
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.

Siesta Key, FL - Casa Berano
Quiet, private home on lovely Siesta Key. 1.6 miles from lovely #1 Beach in the country. 1.9 miles to Siesta Key Village. FREE shuttle to village & beach 7 days a week. Private saltwater pool/enclosed lanai. Spacious 3bd/3b. Pets, dogs only, welcome, pls add to your total guest reservation. Open floor plan, large living area. Kitchen opens into living area & 2 dining areas w/ large tables. 2 car gar. brick paved driveway, in home laundry. 6 Guests Max 2 pets Max (dogs only), under 50lbs

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!

Sunshine Retreat with heated saltwater pool
A beautiful 4 bedroom 2 bath home in a very quiet neighborhood in NW Bradenton. Quiet hours from 9pm to 7am. This ideal location is minutes away from the beautiful beaches of Anna Maria Island and IMG academy. Less than a mile to grocery stores, restaurants and shopping. The house has WIFI and cable TV. Fully stocked kitchen: Pots, pans, utensils, new stainless steel appliances, coffee maker, Keurig, etc.). New saltwater pool and privacy fenced in back yard. Two stall garage for parking.

The Sweet Spot! Walk to DT & Free Trolley to Beach
Looking for the Sweet Spot in Sarasota? Look no further! This artistically updated cottage, nestled in the quiet, historic downtown neighborhood of Laurel Park is a just a short walking distance to some of the best downtown dining, shopping, arts venues and the renowned Selby Gardens. Take the free Breeze Trolley to Siesta Key and Lido beach. Relax in the private outdoor courtyard. It's is the perfect place for a couple's getaway, a family vacation, or a long term stay. So book now and welcome!

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.

Cozy & Beautiful Pool Villa in Sarasota County, FL
Welcome to our home! It’s our pleasure to host you! Your family & friends will be close to everything when you stay at this centrally-located place: shopping, dining, beaches, entertainment, Warm Mineral Springs, Aquatic Center, etc. This charming house located in a beautiful & quiet neighborhood, tastefully furnished & decorated, fenced for your privacy & perfect for making memories with family & friends. Plenty of amenities to make your stay as comfortable as possible. Great location.

Your private retreat near Siesta Key Beach.
Completely Remodeled Private Retreat. COME RELAX, UNWIND, AND MAKE LASTING MEMORIES! From the moment you arrive, you’ll feel the calm, welcoming atmosphere that makes this property stand out. This spacious 3brm 2-bath features an amazing heated pool, a private backyard, and stylish finishes throughout. Whether you’re lounging by the heated pool, enjoying meals in the bright open-concept living space, or exploring the nearby beaches this home is perfect for an unforgettable vacation

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.

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 Gold: Luxury Edition of #1 Rental
High end, luxury 3/2 pool home! 7 4k TVs w/ Netflix and cable (75" in living room), SONOS throughout house/pool, wifi, PS5, private heated salt water pool/Spa, putt putt, foosball, beach gear, Pack & Play, Game room (board games, billiards, shuffle board, arcade), massive kitchen/bar, washer & dryer, garage parking-- all in a quiet and safe neighborhood. Just 5 miles to the best beaches and restaurants. Entire home with no shared amenities!

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.

The Sea is Calling
Our home, The Sea is Calling, is located on a cul de sac in Whitfield Estates. It is a short drive to many world class beaches and attractions like Lido Beach, Siesta Key, Longboat Key, Mote Marine, Ringling Museum and Sarasota Jungle Gardens. Our home is welcoming and we hope you decide to let us share a bit of paradise with you. When The Sea is Calling, you must go! We hope to see you soon.
Popular amenities for Longboat Key house rentals
House rentals with a pool

Spacious Cozy Tropical Retreat!

Cozy Cottage - POOL HOME! 3/3

Allison Palms Luxury Tampa Townhome + Pool

Condor's Nest-Walk to Downtown, Heated Pool!

Stylish Pool Home • Near IMG & Beaches • Top Rated

Bean Pt. Bungalow - Half duplex w/private pool

8 min Beach, Hot Tub, Pool & Games @ Snook Haven

Saltwater Pool, Near MLB Spring Training & Beach!
House rentals with a hot tub

Steps to IMG Golf! Heated Pool, Spa, Game Room!

Modern 3BR Retreat + Anna Maria Beaches + IMG!

Be an AMI

Mobility accessible home swim jacuzzi near beach

Relax+ Jacuzzi | 9 Min to Siesta Key Beach

Cozy Boho Bungalow Pool/Spa QR Code Walkthrough

Hidden Haven / Private Pool & Hot Tub

Near Lido Beach w Hot tub + Fire Pit
House rentals with free parking

AMI Retreat

Gorgeous renovation with pool, minutes from beach

The Lovely Family House

Entire Home Sweet Home in Riverview Florida 33578

Sunny Tampa Gem, Has It All!

Townhouse in Clearwater

The Surf Shack

Pirates Nest - 2 Minute Stroll To The Beach & Pet
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
- Siesta Beach
- Crescent Beach
- Raymond James Stadium
- Busch Gardens Tampa Bay
- John's Pass
- Turtle Beach
- Coquina Beach
- Vinoy Park
- Caspersen Beach
- Lido Key Beach
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- Amalie Arena
- Cortez Beach
- Bean Point Beach
- Anna Maria Public Beach
- Jannus Live
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- Hard Rock Casino
- Englewood Beach
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