Villa vacation rentals in Pine Island

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Popular amenities for Pine Island villa rentals

Private villa rentals

Guest favorite
Villa in Kissimmee
4.73 out of 5 average rating, 74 reviews

Stunning Private Courtyard 3 Bed Villa

LeahRating, 5 stars6 months ago
The Villa was very nice and lovely location. Close to plenty of places to eat and an easy drive to Disney and universal!
Top guest favorite
Villa in Zephyrhills
4.86 out of 5 average rating, 37 reviews

3 Bed 2 Bath private golf course villa

RhiannRating, 5 stars2 weeks ago
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!
Top guest favorite
Villa in Indian Rocks Beach
5 out of 5 average rating, 37 reviews

Villa Blanca - Waterfront Midcentury Modern Home

BeckyRating, 5 stars1 month ago
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!
Superhost
Villa in Davenport
4.95 out of 5 average rating, 42 reviews

Graystone Villa, 3 bedrooms with private pool

GayleRating, 5 stars1 month ago
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!!
Superhost
Villa in Largo
4.89 out of 5 average rating, 38 reviews

More Than A Stay – 1B_High-End Romance Experience!

MorganneRating, 5 stars2 weeks ago
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.
Superhost
Villa in Kissimmee
4.83 out of 5 average rating, 69 reviews

Luxury 9Beds Villas With Pool Spa In Solara

SusanRating, 5 stars5 months ago
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!
Guest favorite
Villa in Davenport
4.73 out of 5 average rating, 56 reviews

Private Villa with Pool near Disney

PhilipRating, 5 stars4 months ago
It was a great place to stay. We would not hesitate to stay here again if we are in the area.
Guest favorite
Villa in Kissimmee
5 out of 5 average rating, 17 reviews

Luxurious home 2 miles from Disney - Windsor Hills

Mary-BethRating, 5 stars3 months ago
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

Superhost
Villa in Davenport
4.93 out of 5 average rating, 94 reviews

Blue Paradise-15 Bdrms, Sleeps 32-Theater, GameRm

KristyRating, 5 stars1 week ago
If I can give more than 5 stars, I would. My family and I felt right at home. From check in to check out, we were very pleased. Parmi’s home was bigger than I thought it would and accommodated my family of 20 with ease. The kids loved the heated pool, the arcade, the themed room with the slide, and the spacious flooring. Every adult was accommodated with their own room and bathroom which so top tier or myself. Not only will my family and I would be returning, but I just sent this home to my friends as well. Thanks Parmi.
Superhost
Villa in Kissimmee
4.95 out of 5 average rating, 56 reviews

Luxury Family Villa + Private Pool & 10 min Disney

JessicaRating, 5 stars1 month ago
My friends and I had a great stay at Joe’s place! The house was exactly as described—clean, comfortable, and well-equipped with everything we needed. The location was great, an easy drive to Orlando/ Kissimmee attractions. Joe was an excellent host—very responsive and helpful. We did have some issues with the cable and the AC at one point, but he quickly responded and addressed the issues; making sure we were comfortable throughout our stay. Overall, I definitely recommend this place to anyone looking for a great stay in Orlando/ Kissimmee!
Superhost
Villa in Osceola County
4.99 out of 5 average rating, 115 reviews

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

Joo EunRating, 5 stars2 weeks ago
Michael’s place was very nice and spacious. Checking in and out was easy. We enjoyed the coffee station each morning, the spacious dining area with plenty of seating, and the play room which had a pool table and a movie screen sized tv to watch movies with amazing surround sound! We took an uber to the Disney parks for the 3 out of 4 days we were there. Make sure you bring the security card to come in and out of the gates for entry back in the Reunion area. We did not end up going to any of the Reunion resort pools. Although we were mostly busy and tired from the Disney Park days, we enjoyed a day at the jacuzzi and private pool with the pool basketball net at the house just relaxing.
Superhost
Villa in Davenport
5 out of 5 average rating, 22 reviews

Windsor Island Villa

NicholasRating, 5 stars2 months ago
The house was wonderful, and exactly as pictured. Comfortable for both kids and adults. The beds were comfortable and everything was spotless clean. There was a little miscommunication on pool heat, but the host was very responsive and remedied almost immediately which was greatly appreciated. The only real issue was traffic upon arrival. “Saturday is arrival day” is the only answer we got, as it wasn’t bad the rest of the week. We sat on the road outside of the resort for an hour waiting to get in after a long day of travel.
Superhost
Villa in Kissimmee
4.95 out of 5 average rating, 127 reviews

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

JeremyRating, 5 stars2 weeks ago
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.
Superhost
Villa in Davenport
4.73 out of 5 average rating, 15 reviews

Luxury Wellness Villa - Private Spa & Pool

JessicaRating, 5 stars22 months ago
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!
Superhost
Villa in Four Corners
5 out of 5 average rating, 7 reviews

Resort & Private Pools, Game Room, Near Disney

MiguelRating, 5 stars1 month ago
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!
Superhost
Villa in Indian Rocks Beach
4.94 out of 5 average rating, 68 reviews

The Emerald Villa, Eco-Luxury by the Sea

RobinRating, 5 stars1 week ago
Enjoyed our stay. The house worked well for our family of six adults and one child. Nix was very responsive. The public beach access was an easy walk across the street from the house.

Villa rentals with a pool

Guest favorite
Villa in Davenport
4.84 out of 5 average rating, 86 reviews

5bedroom,pool,18min to Disney, Kissimmee davenport

OliviaRating, 5 stars1 week ago
Very satisfied with our stay! Thank you Miguel for providing a clean, beautiful home for us to stay with our kids. ⭐️⭐️⭐️⭐️⭐️
Superhost
Villa in Davenport
4.79 out of 5 average rating, 47 reviews

4 Bedroom Villa - with Pool - Near Disney & More

ChristinaRating, 5 stars1 month ago
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!!❤️
Top guest favorite
Villa in Davenport
5 out of 5 average rating, 25 reviews

Luxury Villa Pool/Spa 2 Masters, Highlands Reserve

MelanieRating, 5 stars3 months ago
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!
Superhost
Villa in Clermont
4.76 out of 5 average rating, 85 reviews

4-bed villa w/ beautiful pool 15 mins from Disney!

BrittniRating, 5 stars5 months ago
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
Superhost
Villa in Davenport
4.74 out of 5 average rating, 31 reviews

Home in Davenport FL, near Disney

CorinneRating, 5 stars2 weeks ago
The house was spacious in a convenient location and exactly what we were looking for.
Guest favorite
Villa in Kissimmee
4.81 out of 5 average rating, 90 reviews

Seasons Retreat, 5 Bed, 4 Bath, Private Pool Villa

TaylorRating, 5 stars3 weeks ago
Great home and very comfortable! We enjoyed our stay! Mr. George is a great host and very accommodating.
Guest favorite
Villa in Davenport
4.96 out of 5 average rating, 23 reviews

Elegant 5 Bedroom South Facing Villa with Pool

GillianRating, 5 stars2 weeks ago
Lovely stay in this large and comfortable villa. Lots of towels, nice pool and games room. Everything we expected and more. Thank you for your hospitality.
Superhost
Villa in Davenport
4.67 out of 5 average rating, 58 reviews

4 Bedroom Villa with Private Pool Near Disney!

ReneeRating, 5 stars3 weeks ago
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.

Destinations to explore

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  4. Hernando County
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