
House holiday rentals in Longboat Key
Find and book unique houses on Airbnb
Quick stats about house rentals in Longboat Key

Total holiday rentals
Explore 260 holiday rentals in Longboat Key

Nightly prices starting at
Longboat Key holiday rentals start at $51 NZD per night before taxes and fees

Verified guest reviews
Over 5,390 verified reviews to help you choose

Family-friendly holiday rentals
220 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 120 rentals that welcome pets

Holiday 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 holiday 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.

Carissa A | Beachside Retreat | Golf Cart | Pool
Carissa Loft A🏝️ A well-designed home offering comfortable spaces to relax, reconnect & experience all that AMI has to offer! Step inside to discover a private lower level retreat featuring a queen bed, sofa, TV and game table. Upstairs you'll find the fully stocked kitchen, inviting family room, 2-bedrooms & 2-full baths. The private outdoor oasis features a heated/cooled cocktail pool. 🚙Park the car & let the island adventures begin! The 6-person golf cart is complimentary with your stay!
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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
LocationFamilyTV

Stunning beach house with heated pool and hot tub!
Welcome to The Colony, a stunning vacation rental on Anna Maria Island, designed to capture the essence of Palm Beach living. This spacious 4-bedroom, 4.5-bathroom house features elegant decor and modern amenities. Step outside to discover a beautiful backyard oasis, complete with a large pool, hot tub, and a well-appointed patio that invites relaxation. Just a 5 minute walk to the pristine beaches of AMI, The Colony is perfectly situated in charming Holmes Beach for an unforgettable getaway.
ValueLocationIndoor spaces

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
FamilyLocationSleep quality

Private Heated Pool Retreat for Two Families
🌴 Welcome to your private Sarasota escape - designed for easy, extended stays, where two families can relax together around a private heated pool. With generous living spaces and thoughtful touches throughout, the home balances comfort and connection. Located minutes from Siesta Key, Lido Beach, and downtown Sarasota, and within walking distance of a park with playground, public pool, courts, fitness areas, and scenic trails. Relaxed, comfortable, and ideal for memorable family getaways.
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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.
LocationValueOutdoor spaces

Modern, Bright Downtown SRQ A-Frame West of Trail
Enjoy this bright, newly renovated unique pool home on a street with mostly waterfront homes featuring 4 beds & 3 baths, office area options, loft reading nook, Bosch appliances, bedroom skylights, artful light fixtures and fully fenced with heated pool. Central to & minutes from Siesta Key, St. Armand's Circle/Lido Key, downtown. Walk to the Sarasota Arts Museum, grocery, Southside and downtown Restaurants & shops, Selby Botanical Gardens, Bayfront Park, & Marina Jack. VR24-00157
ValueFamilyCheck-in

NEW! w/ Pool - The Pearl Unit 2 on AMI
The Pearl (Unit 2) is a newly renovated oasis in the heart of Holmes Beach on Anna Maria Island. Just a 3–5 minute walk to the beach, this sunny AMI duplex home has everything — sparkling saltwater pool, fresh interiors, no stairs, beach gear, and parrots that may say hi on your morning walk! Centrally located and steps away from the AMI trolley to whisk you around the island! Relax, explore, and live your best island life. *pool is shared with one other unit in the duplex home*
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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.
LocationValueAccess

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!
ValueLocationGetting around

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.
FamilyLocationQuiet

Your DreamOasisAwaits: SiestaKeyEscape with Pool!
Welcome to your dream oasis near the world-famous Siesta Key! ✨ This immaculate 2BD/2BA home is a true coastal gem, offering a serene retreat with stylish design and luxurious amenities. Just 1 mile from the sugar-white sands of Siesta Key Beach, this home provides the perfect blend of comfort and convenience—an ideal spot to embrace relaxed Florida living at its finest. 🌴
LocationFamilyParking
Popular amenities for Longboat Key house rentals
House rentals with a pool

Retreat by the Bay-Heated Saltwater Pool
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Tiki Bar Paradise! Heated Pool & Gaming Oasis!
ValueLocationDecor

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

Lux Pelican's Perch | Heated Pool + Hot Tub + Gym
LocationFamilyHot tub

Coastal Luxe, SaltPool/heatSpa, 5 miles to Siesta
ValueLocationAmenities

Under the Foxtails by Beach Boutique Rentals
FamilyLocationAmenities

Hidden Gem, Pool, Steps to Beach and St Armands
LocationViewGetting around

Gorgeous Canalfront Home w/ Dock | Walk to Beach!
LocationValueWalkability
Weekly house rentals

Short walk to beach + Boat dock
FamilyValueNearby

Seaquel A Tropical Retreat - Private Pool Home
FamilyLocationAmenities

Pergola Oasis | Walk to Beach + Outdoor Living
LocationFamilyOutdoor spaces

The Siesta Key Retreat - An Island Garden Oasis!
LocationFamilyPool

The Florida Rooms
LocationFamilyCheckout

Magnolia Palms: Family Retreat w/ Backyard Oasis
FamilyLocationHospitality

Bayfront Beach access with Heated Pool!
FamilyValueSleep quality

10 min AMI | 15 min IMG | Heated Pool
FamilyLocationSleep quality
Private house rentals

Ocean Air Oasis-New Centrally Located AMI Luxury
FamilyLocationBathroom

Renovated 2bed /2 bath North End, beach 2 min walk
FamilyValueBeach

Providence Cove | Heated Salt Pool • Sleeps 12
FamilyTVOutdoor spaces

Payton's Place | Private Heated Saltwater Pool/Spa
LocationFamilyBeach

Manatee Sanctuary - in the heart of Anna Maria
FamilyLocationTV

Birds and Sunsets
FamilyValueBeach

TOES IN THE SAND!
FamilyValueWalkability

New! Pool + Rooftop+ 2 Min Walk to Beach & Bay!
LocationFamilyOutdoor spaces
When is the best time to visit Longboat Key?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $472 NZD | $485 NZD | $509 NZD | $380 NZD | $368 NZD | $368 NZD | $349 NZD | $346 NZD | $333 NZD | $324 NZD | $382 NZD | $436 NZD |
| 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 |
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- Anna Maria Island
- Siesta Beach
- Anna Maria Island Beach
- Raymond James Stadium
- Busch Gardens Tampa Bay
- Coquina Beach
- Lido Key Beach
- Bean Point Beach
- Turtle Beach
- Amalie Arena
- Caspersen Beach
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- Manasota Key Beach
- Hard Rock Casino
- University of South Florida
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- Crescent Beach
- John's Pass
- Fort De Soto Park
- Englewood Beach
- Sand Key Beach
- MidFlorida Credit Union Amphitheatre
- Anna Maria Public Beach
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