--- title: "Osprey Holiday Rentals : Private House Rentals | No Hidden Fees - Vrbo" description: "Long stay discounts available for Osprey holiday rentals. Choose from over 7,828 properties and rent an entire home in Osprey with Vrbo." canonical: "https://www.vrbo.com/en-gb/holiday-rentals/united-states/florida/sarasota-county/osprey" language: en-GB market: GB currency: GBP prices_as_of: 2026-11-13T02:37:17Z --- # Osprey holiday lettings ![A nest on a wooden platform by a lake at sunset with birds flying around.](https://images.trvl-media.com/place/55888/a41b6dcc-976b-420f-8203-78fee502b493.jpg?impolicy=resizecrop&rw=1920&ra=fit&ch=480) We found 7,828 holiday rentals — enter your dates for availability Discover a selection of 13 homes and other holiday rentals in Osprey that are perfect for your trip. Whether you're going on holiday with family or friends, holiday rentals have the amenities that you expect for your stay, which might include a garden and hot tub. You'll be able to choose a property to rent for everyone's needs, including places that are non-smoking or accessible. ## Holiday rentals with weekly discounts – Osprey ### Showing deals for:**12 Feb - 19 Feb** ### [Rare private beachfront estate on the Gulf.](https://www.vrbo.com/search?startDate=2027-02-12&endDate=2027-02-19&selected=69252715&adults=2) ![Pool](https://images.trvl-media.com/lodging/70000000/69260000/69252800/69252715/36cb4bec.jpg?impolicy=fcrop&w=600&h=400&p=1&q=high) - Location: Nokomis - Guest rating: 10/10 (Exceptional, 28 reviews) - Price: £20,973 (was £22,825, 8% off), for 7 nights, 1 home, £2,996 per night, includes taxes & fees ### [BEAUTIFUL 2/2 VILLAS, KING BED, High speed Wi-Fi, Heated Pool and Jacuzzi!](https://www.vrbo.com/search?startDate=2027-02-12&endDate=2027-02-19&selected=34444952&adults=2) ![Property grounds](https://images.trvl-media.com/lodging/35000000/34450000/34445000/34444952/80554812.jpg?impolicy=fcrop&w=600&h=400&p=1&q=high) - Location: Sarasota - Guest rating: 9.6/10 (Exceptional, 53 reviews) - Price: £16,708 (was £18,216, 8% off), for 7 nights, 1 villa, £2,387 per night, includes taxes & fees ### [Sarasota Bayfront Estate - Sunset Views, Near Crescent Beach & Siesta Key Beach](https://www.vrbo.com/search?startDate=2027-02-12&endDate=2027-02-19&selected=66414734&adults=2) ![Luxury Estate By The Bay - Close to Beach image 25](https://images.trvl-media.com/lodging/67000000/66420000/66414800/66414734/5465df5e.jpg?impolicy=fcrop&w=600&h=400&p=1&q=high) - Location: Sarasota - Guest rating: 9.4/10 (Exceptional, 18 reviews) - Price: £8,035 (was £8,722, 8% off), for 7 nights, 1 home, £1,148 per night, includes taxes & fees ### [Siesta Coastal Oasis - 5 Min Paved Walk to the Private Beach](https://www.vrbo.com/search?startDate=2027-02-12&endDate=2027-02-19&selected=75810877&adults=2) ![BACKYARD OASIS WITH PRIVATE POOL](https://images.trvl-media.com/lodging/76000000/75820000/75810900/75810877/793a5bc9.jpg?impolicy=fcrop&w=600&h=400&p=1&q=high) - Location: Siesta Key - Guest rating: 10/10 (Exceptional, 53 reviews) - Price: £17,543 (was £19,062, 8% off), for 7 nights, 1 home, £2,506 per night, includes taxes & fees ### [Luxury HEATED Salt-Water Pool Oasis Close to Beaches and Downtown!!](https://www.vrbo.com/search?startDate=2027-02-12&endDate=2027-02-19&selected=68203481&adults=2) ![Pool](https://images.trvl-media.com/lodging/69000000/68210000/68203500/68203481/efd3d11d.jpg?impolicy=fcrop&w=600&h=400&p=1&q=high) - Location: Sarasota - Guest rating: 8.4/10 (Very good, 17 reviews) - Price: £5,463 (was £5,929, 8% off), for 7 nights, 1 home, £780 per night, includes taxes & fees ### [1 mile to Siesta Key! Early Bird Special & Low Wkly Rates! Heated Pool! BBQ](https://www.vrbo.com/search?startDate=2027-02-12&endDate=2027-02-19&selected=33549408&adults=2) ![Marina Jack's Park](https://images.trvl-media.com/lodging/34000000/33550000/33549500/33549408/b22d0b48.jpg?impolicy=fcrop&w=600&h=400&p=1&q=high) - Location: Sarasota - Guest rating: 9.4/10 (Exceptional, 132 reviews) - Price: £3,064 (was £3,311, 7% off), for 7 nights, 1 home, £438 per night, includes taxes & fees ### [AUTUMN SPECIAL!!! 2/2 BEAUTIFUL VILLA! 2 BR, 2 BA, Heated pool and Jacuzzi! WiFi](https://www.vrbo.com/search?startDate=2027-02-12&endDate=2027-02-19&selected=33495166&adults=2) ![Pool](https://images.trvl-media.com/lodging/34000000/33500000/33495200/33495166/89df40a4.jpg?impolicy=fcrop&w=600&h=400&p=1&q=high) - Location: Sarasota - Guest rating: 9.4/10 (Exceptional, 51 reviews) - Price: £3,319 (was £3,583, 7% off), for 7 nights, 1 villa, £474 per night, includes taxes & fees ### [Family Poolside Paradise on Quiet Cul-de-Sac 4.7 Miles from Siesta Key Beach](https://www.vrbo.com/search?startDate=2027-02-12&endDate=2027-02-19&selected=105886634&adults=2) ![Interior](https://images.trvl-media.com/lodging/106000000/105890000/105886700/105886634/c60365f2.jpg?impolicy=fcrop&w=600&h=400&p=1&q=high) - Location: Sarasota - Guest rating: 9.8/10 (Exceptional, 29 reviews) - Price: £4,613 (was £5,012, 8% off), for 7 nights, 1 home, £659 per night, includes taxes & fees ### [Free Heated Pool, Baby Gear, Shuffleboard, EV charger, Near beach, UTC mall, SRQ](https://www.vrbo.com/search?startDate=2027-02-12&endDate=2027-02-19&selected=99514807&adults=2) ![Pool](https://images.trvl-media.com/lodging/100000000/99520000/99514900/99514807/e79e0759.jpg?impolicy=fcrop&w=600&h=400&p=1&q=high) - Location: Sarasota - Guest rating: 9.8/10 (Exceptional, 7 reviews) - Price: £3,866 (was £4,183, 8% off), for 7 nights, 1 home, £552 per night, includes taxes & fees ### [Literally 3 mins from Siesta with its number 1 beaches!!!! Location! Location!](https://www.vrbo.com/search?startDate=2027-02-12&endDate=2027-02-19&selected=112247070&adults=2) ![Private kitchen](https://images.trvl-media.com/lodging/113000000/112250000/112247100/112247070/04fda2f3.jpg?impolicy=fcrop&w=600&h=400&p=1&q=high) - Location: Sarasota - Guest rating: 10/10 (Exceptional, 5 reviews) - Price: £2,837 (was £3,049, 7% off), for 7 nights, 1 apartment, £405 per night, includes taxes & fees ### [Private, cozy, beach guest-suite B](https://www.vrbo.com/search?startDate=2027-02-12&endDate=2027-02-19&selected=100114424&adults=2) ![Private kitchen](https://images.trvl-media.com/lodging/101000000/100120000/100114500/100114424/787c7b63.jpg?impolicy=fcrop&w=600&h=400&p=1&q=high) - Location: Venice - Guest rating: 9.8/10 (Exceptional, 6 reviews) - Price: £775 (was £843, 8% off), for 7 nights, 1 apartment, £111 per night, includes taxes & fees ### [Centrally Located Charming Beach Suite in Sarasota](https://www.vrbo.com/search?startDate=2027-02-12&endDate=2027-02-19&selected=59957727&adults=2) ![Dining](https://images.trvl-media.com/lodging/60000000/59960000/59957800/59957727/1e2e2005.jpg?impolicy=fcrop&w=600&h=400&p=1&q=high) - Location: Sarasota - Guest rating: 8.6/10 (Excellent, 26 reviews) - Price: £649 (was £705, 8% off), for 7 nights, 1 apartment, £93 per night, includes taxes & fees ## Find spaces that suit your style [Search for Houses](https://www.vrbo.com/search?destination=Osprey%2C+Florida%2C+United+States+of+America®ionId=55888&latLong=27.196163%2C-82.490372&adults=2&startDate=2026-11-26&d1=2026-11-26&endDate=2026-11-28&d2=2026-11-28&property%5Ftype%5Fgroup=house) House [Search for Condos/Apartments](https://www.vrbo.com/search?destination=Osprey%2C+Florida%2C+United+States+of+America®ionId=55888&latLong=27.196163%2C-82.490372&adults=2&startDate=2026-11-26&d1=2026-11-26&endDate=2026-11-28&d2=2026-11-28&property%5Ftype%5Fgroup=apartment%5For%5Fcondo) Condo/Apartment [search for cabins](https://www.vrbo.com/search?destination=Osprey%2C+Florida%2C+United+States+of+America®ionId=55888&latLong=27.196163%2C-82.490372&adults=2&startDate=2026-11-26&d1=2026-11-26&endDate=2026-11-28&d2=2026-11-28&property%5Ftype%5Fgroup=cabin) Cabin [search for cottages](https://www.vrbo.com/search?destination=Osprey%2C+Florida%2C+United+States+of+America®ionId=55888&latLong=27.196163%2C-82.490372&adults=2&startDate=2026-11-26&d1=2026-11-26&endDate=2026-11-28&d2=2026-11-28&property%5Ftype%5Fgroup=cottage) Cottage [search for villas](https://www.vrbo.com/search?destination=Osprey%2C+Florida%2C+United+States+of+America®ionId=55888&latLong=27.196163%2C-82.490372&adults=2&startDate=2026-11-26&d1=2026-11-26&endDate=2026-11-28&d2=2026-11-28&property%5Ftype%5Fgroup=villa) Villa [search for chalets](https://www.vrbo.com/search?destination=Osprey%2C+Florida%2C+United+States+of+America®ionId=55888&latLong=27.196163%2C-82.490372&adults=2&startDate=2026-11-26&d1=2026-11-26&endDate=2026-11-28&d2=2026-11-28&property%5Ftype%5Fgroup=chalet) Chalet ## Find properties near top attractions in Osprey ![A forest with tall trees and a dirt path.](https://images.trvl-media.com/place/55888/ca315bf1-6b48-4e36-9bdd-18ae2b73f28a.jpg?impolicy=fcrop&w=600&h=400&p=1&q=medium) 1 ###### [Oscar Scherer State Park](https://www.vrbo.com/en-gb/search?regionId=6296013&startDate=&endDate=&locale=en%5FGB&rfrrid=slp) ![A white wooden chapel with a triangular roof, surrounded by trees.](https://images.trvl-media.com/place/55888/86eaf4f3-0ab2-42a0-88c7-d2ecaa8703a2.jpg?impolicy=fcrop&w=600&h=400&p=1&q=medium) 2 ###### [Historic Spanish Point](https://www.vrbo.com/en-gb/search?regionId=6295820&startDate=&endDate=&locale=en%5FGB&rfrrid=slp) ## Find the best place to stay - Osprey ### [Charming Osprey Home](https://www.vrbo.com/en-gb/p4848553vb?containsVideo=false) ![Image of Charming Osprey Home](https://media.vrbo.com/lodging/121000000/120690000/120681800/120681763/68ecfea1.jpg?impolicy=resizecrop&ra=fit&rw=455&rh=455) - Address: Osprey, FL - Guest rating: 10/10 (Exceptional, 2 reviews) Sleeps 6 · 2 bedrooms · 2 bathrooms ### [Sarasota Vacation paradise!](https://www.vrbo.com/en-gb/p4236442vb?containsVideo=false) ![Image of Sarasota Vacation paradise!](https://media.vrbo.com/lodging/110000000/109690000/109684500/109684411/95ab356d.jpg?impolicy=resizecrop&ra=fit&rw=455&rh=455) - Address: Osprey, FL - Guest rating: 10/10 (Exceptional, 12 reviews) Premier Host Sleeps 8 · 3 bedrooms · 2+ bathrooms ### [Beach-House, wonderful elec. heated Pool with a Natural Waterfall, Jacuzzi, Wifi](https://www.vrbo.com/en-gb/p315684vb?containsVideo=false) ![Image of Beach-House, wonderful elec. heated Pool with a Natural Waterfall, Jacuzzi, Wifi](https://media.vrbo.com/lodging/34000000/33980000/33972900/33972811/1649d5fa.jpg?impolicy=resizecrop&ra=fit&rw=455&rh=455) - Address: Osprey, FL - Guest rating: 8.8/10 (Excellent, 32 reviews) Sleeps 8 · 4 bedrooms · 2 bathrooms ### [Windsor Lodge 18 | Charming Florida Stay Pool](https://www.vrbo.com/en-gb/p4059167vb?containsVideo=false) ![Image of Windsor Lodge 18 | Charming Florida Stay Pool](https://media.vrbo.com/lodging/107000000/106240000/106232100/106232030/701d1f1d.jpg?impolicy=resizecrop&ra=fit&rw=455&rh=455) - Address: Osprey, FL - Guest rating: 9.2/10 (Wonderful, 5 reviews) Premier Host Sleeps 4 · 1 bedroom · 1 bathroom ### [Idyllic Beach House on Casey Key](https://www.vrbo.com/en-gb/p381010vb?containsVideo=false) ![Image of Idyllic Beach House on Casey Key](https://media.vrbo.com/lodging/35000000/34160000/34153000/34152961/d6e71d46.jpg?impolicy=resizecrop&ra=fit&rw=455&rh=455) - Address: Osprey, FL - Guest rating: 9.6/10 (Exceptional, 39 reviews) Sleeps 6 · 3 bedrooms · 2 bathrooms ### [Renovated Tranquil 3-Bdrm- w/ yard, workspace, great kitchen in Osprey dogs ok](https://www.vrbo.com/en-gb/p4825810vb?containsVideo=false) ![Image of Renovated Tranquil 3-Bdrm- w/ yard, workspace, great kitchen in Osprey dogs ok](https://media.vrbo.com/lodging/121000000/120470000/120461700/120461624/18d2ea3d.jpg?impolicy=resizecrop&ra=fit&rw=455&rh=455) - Address: Osprey, FL - Guest rating: 10/10 (Exceptional, 4 reviews) Sleeps 5 · 3 bedrooms · 2 bathrooms ## Top rated rentals - Osprey ### [Kon Tiki Inn](https://www.vrbo.com/en-gb/pdp/lo/90021825?containsVideo=false) ![Image of Kon Tiki Inn](https://media.vrbo.com/lodging/91000000/90030000/90021900/90021825/9a646a3f.jpg?impolicy=resizecrop&ra=fit&rw=455&rh=455) - Guest rating: 10/10 (Exceptional, 320 reviews) - Review: Great. Great place. They have done a good job of refurbishing it, very comfortable, good facilities, with pool and patio with tables and chairs, easy to find, plenty of parking. Restaurant next door Salty Dawgs is good too. Great hosts, friendly and helpful. Really enjoyed our stay., by Stephen, Stayed Feb 2024 ### [Hibiscus Suites - Gateway to Siesta Key](https://www.vrbo.com/en-gb/pdp/lo/1212924?containsVideo=false) ![Image of Hibiscus Suites - Gateway to Siesta Key](https://media.vrbo.com/lodging/2000000/1220000/1213000/1212924/b278ba9a.jpg?impolicy=resizecrop&ra=fit&rw=455&rh=455) - Guest rating: 8.8/10 (Excellent, 2485 reviews) - Review: Gem of a place. What a gem of a place would highly recommend, by Keith, Stayed May 2023 ### [Siesta Heron Suites & Villas](https://www.vrbo.com/en-gb/pdp/lo/59661429?containsVideo=false) ![Image of Siesta Heron Suites & Villas](https://media.vrbo.com/lodging/60000000/59670000/59661500/59661429/6efe649f.jpg?impolicy=resizecrop&ra=fit&rw=455&rh=455) - Guest rating: 8.4/10 (Very good, 46 reviews) - Review: Fine time in Siesta Key. A very comfortable stay in Siesta Key. Our apartment had been fully redeveloped since Hurricane Milton. Excellent job. Pool was really good. Nikes to ride. Kayaks to addle in the lagoon. All in allan exceptional choice., by Ronald, Stayed Mar 2025 ### Peace of mind Our Book with Confidence Guarantee gives you 24/7 support ### More quality time From booking to staying, the whole process is simple and enjoyable ### All the privacy of home Enjoy full kitchens, pools, gardens and more ### More for less More space, more privacy, more amenities — more value ## Find out more about Osprey ### Why visit Osprey - **Scenic Waterfront:** Osprey boasts beautiful waterfront views, perfect for leisurely strolls and relaxation. - **Outdoor Adventures:** The town is ideal for outdoor activities, including beach outings and exploring local parks. - **Stoneybrook Golf Club:** Enjoy a round of golf at this renowned course, set amidst picturesque landscapes. - **Family-Friendly Atmosphere:** Osprey offers a welcoming environment, making it perfect for family vacations and memorable experiences. - **Charming Accommodations:** Choose from a variety of vacation rentals to ensure a comfortable stay during your visit. ### Popular types of accommodation in Osprey Discover the charm of Osprey, Florida, a delightful town brimming with natural beauty and local attractions. From scenic parks to vibrant waterways, this picturesque destination offers a range of experiences for every traveller. When it comes to accommodation, you’ll find a variety of options including houses, condos, and apartments, perfect for a relaxing getaway. Enjoy the comfort of home with Osprey rentals that cater to your needs and ensure a memorable stay. - **[Houses: ](https://www.vrbo.com/en-gb/holiday-rentals/houses/united-states/florida/sarasota-county/osprey)** The top choice for holidaymakers in Osprey, offering spacious accommodations with the comforts of home. - **Condos:** A popular option, these stylish units provide modern amenities and often stunning views. - **Apartments:** Ideal for couples or solo travellers, these self-contained spaces are conveniently located. - **[Villas: ](https://www.vrbo.com/en-gb/holiday-rentals/villas/united-states/florida/sarasota-county/osprey)** Luxurious and often set in picturesque surroundings, villas cater to those seeking an upscale experience. - **Cottages:** Quaint and charming, these delightful retreats offer a cosy atmosphere for a relaxing getaway.\*\* ### Top attractions in and around Osprey Osprey, Florida, is a charming destination perfect for beach and outdoor family vacations. Visitors can enjoy picturesque beaches, explore urban parks, and stroll along the jetty pier. This vibrant area offers a variety of attractions tailored for those seeking outdoor adventures and family-friendly experiences, ensuring that every traveller can create lasting memories in this delightful coastal town. - **[Siesta Key Beach: ](https://www.vrbo.com/en-gb/holiday-rentals/united-states/florida/sarasota-county/siesta-key/siesta-key-public-beach)** Located a mere 10km from Osprey, this pristine beach is renowned for its powdery white sands and vibrant beach vibes, perfect for sunbathing and water sports. - **[Historic Spanish Point: ](https://www.vrbo.com/en-gb/holiday-rentals/united-states/florida/sarasota-county/osprey/osprey-village/historic-spanish-point)** Situated within Osprey, this archaeological site offers a fascinating glimpse into the region's rich history and culture, featuring beautiful gardens and ancient artifacts. - **[Point of Rocks: ](https://www.vrbo.com/en-gb/holiday-rentals/united-states/florida/sarasota-county/siesta-key/point-of-rocks)** Just 6km away, this unique rock formation provides stunning outdoor scenery, ideal for photography and exploring marine life during low tide. ### Things to do recommended for couples Osprey offers a charming escape for couples. Enjoy a romantic sunset at Nokomis Beach or take a leisurely kayak tour through serene waters. Don't miss a delightful dinner at a waterfront restaurant, where you can savour fresh seafood while watching the sun dip below the horizon. ### Things to do recommended for families Families visiting Osprey can explore the beautiful Oscar Scherer State Park, perfect for hiking and spotting wildlife, or enjoy a fun-filled day at Sharky's on the Pier, where kids can play on the beach and savour delicious seafood. ### Things to do recommended for groups Experience the thrill of the TreeUmph. Adventure Course, an exciting zipline and ropes course located 29km from Osprey. Perfect for groups seeking adventure and outdoor fun, it offers a unique way to bond while enjoying Florida's beautiful scenery. *\*Distances are measured in a straight line; actual driving distances may vary depending on the route.* ### What do I need to keep in mind when booking a vacation in Osprey If you're travelling with a group, family, pets, or planning an extended stay, it’s important to refine your search according to your specific needs. Here are some helpful booking tips for Vrbo. - **[Traveling to Osprey with a group: ](https://www.vrbo.com/en-gb/search?bedroom%5Fcount%5Fgt=3®ionId=55888&rooms%5Fspaces%5Fgroup=kitchen&rfrr=crcontent)** Think about how many bedrooms you'll require, as well as amenities like a fully equipped kitchen or outdoor space for group gatherings. Thankfully, you can easily filter for all of these options and more on Vrbo. - **[Traveling to Osprey with young kids: ](https://www.vrbo.com/en-gb/search?house%5Frules%5Fgroup=children%5Fallowed&properties%5Fgood%5Ffor%5Fgroup=families®ionId=55888&rfrr=crcontent)** Travelling with young children can be demanding. It's important to prioritise their comfort and safety, along with suitable amenities, such as a private swimming pool. Additionally, it’s wise to think about how close you are to family-friendly attractions. - **[Taking your pets with you to Osprey: ](https://www.vrbo.com/en-gb/search?house%5Frules%5Fgroup=pets%5Fallowed®ionId=55888&amenities=PETS&rfrr=crcontent)** For many families, a holiday isn’t truly finished without their furry companions. If this resonates with you, take a look at Vrbo properties that welcome pets. Most pet-friendly accommodations offer feeding bowls and beds to ensure that everyone feels completely at home. - **Planning for a long term stay visiting Osprey:** If you're in search of holiday rentals offering discounts for stays of a month or more, you've come to the right place. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to include options like a parking space, a well-equipped kitchen, or even a private pool in your search criteria. ### Where to stay near Osprey Osprey, Florida, is a delightful destination perfect for beach and outdoor family vacations. Visitors can immerse themselves in its historical charm while enjoying the friendly atmosphere. Explore the scenic waterfront, relax in the sunny weather, or indulge in a round of golf at the renowned Stoneybrook Golf Club. With its inviting vibe and opportunities for romantic strolls, Osprey offers a unique blend of relaxation and adventure for every traveller. - **[Siesta Key: ](https://www.vrbo.com/en-gb/holiday-rentals/united-states/florida/sarasota-county/siesta-key)** Siesta Key is a stunning island city located 11km from Osprey, renowned for its powdery white sandy beaches and vibrant outdoor activities. This tropical paradise is perfect for families seeking a fun-filled experience, with numerous recreational areas and resorts to choose from. Visitors can enjoy beach volleyball, water sports, and sunbathing on the picturesque shoreline. Siesta Key is also home to charming shops and eateries, making it a delightful spot to explore. The local landmark, the Siesta Key Beach, is consistently ranked among the best beaches in the USA, offering a perfect blend of relaxation and adventure. - **[Venice: ](https://www.vrbo.com/en-gb/holiday-rentals/united-states/florida/sarasota-county/venice)** Located 11km from Osprey, Venice is a quaint city known for its lovely beaches and family-friendly atmosphere. This charming coastal town offers visitors a variety of outdoor activities, including golf at its scenic courses and relaxing afternoons at the beach. Venice's downtown area is filled with delightful shops and restaurants, creating a vibrant community spirit. The local landmarks, such as the Venice Beach and the picturesque town neighbourhood, provide a perfect backdrop for family outings and leisurely strolls. Venice is an ideal destination for those seeking a blend of excitement and tranquillity. - **[Vamo: ](https://www.vrbo.com/en-gb/holiday-rentals/united-states/florida/sarasota-county/vamo)** Just 3km from Osprey, Vamo is a serene neighbourhood that offers a peaceful retreat for families and outdoor enthusiasts. With easy access to beautiful beaches and recreational areas, visitors can indulge in activities such as golf and leisurely walks along the shore. The local atmosphere is relaxed, making it a great place to unwind and connect with nature. Vamo is an excellent choice for those looking to enjoy the charm of Florida's coast while still being close to the vibrant attractions of nearby cities. ### Best time to go to Osprey If you're planning a trip to Osprey, it's a good idea to check both the weather and property rates. The warmest month is August. Peak season runs in March to April and September, while off-peak times, like October to December tend to have fewer bookings and better deals. | **Calendar Month** | **Temperature** | **Precipitation** | **Cloudiness** | **Occupancy** | **Pricing** | | ------------------ | --------------- | ----------------- | -------------- | ------------- | ------------- | | January | 62.6°F (17.0°C) | Light Rain | Mostly Sunny | Average | Slightly Low | | February | 65.1°F (18.4°C) | No Rain (Dry) | Mostly Sunny | Average | Average | | March | 68.0°F (20.0°C) | No Rain (Dry) | Sunny | Slightly High | Slightly High | | April | 73.4°F (23.0°C) | Light Rain | Mostly Sunny | Slightly High | Slightly High | | May | 77.7°F (25.4°C) | Light Rain | Mostly Sunny | Average | Average | | June | 81.7°F (27.6°C) | Light Rain | Mostly Sunny | Average | Average | | July | 82.9°F (28.3°C) | Light Rain | Mostly Sunny | Average | Slightly High | | August | 83.3°F (28.5°C) | Light Rain | Mostly Sunny | Average | Average | | September | F (27.5°C) | Light Rain | Mostly Sunny | Slightly High | Slightly Low | | October | 77.2°F (25.1°C) | Light Rain | Mostly Sunny | Slightly Low | Slightly Low | | November | 70.7°F (21.5°C) | No Rain (Dry) | Mostly Sunny | Slightly Low | Average | | December | 66.6°F (19.2°C) | No Rain (Dry) | Mostly Sunny | Slightly Low | Average | ### Booking with Vrbo is simple Looking to save on your next holiday? Consider being flexible with your travel dates, as prices can fluctuate. Moreover, extending your stay often results in significant savings. To discover the ideal Vrbo property that fits your budget, utilise our filters to search by price, location, and type of holiday rental. ### Vrbo Trips: Planning as easy as it gets Vrbo's Trip Board offers an easy-to-use platform for planning your journeys. You can start new trips, resume from where you last left off, or manage your existing plans all in one place. You'll find your saved or booked properties neatly organised under Potential, Upcoming, or Current Trips. To begin exploring Trip Boards, please visit: https://www.vrbo.com/en-gb/trips. \*\*Based on Vrbo properties bookings. ## Frequently Asked Questions ### What is the best area to stay in Osprey when booking a holiday rental? When considering a holiday rental in Osprey, Florida, a popular area to stay is near the charming coastal community of Casey Key. This picturesque neighbourhood offers a serene atmosphere and stunning waterfront views, making it an ideal spot for those looking to unwind. Visitors can enjoy the natural beauty of the nearby beaches, such as Nokomis Beach, which is superb for sunbathing or taking a leisurely stroll along the shore. In addition to the beaches, the area is close to the Oscar Scherer State Park, where you can explore scenic trails and observe local wildlife, adding a touch of adventure to your stay. Osprey has a variety of properties available, from quaint cottages to luxurious waterfront homes, ensuring that you can find accommodation that suits your needs and preferences. ### How much does it cost to rent a holiday home in Osprey? Prices for holiday rentals in Osprey vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from [affordable rentals in Osprey](https://www.vrbo.com/en-gb/search?regionId=55888&sort=PRICE%5FLOW%5FTO%5FHIGH) to more spacious homes. To get the best value, book early and take advantage of [Vrbo’s free rewards program](https://www.vrbo.com/en-gb/welcome-one-key). ### Are there any discounts for Osprey holiday house rentals? You can find great discounts on house rentals in Osprey on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates. ### Where are the best areas for renting a beach house in Osprey? For renting a beach house in Osprey, Florida, the area around Casey Key is particularly desirable. This charming barrier island is known for its stunning sandy beaches and a laid-back atmosphere. Properties here often feature direct beach access, spacious decks for outdoor dining, and amenities such as private pools and hot tubs, great for relaxing after a day in the sun. Many of these beach houses also come equipped with modern kitchens and laundry facilities, suiting families or groups looking for a comfortable stay. The nearby Siesta Key, renowned for its powdery white sand beaches, is also a fantastic option. Here, visitors can find a variety of rentals, from beachfront condos to larger family homes, often boasting amenities like beach gear, outdoor showers, and community pools. The vibrant local area offers plenty of dining and shopping choices, making it easy for travellers to enjoy the local culture. Additionally, the proximity to the scenic Myakka River State Park provides opportunities for outdoor activities such as kayaking and hiking, enhancing the appeal of the Osprey area for nature lovers. ### What is the most popular type of holiday rental accomodation in Osprey? In Osprey, holiday houses are the most popular type of holiday rental, with around 116 available in the area. These properties typically feature spacious layouts, multiple bedrooms, fully equipped kitchens, and private outdoor areas, making them ideal for families or groups looking to enjoy the sunny Florida weather. Many of these houses are located near attractions such as the historic Spanish Point and the beautiful beaches along the Gulf Coast. In addition to holiday houses, there are approximately 52 condos and 36 apartments available, offering a more compact living option with amenities like community pools, fitness centres, and easy access to local dining and shopping. For those seeking a quaint escape, several cottages and villas provide a charming and intimate atmosphere, often set in picturesque surroundings. ### Are there any family house rentals in Osprey? In Osprey, Florida, there are numerous family-friendly house rentals available, with around 25 options to choose from. This charming area is known for its proximity to beautiful beaches and vibrant outdoor activities, making it an ideal spot for families. Many of these properties feature spacious living areas, fully equipped kitchens for preparing meals, and outdoor spaces great for children to play. Visitors can enjoy amenities such as private pools, game rooms, and access to nearby parks. The locale is conveniently situated near attractions like the Oscar Scherer State Park, which offers hiking trails and wildlife viewing, as well as the stunning Gulf Coast beaches, great for a day of sun and sand. ### Can I rent a holiday home with a pool or hot tub in Osprey? In Osprey, there are plenty of holiday homes available for rent that come equipped with pools and hot tubs, with around 32 options to choose from. This charming area, located near the beautiful Gulf Coast of Florida, offers a range of neighbourhoods where travellers can find these properties, including the serene Bay Preserve and the picturesque Osprey Harbour. Guests can expect a variety of amenities in these rentals, such as private pools, relaxing hot tubs, spacious outdoor areas for lounging, and fully equipped kitchens great for preparing meals after a day of exploring. Many properties also feature additional comforts like barbecue grills and outdoor dining spaces, allowing for enjoyable evenings under the stars. ### Can I find long-stay holiday rentals in Osprey? A [long-stay holiday rental in Osprey](https://www.vrbo.com/en-gb/tgp/lodging/theme/longstay/55888/osprey) is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search. ### Are there pet-friendly house rentals in Osprey? In Osprey, Florida, there are several pet-friendly house rentals available, with a good selection to choose from. Many of these properties are equipped with amenities such as spacious backyards, fully equipped kitchens, and comfortable living areas, making them ideal for families or groups travelling with pets. The area offers easy access to beautiful parks and beaches, including nearby Oscar Scherer State Park, which is known for its scenic trails and opportunities for outdoor activities, great for walks with your furry companions. Additionally, the charming waterfront neighbourhood provides a relaxing atmosphere, and many rentals are conveniently located near local shops and dining options, adding to the convenience for travellers. ### Are there any remote work holiday rentals in Osprey? In Osprey, Florida, there are numerous holiday rentals suitable for remote work, with around 168 options available. This charming area, located near the stunning Gulf Coast, offers properties that cater to the needs of remote workers. Many rentals come equipped with high-speed internet and Wi-Fi, ensuring that guests can stay connected while enjoying the serenity of their surroundings. Travellers can expect amenities such as spacious workspaces, comfortable seating areas, and fully equipped kitchens, allowing for both productivity and relaxation. The proximity to beautiful beaches and parks, like the nearby Oscar Scherer State Park, provides excellent opportunities for outdoor activities during breaks. To help narrow your search, insert your dates and apply the "[WiFi](https://www.vrbo.com/en-gb/search?regionId=55888&amenities%5Ffacilities%5Fgroup=internet%5Favailable)" filter on Vrbo. ### Are there any Osprey holiday rentals with parking? Vrbo offers a wide selection of [holiday rentals in Osprey with parking](https://www.vrbo.com/en-gb/search?regionId=55888&amenities%5Ffacilities%5Fgroup=parking) available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the “Parking available” filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay. ### What are popular rental amenities in Osprey? In Osprey, popular holiday rental amenities include fully-equipped kitchens, allowing guests to prepare their own meals with ease. Onsite parking is also a common feature, providing convenience for those travelling by car. Many properties offer decks or patios, great for enjoying the warm Florida weather and outdoor relaxation. Additionally, coffee and tea makers are typically provided for guests who enjoy their morning brew. Notably, some rentals permit pets, making it easier for travellers to bring their furry friends along for the stay. ### When is the best time to visit Osprey for a holiday rental? The best time to visit Osprey for a holiday rental is during the peak season from February to April, with March being particularly popular. This period attracts sun seekers and outdoor enthusiasts, keen to enjoy the stunning beaches and nature parks that Osprey has to offer. With pleasant temperatures averaging between 15 to 25 degrees Celsius, visitors can comfortably engage in a variety of activities like kayaking, fishing, and exploring the scenic Myakka River State Park. During these months, the area bustles with activity, providing ample opportunities for sightseeing and relaxation. The pleasant climate encourages leisurely strolls along the picturesque Gulf Coast beaches, where you can soak up the sun or enjoy a refreshing swim in the ocean. If you're looking for a more budget-friendly option, consider visiting in October. This month offers a quieter atmosphere and is superb for enjoying the beauty of Osprey without the crowds. The weather is still warm, making it an excellent time for outdoor adventures and peaceful beach days. Ultimately, your choice of when to visit Osprey will depend on whether you prefer the vibrant energy of peak season or the tranquil charm of the shoulder months. ### How early should I book a Osprey holiday rental? Book your Osprey holiday rental at least two months before you travel for the best selection of properties.\* Plus, you'll typically find that the earlier you book your holiday rental, the better the price. \*Based on analysis of Vrbo booking and occupancy data for 2024 stays. ### What are the top attractions in Osprey? In Osprey, visitors can enjoy a range of attractions that highlight both natural beauty and cultural experiences. The serene Oscar Scherer State Park is a prominent feature, offering hiking trails, wildlife viewing, and access to the lovely South Creek, ideal for canoeing and kayaking. This park is a great spot for nature enthusiasts and those looking to explore Florida's natural habitats. Another top attraction is the historic Spanish Point, an archaeological site that provides insight into the area's history and early Native American cultures. Visitors can wander through beautiful gardens, see historical buildings, and learn about the region's past. For beach lovers, Siesta Key is just a short drive away, famed for its powdery white sands and vibrant beach atmosphere, making it great for sunbathing and water activities. The nearby Legacy Trail is great for cycling and walking, connecting Osprey to Sarasota and providing scenic views along the way. ### Can I change or cancel my Osprey home rental booking on Vrbo? To find Osprey holiday rentals with free cancellation, just use Vrbo's handy "[Free cancellation](https://www.vrbo.com/en-gb/search?regionId=55888&free%5Fcancellation%5Fgroup=free%5Fcancellation)" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo makes it easy to book with confidence. ### Why should I join Vrbo as a host? Joining Vrbo as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, [become a host](https://www.vrbo.com/en-gb/list) and let Vrbo handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences. ### Are all fees included in the Osprey holiday rental prices shown on Vrbo? Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence. ### What is VrboCare™ and how does it work? Vrbo’s mission is to help guests relax, reconnect, and enjoy precious time together. With [VrboCare™](https://www.vrbo.com/en-gb/tlp/trust-and-safety/care-guarantee), you can have peace of mind knowing you’re protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can’t resolve, we’ll help you address it, find a similar property, or get your reservation refunded if applicable. That’s our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable. ### What can I expect from Vrbo customer service and VrboCare™ support? Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way. Vrbo also offers support via live chat through our [Help Centre](https://www.vrbo.com/en-gb/helpcenter/?articleId=40104), where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions. ### Can I plan a group trip on Vrbo? Vrbo's [Trip Planner](https://www.vrbo.com/en-gb/why/trip-planning) makes organising group trips easy and stress-free. 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[Ski-In/Ski-Out rentals near Pinelands Reserve](https://www.vrbo.com/en-gb/tgp/lodging/theme/ski/553248621532652550/pinelands-reserve) - [Rentals with pool near Lido Beach](https://www.vrbo.com/en-gb/holiday-rentals/pools/united-states/florida/sarasota-county/sarasota/lido-key/lido-key-beach) - [Longstay Hotels near Lido Beach](https://www.vrbo.com/en-gb/tgp/lodging/theme/longstay/6145141/lido-key-beach) - [Villas in Orlando](https://www.vrbo.com/en-gb/holiday-rentals/villas/united-states/florida/orange-county/orlando) - [Houses in St. Armands Circle](https://www.vrbo.com/en-gb/holiday-rentals/houses/united-states/florida/sarasota-county/sarasota/saint-armands-key/st-armands-circle) - [Villas in St. Armands Circle](https://www.vrbo.com/en-gb/holiday-rentals/villas/united-states/florida/sarasota-county/sarasota/saint-armands-key/st-armands-circle) - [Palmer Ranch Holiday Rentals](https://www.vrbo.com/en-gb/holiday-rentals/united-states/florida/sarasota-county/sarasota/palmer-ranch) - [University Park Country Club Holiday Rentals](https://www.vrbo.com/en-gb/holiday-rentals/united-states/florida/sarasota-county/sarasota/university-park-country-club) - [Siesta Key Holiday Rentals](https://www.vrbo.com/en-gb/holiday-rentals/united-states/florida/sarasota-county/siesta-key) - [Historic Spanish Point Holiday Rentals](https://www.vrbo.com/en-gb/holiday-rentals/united-states/florida/sarasota-county/osprey/osprey-village/historic-spanish-point) - [Fisherman's Haven Holiday Rentals](https://www.vrbo.com/en-gb/holiday-rentals/united-states/florida/sarasota-county/siesta-key/fishermans-haven) - [Turtle Beach Holiday Rentals](https://www.vrbo.com/en-gb/holiday-rentals/united-states/florida/sarasota-county/siesta-key/turtle-beach) - [Sunrise Cove Holiday Rentals](https://www.vrbo.com/en-gb/holiday-rentals/united-states/florida/sarasota-county/siesta-key/sunrise-cove) - [Gulf Gate Woods Holiday Rentals](https://www.vrbo.com/en-gb/holiday-rentals/united-states/florida/sarasota-county/sarasota/gulf-gate-woods) - [Rivendell Holiday Rentals](https://www.vrbo.com/en-gb/holiday-rentals/united-states/florida/sarasota-county/osprey/rivendell) - [Jim Neville Marine Preserve Holiday Rentals](https://www.vrbo.com/en-gb/holiday-rentals/united-states/florida/sarasota-county/siesta-key/jim-neville-marine-preserve) - [Inlets Holiday Rentals](https://www.vrbo.com/en-gb/holiday-rentals/united-states/florida/sarasota-county/siesta-key/inlets) - [Banana Bay Club Waterside Holiday Rentals](https://www.vrbo.com/en-gb/holiday-rentals/united-states/florida/sarasota-county/siesta-key/banana-bay-club-waterside) - [Sorrento Shores Holiday Rentals](https://www.vrbo.com/en-gb/holiday-rentals/united-states/florida/sarasota-county/osprey/sorrento-shores) - [Venice Holiday Rentals](https://www.vrbo.com/en-gb/holiday-rentals/united-states/florida/sarasota-county/venice) - [Disney's Maingate West Holiday Rentals](https://www.vrbo.com/en-gb/holiday-rentals/united-states/florida/disneys-maingate-west) - [Bay Acres Holiday Rentals](https://www.vrbo.com/en-gb/holiday-rentals/united-states/florida/sarasota-county/osprey/bay-acres) - [Village des Pins Holiday Rentals](https://www.vrbo.com/en-gb/holiday-rentals/united-states/florida/sarasota-county/sarasota/village-des-pins) - [The Oaks Club Holiday Rentals](https://www.vrbo.com/en-gb/holiday-rentals/united-states/florida/sarasota-county/osprey/the-oaks) - [Island Reef Holiday Rentals](https://www.vrbo.com/en-gb/holiday-rentals/united-states/florida/sarasota-county/siesta-key/island-reef) - [Coral Cove Holiday Rentals](https://www.vrbo.com/en-gb/holiday-rentals/united-states/florida/sarasota-county/sarasota/coral-cove) - [Osprey Village Holiday Rentals](https://www.vrbo.com/en-gb/holiday-rentals/united-states/florida/sarasota-county/osprey/osprey-village) - [Vamo Holiday Rentals](https://www.vrbo.com/en-gb/holiday-rentals/united-states/florida/sarasota-county/vamo) - [Stoneybrook Golf and Country Club Holiday Rentals](https://www.vrbo.com/en-gb/holiday-rentals/united-states/florida/sarasota-county/sarasota/palmer-ranch/stoneybrook-golf-and-country-club) - [Stoneybrook Golf & Country Club Holiday Rentals](https://www.vrbo.com/en-gb/holiday-rentals/united-states/florida/sarasota-county/sarasota/palmer-ranch/stoneybrook-golf-and-country-club/stoneybrook-golf-country-club) - [Bay Tree Club Holiday Rentals](https://www.vrbo.com/en-gb/holiday-rentals/united-states/florida/sarasota-county/siesta-key/bay-tree-club) - [Vista Hermosa Holiday Rentals](https://www.vrbo.com/en-gb/holiday-rentals/united-states/florida/sarasota-county/siesta-key/vista-hermosa) - [Tortuga Holiday Rentals](https://www.vrbo.com/en-gb/holiday-rentals/united-states/florida/sarasota-county/siesta-key/tortuga) - [Sarasota Holiday Rentals](https://www.vrbo.com/en-gb/holiday-rentals/united-states/florida/sarasota-county/sarasota) - [Casey Key Holiday Rentals](https://www.vrbo.com/en-gb/holiday-rentals/united-states/florida/sarasota-county/nokomis/casey-key) - [Pelican Cove Holiday Rentals](https://www.vrbo.com/en-gb/holiday-rentals/united-states/florida/sarasota-county/sarasota/pelican-cove) - [Fisherman's Cove Holiday Rentals](https://www.vrbo.com/en-gb/holiday-rentals/united-states/florida/sarasota-county/siesta-key/fishermans-cove) - [Sarasota Square Holiday Rentals](https://www.vrbo.com/en-gb/holiday-rentals/united-states/florida/sarasota-county/sarasota/palmer-ranch/palmer-square-west/sarasota-square) ## Other language versions ```yaml hreflang: x-default: https://www.vrbo.com/vacation-rentals/usa/florida/south-west/osprey de-AT: https://www.vrbo.com/de-at/urlaubsunterkunft/vereinigte-staaten/florida/sarasota-county/osprey fr-CA: https://www.vrbo.com/fr-ca/location-vacances/%C3%A9tats-unis-dam%C3%A9rique/floride/comt%C3%A9-de-sarasota/osprey fr: https://www.abritel.fr/d/1752/osprey en-CA: https://www.vrbo.com/en-ca/vacation-rentals/united-states/florida/sarasota-county/osprey it-IT: https://www.vrbo.com/it-it/case-vacanze/stati-uniti-damerica/florida/contea-di-sarasota/osprey de: https://www.fewo-direkt.de/d/1752/osprey en-SG: https://www.vrbo.com/en-sg/holiday-accommodation/united-states/florida/sarasota-county/osprey sv-SE: https://www.vrbo.com/sv-se/semesterbostad/usa/florida/sarasota-county/osprey en-AU: https://www.stayz.com.au/d/1752/osprey es-ES: https://www.vrbo.com/es-es/alquiler-vacacional/estados-unidos/florida/condado-de-sarasota/osprey en-GB: https://www.vrbo.com/en-gb/holiday-rentals/united-states/florida/sarasota-county/osprey nl-NL: https://www.vrbo.com/nl-nl/vakantiehuizen/verenigde-staten/florida/sarasota-county/osprey en-NZ: https://www.bookabach.co.nz/d/1752/osprey no-NO: https://www.vrbo.com/no-no/overnatting/forente-stater/florida/sarasota-county/osprey en-US: https://www.vrbo.com/vacation-rentals/usa/florida/south-west/osprey pt-BR: https://www.vrbo.com/pt-br/alugue-temporada/estados-unidos/fl%C3%B3rida/sarasota-county/osprey ```