Longboat Key vacation rentals

We found 11,510 vacation rentals — enter your dates for availability

Discover a selection of 23 homes, 18 apartments, and other vacation rentals in Longboat Key that are perfect for your trip. Whether you're going on vacation with family or friends, vacation rentals have the best amenities for spending time at your vacation home, which might include a garden and hot tub. No matter what you're looking for, you'll be sure to find a rental for everyone's needs, including a place that is accessible or non-smoking.

Vacation rentals with weekly discounts - Longboat Key

Showing deals for:Mar 20 - Mar 27

Image gallery for Charm | Comfy | Tiki | Pool Private Beach

Full Kitchen
9.6 out of 10, Exceptional, (193 reviews)
Exceptional
(193 reviews)

Charm | Comfy | Tiki | Pool Private Beach

Siesta Key

5% off
Price is CA $430
CA $4,070 total
includes taxes & fees
Charm | Comfy | Tiki | Pool Private Beach

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Find out more about Longboat Key

Why visit Longboat Key

  • Stunning Beaches: Longboat Key boasts beautiful sandy shores perfect for sunbathing and relaxation.
  • Family-Friendly Activities: The area offers various attractions suitable for all ages, ensuring a fun-filled vacation.
  • Charming Coastal Vibe: Enjoy the serene atmosphere and picturesque palm-lined streets that enhance your getaway experience.
  • Outdoor Adventures: Explore nearby marinas and nature trails for exciting outdoor experiences and local wildlife.
  • Diverse Accommodations: Choose from a range of vacation rentals, including condos and private homes, for a comfortable stay.

Popular types of accommodation in Longboat Key

Planning a getaway to Longboat Key? You're in for a treat. With a variety of top-notch accommodations, including condos, houses, and apartments, you’ll find the perfect spot to unwind. Explore Longboat Key vacation rentals that offer transparency and savings, ensuring a stress-free experience. Discover the best beach condo rentals in Florida for a memorable stay on the stunning Gulf Coast.

  • Condos: The top choice for vacation rentals in Longboat Key, offering modern amenities and stunning views.
  • Houses: A popular option for families and groups, providing ample space and privacy for your stay.
  • Apartments: Ideal for solo travellers or couples, these rentals offer convenient locations and essential comforts.
  • Cottages: A charming selection for those seeking a quaint, homey atmosphere near the beach.
  • Villas: Luxurious accommodations perfect for a lavish getaway, featuring upscale facilities and beautiful surroundings.**

Top attractions near Longboat Key

Longboat Key, Florida, is perfect for beach, family, and city-themed vacations. Visitors can explore beautiful beaches, modern colleges, and marinas, catering to those seeking culture and outdoor experiences. Whether you're interested in sunbathing on the sandy shores or enjoying local attractions, Longboat Key offers a delightful getaway for everyone. Be sure to discover all that this charming locale has to offer during your visit.

  • IMG Academy: A premier sports training facility, IMG Academy offers a unique opportunity to witness aspiring athletes hone their skills. Engage in various sports events, training camps, and workshops, making it a great spot for sports enthusiasts.
  • Lido Beach: Known for its stunning white sand and vibrant beach vibes, Lido Beach is perfect for sunbathing, swimming, and water activities. Enjoy the natural beauty and relax in a tranquil atmosphere.
  • St. Armands Circle: This charming street offers a lively atmosphere with upscale shops, dining, and art galleries. Experience the city vibes while strolling through this vibrant hub, perfect for shopping and leisure.

Things to do recommended for couples

For a romantic escape in Longboat Key, indulge in relaxation at Aluna Wellness Center & Spa, only 8.0km away. Challenge each other at the nearby Fish Hole Adventure Golf, 6.4km away, or enjoy outdoor thrills with H2O Watersportz, also 6.4km from your stay.

Things to do recommended for families

Families vacationing in Longboat Key can enjoy a day at LECOM Park for exciting sports, visit the Astro Skate and Fun Center for thrilling arcade adventures, or relax at the Robert L. Taylor Community Complex, which offers wellness and recreational activities, all within a short drive.

Things to do recommended for groups

Groups visiting Longboat Key can enjoy a captivating show at the Asolo Theatre for the Performing Arts, explore unique finds at the West Coast Surf Shop, and experience the vibrant atmosphere of the Red Barn Flea Market Plaza. These activities promise a memorable local experience.

*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 Longboat Key

When planning your trip—whether you're traveling with a group, family, pets, or seeking extended stays—be sure to use the appropriate filters to match your priorities. Here are some helpful Vrbo booking tips for you.

  • Traveling to Longboat Key with a group: Think about how many bedrooms you require and any specific amenities, like a full kitchen or outdoor area for group gatherings. The good news is that you can easily filter for these options and much more on Vrbo.
  • Traveling to Longboat Key with young kids: Traveling with young children can present its own set of challenges. It's important to prioritize their comfort and safety, along with suitable amenities like 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 Longboat Key: For many, a family vacation isn’t truly fulfilling without their furry companion by their side. If you can relate, take a look at Vrbo properties that welcome pets. Most of these pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Longboat Key: If you're seeking vacation rentals that offer discounts for stays of a month or more, you've come to the right spot. 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 a private pool in your search as well.

Where to stay near Longboat Key

Longboat Key, Florida, is a delightful coastal escape perfect for beach lovers and families alike. With its serene vibe, this charming island offers unique spots adorned with palm trees and summer sun. Explore nearby towns for a friendly atmosphere and budget-friendly excursions, all while soaking in the beautiful coastal charm. Whether you're looking to relax or embark on adventures, Longboat Key promises a memorable vacation experience in the heart of Florida.

  • Sarasota: Located 14.5km away from Longboat Key, Sarasota is a vibrant city known for its blend of beach charm and urban sophistication. Visitors flock to this locale for its beautiful beaches and family-friendly attractions. The city boasts a variety of shopping options, from chic boutiques to larger shopping centres, ensuring a delightful retail experience. Sarasota is also home to cultural landmarks like the Ringling Museum, offering a taste of art and history. With its lively downtown area, numerous parks, and family-oriented beaches, Sarasota offers something for everyone, making it a perfect day trip from Longboat Key.
  • Anna Maria Island: Just 11.3km from Longboat Key, Anna Maria Island is a picturesque destination celebrated for its stunning beaches and outdoor activities. This charming island features a laid-back atmosphere, making it ideal for families seeking relaxation and fun. Visitors can enjoy various recreational areas and shopping malls, while the pristine beaches are perfect for sunbathing and swimming. With its quaint shops, delicious dining options, and nearby theme parks, Anna Maria Island is a delightful escape for those wanting to immerse themselves in natural beauty and family-friendly fun.
  • Anna Maria: Situated 14.5km from Longboat Key, Anna Maria is a quaint city that offers breathtaking scenery and outdoor adventures. Known for its serene beaches and stunning landscapes, it provides a peaceful retreat for nature lovers. Visitors can explore various recreational areas, indulge in shopping, and enjoy the local resorts. The scenic beaches and family-friendly atmosphere make Anna Maria a wonderful spot for a relaxing getaway. With its charming streets and captivating views, Anna Maria captures the essence of coastal living, ensuring a memorable experience for all.

Best time to go to Longboat Key

If you're planning a trip to Longboat Key, 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 July, while off-peak times, like October to December tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January62.6°F (17.0°C)Light RainMostly SunnyAverageSlightly Low
February65.5°F (18.6°C)No Rain (Dry)Mostly SunnyAverageAverage
March68.4°F (20.2°C)Light RainMostly SunnyModerately HighSlightly High
April73.8°F (23.2°C)Light RainMostly SunnyModerately HighSlightly High
May78.1°F (25.6°C)Light RainMostly SunnyAverageAverage
June82.0°F (27.8°C)Light RainMostly SunnyAverageAverage
July83.1°F (28.4°C)Moderate RainMostly SunnyModerately HighSlightly High
August83.5°F (28.6°C)Moderate RainMostly SunnyAverageAverage
September81.5°F (27.5°C)Moderate RainMostly SunnyAverageSlightly Low
October77.0°F (25.0°C)Light RainMostly SunnyModerately LowSlightly Low
November70.5°F (21.4°C)Light RainMostly SunnyModerately LowAverage
December66.4°F (19.1°C)Light RainMostly SunnyModerately LowAverage

Booking with Vrbo is a breeze

Are you hoping to save on your upcoming journey? Being flexible with your travel dates can make a significant difference, as prices often fluctuate. Additionally, consider booking a longer stay to unlock even greater savings. To discover a Vrbo property that aligns with your budget, utilize our filters to sort by price, location, and type of vacation rental. We're here to help you find the best options for your travel needs.

Vrbo Trips: Planning made easy

Vrbo’s Trip Board offers a user-friendly platform where you can easily plan new trips, continue from where you last stopped, or manage your travel arrangements. You’ll see your saved or booked properties neatly organized into categories like Potential, Upcoming, or Current Trips. To begin exploring Trip Boards, please visit: https://www.vrbo.com/en-ca/trips.

**Based on Vrbo properties bookings.

Tranquil Longboat Key will entice you

Enjoy the monuments and other features of Longboat Key. This relaxing city is known for its beaches, bird watching and seaside. Lido Beach and Siesta Key Beach are just a couple of the must-sees in the area. Many rental homes come with outdoor spaces, separate dining areas and full kitchens, perfect if you want to enjoy some home-cooked meals.

Activities and attractions in and around Longboat Key

Are you hoping to find attractions to visit during your stay? Venture out of your vacation home and experience everything that makes Longboat Key a fun place to get away. Here are some of the top attractions to explore, all within 30 miles (48.2 km) of the city center:

  • Sarasota Jungle Gardens (7.1 mi / 11.4 km)
  • Mote Marine Laboratory & Aquarium (7.4 mi / 12 km)
  • Premier Sports Campus at Lakewood Ranch (16.9 mi / 27.3 km)
  • Aluna Wellness Center & Spa (5.3 mi / 8.6 km)
  • Harborside Golf Course at Longboat Key Club (6.9 mi / 11.2 km)
  • Islandside Golf Course at Longboat Key Club (7 mi / 11.2 km)

Exploring the beaches and other natural features in Longboat Key

Travelers enjoy Longboat Key for its sunsets and seaside. Whether you're looking for adventure or just want to spend some time taking in the scenery, Longboat Key is a great place to get out in nature. Here are a few of the area's most eye-catching features, all within 30 miles (48.2 km) of the city center:

  • Lido Beach (8.8 mi / 14.2 km)
  • Siesta Key Beach (12 mi / 19.4 km)
  • Tampa Bay (25.2 mi / 40.6 km)
  • Longboat Key Beaches (2.8 mi / 4.6 km)
  • Coquina Beach (3.2 mi / 5.2 km)
  • Cortez Beach (4.2 mi / 6.7 km)

Seasonal weather averages in Longboat Key

Travelers enjoy Longboat Key for its boating. If you're hoping to enjoy some warm-weather activities on your vacation, August, July, June and September are the hottest months to visit, when temperatures average 83°F.

How to get to and around Longboat Key

The nearest airport is in Sarasota-Bradenton Intl. Airport (SRQ), located 6.7 mi (10.8 km) from the city center. If you can't find a flight that works for your travel itinerary, you could book a flight to St. Petersburg, FL (SPG-Albert Whitted), which is 24.4 mi (39.2 km) away.

Frequently asked questions

What is the best area to stay in Longboat Key when booking a vacation rental?
When considering a vacation rental in Longboat Key, Florida, a popular area to stay is the northern part of the island, particularly around the neighbourhood of Longboat Key Village. This charming area offers a more laid-back atmosphere while still providing easy access to beautiful beaches and delightful local dining options. You can enjoy the picturesque scenery at the nearby Joan M. Durante Park, which is superb for leisurely walks and enjoying nature.

Another fantastic option is the southern section of Longboat Key, near the renowned Longboat Key Club. This area boasts stunning waterfront views and is close to several upscale dining venues, as well as the popular St. Armands Circle, known for its unique shops and vibrant atmosphere. Here, visitors can explore a variety of boutiques and enjoy a delightful dining experience.
How much does it cost to rent a vacation home in Longboat Key?
Prices for vacation rentals in Longboat Key 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 travelling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Longboat Key to more spacious homes.
Are there any discounts for Longboat Key vacation house rentals?
You can find great discounts on house rentals in Longboat Key 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 Longboat Key?
For renting a beach house in Longboat Key, the area along Gulf of Mexico Drive is particularly appealing. This stretch features beautiful sandy beaches and is ideal for those looking to enjoy beachfront living. Properties here often come with amenities like private balconies with ocean views, outdoor grills, and direct beach access, making them superb for families or groups wanting to soak up the sun.

The northern part of Longboat Key, closer to the Longboat Key Club, offers more upscale vacation rentals, where you can find luxurious condominiums and houses with resort-style amenities. Many of these properties feature swimming pools, tennis courts, and fitness centres, as well as easy access to fine dining and shopping options nearby.

For those seeking a more tranquil experience, the southern end of Longboat Key near the village of Longboat Key provides quaint houses surrounded by lush landscaping. Here, you can expect amenities such as private docks, outdoor dining areas, and spacious living rooms, ideal for relaxed gatherings after a day at the beach. The charm of this area is complemented by proximity to local parks and the Longboat Key Centre, which has shops and restaurants. Find your rental near the beach in Longboat Key.
What is the most popular type of vacation rental accomodation in Longboat Key?
In Longboat Key, condos are the most popular type of vacation rental, with approximately 531 available in appealing locations close to the beach and local amenities. These properties often come equipped with modern kitchens, spacious living areas, and access to communal pools, making them ideal for couples or families looking for convenience and comfort.
Are there any family house rentals in Longboat Key?
In Longboat Key, Florida, families will be pleased to discover a wealth of vacation rentals available—around 499 to choose from. This scenic coastal area is superb for family getaways, offering spacious homes that often come with multiple bedrooms, expansive living areas, and fully equipped kitchens, making it easy for families to enjoy home-cooked meals together. Many properties also feature private pools and outdoor spaces, ideal for children to play and for parents to relax.

The locale is well-known for its stunning beaches, with easy access to activities such as kayaking and paddleboarding. Nearby, the beautiful Marie Selby Botanical Gardens provide a lovely setting for leisurely strolls and family outings. Additionally, the vibrant St. Armands Circle, with its shops and dining options, is just a short drive away, offering a variety of entertainment for all ages.
Can I rent a vacation home with a pool or hot tub in Longboat Key?
In Longboat Key, there are plenty of vacation homes available for rent that feature pools and hot tubs, with around 639 options to choose from. This beautiful barrier island offers a range of neighbourhoods, such as the tranquil residential areas along the Gulf of Mexico and the more bustling parts near St. Armands Circle, where you can find a blend of relaxation and local amenities. Find your rental in Longboat Key with a pool or a hot tub.
Can I find long-stay vacation rentals in Longboat Key?
A long-stay vacation rental in Longboat Key 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 Longboat Key?
In Longboat Key, there are numerous pet-friendly house rentals available, with around 98 options to choose from. This charming barrier island is known for its stunning beaches and relaxed atmosphere, making it a great destination for travellers with pets. Many of these vacation rentals feature amenities such as private pools, outdoor patios, and fully equipped kitchens, ensuring a comfortable stay for families and their furry companions. See all pet-friendly rentals in Longboat Key.
Are there any remote work vacation rentals in Longboat Key?
In Longboat Key, Florida, there is a substantial selection of remote work vacation rentals available, with around 697 options for travellers seeking a work-friendly environment. This picturesque barrier island offers a blend of serene beaches and vibrant local culture, making it an ideal location for those balancing work and leisure.

Many of the properties cater specifically to remote workers, featuring dedicated office spaces, desks, and comfortable chairs to ensure productivity during your stay. Additionally, travellers can expect high-speed Wi-Fi, laptop workspaces, and sometimes even computer monitors, allowing for a seamless work experience. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Longboat Key vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Longboat Key with 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 Longboat Key?
In Longboat Key, popular rental amenities include heated pools, kitchens, and shared pools, suiting the preferences of vacationers seeking both relaxation and convenience. Many vacation rentals feature fully equipped kitchens, allowing guests to prepare their meals and enjoy dining in comfort. Additionally, properties often come with microwaves for quick snacks and meals.
When is the best time to visit Longboat Key for a vacation rental?
March is the most popular month to visit Longboat Key, as it falls within the peak season from February to April. This time of year attracts vacationmakers seeking a warm escape, with average temperatures hovering around the mid-20s Celsius, superb for sunbathing and indulging in water sports. Visitors can enjoy pristine beaches, delightful seafood dining, and vibrant local culture, making it an ideal setting for both relaxation and adventure.

During these peak months, outdoor activities abound. From kayaking in the calm waters to exploring the scenic walking trails, there's something for everyone who values quality experiences in a stunning coastal environment. Whether you're lounging on the beach or embarking on a dolphin-watching tour, the opportunities for enjoyment are plentiful.

If you're looking for a more budget-friendly option, consider planning your visit in November. This month offers a lovely climate with fewer crowds, allowing you to savour the tranquil beauty of Longboat Key without the hustle and bustle of peak season. The beaches remain inviting, and you can still experience the charm of the local shops and restaurants at a more leisurely pace.
How early should I book a Longboat Key vacation rental?
Book your Longboat Key vacation 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 vacation rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Can I change or cancel my Longboat Key home rental booking on Vrbo?
To find Longboat Key vacation rentals with free cancellation, just use Vrbo's handy "Free cancellation" 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 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 Longboat Key vacation 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™, 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.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, 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 makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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