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House vacation 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

Home in Holmes Beach

4.87 out of 5 average rating, 103 reviews

New Golf cart + 4bd/3b w pool/2100 sq ft home

Urban Oasis is a privately owned 2100 sq ft 4 bd, 3 bth on Anna Maria Island. 4 minute walk on a quiet residential street to walk to the beach.This home features grey blue hues, coastal furniture, driftwood accents, themed rooms and designer accents. A brand new 2024 6 str golf cart is included in your rental as well as a premium linen service including all towels and linens. Urban Oasis is truly a turnkey Vacation Rental! We also have a second property, Urban Oasis Too, if you like our style!

Home in Sarasota

4.94 out of 5 average rating, 267 reviews

Lovely guest house

Come get away from everyday life & enjoy this cozy studio located in the heart of Sarasota. This studio is a breath of fresh air- you’ll feel calm and at peace. Sparkling clean & spacious with queen-sized, comfortable bed, a full bathroom and kitchenette. A great location to have the city life, but also quiet enough to relax. Whether you’re here for business or pleasure, this cozy studio is sure to be a highlight.The studio is separate 100 feet from the main house, and It has a private entrance

Home in Bradenton

4.94 out of 5 average rating, 171 reviews

Peaceful Braden River Oasis: Cottage

Come get away to this river retreat just outside of Lakewood Ranch. This property has three separate rental units on it including this charming single bedroom cottage with access to the river. It comes with everything you need to enjoy a wonderful vacation! The other units on this property are the Guest House, a larger studio unit 1 bed/1 bath sleeps 2 (Search Peaceful Braden River Oasis: Guest House) and the Main House, a 2 bed/2 bath sleeps 7 (search Peaceful Braden River Oasis: Main House).

Home in Sarasota

4.85 out of 5 average rating, 181 reviews

Authentic Florida Bungalow near Downtown and Beach

Revisit the charm of old Florida in this 1943 cottage that has been lovingly restored. Relax on the indoor screened porch with a book or a game of cards. New air conditioning, beautiful quartz countertop in kitchen with newer appliances.Super comfy king size bed and full beds will sleep up to 4 in 2 bedrooms. Fabulous location with only 16 blocks to downtown, 10 minutes to St. Armands Circle, beautiful Lido Key . Directly on bus line for public transportation and 10 minutes to SRQ airport.

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!

Home in Sarasota

4.96 out of 5 average rating, 142 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.

Home in Sarasota

4.96 out of 5 average rating, 224 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 .

Home in Bradenton Beach

4.97 out of 5 average rating, 159 reviews

BACK Jan 1! Newly Renovated! STEPS 2 Private Beach

NEW Pics Coming! 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.

Home in Indian Beach-Sapphire Shores

4.92 out of 5 average rating, 102 reviews

Pool Courtyard, patio w/ fire pit, 2 mls downtown

Enjoy this unique courtyard-style Spanish colonial home just steps to Sarasota Bay and 2 miles from downtown. The property consists of a 2 bed / 1 bath main house AND a detached studio. Everything pictured is yours to enjoy, nothing is shared. The houses are separated by a quaint & private pool courtyard w/ outdoor shower. Capture a photo of the local peacocks, eat fresh mangos from the yard, catch a sunset over the bay, or enjoy the sun by the pool listening to the Zen fountains.

Home in Anna Maria

4.99 out of 5 average rating, 102 reviews

1 block to Beach on Pine Ave! Private Pool Oasis

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!

Home in Sarasota

4.93 out of 5 average rating, 110 reviews

The Sunkissed Haven- cheerful 3/2 near beaches.

Unwind in this serene, stylish 3-bedroom, 2-bathroom haven drenched in sunlight and adorned with thoughtful decor. Enjoy plush bedding – a king and two queens – perfect for your family retreat. The well-equipped kitchen and fully fenced backyard make it an ideal spot for relaxation. Just 5.4 miles to Lido Beach and 7.5 miles to Siesta Key Beach, minutes from Downtown Sarasota, the Sarasota Airport, and the charming Amish Village of Pinecraft, your getaway awaits.

Vacation rentals for every style

Get the amount of space that is right for you

Apartments

Convenient locations with everyday essentials

Cottages

Quaint homes, peaceful surroundings

Villas

Luxurious estates for the ultimate escape

Popular amenities for Longboat Key house rentals

Free parking on premises

Air conditioning

House rentals with a pool

Home in Sarasota

4.99 out of 5 average rating, 70 reviews

Sea Esta | Private Saltwater POOL + Putting Green!

Home in Anna Maria

5 out of 5 average rating, 22 reviews

Veselka - Canal front w private heated pool & dock

Home in Holmes Beach

5 out of 5 average rating, 9 reviews

Beachy Blue by Beach Boutique Rentals

Home in Holmes Beach

4.93 out of 5 average rating, 41 reviews

Backyard Bliss Anna Maria Island

Home in Bradenton

5 out of 5 average rating, 118 reviews

HTDPool~2KingSuites~3BathRm~FIREpit~Airhockey~CRIB

Home in Anna Maria

5 out of 5 average rating, 22 reviews

༄ Sunset Shore on Anna Maria Island ༄

Home in Holmes Beach

5 out of 5 average rating, 61 reviews

Private Luxurious Ground Level Home

Home in Sarasota

4.95 out of 5 average rating, 65 reviews

True Island Living House

Weekly house rentals

Home in Sarasota

4.97 out of 5 average rating, 65 reviews

Minutes to downtown renovated oasis with nostalgia

Home in Holmes Beach

5 out of 5 average rating, 14 reviews

Castaway Cottage

Home in Holmes Beach

4.96 out of 5 average rating, 75 reviews

Salty Harbor AMI pool retreat near the Beach

Home in Sarasota

5 out of 5 average rating, 14 reviews

Private Guest Cottage on 5 acres

Home in Anna Maria

5 out of 5 average rating, 9 reviews

Bateman's - Renting 12/2024!

Home in Anna Maria

5 out of 5 average rating, 9 reviews

Ocean Air Oasis-New Centrally Located AMI Luxury

Home in Holmes Beach

5 out of 5 average rating, 45 reviews

Luxury Home Steps to Quiet Beach on 78th St

Home in Sarasota

4.98 out of 5 average rating, 51 reviews

The Mango House Beach Cottage

Private house rentals

Home in Sarasota

4.96 out of 5 average rating, 54 reviews

Sun-filled cottage with pool, walk to beach

Home in Anna Maria

4.9 out of 5 average rating, 50 reviews

Island in the Sun

Home in Holmes Beach

5 out of 5 average rating, 13 reviews

6 Bed/5.5 Bath Heated Pool -1 Minute Walk to Beach

Home in Indian Beach-Sapphire Shores

5 out of 5 average rating, 67 reviews

Magical Secluded Retreat

Home in Holmes Beach

5 out of 5 average rating, 37 reviews

Couple’s Seatreat Summer Rate Specials

Home in Sarasota

5 out of 5 average rating, 15 reviews

Luxe Oasis Mins to Beach & Downtown w/Heated Pool

Home in Siesta Key

5 out of 5 average rating, 25 reviews

Paradise In Siesta!

Home in Siesta Key

5 out of 5 average rating, 25 reviews

Beachfront 180-Degree View, Walk to Village!

Quick stats about house rentals in Longboat Key

Total rentals
230 properties
Nightly prices starting at
$30 before taxes and fees
Total number of reviews
3.5K 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