Villa holiday rentals in Pine Island

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Popular amenities for Pine Island villa rentals

Private villa rentals

Top Guest favourite
Villa in Indian Rocks Beach
5 out of 5 average rating, 22 reviews

IRB Harbor House Semiprivate Waterfront Pool Villa

JordanaRating, 5 stars2 weeks ago
This is a GEM of a house, you’re a minutes drive from the most gorgeous white sand beach AND on the waterfront with a pool. We saw dolphins a few times each day and so many cool birds. We loved the bathrooms and the kitchen, new and modern. Comfy beds—and I appreciate the high quality percale cotton bed linens and pillows. The house was spotless, stocked well if you wanted to cook a few things, and the backyard was just heaven. Keith was super responsive and helpful with anything and everything. We will absolutely be returning!
Top Guest favourite
Villa in Spring Hill
4.96 out of 5 average rating, 23 reviews

Cabana pool home. 3400sq ft Of luxury!

MaureenRating, 5 stars7 months ago
The house was perfect for our stay. The beds were very comfortable, linens and towels were soft and plentiful and there was tons space for everyone to relax. We spent most of our time hanging around the pool - which is exactly what you want when visiting Florida! The kitchen is very nice and although we didn’t cook there’s everything you would need to prepare meals. Communication with Sandra was great too!
Top Guest favourite
Villa in Four Corners
5 out of 5 average rating, 90 reviews

The Golden Bear Villa | Private Pool & Theater

BrittanyRating, 5 stars4 days ago
Stayed at Dan’s home for about 8 days with my family to celebrate my wedding weekend. The home was so beautiful, pool was fun and the kitchen was stocked up with seasonings, tons of pots and pans for us to cook at home and the movie theater/game room was a great bonus, the kids had a great time! Everything was exactly like the pictures although I did think the pool was a bit smaller than I expected in the photos but it was still super fun and comfortably fit 7 people. I would definitely stay at Dan’s home again!
Top Guest favourite
Villa in Tampa
5 out of 5 average rating, 75 reviews

Luxury home in the heart of South Tampa & POOL!

OscarRating, 5 stars1 week ago
We had a wonderful stay at Isabella’s home! It was the perfect place for a family getaway. The house is beautiful, clean, and very well maintained. The beds were extremely comfortable, which made for a great night's sleep. The pool area was awesome — a great spot to relax and enjoy the Florida weather. Isabella was a fantastic host, very responsive and welcoming. We would definitely stay here again and highly recommend it to anyone visiting the area!
Superhost
Villa in The Villages
4.82 out of 5 average rating, 89 reviews

Location Can’t be Beat! With cart!

LindaRating, 5 stars2 weeks ago
It was effortless and enjoyable to stay at this home while we were considering a future purchase in the Villages!
Guest favourite
Villa in Kissimmee
4.95 out of 5 average rating, 81 reviews

Luxury Villa! /Game Room/ Pool Heater

AntoinetteRating, 5 stars2 weeks ago
Love the beautiful home will come again.
Guest favourite
Villa in Clermont
5 out of 5 average rating, 20 reviews

Luxury home | Lakeside Landing

LoriRating, 5 stars3 weeks ago
5 stars all around. I can’t rave enough about how this place had everything we needed. Everything was high quality from the towels to the sheets to the pillows and even the appliances. Every detail was well-thought thru from the kitchen being well-stocked to even baby shampoo/body wash in the master bedroom. Thank you thank you for making our stay incredibly relaxing and stress/worry free.
Guest favourite
Villa in Kissimmee
4.95 out of 5 average rating, 77 reviews

Private Pool & Free Heat - Close to Disney!

LavedaRating, 5 stars2 weeks ago
The stay was amazing we loved every second of it from the pool to cooking in the house and playing game we loved that akilia accommodated to our schedule and made us feel so welcomed

Luxury villa rentals

Top Guest favourite
Villa in Davenport
4.97 out of 5 average rating, 103 reviews

Pickleball PoolsideMovies |WalkToWaterpark| Arcade

VivianaRating, 5 stars4 weeks ago
The place was really nice felt right at home. It was very clean. Loved how everything was baby proof, so I felt comfortable with my one year old crawling around. Loved how they had everything to accommodate children. floaters for all ages, baby carriage, play pen, crib etc. the pool was huge and we loved the big screen. The kids can’t stop talking about their experience there. If you’re hesitating to book trust me you just book it.
Top Guest favourite
Villa in Osceola County
4.99 out of 5 average rating, 118 reviews

*Private Resort Oasis: Golf-Front, Pool/Spa/Cinema

MatthewRating, 5 stars2 weeks ago
We had a fantastic stay, Reunion resort is an excellent location close to all the parks and very safe and spotlessly clean, the house was easy to find and straightforward to access. Michael had provided clear instructions prior to our arrival, the house was spotlessly clean and had all the amenities we needed for a fantastic stay. The balcony from the main bedroom was great to sit and enjoy a sunrise with an excellent coffee and our teenagers loved having their own house and games area in the pool house, which had a pool table, pin ball, space invaders and a karaoke machine, If we travel to Orlando again we will certainly re book the house and would whole heartedly recommend it as a great place to stay in Orlando.
Guest favourite
Villa in Davenport
4.94 out of 5 average rating, 158 reviews

Free Pool Heat! Disney Themes, Arcade, Sleeps 22

RogerRating, 5 stars5 days ago
Ryan was a great host. His instructions were very helpful. The house was warm and inviting. The kids had a great time in the game room, pool and even the Star Wars bedroom. We would definitely return.
Guest favourite
Villa in Kissimmee
4.88 out of 5 average rating, 126 reviews

NEW Unique 6BR,private pool,Full game room, + MORE

DanaRating, 5 stars3 months ago
This was a fabulous house. The themed rooms were so much fun. Each room was so carefully and wonderfully decorated. From the cloud room to the camp room to the avatar room. The game room was a blast with its bunk house and slide and movie projector screen. The pool and outdoor area was great to hang out. And the kitchen had everything you could need. We had such an amazing time. Plus our host, Tati, was so accommodating and great to work with. Definitley the best house to stay at.
Guest favourite
Villa in Kissimmee
4.95 out of 5 average rating, 137 reviews

"Disney Serenity": Luxe 8BR Villa/ Privacy/ Pool

JonathanRating, 5 stars4 days ago
The place was amazing and very comfortable. Very nice and clean space. The pool was always at the right temperature. We had an amazing time at the place and its facilities. The hosts are very helpful and responsive. They are also very patient and kind. Thank you again for our stay!
Guest favourite
Villa in Indian Rocks Beach
4.9 out of 5 average rating, 42 reviews

Villa Blanca - Waterfront Midcentury Modern Home

CarrieRating, 5 stars3 weeks ago
Villa Blanca was everything we could ask for and then some! We were greeted with a bottle of wine, chocolates and a note from Debbie on the counter. Not many Airbnb's offer that type of personal touch and we appreciated it. The home and grounds are well maintained, the house was clean, everything you could need in the kitchen was available. This is the perfect getaway home! Thank you Debbie for your hospitality!
Guest favourite
Villa in Kissimmee
4.91 out of 5 average rating, 110 reviews

33 Disney Villa Game Room Movie Theater Pool

MairaRating, 5 stars1 month ago
We had a great two night stay at Cal’s home in Orlando for my son’s birthday. The house was clean, cozy, and just like the photos. The game room and theater were amazing our kids had a blast playing and watching movies. Cal was a responsive host, and we’d happily stay again.
Top Guest favourite
Villa in Kissimmee
4.97 out of 5 average rating, 105 reviews

Luxury Themed Villa 9 BR | Close to Disney

MikeRating, 5 stars5 days ago
Beautifully themed and well appointed home that accommodates a large group. Everything was as described. Communication was proactive and detailed. Thanks for the great hospitality!

Villa rentals with a pool

Top Guest favourite
Villa in Davenport
5 out of 5 average rating, 7 reviews

Lux 4BD/2BAVilla/Heated Pool/Private Backyard

ChristineRating, 5 stars1 month ago
Our stay at Semen’s place was fantastic. The house was beautiful, modern and had all the amenities we could ever hope for. The house was impeccably clean and well-stocked with everything we needed. We also appreciated the quick response time when a question came up. Highly recommend Semen’s house!
Top Guest favourite
Villa in The Villages
4.98 out of 5 average rating, 64 reviews

Perfect location Lake Sumpter Villa w/ Golf Cart

PatriciaRating, 5 stars4 months ago
We are so lucky to have been guests at this property. Stephen & Amanda are very considerate and accommodating hosts. The home is spotless clean, fabulous location, furnishings comfortable, especially the Master King size bed. The private backyard space is an oasis that provides tranquil serenity to reboot one's self. We spent each morning on cozy screened in patio siping coffee enjoying the palm trees and blue skies overhead. The golf cart (and bikes) an added plus. A great ride is; cross the Sumter Landing bridge and take first left to circle around Arnold Palmer course. Just beautiful for sunsets. The neighborhood is surprising quiet given proximity to town squares. We just had a memorable week staying at this Villa. Felt right at home, didn't want to leave. IF you're able to book this property, as it's very popular, Grab it. A BIG Thank You to Stephen & Amanda for having us at your Villa, hope to return again. ~ Pati & Steve
Top Guest favourite
Villa in Kissimmee
5 out of 5 average rating, 35 reviews

Crete Prestige Villa - Windsor Palms Resort

TonyehnRating, 5 stars11 months ago
I could not rave more about this home. I rented this villa after another home I was interested in became unavailable. I'm so thrilled this showed up in my second search because it was so much more convenient for drop offs and pick ups at the park. While the kids were at the park I spent days exploring the area or just floating in the pool. If I ever go back to disney this will be my home away from home.
Top Guest favourite
Villa in The Villages
5 out of 5 average rating, 27 reviews

The Coconut Courtyard-Private saltwater Pool-clean

DerrickRating, 5 stars1 week ago
Kim has a top-notch place here that is very welcoming. The house is wonderful and this is our second time staying here and we will continue to stay here with Kim. The house may not be close to a beach but it is close enough to Daytona, Orlando, and to the Gulf Coast that there are a lot of different things you can do within an hour that are great. this place really gets you out of the hustle and bustle of the beach crowds. it is wonderfully laid back and quiet.
Top Guest favourite
Villa in Davenport
5 out of 5 average rating, 41 reviews

Themed Bedrooms, Pvt Pool, BBQ, Game Room & PS5

ChynaRating, 5 stars2 weeks ago
Rennata’s home was great for my family. She was very proactive with her communication leading up to and during the trip. The location was very convenient and the neighborhood was family friendly. I would recommend this home and would return. Thanks Rennata.
Guest favourite
Villa in Kissimmee
4.96 out of 5 average rating, 52 reviews

Luxury Villa Near Disney -Hot Tub/Private Pool/BBQ

AlexandriaRating, 5 stars1 week ago
The house was beautiful and clean! We felt right at home, and the area is super nice as well! Frank was super friendly and responsive!
Top Guest favourite
Villa in Kissimmee
5 out of 5 average rating, 17 reviews

NEW* villa w/ pool, spa, theater & themed spaces

VictoriaRating, 5 stars1 week ago
Wonderful location, beautiful home that was well equipped. A great choice if your group has kids or just adults. We had a wonderful time and Kimberly was very nice.
Top Guest favourite
Villa in Davenport
4.98 out of 5 average rating, 60 reviews

Quiet Villa w/ pool close to Theme Parks and golf!

LeannaRating, 5 stars2 weeks ago
We stayed on vacation to celebrate our daughter’s birthday and had an absolute blast. We relaxed at the house about three days and the rest of the time we had some pretty fun things planned. The house itself was amazing and had everything you would possibly need. Its was really well stocked with pots, pans, silverware, and cups. We really enjoyed the pool and game garage. The pool was also very well stocked with pool noodles and swim rings. Along with the garage having plenty of games and the board games too. The house was centrally located in a nice quiet neighborhood with everything you would need and more pretty close by. Pam was also very friendly and helpful throughout our entire trip. Her communication was amazing. She went above and beyond for us and that truly meant a lot. We will definitely be staying here the next time we are in the area.

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