Villa vacation rentals in Big Pine Key

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Popular amenities for Big Pine Key villa rentals

Luxury villa rentals

Villa in Marathon
4.67 out of 5 average rating, 3 reviews

Villa Sombrero

NikkiRating, 5 stars28 months ago
We had a wonderful time. The neighborhood is beautiful, super quiet and nice to walk around. We used the provided paddle boards to go to nearby Sombrero Beach which was lovely. We also walked to Publix and Walgreens. The house itself is really two houses - one upstairs and one downstairs - each with their own kitchens, bedrooms and bathrooms. The house itself is simple and utilitarian, but backyard area is really spectacular. We spent the vast majority of our time outside lounging, playing tennis or swimming in the pool. The location also makes for an easy day trip to Key West. The property manager Jesús was extremely responsive and took care of everything we needed.
Top guest favorite
Villa in Marathon
5 out of 5 average rating, 21 reviews

Indigo Reef water view Villa- #1 Guest Favorite

CaitlinRating, 5 stars1 week ago
We absolutely loved our stay and can’t wait to return! The unit was pristine and we loved watching the sunsets from the porches. The pool was pristine and never crowded. The hosts were amazingly responsive and helpful.
Villa in Islamorada
5 out of 5 average rating, 3 reviews

2 Spacious Villa Perfect For Family Beach Retreat

LanceRating, 5 stars4 months ago
All was great and as expected! Would stay again! Beautiful views.
Villa in Islamorada
5 out of 5 average rating, 3 reviews

Isla Lychee: Little Basin Villas, Waterfront

NathanielRating, 5 stars3 weeks ago
The villa was squeaky clean when we arrived, our family really loved the pool, grill and docks for fishing and paddle boarding. Thank you for having us.
Guest favorite
Villa in Marathon
5 out of 5 average rating, 10 reviews

Waterfront Villa (38) w/ sunset views & boat slip

KatrinRating, 5 stars3 weeks ago
Great location on the property. Beautiful view of the water and the pool. Nice big porch to relax on with plenty of chairs. Provided plenty of towels and the kitchen had everything you needed. Could have used more TB, PT and some dishwasher soap but all good. This place is a favorite of ours to just relax and go boating! Highly recommend!!
Villa in Marathon
4.83 out of 5 average rating, 24 reviews

"Casa Azul Villa" Oceanfront-Marathon-8Guests-Dock

EdithRating, 5 stars2 months ago
This place was decorated beautifully! Very unique furnishings and decorations were fun! Outside area was beautiful. Spent every day there! Sunsets from the end of the dock were beautiful! The landscaping was spot on, even some orchids in the trees! Loved the colorful dishes and modern appliances, and the coffee pods were awesome! I am getting the same machine now! Privacy and quiet neighborhood is hard to find in some areas of the keys. Walked several days on the street. Nice towels, beach towels and comfortable sheets, pillows and throws. My husband loved the fake fur one in the LR! Thank you for the lovely stay!
Guest favorite
Villa in Marathon
4.96 out of 5 average rating, 27 reviews

4/3 Private Pool, Private Dock, Bikes, Kayaks!

KathieRating, 5 stars2 months ago
The place was perfect for our group of 9. We enjoyed the pool and the view. The kitchen was very well stocked as we cooked most of the time. Loved the outside sitting area with the TV. So glad we found this place!

Villa rentals with a pool

Guest favorite
Villa in Islamorada
5 out of 5 average rating, 32 reviews

Anglers Reef Islamorada

NicoleRating, 5 stars1 month ago
Our family of 5 loved our time in Islamorada. The community was beautiful and quiet. It was definitely mostly retired couples but everyone was friendly with our young kids. The condo was bigger than the pictures made it seem- we had more than enough space. Everything was clean and we had everything we needed.
Top guest favorite
Villa in Islamorada
5 out of 5 average rating, 6 reviews

Isla Key Lime: Waterfront Htd Pool, Dock, Walkable

LeighAnnaRating, 5 stars2 weeks ago
we have been to islamorada several times and this is my favorite place we have stayed! it was clean, beautiful, and in the perfect location! right in the middle everything! we enjoyed it and will definitely be back!
Villa in Duck Key
4.35 out of 5 average rating, 20 reviews

2BR water view with private pool, balcony & kayak

JennaRating, 5 stars2 months ago
very comfortable villa. Absolutely loved the little swimming pool. Clean and comfortable villa.
Villa in Islamorada
5 out of 5 average rating, 3 reviews

Isla Mamey: Waterfront Htd Pool, Dock, Walkable

TanyaRating, 5 stars8 months ago
Our family of 4 stayed for 11 nights to celebrate our twins 10th birthday. We live in Miami and brought most of our kitchen but totally wasn’t needed! Villa #5 has anything and everything kitchen wise! Everything was so clean and comfortable - need to upgrade our home pillows to match! Shared pool was always clean and warm, met so many nice people. Evening dock was awesome for catching small fish with the kids. Location is perfect for all the dining Islamorada has to offer. We can’t wait to go back! Thanks again!
Villa in Islamorada
4.5 out of 5 average rating, 4 reviews

Isla Acai: Waterfront Htd Pool, Dock, Walkable

AmandaRating, 5 stars6 months ago
We really enjoyed our stay at this villa. The location was great. The villa is bright and clean. We enjoyed the dock a lot. We saw many types of fish and even manatees at the dock.! We used the gas grill 2 nights and that was an amazing amenity to have! The villa is close to grocery stores and a good midway point on the island to see many things and visit great snorkeling spots. We enjoyed a fishing charter nearby and caught tuna! We also did a snorkeling trip and ended our stay with a private sunset charter by a local family.
Guest favorite
Villa in Islamorada
4.83 out of 5 average rating, 6 reviews

Isla Mirabelle: Waterfront Pool, Dock, Walkable

JeffryRating, 5 stars2 months ago
The property was better than described. A great quiet getaway. At the same time a lot to do for all. For kids, a playground, park and library adjacent to the property. This is beyond what is available throughout the Keys. Looking forward to our next stay.
Superhost
Villa in Key West
4.6 out of 5 average rating, 43 reviews

Coral Villa by AvantStay| Close 2 DT Key West!

RyanRating, 5 stars1 week ago
Amazing location next to good food

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