Villa vacation rentals in Longboat Key

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Popular amenities for Longboat Key villa rentals

Private villa rentals

Top guest favorite
Villa in Indian Rocks Beach
5 out of 5 average rating, 17 reviews

IRB Harbor House Semiprivate Waterfront Pool Villa

ReneeRating, 5 stars3 weeks ago
Will 100% be back! The home was beautiful and felt like we were at our own private resort. Thoughtful touches throughout. To be on the water but walkable to the beach - all around an incredible week. It was private. The host was awesome, great at anticipating our needs and super responsive when needed. Takes great pride in a well maintained and updated home. Home was stocked with all that we needed. Didn’t want to leave! Hard to believe it was better in person than the photos show!
Guest favorite
The dining area features a modern table with gold accents, surrounded by plush gray chairs. A stylish chandelier hangs above, illuminating the space. The open-concept layout offers a clear view of the adjacent kitchen and a spacious living area with a large television.
Villa in Palm Harbor
4.91 out of 5 average rating, 33 reviews

Villa Luxe~Heated Saltwater Pool~Near Beaches

LacyRating, 5 stars1 month ago
Absolutely one of the best hosts we have had. They went above and beyond to make sure we had everything we needed. Came over when the outdoor grill would not work, made a special trip to bring a new net for the pool, and even reached out before we arrived to see if we had a need for a stroller that she wanted to drop off. The house was very, very nice. The only area that I could see for improvement is maybe a little bit of updating to the pool area. However, our kids still really enjoyed it. I would definitely recommend this place and the hosts!
Guest favorite
A clear blue pool is surrounded by a decorative stone patio. Comfortable lounge chairs are positioned nearby, inviting relaxation. A covered outdoor dining area with a table and chairs is visible under a shaded awning. Lush greenery complements the serene atmosphere.
Villa in Sarasota
4.97 out of 5 average rating, 29 reviews

Luxurious Poolside Retreat in Sarasota

DavidRating, 5 stars1 month ago
Alex was very professional and promptly addressed any issues we had. By issues I mean, getting us more towels and fixing the pool where it was losing water. Would definitely recommend this place!
Top guest favorite
A screened-in outdoor seating area is featured, furnished with a large sectional sofa adorned with red accent pillows. A low coffee table holds a bowl of fresh fruit and drinks, overlooking a sparkling pool surrounded by lush greenery.
Villa in Sarasota
4.97 out of 5 average rating, 59 reviews

SEALAND 3/2 Modern Villa w/ Pool near Siesta

SarahRating, 5 stars1 week ago
This was one of the BEST air b&b’s I have stayed at in Sarasota so far!! Aside from the beautiful weather Inas home was very clean, and had all the amenities needed!! The pictures look exactly like what her home has to offer. She was very responsive and kind. We asked for the pool heated for the extra daily charge and she did it immediately! Very close and convenient to all grocery stores, gas stations and restaurants. About a 10 minute ride to beautiful siesta key beach. I give 10 Stars !!! Highly recommend!! Thank you Ina for hosting us and we hope to be back soon !!!! For the next guests enjoy!!
Guest favorite
A cozy living area features a dark gray sofa adorned with colorful cushions. A vibrant area rug sits beneath a rectangular coffee table. Bright orange chairs add a pop of color, while a large mirror and framed artwork enhance the space's brightness.
Villa in Clearwater Beach
4.91 out of 5 average rating, 222 reviews

V3- 1 BR, waterfront villa, 2 min walk 2 beach

JennyRating, 5 stars2 weeks ago
We had a great stay! We would definitely stay again!
Superhost
A spacious outdoor area featuring a pool surrounded by lounge chairs. Lush greenery and palm trees enhance the setting, while a nearby area is prepared for games. A light-colored non-slip surface provides a safe space for relaxation and enjoyment under the clear sky.
Villa in Bradenton
4.87 out of 5 average rating, 97 reviews

Florida Living

CallahanRating, 5 stars2 weeks ago
Had a great stay at this clean and relaxing property! The pool was great and everything met or exceeded expectations.
Guest favorite
A fire pit made of stone is surrounded by two white adirondack chairs. Flames rise energetically from the center, surrounded by logs in a gravel setting. Lush green plants are visible in the background, creating a cozy outdoor ambiance.
Villa in Sarasota
4.86 out of 5 average rating, 37 reviews

The Olive Turtle

JulietRating, 5 stars2 months ago
VERY spacious. Great entrance with chairs so easily put on and off shoes which was requested. Bathrooms very clean. Master bedroom very spacious. Very nicely stocked for us to enjoy coffee and some snacks the next morning. Close to our extended family near Botanic garden. We were comfortable, beds were nice. Quiet street. Did not end up walking anywhere but close to a great and popular pickleball public park. For the few questions we did have, owners were incredibly friendly and responded quickly. Unusual layout with stairs into different parts of the house. Kitchen sort of off to the side in a nook but we were there for extended family events so not really an issue.
Guest favorite
A shaded outdoor seating area features two wicker chairs surrounding a small table, set against a backdrop of a brick wall and a light-colored building. The garage doors are visible, along with a partially covered patio area, creating a welcoming atmosphere.
Villa in Bayshore Beautiful
4.99 out of 5 average rating, 68 reviews

Southern Charm Villa with Pool

CodyRating, 5 stars1 month ago
Our stay at Adina’s was great! Very clean and spacious bedroom. Walkable to Bayshore and quick drive to Hyde Park. Adina was very responsive and flexible with a late check out to accommodate our later flight. The baked goodies she made were an added bonus!

Luxury villa rentals

Guest favorite
The charming exterior of a beautifully restored duplex features a welcoming entrance with decorative columns and a spacious balcony. Warm lights illuminate the facade, while lush greenery surrounds the property, creating an inviting atmosphere complemented by the architectural details typical of the historic Ybor City neighborhood.
Villa in Ybor City Historic District
4.95 out of 5 average rating, 19 reviews

Luxury 5BR Ybor City Duplex Near 7th

TracieRating, 5 stars3 days ago
Beautiful villas, newly renovations, spacious living area & Kitchen, VERY clean. Would definitely stay here again!! Thank you for a great stay!!
Guest favorite
A serene outdoor space features a circular fire pit surrounded by several adirondack chairs. Lush greenery and trees frame the area, while a vibrant sunset paints the sky in soft pastel hues. The lake is visible in the distance, enhancing the peaceful ambiance.
Villa in Thonotosassa
4.95 out of 5 average rating, 41 reviews

Lakeside Villa

AviRating, 5 stars3 weeks ago
This was not only an incredible house, but Kyle was also an amazing host. He was extremely responsive and genuinely cared about our stay. We can’t stop raving about how lovely this place was—gorgeous views, cozy cabin vibes, peaceful, and private. We’d definitely come back.
Guest favorite
Villa in Seminole
4.95 out of 5 average rating, 41 reviews

Modern Luxury Retreat - Heated Pool Spa, Game Room

LoriRating, 5 stars4 weeks ago
Our stay at the Luxury Ultra Modern Villa in Seminole, Florida, was absolutely fantastic! Perfect for our party of five, the villa exceeded our expectations in every way. The location was ideal, just minutes from stunning beaches—only a 5-minute drive to beach access and 13 minutes to Indian Rocks Beach. The villa itself featured a sleek, modern design with an open layout that brought everyone together. The three stylish bedrooms were beautifully decorated, each with super comfortable memory foam mattresses, we all slept like babies. The highlight was the stunning backyard. The heated pool was a true oasis, perfect for cooling off during sunny days, while the spa offered a relaxing retreat in the evenings. We loved this space so much and spent most of our time out there. With beach accessories provided, we were well-equipped for the beach. The owners are great people and very responsive. We will for sure come back in the future!
Superhost
A wooden deck leads down to a lush green area with artificial turf, adjacent to a tranquil canal. The water reflects the surrounding greenery and blue sky, creating a peaceful outdoor setting, ideal for relaxation.
Villa in Largo
4.86 out of 5 average rating, 63 reviews

Best deal in town!

BarbaraRating, 5 stars2 weeks ago
The residence was clean and met our needs for the 9 family members that stayed (3 nights). The kitchen has plenty of counter space. The home was roomy enough for all, but some of the seating (blue chairs in photos) was not in the home. If you are traveling with elders, just note that 2 of the 3 bathrooms have smaller than standard doors. My mom’s walker would not fit through them. The beds are very comfortable. We would stay here again if coming to town.
Guest favorite
The exterior of the villa is showcased under a sunset sky, featuring a two-story gray structure with large windows. The well-maintained lawn is complemented by shrubs and tropical plants, while a wooden fence marks the boundary of the property.
Villa in Seminole
4.86 out of 5 average rating, 22 reviews

5BR LUX Pool Villa | w/ Sauna | Near The Beach

GaryRating, 5 stars1 month ago
this place was so beautiful. we definitely recommend if you were in the area this is where you want to be. thanks again for being a great host.
Top guest favorite
A vibrant outdoor scene showcasing a poolside setting with plush lounge chairs and colorful pool floats. A straw hat and sunglasses rest on a striped towel next to a wicker table adorned with tropical-themed items. Refreshing drinks and fruits are nearby, surrounded by lush greenery.
Villa in Sarasota
5 out of 5 average rating, 11 reviews

Close to Beaches|Pool|Fire Pit|Game Room|King Beds

KellyRating, 5 stars3 weeks ago
Great stay in Florida! House was clean and Paula and Roberto were very responsive when we had questions! Pool and backyard were amazing. Lots of space in the house for 9 guests too! Thanks for having us!
Guest favorite
Villa in Seminole
4.97 out of 5 average rating, 58 reviews

5 BR Luxury Beach Villa: Heated Pool & Games Room

JenniferRating, 5 stars4 months ago
We had a great stay, close to the beaches and just as described!
Guest favorite
A serene pool area surrounded by lush greenery is highlighted, featuring a waterfall cascading over rocks into the crystal-clear water. A colorful donut-shaped float lies in the pool, alongside a rustic wooden table holding a mug with a mermaid design.
Villa in Holmes Beach
4.97 out of 5 average rating, 70 reviews

Calico AMI – Steps to Sand, Family Paradise!

SamanthaRating, 5 stars1 month ago
Céline's home was perfect for our family of 7. Celine was proactive in making sure we had everything we needed. She went the extra mile with details around the house for us to have a such an enjoyable stay. The house is walkable to a grocery store and the public beach. Sometimes you can hear traffic but she does an amazing job with the pool and waterfall to drown out the traffic and it makes you feel like you are in your own backyard oasis! We definitely recommend staying here. We absolutely loved it and can't wait to be back. Thank you for everything Céline!

Villa rentals with a pool

A screened lanai houses a private heated pool, surrounded by a spacious deck. Two chaise lounge chairs are positioned near the water, while a cozy seating area nearby invites relaxation. A green backdrop of lush vegetation enhances the tranquil outdoor setting.
Villa in North Port
4.83 out of 5 average rating, 24 reviews

Cheerful 3-bed villa with heated pool+beach staff

AmyRating, 5 stars2 months ago
We really enjoyed our stay! The house was very clean, comfortable and had everything we needed. We really appreciated having the beach gear, including a wagon the transport everything. Very convenient! Beautiful beaches within 30 minutes. Wellen Park and Warm Mineral Springs worth checking out! Irina was very responsive. Pool temp was a little cooler than our comfort level and some of the outdoor things are a bit warn (basketball hoop broken, pool floats, etc.). Other than that the place was just perfect! Highly recommend!
Guest favorite
Villa in Dunedin
5 out of 5 average rating, 12 reviews

NEW Family Haven: Near Honeymoon Island

JenningsRating, 5 stars3 weeks ago
Karie and Chris's home provided a great place to get the family together. The home was spacious which gave our families plenty of privacy. The toy rooms were a hit with our grandchildren! The kitchen and grill were great. We cooked all our meals at home. The pool provided a bonus which we all enjoyed. A very enjoyable vacation made possible by their home!
Superhost
Villa in Venice
4.83 out of 5 average rating, 29 reviews

Peaceful bright home minutes from the beach

JoeRating, 5 stars2 months ago
Great Home. The pool made my stay, it felt like an oasis in the Florida heat.
Superhost
Villa in Largo
4.89 out of 5 average rating, 98 reviews

Solar Heated Pool Paradise/5mins 2 beach/Games/BBQ

ScottRating, 5 stars2 weeks ago
The place was really cute and comfortable. The only thing , and this is not criticism just a suggestion , a clothes line outside to hang dry your clothes would be super helpful so you don’t have to use the dryer all the time . Apart from that all was great 🥰🥰🥰
Top guest favorite
Villa in Tampa
5 out of 5 average rating, 72 reviews

Luxury home in the heart of South Tampa & POOL!

KelseyRating, 5 stars1 day ago
Even better than the pictures! This place was absolutely fantastic. All of my guests loved the property and the backyard was incredible! We had a great time grilling and swimming in the pool! The pool bath is a super nice feature and it’s beautiful! The house was super clean and had plenty of parking. The street was quiet and the neighborhood felt safe. You could even take a morning walk to Wawa for coffee if you wanted to. It’s also a 3 minute car ride to Target and Publix so it’s super easy to get anything you need. Isabella was very sweet and responsive. 10/10 I would absolutely rebook again.
Guest favorite
A vibrant game room features colorful lighting and playful wall art. Various entertainment options are included, such as a foosball table, ping pong table, and lounge area. A refrigerator for refreshments is positioned alongside seating for relaxation.
Villa in Largo
4.89 out of 5 average rating, 36 reviews

Waterfront-6 BR-Heated Pool-Game Room-Fire Pit

JordanRating, 5 stars2 weeks ago
Bee & Peter’s place is amazing! Such a personal and charming house which guarantees you to have fun. Also communication is fantastic with responses being close to instant. Very pleasant experience
Villa in St. Petersburg
4.8 out of 5 average rating, 127 reviews

Dolphin Cove Waterfront St. Pete Beach w/ Pool

TerryRating, 5 stars2 weeks ago
Beautiful home with a great water view with lots of wild life to observe. Easy to get food delivered and off street parking. We loved this place!
Guest favorite
A saltwater pool is featured with a large yellow inflatable duck wearing sunglasses. Water splashes create a lively ambiance, while a shaded patio area is visible in the background. Roller coasters can be seen beyond the pool area, highlighting the proximity to attractions.
Villa in Tampa
4.89 out of 5 average rating, 102 reviews

Busch Gardens Deluxe Edition w/heatedpool

AmandaRating, 5 stars2 days ago
House was perfect for me and my family, easily able to locate restaurants, bush gardens 3 minutes away, door dash and uber easily found home with no difficulties. Will stay again

Quick stats about villa rentals in Longboat Key

  • Total rentals

    10 properties

  • Nightly prices starting at

    ﺩ.ﺇ367 before taxes and fees

  • Total number of reviews

    300 reviews

  • Family-friendly rentals

    10 properties are a good fit for families

  • Rentals with a pool

    10 properties have a pool

  • Wifi availability

    10 properties include access to wifi

Destinations to explore

  1. Airbnb
  2. United States
  3. Florida
  4. Manatee County
  5. Longboat Key
  6. Villa rentals