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House holiday rentals in Longboat Key

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Top-rated house rentals in Longboat Key

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Home in Longboat Key

4.86 out of 5 average rating, 110 reviews

Summer House longboat key

Luxurious waterfront 3 Bedroom home with bay and and canal view with extra dock that can accommodate up to 21 ft+-heated pool, tropical landscaping with coconut palms, outside patio and grill. Fish on the dock and watch dolphins and manatee. Truly a tropical paradise just 7 minute Walk to your own private beach, It is a private home nestled on a canal that is 2 houses from Sarasota Bay. Our home is situated in the desirable quiet neighborhood of Country Club Shore minutes from at Armand’s circle

Guest favourite

Home in Bradenton

4.97 out of 5 average rating, 109 reviews

WOW-King Bed w/86° Pool, Turf Golf green, Beaches

Location!! Have fun with the whole family at this stylish home. Just minutes to Anna Maria Island beaches. This incredible newly built home sets the highest standards of luxury living. It’s the ideal retreat with its expansive views of the outdoors from the moment you enter. Open concept with large French doors throughout the home creates the perfect indoor-outdoor lifestyle. Spend the day lounging by the heated pool with a cold drink in your hand. Fun turf yard area with games and putting green

Guest favourite

Home in Indian Beach-Sapphire Shores

4.96 out of 5 average rating, 142 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.

Guest favourite

Home in Bradenton

4.94 out of 5 average rating, 247 reviews

Home near Anna Maria Beach w/ Hot Tub + Fire Pit

* Place is ready & available post Hurricane Milton, with 5 Star review from recent guest Come find a space away in this 1 bedroom Guest House with a private patio and inflatable hot tub located less than 15 Minutes away from Anna Maria Island Beach. Enjoy all that the area has to offer, and come home to the private ambience of an outdoor fire pit and relaxing hot tub, or play a fun game of corn-hole on the back patio. The home is a quaint 627 square feet in a safe and friendly neighborhood

Guest favourite

Home in Holmes Beach

4.97 out of 5 average rating, 128 reviews

Twin Palms: Big House Steps to Beach w/Lush Pool

Twin Palms is home to NY Times best-selling food writer and chef and her tech husband. Infant/kid/pet-friendly (to 35 lbs) in a great location 5 min. walk to the beach. Private lagoon-style *heated* pool amid lush landscaping with gorgeous rock waterfall. Fully updated kitchen, 60-inch Sony HDTV, 55'' Samsung Frame TV, Italian leather reclining sofas, BBQ, beach gear, updated bathrooms, three king bedrooms. Classic Florida one-level home - no stairs. Managed directly by owners. No crazy fees!

Guest favourite

Home in Bradenton Beach

4.97 out of 5 average rating, 159 reviews

Welcoming Back Guest: Jan 1, 2025!

Less than a 2 minute WALK from the white sand beaches of the Gulf, this 4 BR home comfortably sleeps 8. With 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 a bathroom on opposite ends of the house (a pocket door adds privacy). Private heated salt water pool sits amidst the lush tropical yard. Hop on the free A/C'ed trolley and explore Florida's gorgeous Anna Maria Island.

Guest favourite

Home in Sarasota

4.96 out of 5 average rating, 139 reviews

Sarasota Florida -Wild Orchid Creek Cottage Home

Come enjoy old Florida living at this completely renovated cottage style home on nearly seven acres. Relax and unwind in this 1000 square foot private home with king bed and queen sleeper to accommodate up to four people. Open concept living, dining room and full kitchen. Laundry facilities available. Equipped with WiFi and direct tv. While enjoying the private backyard space, it is common to spot abundant wildlife and wildflowers. Wild orchids in many of the oak trees bloom in early summer.

Guest favourite

Home in Sarasota

4.98 out of 5 average rating, 221 reviews

The Key Lime Cottage 2 miles from Siesta Key Beach

Great location. 2 miles from the # 1 rated Beach in America , Siesta Key . The cottage is near several other beaches as well. Close to restaurants and shopping. 1 hour from Tampa and 2 hours from Orlando. The Key Lime Cottage is totally updated with new stainless steel & granite in the kitchen . There are two new beds ..... one is a queen size and the other is a full size. (URL HIDDEN) Linens & towels are all new. New tile and wood floors throughout. Quite neighborhood for walking .

Guest favourite

Home in Anna Maria

4.99 out of 5 average rating, 102 reviews

1 block to Beach on Pine Ave! Private Heated Pool

Sat-Sat rentals, usually... Our 3 bedroom, 2 bath townhouse, with a private heated-pool oasis, is on Pine Ave in the heart of Anna Maria - 1 ½ blocks from the best white sand beach on the island - 3 blocks in the other direction to the bay - from sunrise at the City Pier to Sunset on the Gulf of Mexico. Walk or ride a bike to all the quaint stores, shopping and restaurants (plus the local doughnut, taco shop and Northshore Cafe next door) without ever getting in your car!

Guest favourite

Home in Bradenton Beach

4.82 out of 5 average rating, 133 reviews

50 Steps to Beach Villa Hot Tub 1bd modern cottage

Luxury Beach Cottage w/ HOT TUB, Fire Pit & BBQ. 1 bed/2bath sleeps 4 This is your chance to enjoy a unique getaway on the nicest beach! Stay in our newly remodeled beach cottage. White sandy beach & turquoise water is literally 50 ft from the door. Everything you need for a delightful & relaxing day at the beach is included. Chairs, beach towels, umbrella, snorkels, masks & a cooler. Enjoy the convenience of this premium location across Gulf blvd to Beach.

Guest favourite

Home in Indian Beach-Sapphire Shores

4.89 out of 5 average rating, 615 reviews

Charming Apt. in old Florida home

Cozy, charming suite in a historic 1920's home. Lots of character and charm. Amazing location. One block from the bay with beautiful sunsets. And just a few miles to the beach and downtown. Clean, comfy and a welcoming host. Great for 1 or up to 3 guests. ****Please read the full detailed description for more information before booking. This is very old home, not fully restored, old Florida house. Owner occupied Non- Smoking guests 🙏 Hope to see you soon

Guest favourite

Home in Anna Maria

4.94 out of 5 average rating, 167 reviews

Re-Modeled & Now Ready for Post-Hurricane Visits!

* It doesn't get much better than being right on the water, located on a wide canal, and ½ block from the beach. * Enjoy the large 16' x 30' private pool in a picturesque tropical landscape along with a 30' fishing/boat dock. * Within walking distance of Pine Avenue, City Pier, Two Scoops, Waterfront Restaurant, Galati's Marina, and Island Ocean Star Restaurant. *Less than a 3 minute walk to Bay Beach and a 15 minute walk to Bean Point.

Holiday rentals for every style

Get the amount of space that is right for you

Flats

Convenient locations with everyday essentials

Villas

Luxurious estates for the ultimate escape

Cottages

Quaint homes, peaceful surroundings

Popular amenities for house rentals in Longboat Key

Free parking on premises

Air conditioning

House rentals with a pool

Guest favourite

Home in Sarasota

4.95 out of 5 average rating, 194 reviews

The Oasis-Heated Private Pool Hot Tub-5mi to beach

Guest favourite

Home in Bradenton Beach

5 out of 5 average rating, 44 reviews

AMI*Steps to the beach-Modern luxury POOL SPA

Guest favourite

Home in Holmes Beach

5 out of 5 average rating, 14 reviews

Castaway Cottage

Guest favourite

Home in Bradenton

5 out of 5 average rating, 117 reviews

No Storm Damage! We Have Power!HeatedPool.Firepit!

Guest favourite

Home in Holmes Beach

4.95 out of 5 average rating, 94 reviews

The Peachy Beach House, steps to the gulf

Home in Sarasota

4.82 out of 5 average rating, 222 reviews

Private Siesta Beach House Oasis with Heated Pool.

Guest favourite

Home in Holmes Beach

5 out of 5 average rating, 61 reviews

Private Luxurious Ground Level Home

Guest favourite

Home in Sarasota

4.94 out of 5 average rating, 68 reviews

The Wisteria Oasis W/ heated pool & hot tub

Weekly house rentals

Guest favourite

Home in Bradenton Beach

5 out of 5 average rating, 45 reviews

Beach front! Trolley/Sunsets/Pier/Restaurants!

Guest favourite

Home in Bradenton Beach

4.94 out of 5 average rating, 33 reviews

Beach Bliss! Short stay specials! Walk to beach!

Guest favourite

Home in Siesta Key

4.93 out of 5 average rating, 27 reviews

Stunning Siesta Home | 4 Bedroom | Walk to Village

Guest favourite

Home in Sarasota

4.91 out of 5 average rating, 81 reviews

Tangerine House | Sauna | Near Downtown

Guest favourite

Home in Holmes Beach

5 out of 5 average rating, 45 reviews

Luxury Home Steps to Quiet Beach on 78th St

Guest favourite

Home in Sarasota

5 out of 5 average rating, 14 reviews

Swim & Soak Retreat w/Pool, Spa & Master Suite

Guest favourite

Home in Sarasota

4.95 out of 5 average rating, 78 reviews

Mid-Century Oasis with Pool in Arlington Park 1

Guest favourite

Home in Indian Beach-Sapphire Shores

4.95 out of 5 average rating, 42 reviews

Large and Beautiful, Steps from Bay, Ringling!!

Private house rentals

Guest favourite

Home in Sarasota

4.98 out of 5 average rating, 52 reviews

Sun-filled cottage with pool, walk to beach

Guest favourite

Home in Holmes Beach

4.94 out of 5 average rating, 89 reviews

Breezy Harbor AMI pool retreat near the Beach

Guest favourite

Home in Sarasota

5 out of 5 average rating, 6 reviews

Arlington Ocean Oasis 5br 5ba Htd Saltwater Pool

Guest favourite

Home in Indian Beach-Sapphire Shores

5 out of 5 average rating, 66 reviews

Magical Secluded Retreat

Guest favourite

Home in Sarasota

4.98 out of 5 average rating, 54 reviews

Stunning New 3 bed 3 bath pool home by Siesta Key!

Guest favourite

Home in Sarasota

5 out of 5 average rating, 52 reviews

The Blessing House- Htd Pool/Spa, Close to Beaches

Guest favourite

Home in Bradenton

5 out of 5 average rating, 14 reviews

Canal front, dock, heated Pool, near AMI+IMG

Guest favourite

Home in Bradenton

5 out of 5 average rating, 14 reviews

The Lazy Palm

Quick stats about house rentals in Longboat Key

Total rentals
230 properties
Nightly prices starting at
₹2,543 before taxes and fees
Total number of reviews
3.5T reviews
Family-friendly rentals
200 properties are a good fit for families
Pet-friendly rentals
100 properties allow pets
Rentals with a pool
140 properties have a pool

Destinations to explore