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House vacation rentals in Longboat Key

Find and book unique houses on Airbnb

Quick stats about house rentals in Longboat Key

  • Total vacation rentals

    Explore 260 vacation rentals in Longboat Key

  • Nightly prices starting at

    Longboat Key vacation rentals start at ﺩ.ﺇ 110 per night before taxes and fees

  • Verified guest reviews

    Over 5,390 verified reviews to help you choose

  • Family-friendly vacation rentals

    220 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 120 rentals that welcome pets

  • Vacation rentals with a pool

    170 properties feature pools

  • Rentals with dedicated workspaces

    140 properties have a dedicated workspace

  • Wi-Fi availability

    260 of Longboat Key vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Longboat Key rentals

  • 4.9 Average rating

    Longboat Key stays are highly rated by guests—averaging 4.9 out of 5!

Top-rated house rentals in Longboat Key

Guests agree: these houses are highly rated for location, cleanliness, and more.

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Top guest favorite
A private heated pool is enclosed by a screened lanai, surrounded by lush tropical plants. Soft purple lights create a relaxed ambiance. Comfortable seating and dining areas are positioned nearby, inviting leisurely moments by the water.
Home in Sarasota
4.97 out of 5 average rating, 179 reviews

ROYS PLACE private, tropical, romantic paradise.

NAMED #1 BEST AIRBNB WITH POOL IN SARASOTA BY TRIP 101 TRAVEL GUIDE FOR 2022, 2023, 2024. An exceptional vacation is a frame for an exceptional life. Offered for you, a romantic boutique home. Sarasota Chic decor, quality furnishings, lush tropical landscaping. Only property in urban Sarasota with your own private (EXCLUSIVE to you, NOT shared) CLOTHING OPTIONAL heated pool for tropical fun. One block walk to beautiful sunsets over Sarasota Bay. All tropical serenity yet close to everything.

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Top guest favorite
The exterior of the beach house is depicted, showcasing a blue structure with a metal roof surrounded by tropical landscaping. A gravel driveway leads to the entrance, flanked by palm trees and vibrant foliage, emphasizing the inviting coastal atmosphere.
Home in Longboat Key
4.97 out of 5 average rating, 112 reviews

Beautiful Beach House

Beautiful, updated 1937 beach house. Original LongBeach cottage. Gated entrance to property. Three bedroom, two bath. Master bathroom has bathroom en suite. Hardwood floors throughout. Kitchen updated. Beautiful front and back porches to enjoy the sunshine. Private access to beach and Gulf of Mexico. Walking distance to shops and Tennis. Bedrooms include master with King, second bedroom with queen, third bedroom with two twins. Come join us in longboat key for sunshine, beaches,culture,tennis

LocationFamilySleep quality

Top guest favorite
A Tiki bar with a thatched roof provides a stylish overlook of a heated pool surrounded by lounge chairs. The design features natural wood accents and vibrant decorations, inviting relaxation and leisure. Sunlight reflects off the water, adding to the serene outdoor atmosphere.
Home in South Sarasota
4.94 out of 5 average rating, 104 reviews

Tiki Bar Paradise! Heated Pool & Gaming Oasis!

Welcome to one of our beautiful properties, only 9 minutes to Siesta Key Beach! 24/7 Host Support - no AI messaging or hidden fees. Gorgeous HEATED POOL & Tiki Bar. Corn hole, ring game, or water pong on dry land or play volleyball, basketball, or beer pong in the pool. Bring the competition inside to the Game Room to play billiards or any number of family card/board games. Relax in the cozy living room w/ fireplace & fully equipped kitchen. Minutes to Siesta Key, the Village & Downtown SRQ.

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Top guest favorite
Home in Sarasota
4.95 out of 5 average rating, 199 reviews

Modern 4BR Home *Heated Pool & Spa*

Discover elegance in this centrally located Sarasota gem, featuring four bedrooms and two bathrooms to accommodate up to eight guests. Enjoy a laid-back vibe while lounging at Sarasota's beaches or immersing yourself in local attractions. Siesta Beach and Lido Beach are within easy reach at 7.6 and 6.4 miles respectively. Rest easy knowing commitment to cleanliness aligns with your travel priorities. Your serene vacation awaits in this beautifully adorned home. *Brand new pool* VR24-00265

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Top guest favorite
Home in Bradenton Beach
4.98 out of 5 average rating, 128 reviews

Gulf Front! Sunset Deck! + Walk to Bridge St Pier!

🌊🏄Welcome to The Surof House - where panoramic views of the Gulf of Mexico welcome you from almost every corner! 🏖️Experience the ultimate beachfront retreat at this unique & stunning property nestled across from one of the top beaches in the world. A perfect blend of luxury, comfort, & unparalleled views awaites. With an upstairs loft featuring 3 single beds & 2 downstairs rooms with king beds, it's an ideal getaway for families, friends, or anyone seeking a slice of paradise.

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Top guest favorite
A heated saltwater pool is surrounded by lush tropical vegetation, creating a serene atmosphere. Poolside seating is offered by several lounge chairs, alongside a shaded area with an umbrella. Sunlight reflects off the water's surface, enhancing the tranquil setting.
Home in Bradenton Beach
4.98 out of 5 average rating, 205 reviews

STEPs to BEACH! /Heated Salt Pool/Sunsets/5 STAR!

Less than a 2 min WALK to the white sand beaches of the Gulf, this 4 BR home comfortably sleeps 8. Large bedrooms & a spacious floor plan (the kitchen, dining and living rooms flow together), the house is perfect for families. The bedrooms are split 2+2 & paired with bathrooms on opposite ends of the house (a pocket door adds privacy). Private heated saltwater pool sits amidst the tropical yard. Hop on the free trolley and explore Florida's gorgeous Anna Maria Island.

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Guest favorite
Home in Longboat Key
4.9 out of 5 average rating, 20 reviews

Dog friendly LBK home with deeded access to beach!

**Calendar not always up to date. Please message me for specific dates. Newly renovated 3/2. Location, location, location. Walk or ride bikes to some of the top restaurants on LBK. Perfect for a small family or two couples. Beautiful outdoor screened in porch with grill, couches, dining room set and and ping ping table, outdoor living at its best. Tenants also get to enjoy Cedar’s Racquet Club membership with pool, tennis, pickle ball, full gym and bikes.

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Guest favorite
An outdoor dining area is set with a glass table and six blue chairs, shaded by a blue umbrella. In the background, a swimming pool with surrounding tropical plants invites relaxation, while a spa is visible nearby, offering a serene ambiance.
Home in Holmes Beach
4.82 out of 5 average rating, 104 reviews

Private pool, only two blocks .3 miles from beach!

Just two blocks away from the beautiful white sands of Holmes Beach. Restaurants & night life even closer. Swimming pool and spa are inviting for both romantic getaways as well as families. You will have access to the entire beautiful two story townhouse. The property has a shared wall, but all space is private and quiet. The outdoors are separated and private as well. Plenty of parking, sun, & fun. New mattresses, new couch, and other furniture.

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Guest favorite
Home in South Bradenton
4.94 out of 5 average rating, 104 reviews

Stylish Pool Home • Near IMG & Beaches • Top Rated

Just 2.2 miles from IMG Academy and 6.5 miles from Sarasota Airport! Near beautiful Coquina and Anna Maria beaches. Enjoy a private pool, ping pong table, and modern comforts in this stylish 3-bedroom, 2-bath home. Fully equipped kitchen, washer/dryer, smart TV, and fast Wi-Fi. One pet allowed with a $200 fee. Relax or entertain in the spacious fenced backyard. Ideal for families or couples seeking comfort, sun, and fun in Bradenton!

LocationValueTV

Top guest favorite
A serene outdoor space is highlighted by a heated saltwater pool and a six-person spa. Comfortable lounge chairs line the pool area, and an outdoor grill is situated nearby. The setting is complemented by a vibrant sunset, enhancing the tranquil atmosphere.
Home in Sarasota
5.0 out of 5 average rating, 109 reviews

Luxury 3/3 with Heated Pool, Spa, & Putting Green!

Experience luxury at this newly remodeled home with a brand-new pool, spa, and putting green. Centrally-located near downtown Sarasota, Siesta Key, Lido Key beaches, and St. Armand’s Circle, it features a full kitchen, 3 king bedrooms, 3 full bathrooms, outdoor dining, high speed internet, a 75” outdoor TV, fire pit, and EV charger. Pet-friendly with a fenced yard, pet crate, bowls & treats. License # VR24-00208

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Guest favorite
A serene sunset view is captured over the bay, with the sun sinking just above the horizon. Lush green grass stretches across the foreground, leading to calm waters. A private dock is visible, framed by coastal vegetation.
Home in Longboat Key
4.96 out of 5 average rating, 54 reviews

Right on the water with private boat slip

Beautifully furnished 2,500 sq ft 3bdrm/3bath (4 beds total) bayfront home with fabulous water views from nearly every room. Private slip & garage storage for your trailer. Bring your boat & leave it at the dock for your entire vacation. Gourmet kitchen. Spacious family room. Covered lanai. Private beach with chairs provided & community pool w/in a 3 minute walk. By far the premier home in the complex.

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Top guest favorite
Home in Anna Maria
5.0 out of 5 average rating, 109 reviews

Bean Pt. Bungalow - Half duplex w/private pool

Welcome to Bean Pt. Bungalow! A charming 3/2 villa with a private saltwater pool in the heart of Anna Maria. You're only 0.2 miles from the nearest beach access and 0.2 miles from the Rod and Reel Pier. The home comes equipped with 6 beach chairs and cart. This boutique rental is the perfect place for your next getaway! Primary - King Bed Front bedroom - King bed Bunk room - 4 twin beds

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Popular amenities for Longboat Key house rentals

When is the best time to visit Longboat Key?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceﺩ.ﺇ 1,021ﺩ.ﺇ 1,050ﺩ.ﺇ 1,102ﺩ.ﺇ 823ﺩ.ﺇ 797ﺩ.ﺇ 797ﺩ.ﺇ 757ﺩ.ﺇ 749ﺩ.ﺇ 720ﺩ.ﺇ 701ﺩ.ﺇ 826ﺩ.ﺇ 944
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Destinations to explore