
Villa vacation rentals in Pine Island
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Top-rated villa rentals in Pine Island
Guests agree: these villas are highly rated for location, cleanliness, and more.
Vacation rentals for every style
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Popular amenities for Pine Island villa rentals
Private villa rentals

Stunning Private Courtyard 3 Bed Villa
The Villa was very nice and lovely location. Close to plenty of places to eat and an easy drive to Disney and universal!

3 Bed 2 Bath private golf course villa
Absolutely loved staying here! Me and two other people came into town for a tennis tournament and found this Airbnb to stay at. The Airbnb was very clean and very comfortable, we all felt right at home staying here. I also loved how close this place was to the tournament site we were playing at. We will definitely stay here again!

Villa Blanca - Waterfront Midcentury Modern Home
My family of 4 and my parents stayed for 4 nights and enjoyed both the beach and intercostal waters! The house was very comfortable for the 6 of us, with ample bathroom and bedroom space. Very clean and tidy. The neighborhood was quiet and beautiful. It is a 14 minute easy stroll to the beach. We packed the provided beach chairs on our backs and were able to spend several hours at the beach. Driving to the beach is an option but beach access parking is a bit difficult during spring break. We loved the intercostal location, with the pool and spa! We were able to fish and enjoy the beautiful breeze and view. The house is exactly what Debbie has described and pictured. Highly recommend!

Graystone Villa, 3 bedrooms with private pool
Can’t say enough about Nicola and her property. Our vacation started out rocky at a not so stellar condo. Thankfully we found her property and she was able to accommodate my family the very next day. The house is just as described, very spacious and clean! The location was perfect and close to many restaurants and shopping. Nicola was quick to respond to any of our needs. I will definitely be booking here if we are ever in the area. THANK YOU for being amazing!!

This New Pinnacle of Relaxation – 1B Vila Awaits!
We enjoyed ourselves! It was a private, peaceful location. We loved being able to enjoy the pool and the lights so we could swim at night. Would definitely come to stay again.

Luxury 9Beds Villas With Pool Spa In Solara
This was our second time staying at Chuck’s place. The resort amenities are great and our family utilized the splash pad, pool, gym, basketball courts and restaurant. The house is great and accommodates our family of 14 perfectly. We had a great stay!

Private Villa with Pool near Disney
It was a great place to stay. We would not hesitate to stay here again if we are in the area.

Luxurious home 2 miles from Disney - Windsor Hills
The house was wonderful and exactly as described. It was spacious enough for our big group. Andreanne responded promptly most of the time. Our only negative was the batteries ran out in the keypad and my parents were locked out at night in the (Florida) cold. The management company sent a locksmith who let them in after about 1.5 hours. However, the management company brought the new batteries and dropped them on the porch instead of fixing the keypad. My dad installed the batteries in the keypad so it didn’t happen to the next guests or the cleaners. Andreanne didn’t respond to my messages regarding the lock out or the key pad, but had been responsive prior to that. The battery pad was most likely a fluke, but it showed no signs of issues leading up to that. Otherwise, our stay was great and would recommend.
Luxury villa rentals

Prestige 5: Lux Windsor West, S Fc Pool, Lake View
We’ve just returned from a large family holiday! With family flying in from Boston and Las Vegas, Orlando was a central location for us to kick back & enjoy each other’s company. Plenty of space for our 13 person group! The pool and hot tub were perfect, large kitchen where we cooked big meals & fun game space on the 2nd floor! We enjoyed a day at the club house & pool - a quick walk from the home we stayed in. Loved having a lake behind us, making it feel peaceful and private. Communication before, during & after was easy and prompt.

Clearwater Villa Heated Pool, Golf, 4K Projector
Amazing house, with great amenities, the perfect place for family vacations. Lots of entertainment for the children. Responsive and flexible host. I highly recommend this listing.

*Private Resort Oasis: Golf-Front, Pool/Spa/Cinema
Really enjoyed our time at this lovely home. We were spoiled with a few pleasant surprises to welcome us and make our children feel at home too which was really nice. Great games room and cinema area, direct sunlight (if you want it) from lots of different outdoor areas within the boundary, very spacious throughout. Fantastically equipped kitchen! Bedrooms were very suitable for our needs and decorated beautifully. Beds clean and comfy. Very peaceful at night time. I can’t really fault it in any way. Would certainly recommend staying in this place.

"Disney Serenity": Luxe 8BR Villa/ Privacy/ Pool
Everyone in our group thoroughly enjoyed our stay at Dexter & Misty's Villa! No complaints and would love to stay here again in the future. The kitchen was stocked with everything we could need for cooking any meal. The hot tub and pool were used every day and everybody loved them! They layout of the house is great, with common areas, yet bedrooms split up for pivacy. Any host communication was very fast! We had one minor issue with the pool the first day that was quickly resolved with them going above and beyond to make sure our stay was perfect! FYI - delivery services such as Doordash, groceries, etc easily dropped off inside the gated community, so we had groceries ready for us upon arrival.

Luxury Wellness Villa - Private Spa & Pool
We had such a lovely stay! The place was just as pictured. Plenty of space for the 9 of us to lounge around the house and hangout by the pool. We will definitely be back!

Resort & Private Pools, Game Room, Near Disney
Lissette was an amazing host she was very responsive to any questions we had and her home was amazing our kids loved it the house was spotless!

The Emerald Villa, Eco-Luxury by the Sea
Home looks exactly like the pictures and the location was better than I had expected! Beach access is directly across the street with several restaurants/ coffee shops also within walking distance. We loved that we were ~15 minutes away from Clearwater but had such easy access to Indian Rocks Beach which was less crowded. There is also easy access to rent a cabana on IRB for $45 for a full day or $25 for a half day that comes with chairs and the cabana cover. The outdoor area at the home was lovely and we loved having access to the outdoor shower and beach chairs / cart to bring everything to the beach. Overall a fantastic stay for our group of 7 adults and would absolutely book here again next time we are in the area!

Jas Vacation Home 314
Beautiful home ! Stunning neighborhood! Everything was just as pictured. Communication with the owner was easy and he was very quick to respond.
Villa rentals with a pool

5bedroom,pool,18min to Disney, Kissimmee davenport
Very beautiful home and Miguel is very accommodating and responsive. Would definitely stay at his home again.

4 Bedroom Villa - with Pool - Near Disney & More
This house is very comfortable! We have 5 kids and they all enjoyed using the pool and pool table. I recommend highly paying for the pool heat; more so for the evening swim. We still used the pool daily, but I will definitely ask to have it heated before we come next time. We felt very safe in this location. Clean, family-friendly surroundings. Easily accessible to all Disney activities! We also spent time in Clearwater and on the Atlantic coast. About 1.5 hours to Gulf or Ocean from her place. We will definitely be back!!❤️

Luxury Villa Pool/Spa 2 Masters, Highlands Reserve
10/10 would recommend this vacation home! Beautiful, spacious home with an awesome outdoor living area. We thoroughly enjoyed the pool and spa as well as the outdoor dining/fire table area that comfortably seated our entire family. The kids really liked the game room. The beds and pillows throughout the home were very comfortable. Dawn was a great host and she has fully stocked the house with all the supplies you could ever need. Plenty of extra towels, blankets, pillows, kitchen items, etc. She even keeps it stocked with a few convenient snacks as well as essentials like spices, coffee, tea, dishwasher tabs, dish liquid, cleaning supplies, etc. There are even little baskets in the bathrooms filled with things you may have forgotten such as toothbrushes, toothpaste, Q-tips, etc. Since we were there around Christmas time, there was a cute little Christmas tree, stockings and a couple of other decorations around the house. She really has thought of everything!

4-bed villa w/ beautiful pool 15 mins from Disney!
It felt right at home from the moment we arrived to the minute we left. Every thing was clean, comfortable and overall a wonderful experience. We would definitely stay there again. Thank you for your hospitality in letting our family stay in your beautiful home. Brittni

Home in Davenport FL, near Disney
The house was spacious in a convenient location and exactly what we were looking for.

Seasons Retreat, 5 Bed, 4 Bath, Private Pool Villa
Great home and very comfortable! We enjoyed our stay! Mr. George is a great host and very accommodating.

Elegant 5 Bedroom South Facing Villa with Pool
We had a wonderful month at Michelle's place. She is a very responsive host and we would Definitely rent again. She answered all our questions in a timely manner. The house was fully equipped for all our needs. The kitchen was perfect for cooking meals. Very enjoyable!!🌞

4 Bedroom Villa with Private Pool Near Disney!
We really enjoyed our stay with our daughter and grandchildren. The house had everything we needed for the week. We had no complaints. Location was really close to all parks we visited as well as restaurants. We also felt comfortable to take a nice long evening walk with the babies, the neighborhood was very friendly.
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- Busch Gardens Tampa Bay
- Amalie Arena
- Raymond James Stadium
- Clearwater Beach
- Rainbow Springs State Park
- Tampa Theatre
- Curtis Hixon Waterfront Park
- Plantation Inn and Golf Resort
- ZooTampa at Lowry Park
- Adventure Island
- Splash Harbour Water Park
- Fort Island Beach
- Clearwater Marine Aquarium
- Fred Howard Park
- Sand Key Beach
- Tampa Palms Golf & Country Club
- Honeymoon Island Beach
- Black Diamond Ranch
- Honeymoon Island State Park
- Florida Botanical Gardens
- Bayou Club
- Ben T Davis Beach
- Clearwater Country Club
- Honeymoon Island State Park Pet Beach