
House vacation rentals in Longboat Key
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Top-rated house rentals in Longboat Key
Guests agree: these houses are highly rated for location, cleanliness, and more.

Longboat Key Beach House
This quaint beach house with a private backyard and outdoor shower is everything you need to enjoy your relaxing Florida getaway and includes your beach supplies. A 3 minute walk to the beach and to the bay, this house is within a block of restaurants and a deli. Also Included is the use of a membership to Cedars East Tennis Club (5 minute walk), which has 10 HarTru Tennis Courts, a junior Olympic POOL, gym, bicycle rental and tiki bar. Only Minutes to Holmes, Bradenton and Coquina Beaches.

Gulf Front! Beach Sunsets+ 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.

Vacation Rental with private swimming pool
Located in a desirable community of South Venice. Venice, Manasota, Nokomis and Sharky’s beaches are located only 5 miles away. The historic Venice Avenue of unique shops, restaurants, special events. Farmer market, tennis courts, and children fountain are close by. Newly renovated home and swimming pool in a quiet peaceful area in an ideal place for any season gateway.A great place for biking, running and walking. My place great for couples, solo adventurers or families with kids.

The Peachy Beach House, steps to the gulf
The perfect place for a combination family vacation and some romance-when the kids are in bed, turn on the spa and music. June, July and August, Saturday to Saturday only. If custom trip length is wanted- ask Two bedroom, 2 full bathroom, new heated private pool/spa Steps to semi-private gulf beach, on quiet street in N. HB Well-stocked kitchen, 2 TVs, large primary suite and amazing gulf views from bedrooms. Crib, high chair, beach chairs, wagon, umbrella, beach toys and towels

Palm Retreat: #1 Top Rated Rental of Bradenton/AMI
Enjoy Florida sun in a stunning, newly renovated 4/2 pool home! We have provided almost everything we could think of including five 4k TVs w/ Netflix and cable, wifi, heated (optional) salt water pool w/ 7' privacy fencing, adult bikes, beach gear, Pack & Play, office, board games, relaxing lounge chairs, stocked kitchen, washer & dryer, garage parking, dog crate, all in a quiet and safe neighborhood. Oh, and of course it's just 5 miles to world renowned beaches.

Coastal Getaway *With Bikes & NEW Saltwater Pool*
Just outside of Downtown near the Legacy Trail, this home is located in a quiet neighborhood only 15 minutes from the Siesta Key Beach. The home stands out with its bright and airy design, brand new saltwater pool in the private backyard, and its breezy living room. The large master bathroom rain shower is perfect to wash off the leftover sand from the beach. You can also spend your evenings grilling out back or playing corn hole in the patio area.

Relaxing 3BR Retreat+ Hot Tub + Pool +Beaches +IMG
🌴Welcome to Beachway Haven! This 5-Star ⭐️ hideaway is just mins from Anna Maria Island's Pristine Beaches & the Gulf of Mexico. Dive into relaxation with your own Heated Saltwater Pool & Spa Hot Tub, nestled in a tropical oasis. Only a skip away from Golf Courses, Nature Parks, IMG Academy, & Palma Sola Causeway's Beach Access – your gateway to Horseback Riding, Kayaking, & endless sandy adventures. Shopping & dining are only a few mins away too!

Magical Secluded Retreat
Light-filled mid-century gem, newly renovated with cathedral ceilings. A lush canopy of tropical plants and trees offers privacy and calm unusual for its central location in Sarasota's historic neighborhood on the Bay. Relax inside and out, and lose yourself in birdsong, gently swaying bamboo and beautiful nature. Just 10 minutes to world-renowned beaches and even closer to dining, shopping and museums.

Fully remodeled home! Near beaches and restaurants
Step into our fully renovated and tastefully designed Airbnb where we hope you will feel right at home. We hope that from the moment you step inside you will feel peace and know that you’re in for a worry free vacation. Located approximately 20 minutes to pristine beaches with Siesta Key/Lido to the south and Bradenton beaches/Anna Maria Island to the north.

Private Siesta Beach House Oasis with Heated Pool.
Come enjoy the #1 rated beach in the USA. A contemporary style beach house that is located in a very conveniently located 10 min from Siesta Key beach. Within .5 miles you will find a mall, Cinebistro, trendy local bars, all major banks, Trader Joe’s, Publix, and a gas station. Drive way accommodates 2 cars with street parking as well.

Beach Cottage | Heated Pool & Spa | Golf Cart
Newly renovated beach cottage just 2 blocks from IRB with a HEATED saltwater pool, spa, tanning deck, and 4‑passenger golf cart. Pet‑friendly and set in a quiet, safe neighborhood, this cozy 2‑bed retreat is perfect for couples and small families seeking comfort, convenience, and unforgettable Gulf Coast memories. BTR# 2041

The BEACH Life!
Newly remodeled 4 bed/3 full bath - 2200 sq ft. house! 150 yards WALK to the beach. Pool table! Plenty of off-street parking. A cafe and a deli, 3 pub/restaurants, a pizzeria and a local beach shop all 200 yards away. Tennis/Pickleball/Pool Private Club membership included - only a 5 minute stroll from the house.
Popular amenities for Longboat Key house rentals
House rentals with a pool

Sunny Paradise w/Pool&HotTub 5 min to Siesta Key!

Beachfront Getaway in Siesta Key

Heated Pool & Outdoor Kitchen! Close to Lido Beach

ON SALE - Canalfront, Pool, Grill, Dock

Pickleball - Heated Pool - Relax, Play & Grill

Ocean Air Oasis-New Centrally Located AMI Luxury

True Island Living House/beach/water views

Mykonos: Beautifully updated with heated pool
House rentals with a hot tub

Be an AMI

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

Coastal Home in Sarasota-8min from Siesta Key

Private Pool + Hot Tub | Cottage on Bay

Luxury Retreat~Private Hot tub~9 mins to Downtown

Near Lido Beach w Hot tub + Fire Pit

Waterfront Pool Home Steps to Beach

Tampa Waterfront Heated Pool/ Hot Tub Oasis w Dock
House rentals with free parking

Casa Loco - Fun & Whimsical

Charming houseB 2 min walk to beach, 4+, baby pets

Pool, Bikes & BBQ Included! 2min to Beach!

"Little Siesta" - Farm home near Terra Nova

Flamingo 1BR Beach-side Villa in Siesta Key | Pool

Bayou Hammock, Sarasota FL

Emerald Beach Cottage

3 min Walk to The Beach
When is the best time to visit Longboat Key?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ933 | ﺩ.ﺇ1,069 | ﺩ.ﺇ1,102 | ﺩ.ﺇ936 | ﺩ.ﺇ918 | ﺩ.ﺇ808 | ﺩ.ﺇ757 | ﺩ.ﺇ749 | ﺩ.ﺇ720 | ﺩ.ﺇ701 | ﺩ.ﺇ826 | ﺩ.ﺇ944 |
| Avg. temp | 16°C | 18°C | 20°C | 22°C | 25°C | 27°C | 28°C | 28°C | 27°C | 24°C | 20°C | 18°C |
Quick stats about house rentals in Longboat Key

Total vacation rentals
Explore 250 vacation rentals in Longboat Key

Nightly prices starting at
Longboat Key vacation rentals start at ﺩ.ﺇ110 per night before taxes and fees

Verified guest reviews
Over 4,410 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
250 of Longboat Key vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Longboat Key rentals

4.8 Average rating
Longboat Key stays are highly rated by guests—averaging 4.8 out of 5!
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- Anna Maria Island
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- Busch Gardens Tampa Bay
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