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

The Nest Villa & Marina in the heart of Islamorada
This was our second stay at The Nest and we will be back! The interior is so soothing, comfortable, clean and very well stocked. Communication with the host was great and they were very responsive to questions. The surroundings are beautiful and peaceful, and the HUGE patio was so perfect for relaxing at the end of the day. Can’t wait to go back!

Villa 5034 on Duck Key BOAT SLIP available
Frank's place was just as listing shows! Perfect location on Duck Key. Beautiful sunsets right on Tom's Harbour. Would recommend to others!

Sunset Villa in Duck Key
It was one of cleanliness Villas I have stayed in . We have been vacationing on Duck Key for 20 plus years and would definitely recommend 5085 - great location , very reasonable price and very simple easy check in and check out instructions. Thank you .

Family Friendly Sunset Oasis!
Loved the Villa and its location. Host was excellent. A bit disappointed that we were not permitted to use the beautiful pool just behind the Villa. Also, second bedroom is very small (cannot tell from in-line photos) and while twin beds would serve children well, they are not suitable for adults.

Waterfront villa for families * Family friendly*
The place was decorated very cute, it was clean, had all the amenities necessary for a comfortable stay, would definitely book again.

Villa 5086 on Duck Key BOAT SLIP available
Great spot! Frank is very responsive! Highly recommend!

Villa 5028 on Duck Key BOAT SLIP available
This is a great spot. Very quiet and close to everything we wanted to do. The place was spotless and had everything we needed. Frank is very responsive. I highly recommend this place.

Key Lime Cottage - Lovely Duck Key Villa, Dip Pool
Beautiful little townhome on duck key! I had a medical conference, and I walked to it every morning. Very convenient. We would stay again. Our only complaint was that the larger bedroom bed was so uncomfortable. I woke with severe back pain first 2 nights. My husband and I then slept in the twin beds in the other bedroom which were much more comfortable! Other than that, no complaints. It was December, so dipping pool of course was cold, but it would be so nice to have during a summer stay! Quick responses from the owner or manager! We had enough trash bags, toilet paper and paper towels for 2 people for our 6 day stay, which was very nice! Kitchen is fully functional and full size fridge!
Luxury villa rentals

Villa Sombrero
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.

Isla Guava: FREE Boat Dockage Sept-Oct Only!
Amazing place, you can’t beat the location and property. The house was exceptionally clean and the host was very friendly and easy to communicate with. We will definitely return!!

Florida Keys Sanctuary
I celebrated both my mom’s birthday and mine here, and from the moment I booked until check-out, the experience was nothing short of amazing. The property manager was incredibly helpful, responsive, and made everything seamless. Highly recommend!

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

Coral Villa by AvantStay| Close 2 DT Key West!
We had great stay! If we come back to Key West, we will definitely stay here again. The Avant team was highly responsive and great to work with. Check in and check out was extremely easy.

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

Scenic Resort w/ Outdoor Pool | Florida Keys Stay
Very nice townhouse, it was also really convenient to call the golf cart and go to the larger resort, which was beautiful.

Discount Available! 4BR/3BA! Many Extra Amenities!
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

Anglers Reef Islamorada
What a great place to stay! The community was well kept and the amenities were wonderful. There are great restaurants close by and it's location is perfect. We had a wonderful time and met some really wonderful people. We plan on returning, next year!

Isla Key Lime: FREE Boat Dockage Sept-Oct Only!
Key Lime Villa & Newman Hospitality were all around fantastic! We really enjoyed our weeklong stay at this beautiful property! They were a great host, very helpful and easy to deal with, super responsive too. The property itself was just as described, very nice, spacious and squeaky clean, very comfortable, we were able to settle in right away. Being big dog friendly was really nice as well, our boys were very comfortable and really enjoyed the place. We really love the pool and the fire pit area along with the dock area for sunset, it was very peaceful. Also, the location is perfect, it was right in the heart of the island so we were able to do a ton of walking to all of our restaurants and bars. We will definitely be back to stay here again for another trip soon! Thanks again to the team at Newman for making our stay a great one!

2BR water view with private pool, balcony & kayak
We overall had an amazing stay! Beautiful views, clean house, & responsive hosts!

Indigo Reef water view Villa- #1 Guest Favorite
Perfect location in the Middle Keys with easy access to all that Marathon has to offer, Key West or Islamadora. The home is well appointed and the views of the Gulf out the two back porches are spectacular! Very peaceful setting and close to the docks and pool. Would stay here again in a heartbeat!

Isla Mamey: FREE Boat Dockage Sept-Oct Only!
Amazing location and beautiful home! The dock, pool, and fire place seating area were perfect. Would highly suggest this location to anyone.

3 EnSuite Bedrooms,FREE boat dockage Sept-Oct only
This house was perfect for our family of 5 for Spring Break. The canal at the back was perfect for fishing, kayaking and SUP. The pool was lovely and warm. The house and grounds were so beautiful and comfortable! We had a wonderful time and would stay here again in a heartbeat!

Luxury Waterfront Villa, Marathon, Florida Keys
Very clean quiet and an excellent pool area!

Picturesque Villa Near History of Diving Museum
Beautiful place on Islamorada halfway between Key West and Fort Lauderdale...so peaceful and great views... the heated pool was also very nice... the Lavazza coffee maker made our morning since its not really a place you can walk to/from... there is a flight of stairs just in case you have mobility issues... bathroom amenities are very nice!
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