Longboat Key vacation rentals

We found 11,749 vacation rentals — enter your dates for availability

Welcome to Longboat Key, where pristine sandy beaches meet vibrant cultural experiences and breathtaking outdoor adventures. This idyllic destination invites families and groups to soak up the sun while exploring stunning attractions, from the serene shores of Jewfish Key to the lively arts scene in nearby Sarasota. With a variety of accommodations, including luxurious beachfront condos and charming vacation homes, you’ll enjoy the comfort and convenience of a home-like retreat, perfect for making unforgettable memories together.

Holiday rentals with weekly discounts - Longboat Key

Showing deals for:Dec 11 - Dec 18

Living area
Four barstools and large area for eating
dining room with seating for 8
Interior
Exceptional
(87 reviews)

Large pool/spa home minutes from beach with arcade games and canal for fishing.

Bradenton

8% off
$374
$2,617 for 7 nights
All fees included
Large pool/spa home minutes from beach with arcade games and canal for fishing.
Exterior
Exterior
Exterior
Aerial view
Exceptional
(13 reviews)

Modern Home + Heated Pool + Spa + Walkable Downtown + Short Drive to Beaches

Sarasota

9% off
$1,139
$7,975 for 7 nights
All fees included
Modern Home + Heated Pool + Spa + Walkable Downtown + Short Drive to Beaches
Room
Room
Outdoor shower (yes there is one inside also)
Front House from the street view
Exceptional
(30 reviews)

Adorable 1 Bedroom, 1 Bath guesthouse < 1block to Lido Beach

Sarasota

6% off
$273
$1,909 for 7 nights
All fees included
Adorable 1 Bedroom, 1 Bath guesthouse < 1block to Lido Beach
Interior
Marina
Pool
Property grounds
Exceptional
(73 reviews)

Relaxing Lakefront Home: 3BR/2BA, Heated Pool, Near Siesta Key Beach

Sarasota

8% off
$278
$1,945 for 7 nights
All fees included
Relaxing Lakefront Home: 3BR/2BA, Heated Pool, Near Siesta Key Beach
Take An Incredible Stroll Through The Ringling Museum In Sarasota!
Longboat Pass
Front Wrought Iron Private Gates Entering- “Sea La Vie” Pond, Meditation Garden.
Private Swimming Pool & Relaxing Area.
Exceptional
(83 reviews)

Heated Pool~Massive Spanish Home~Water Views~Sunset Deck~Grill~WIFI~Near Beaches

Bradenton

8% off
$625
$4,373 for 7 nights
All fees included
Heated Pool~Massive Spanish Home~Water Views~Sunset Deck~Grill~WIFI~Near Beaches
Living area
Interior
Room
Terrace/patio
Exceptional
(47 reviews)

🌴 Peaceful Sarasota Home with Patio, 2BR, 2BA Near Lido Beach & Downtown

Sarasota

8% off
$150
$1,049 for 7 nights
All fees included
🌴 Peaceful Sarasota Home with Patio, 2BR, 2BA Near Lido Beach & Downtown
Property grounds
Pool
Private kitchen
Private kitchen
Exceptional
(190 reviews)

LAKEFRONT 2bed/2bath with Heated POOL house, JUST 5 min away SIESTA KEY BEACH!

Sarasota

8% off
$203
$1,423 for 7 nights
All fees included
LAKEFRONT 2bed/2bath with Heated POOL house, JUST 5 min away SIESTA KEY BEACH!
Bathroom
Terrace/patio
Living area
Private kitchen
Exceptional
(20 reviews)

Charming 2-bedroom house in the heart of Sarasota—A quaint nature escape

Sarasota

8% off
$158
$1,104 for 7 nights
All fees included
Charming 2-bedroom house in the heart of Sarasota—A quaint nature escape
Interior
Private kitchen
Dining
Pool
Excellent
(18 reviews)

Pool | Hot Tub | Waterfront Views | Sunsets

Bradenton

11% off
$518
$3,628 for 7 nights
All fees included
Pool | Hot Tub | Waterfront Views | Sunsets
Terrace/patio
Private kitchen
Marina
Living area
Exceptional
(111 reviews)

75 ft Canal Front Anna Maria House, Great for Boaters, Newly Renovated

Anna Maria

8% off
$430
$3,013 for 7 nights
All fees included
75 ft Canal Front Anna Maria House, Great for Boaters, Newly Renovated
sliding door in kitchen leads to patio area
additional bar area seating
Pool
Front (living) room
Exceptional
(129 reviews)

HEATED pool, bike to Siesta, quiet street, 1 MILE to SK beach, kayaks & bikes

Sarasota

5% off
$361
$2,529 for 7 nights
All fees included
HEATED pool, bike to Siesta, quiet street, 1 MILE to SK beach, kayaks & bikes
Beach
Exterior
Dining
Private kitchen
Exceptional
(58 reviews)

Happy Turtle A: Cute Beach Cottage, 60 Steps to Sand, Sun Room

Bradenton Beach

9% off
$322
$2,257 for 7 nights
All fees included
Happy Turtle A: Cute Beach Cottage, 60 Steps to Sand, Sun Room
Outdoor Dinner Seating for 12
Pool
Private kitchen
Dining
Exceptional
(44 reviews)

2 Homes, 1 Private Pool Near IMG & AMI

Bradenton

11% off
$313
$2,188 for 7 nights
All fees included
2 Homes, 1 Private Pool Near IMG & AMI
Dining
Interior
Private kitchen
Living area
Exceptional
(44 reviews)

3 Minute walk to beautiful AMI beach! Old Florida Charm with a Modern Flair!

Holmes Beach

8% off
$191
$1,338 for 7 nights
All fees included
3 Minute walk to beautiful AMI beach! Old Florida Charm with a Modern Flair!
Exterior
Sport court
Interior
Terrace/patio
Exceptional
(183 reviews)

Amazing 1 Br/1 Ba Condo at Casa Mar

Siesta Key

8% off
$294
$2,060 for 7 nights
All fees included
Amazing 1 Br/1 Ba Condo at Casa Mar
Condo pool with tables and chairs and large shaded seating area!
Living area / king size bed with balcony, overlooking the beach.
Interior
spare bedding & pillows for the futon is in the closet.
Exceptional
(5 reviews)

The Pelican's Perch, a Beachfront studio condo w/ balcony

Bradenton Beach

13% off
$248
$1,736 for 7 nights
All fees included
The Pelican's Perch, a Beachfront studio condo w/ balcony
Property grounds
Pool
Terrace/patio
Exterior
Exceptional
(17 reviews)

New The BLUE HERON 3 bedroom oasis with heated pool

Bradenton

8% off
$238
$1,663 for 7 nights
All fees included
New The BLUE HERON 3 bedroom oasis with heated pool
Private kitchen
Beach
Room
Outdoor dining
Exceptional
(103 reviews)

Low Rider - Bottom Unit -

Bradenton Beach

9% off
$452
$3,162 for 7 nights
All fees included
Low Rider - Bottom Unit -
Boat/Fishing Deck
Quiet and safe neighborhood for families to swim, walk, bike, and fish
Front Entrance
View of spacious main pool and clubhouse.  Dry sauna and gym inside.
Exceptional
(102 reviews)

Gulf & Bay Club Bayside, 1st Floor, CLEAN, 5 STARS & EXCELLENT REVIEWS!

Siesta Key

6% off
$440
$3,079 for 7 nights
All fees included
Gulf & Bay Club Bayside, 1st Floor, CLEAN, 5 STARS & EXCELLENT REVIEWS!
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Find out more about Longboat Key

Why visit Longboat Key

  • Beautiful Beaches: Longboat Key boasts stunning sandy beaches, perfect for sunbathing and water activities.
  • Cultural Experiences: Explore local history museums and enjoy the vibrant arts scene in nearby neighborhoods.
  • Outdoor Adventures: Engage in activities like kayaking, fishing, and biking amidst scenic natural surroundings.
  • Family-Friendly Atmosphere: The welcoming environment and various attractions make it ideal for family vacations.
  • Top-Notch Accommodations: Choose from luxury resorts, private vacation homes, and beachfront condos for a perfect stay.

Popular types of accommodation in Longboat Key

Planning a getaway to Longboat Key? You're in for a treat. Discover the most popular vacation rental options, including stunning condos, houses, and cozy apartments. Whether you're searching for beachfront condo rentals or the perfect Gulf Coast vacation home, our platform offers a variety of FL vacation rentals to suit your needs. Enjoy the sun, sand, and sea in beautiful beach condo rentals throughout Florida.

  • Condos: The top choice for vacation rentals in Longboat Key, offering a blend of comfort and amenities, perfect for families and couples.
  • Houses: A great option for those seeking space and privacy, ideal for larger groups or families wanting a home-like experience.
  • Apartments: A popular selection for travelers looking for convenience and accessibility, suitable for couples or solo visitors.
  • Cottages: Charming and cozy, these rentals provide a quaint atmosphere, perfect for a peaceful getaway.
  • Villas: Luxurious and spacious, villas offer an upscale experience with stunning views and private amenities.**

Top attractions in and around Longboat Key

Longboat Key, Florida, is an ideal destination for beach and family vacations, offering a mix of cultural experiences and outdoor adventures. Visitors can enjoy quiet beaches, explore marinas, and visit local history museums. With a variety of top-notch resorts, Longboat Key caters to those seeking relaxation and exploration, making it perfect for travelers looking to unwind by the sea while indulging in rich local culture.

  • Jewfish Key: This tranquil island offers stunning outdoor experiences with beautiful beach vibes, perfect for relaxation and sunbathing. Enjoy kayaking or paddleboarding in its serene waters, and explore the natural beauty of the surroundings.
  • Lido Beach: Located 9 miles away, Lido Beach boasts soft, white sands and crystal-clear waters. It's an ideal spot for swimming, sunbathing, and enjoying picturesque sunsets over the Gulf of Mexico.
  • Harborside Golf Course at Longboat Key Club: Nestled within Longboat Key, this beautifully designed golf course offers a challenging yet enjoyable experience for golfers of all levels, complemented by stunning views of the surrounding landscape.

Things to do recommended for couples

Longboat Key offers romantic experiences like attending a polo match at Sarasota Polo, just 16 miles away, or enjoying the luxury vibes at The Oaks Club, located 18 miles away. Both provide a charming atmosphere perfect for couples seeking memorable moments together.

Things to do recommended for families

Families visiting Longboat Key can enjoy a day at the beautiful beaches, explore the nature trails at the nearby Longboat Key Pass, and visit the Mote Marine Laboratory & Aquarium for interactive exhibits that engage kids and spark their curiosity about marine life.

Things to do recommended for groups

Groups visiting Longboat Key can enjoy a relaxing day on the beautiful beaches, indulge in fresh seafood at local restaurants, and explore the lush trails at the nearby nature reserves. For adventure, consider kayaking or paddleboarding in the serene waters of the Gulf of Mexico.

*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

If you’re traveling with a group, family, pets, or planning an extended stay, it’s important to prioritize your preferences when filtering options. Here are some helpful Vrbo booking tips to consider.

  • Traveling to Longboat Key with a group: Think about how many bedrooms you'll require, as well as features like a full kitchen or outdoor area for group gatherings. Luckily, you can easily filter for these options and more on Vrbo.
  • Traveling to Longboat Key with young kids: Traveling with young children can be quite demanding. It's important to prioritize their comfort and safety, along with ensuring access to suitable amenities like a private swimming pool. Additionally, you should think about how close you are to family-friendly attractions.
  • Taking your pets with you to Longboat Key: For many, a family vacation wouldn’t feel complete without their furry companions. If this resonates with you, explore Vrbo listings that welcome pets. Most pet-friendly properties come equipped with feeding bowls and beds, ensuring that every member of your family feels at home.
  • Planning for a long term stay visiting Longboat Key: If you're in search of vacation rentals offering discounts for month-long stays, 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 features like a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay near Longboat Key

Longboat Key, Florida, is a stunning beach getaway that offers a perfect blend of relaxation and family-friendly fun. With its beautiful beaches and welcoming atmosphere, visitors can explore the charming local neighborhoods and experience the vibrant culture. Nearby cities provide additional excursions that highlight the friendly vibe and budget-friendly options. Whether you’re soaking up the sun on Longboat Key Beach or enjoying local attractions, this destination promises a memorable vacation for everyone.

  • Sarasota: Situated 9 miles from Longboat Key, Sarasota is a vibrant city known for its rich cultural scene and beautiful beaches. Travelers flock to Sarasota for a family-friendly atmosphere, with numerous attractions such as the famous Siesta Key Beach, which boasts powdery white sand. The city offers a mix of shopping experiences at local malls and centers, and you can enjoy a leisurely stroll at the Marie Selby Botanical Gardens. Sarasota's lively arts community is highlighted by the Ringling Museum of Art, making it a perfect destination for culture enthusiasts and families alike.
  • Anna Maria Island: Located 7 miles from Longboat Key, Anna Maria Island is a picturesque barrier island known for its stunning natural beauty and laid-back vibe. Visitors are drawn here for outdoor adventures, from kayaking in the tranquil waters to lounging on pristine beaches. The island features charming boutiques and local eateries, as well as recreational areas perfect for family outings. Don't miss the iconic Anna Maria City Pier for breathtaking sunset views and a chance to spot local wildlife. It's an ideal getaway for those looking to connect with nature and enjoy family-friendly activities.
  • Bradenton Beach: Just 5 miles from Longboat Key, Bradenton Beach is a delightful coastal city that offers a mix of outdoor fun and family-oriented experiences. Known for its beautiful beaches, visitors can enjoy sunbathing, swimming, and beachside dining. The area has several recreational spots and shopping centers that cater to all ages. You can explore the charming local neighborhoods, where colorful beach cottages line the streets, creating a welcoming atmosphere. Bradenton Beach is perfect for families looking to unwind and embrace the coastal lifestyle.

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 simple

Are you interested in saving on your upcoming journey? Being flexible with your travel dates can make a difference, as prices often fluctuate. Additionally, you can enjoy considerable savings by opting for a longer stay. To discover a Vrbo property that aligns with your budget, feel free to utilize our filters to sort by price, location, and type of vacation rental. We’re here to help you find the perfect getaway.

Vrbo Trips: Planning as easy as it gets

Vrbo’s Trip Board provides a convenient way to plan your travels, manage your bookings, and keep your trip ideas organized. Your saved or booked properties are neatly categorized into Potential, Upcoming, or Current Trips. To check out Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Experience Longboat Key at vacation home rentals

Vacation treasures are just waiting to be unwrapped on this beach-lined ribbon of land in the Gulf of Mexico west of Bradenton and Sarasota. Known as a great location to pull out your fishing pole, Longboat Key also offers elegant resorts and upscale dining, plus opportunities to see nature up close and personal. It's only 30 minutes away from Bradenton-Sarasota airport, and just as easy to reach the cultural and family-friendly attractions in both communities. A Longboat Key vacation rental is a relaxing place to warm your heart on a midwinter getaway.

Tourist attractions near Longboat Key vacation homes

A Longboat Key vacation rental is a convenient launching place to visit attractions around the area. Mote Marine Aquarium, just over the bridge to the south, has an open-water Shark Zone and exhibits on alligators, sting rays, manatees, sea turtles, and other aquatic life. South Florida Museum in Bradenton features a manatee aquarium and planetarium, plus exhibits on natural and cultural history. In Sarasota, visit the vast collection of the Ringling Museum of Art, plus the Marietta Museum of Art & Whimsy. Sarasota also offers botanical gardens and encounters of the retail kind.

Activities near your Longboat Key summer rental

If you're looking for sport fishing, Longboat Key is the place. Tarpon and cobia can be caught from the beach, and some docks are lighted for nighttime fishing. Redfish and speckled trout lurk in the mangroves. You can book a charter for offshore fishing—or a cruise just to view the dolphins. Gulf-side beaches beg you to loll in the sun, swim, take up windsurfing or parasailing, and rent paddle boards and boogie boards. There's a public tennis center. Beer Can Island is a boat-in stretch of beach for picnicking at the key's northern tip.

Climate for your trip to Longboat Key vacation rentals

Sunshine rules for 256 days a year on Longboat Key, making outdoor activities enjoyable all year from a Longboat Key vacation rental. Summer is the hottest season, and often humid, with July highs around 90. It's also the wettest, with August rainfall around 9 inches. January high temperatures are generally in the 80s, with the average low around 50. May to late fall is actually the slower season, with lower prices. The cooler, busier winter season is when visitors seek escape from cold and snow elsewhere. Spring and fall are in-between, for both weather and crowds.

Good things in a small package on Longboat Key

Longboat Key occupies a narrow barrier island between the Gulf of Mexico and Sarasota Bay. Everything is packed into 4 square miles of dry land, and you could bike the 10 miles from northerly Beer Can Island to Quick Point in about 50 minutes. Sea turtles and shorebirds nest along the Gulf beaches from April to November, but habitats are protected by keeping observers at a distance and outdoor lights off at night. Crabs and conchs, egrets, herons, and osprey are seen from trails and boardwalks through 34 acres of wetland and mangrove lagoons at Quick Point Nature Preserve.

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.

Romantic vacation rentals in Longboat Key

If you're looking for a romantic retreat, Longboat Key has an array of tranquil locations to explore. Vacation rentals are available near places like St. Armands Key, a bay island with serene tropical surrounds and parklands, and Leffis Key, an island nature reserve and tidal habitat with nature trails and boardwalks through the marshland. You could also visit Palma Sola Botanical Park, a landscaped garden with exotic plants and lakes.

Frequently asked questions

What is the most popular type of vacation rental accommodation in Longboat Key?
Condos are the most popular type of vacation rental in Longboat Key, according to our data. Even if you've got a different vision in mind, Vrbo has properties in loads of shapes and sizes. Browse our many options to find your perfect Longboat Key pad.
How much does it cost to rent a vacation rental in Longboat Key?
The average price for a vacation rental in Longboat Key is based on a number of factors, including property type, season and length of stay. Whether you're dreaming about a sprawling villa with lots of bedrooms or a cozy condo just enough for two, just enter your travel dates to find stays with fantastic value.
How much does it cost to rent a beach house in Longboat Key?
When you travel and the style and size of the property will influence how much you'll pay for your beachside escape. Enter your Longboat Key travel dates to view your available options on Vrbo. Can't live without a hot tub, or maybe a private pool? Use our filters to pick the features and amenities you want in your vacation home.
What are popular rental amenities in Longboat Key?
When it comes to rental amenities that guests are on the lookout for in Longboat Key, a barbecue grill, tennis and a nearby waterfront rank the highest. With Vrbo vacation rentals, you'll enjoy choices to suit your style and taste, whether you're taking a trip with family, friends or even pets.
What are the top attractions for families in Longboat Key?
Keep the kids amused at these fantastic family-friendly attractions in Longboat Key:
  • Islandside Golf Course at Longboat Key Club
  • Jewfish Key
  • Harborside Golf Course at Longboat Key Club
Can I find two-bedroom vacation rentals in Longboat Key?
Longboat Key has 408 two-bedroom vacation rentals to choose from. Discover a vacation home with all the comfort and privacy you want at an attractive price on Vrbo.
Are there vacation rentals with WiFi in Longboat Key?
Longboat Key has 237 vacation rentals with WiFi, so you'll be able to stay connected when you're away. Simply check the "WiFi" box in our handy search filter to find the perfect property. From streaming movies with the family to updating your social media, these Vrbo homes make it easy to get online.
How old do you have to be to rent a vacation rental in Longboat Key?
The minimum age permitted can vary across properties on Vrbo, so be sure to look at the rules of the vacation rental in Longboat Key you want to book. But in general, it's 16, 18 or 21.
How long can I rent a vacation rental in Longboat Key for?
It really depends on the Longboat Key property. To browse a list of options offering extended stays, simply type your dates and number of guests into Vrbo's search page. Look forward to having the entire property to yourself, along with home comforts such as a kitchen, air conditioning and outdoor spaces to run around in. Keep an eye out for long-term stays that offer discounted weekly or monthly prices.
Does Vrbo offer discounts for vacation homes in Longboat Key?
On Vrbo, you'll find fantastic discounts and bargains for Longboat Key. Browse our newly listed homes, as well as our weekly and monthly discounts on vacation rentals. Whether you're after a weekend retreat or an extended stay, Vrbo offers options for all styles and budgets.

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