
Villa holiday rentals in Longboat Key
Find and book unique villas on Airbnb
Top-rated villa rentals in Longboat Key
Guests agree: These villas are highly rated for location, cleanliness and more.

Heated Pool! Huge Walk In Shower! 5 min to beach!
Welcome to Coastal Paradise! This modern villa is newly remodelled and professionally furnished with a beautiful coastal theme. It has a very spacious open layout with plenty of space for the whole family. A huge master walk in shower with two shower heads and four body jets! Out back is a private heated pool with lounge chairs, grill, a hammock, corn hole and a beautiful patio set to enjoy a meal outdoors. Madeira beach is only a 5 min drive away! We also provide all your beach necessities!!

Villa Key West "Villas by Christine"
Perfect location, Charming Villa Guests are loving the newly renovated Villa Key West. Christine's goal was to make guests to feel the charm of a Key West Villa while experiencing the amenities of a 5 star hotel The Living room and bedrooms have large smart TV’s with complementary Roku, Netflix, Prime and Hulu. Enjoy the view out back of one of Safety Harbors 150 year old Oak & nature pond. We are per friendly. Please let us know you will be bringing pet. Pet fee of $100.00 due upon arrival.

Entire Standalone Villa,1.2k sf,1 block Lido Beach
Welcome to our cute, spacious, sun filled and newly renovated Beach Villa. A Happy place for sandy feet, friends, and family. The Villa is located 1 block away from world famous Lido Beach, a 7 min walk to St Armand's Circle, and a short 3 mile drive to grocery shopping & the excitement of downtown Sarasota. The 2 bdr villa comfortably sleeps up to 6 people and features a private outdoor patio, spacious dining area, in-unit washer/dryer & dedicated parking. Come enjoy a taste of paradise!

Quiet 3BD Huge Tropical Garden & Patio. 5min Beach
Escape to our tranquil tropical paradise! Our private garden overflows with emerald palm trees, exotic foliage and native blooms, while the covered patio offers a place to relax and savor nature's natural sounds. Grill area, outdoor seating, lounge chairs. 5 minutes to Indian Rocks Beach and downtown amenities. Embark on bike rides on the nearby Pinellas Trail and Tailor Park with our complimentary bikes. Enjoy fun and fishing with our provided kayaks and gear, easily loaded onto your car.

Duplex - just mins to Siesta Beach - Pet Friendly
This is a 2/1 in Sarasota's Historic Laurel Park that offers a great downtown and beach experience! Walk/bike to historic downtown with shops, restaurants, bars, boutiques, parks, and music/theater. Minutes from the best beaches in the U.S. Enjoy the lanai & fenced backyard for privacy . Grill & enjoy your favorite beverage while watching your favorite show on the lanai ! Enjoy taking your pet for a walk & check out the historic homes in the area! Short term rental number VR24-00222

Luxury Villa with Pool, Game Room, Near Beach
Welcome to your tropical luxury escape! Spacious living flows to the heated pool, game room and sunny patio—perfect for family fun. • Bedrooms: 4 private suites, plush linens to ensure restful nights. • Location: Quiet neighborhood just minutes from the sandy beach, dining and shopping hotspots. • Heated pool & sun loungers • Arcade-style game room • Fast Wi-Fi & 5-star cleanliness • Pet friendly with fenced yard Have questions? We reply in under an hour—book your stay today! VR24-00060

Tampa heat pool /hot tub lake view near airport
Welcome to home away from home! This beautiful 4 bedroom 2 bathroom house is new with modern decor and has everything you need for a comfortable and relaxing stay. The house features a sparkling swimming pool and a hot spa, perfect for unwinding after a long day. Located in brandon, you’ll be just 15 minutes away from downtown, where you can experience the city’s vibrant culture and attractions. Get ready to create some unforgettable memories in this charming abode.

A Wave From It All Villa W King Beds
Fully renovated 2 bedrooms with 2 King beds 2bath unit, has all the stainless steel appliances everything you could possibly need for your vacation time. The home is located 7min from buccaneers stadium, 5 mins from St. Joseph hospital, 10 mins to international mall, 10 mins to Soho. Home is in the heart of Tampa Bay! -Tampa International Airport 8.6MI -Tampa Bay Buccaneers Stadium 2.2MI -Aquarium7.6MI -Busch Gardens8.4MI -Clearwater24MI -Adventure Island9.0MI

5 min to Siesta Key, Heated Pool, Grill, WiFi
Welcome to 'Villa Tropicana' 'Villa Tropicana' is a 3BD/2BA home featuring a pool with a deck. Enjoy a beverage in the tropical front garden or sunbathe by the pool out back for a dream vacation. The best part is the location - less than 5 minutes away from the gorgeous beaches of the world famous Siesta Key. In case you need any additional information, please try prefix 941, followed by 376, and finally 8679. Thank you, Ven & The Hacienda Team

Cozy funky duplex with KING bed
Escape to the charming town of Gulfport, Florida, and discover a hidden gem nestled in the heart of this vibrant community. Our eclectic studio offers a one-of-a-kind experience for those seeking comfort, style, and a touch of the extraordinary. The main highlight is the funky wallpaper and the luxurious king-sized bed, adorned with premium linens and plush pillows, ensuring a restful night's sleep after your Gulfport adventures.

Boho -Minimalist villa
Welcome to our Boho Minimalist Villa 4311 unit B with a 2 bedroom and 1 bathroom. Conveniently located in the heart of Tampa, Florida. “Points of interest” to visit and enjoy while you are here: Raymond’s James Stadium, New York Yankees Training Camp, Hillsborough Community College, International Tampa Airport, Downtown Tampa, Midtown within less than 10-minutes’ drive enjoy a great afternoon eating at many local restaurants.

Beachfront Paradise! Ground level with Heated pool
Gulf-front getaway with unbeatable beach access—step out your back door and right onto the sand! Enjoy a king bed, queen sleeper, fully stocked kitchen, in-unit washer/dryer, and professional linen service. Beach towels, two chairs, and an umbrella are included. Relax or grill by the shared heated pool and soak in the stunning Gulf views. Everything you need for the perfect beach escape—just bring your sunscreen and unwind!
Popular amenities for Longboat Key villa rentals
Private villa rentals

Villa Luxe~Heated Saltwater Pool~Near Beaches

Paradise Villa- Sarasota

Northshore BeachHouse West Anna Maria Island

King 1 Br/1Ba, Hot Tub - Close to Beach & Downtown

Remodeled Mid-century POOL house

Coastal Cottage

Oasis Getaway -Beautiful House-Infinity Pool-Beach

Lakefront 2BR • Perfect for IMG & Long Stays
Luxury villa rentals

Mediterranean Villa w/ Beautiful Heated Pool/Spa

(HGR) Heated pool villa. Boat rental available

Luxury home in the heart of South Tampa & POOL!

Best deal in town!

Sleep 28 w/ 14 Beds + Pool | Near Clear Waterbeach

5 BR Luxury Beach Villa: Heated Pool & Games Room

Paradise with a pool, pier and private beach area

Waterfront Heated Pool, Sleeps 20 - 4plex
Villa rentals with a pool

Family Haven/Kid's Amenities Near Honeymoon Island

La Villa, 1 of 3 rentals on-site. Heated Pool!

The Tropical Oasis, w/ Solar Heated Pool and Games

The Sea House

Tiki Bella Villa (Entire home with Pool)

Villa Perdomo Family

Waterfront Villa with heated Pool

4 min Walk to Beach, Pool, Roof Deck
Quick stats about villa rentals in Longboat Key

Total holiday rentals
Explore 10 holiday rentals in Longboat Key

Nightly prices starting at
Longboat Key holiday rentals start at $173 NZD per night before taxes and fees

Verified guest reviews
Over 310 verified reviews to help you choose

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

Wi-Fi availability
10 of Longboat Key holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wi-Fi and Pool across Longboat Key rentals

4.8 Average rating
Longboat Key stays are highly rated by guests—averaging 4.8 out of 5!
Destinations to explore
- Seminole Holiday rentals
- Central Florida Holiday rentals
- Miami Holiday rentals
- St Johns River Holiday rentals
- Orlando Holiday rentals
- Gold Coast Holiday rentals
- Miami Beach Holiday rentals
- Havana Holiday rentals
- Fort Lauderdale Holiday rentals
- Four Corners Holiday rentals
- Tampa Holiday rentals
- Kissimmee Holiday rentals
- Fitness-friendly rentals Longboat Key
- Condo rentals Longboat Key
- Rentals with lake access Longboat Key
- Rentals with pools Longboat Key
- Rentals with an accessible height toilet Longboat Key
- Apartment rentals Longboat Key
- Rentals with beach access Longboat Key
- Beach condo rentals Longboat Key
- Rentals with outdoor seating Longboat Key
- Waterfront rentals Longboat Key
- House rentals Longboat Key
- Beachfront rentals Longboat Key
- Rentals with a fireplace Longboat Key
- Rentals with a washing machine and dryer Longboat Key
- Rentals with a hot tub Longboat Key
- Rentals with an EV charger Longboat Key
- Beach house rentals Longboat Key
- Family-friendly rentals Longboat Key
- Rentals with a patio Longboat Key
- Cottage rentals Longboat Key
- Rentals with a fire pit Longboat Key
- Pet-friendly rentals Longboat Key
- Rentals with a kayak Longboat Key
- Townhouse rentals Longboat Key
- Villa rentals Manatee County
- Villa rentals Florida
- Villa rentals United States
- Anna Maria Island
- Siesta Beach
- Crescent Beach
- Busch Gardens Tampa Bay
- John's Pass
- Raymond James Stadium
- Turtle Beach
- Dunedin Beach
- Caspersen Beach
- Coquina Beach
- Vinoy Park
- Cortez Beach
- Lido Key Beach
- Anna Maria Public Beach
- Amalie Arena
- Bean Point Beach
- Jannus Live
- ZooTampa at Lowry Park
- Manasota Key Beach
- Gulfport Beach Recreation Area
- North Beach
- Tampa Palms Golf & Country Club
- River Strand Golf and Country Club
- Englewood Beach




