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Compare 49 Villas in Big Pine Key with updated reviews, rates, and availability.

Waterfront Beauty 8-guests, Dock, Kayaks and more

10.0 out of 10, Exceptional, (7)
"Wow! We enjoyed this beautiful home and had everything we could possibly need. The house has more than you need and it is clean and the beds are very comfortable. All the furniture was comfortable and the outdoors are amazing. I can’t describe just how special this home feels. I would highly recommend."
Waterfront Beauty 8-guests, Dock, Kayaks and more

203 Sombrero- 4 Bedroom/3 Bath Attached Villa w/ Private Boat Dock

8.8 out of 10, Excellent, (102)
"Great place to stay would definitely go again we had such a good time. "
203 Sombrero- 4 Bedroom/3 Bath Attached Villa w/ Private Boat Dock

129 FIVE STAR REVIEWS!! NEW LOWER PRICES FOR SUMMER ~ELEVATOR BABY~BOAT SLIP!

10.0 out of 10, Exceptional, (129)
"Nice place, can walk to restaurants.loved the top floor patio."
129 FIVE STAR REVIEWS!! NEW LOWER PRICES FOR SUMMER ~ELEVATOR BABY~BOAT SLIP!

Atlantic View Luxury Villa with Pool

3.5 star property
10.0 out of 10, Exceptional, (1)
"We were here for a night and it was great. A nice rustic feel on a big property, with good view. "
The price is SAR 1,899
SAR 3,449 total
includes taxes & fees
5 Apr - 6 Apr
Atlantic View Luxury Villa with Pool

Life in Paradise at #1 Rated Resort in Marathon - Coral Lagoon - Boat Slip Avail

10.0 out of 10, Exceptional, (201)
"Nice location in the middle Keys. Enjoyed a day in Key which was about an hour away. The property itself was nice. Located right on a canal. Saw a Manatee on our second day. Bedrooms are upstairs. Small bathrooms but we could make it work . Would not hesitate to stay again. Many restaurants close by"
Life in Paradise at #1 Rated Resort in Marathon - Coral Lagoon - Boat Slip Avail

Fabulous Canal Front Villa, Private Pool in KCB!

10.0 out of 10, Exceptional, (20)
"Great property! Very spacious and well stocked. We enjoyed our two week vacation and would definitely stay here again! A gem of a property in Key Colony."
Fabulous Canal Front Villa, Private Pool in KCB!

Emerald Seas - Florida Keys Ocean Front Paradise!

10.0 out of 10, Exceptional, (14)
"What a great place to stay!!! We enjoyed watching the fish every night right off the dock. Shawn and Cindy were very accommodating when we wanted to extend our stay."
Emerald Seas - Florida Keys Ocean Front Paradise!

Luxury Oceanview Pool Eco-friendly Villa Near Key West

2.0 star property
Luxury Oceanview Pool Eco-friendly Villa Near Key West

Oceanfront Spanish Villa: 4 bed, loft, 8 guests

2.0 star property
10.0 out of 10, Exceptional, (1)
"Best house ever. Very friendly host and ready to please with any requests. The beds were top quality. The house is perfect for families, the kitchen is great to cook, they have games, fishing poles and is very clean. We have never seen such beautiful sunsets. Easy to get to from anywhere in the country. Marathon is a unique destination, great food, quaint and you don’t get tired of coming back every year. WE RECOMMEND THIS HOUSE."
Oceanfront Spanish Villa: 4 bed, loft, 8 guests

Sombrero Beach Villa with Private Pool and Dock

10.0 out of 10, Exceptional, (120)
"Convenient location and well equipped property."
Sombrero Beach Villa with Private Pool and Dock

Canal Front, Tiki Hut w/TV, Private Pool, Beach!

9.8 out of 10, Exceptional, (49)
"The property is nice and all issues were promptly addressed. I recommend this property."
Canal Front, Tiki Hut w/TV, Private Pool, Beach!

Canal Front, Private Custom Pool, Hot Tub, Private Dock & Neighoborhood Beach!

10.0 out of 10, Exceptional, (86)
"Loved this property. Property was clean, close to all of our favorite places. Meredith with Pineapple properties was great to work with. Plan to book again. "
Canal Front, Private Custom Pool, Hot Tub, Private Dock & Neighoborhood Beach!

4 Bedrooms, 3 Baths! Bikes, Private Pool, Dock, Canal Front, Neighborhood Beach!

9.8 out of 10, Exceptional, (65)
"We loved our stay, the pool felt amazing every day! The home was very clean. "
4 Bedrooms, 3 Baths! Bikes, Private Pool, Dock, Canal Front, Neighborhood Beach!

Brand New Single Family 5/5 -90ft dock, pool, paddle boards, bicycles plus more!

10.0 out of 10, Exceptional, (25)
"We had a wonderful week at this unbelievable home. As advertised…spacious rooms throughout the house, gorgeous views, large pool & many other amenities. Dennis was quick to respond to any & all questions we had. "
Brand New Single Family 5/5 -90ft dock, pool, paddle boards, bicycles plus more!

Marlin House 52: Gated Luxury Villa w/ Dockage, Sunset Views and Pool

10.0 out of 10, Exceptional, (47)
"We had an amazing stay at this VRBO in Marathon Shores! The condo was incredibly well-stocked—just like home—with everything we could possibly need. From the fully equipped kitchen to the cozy living space, every detail was thoughtfully taken care of. The location was perfect, and the host was absolutely wonderful—responsive, friendly, and truly made us feel welcome. One of the highlights was relaxing on the deck and balcony, watching the breathtaking sunsets over the water. It was the perfect...
Marlin House 52: Gated Luxury Villa w/ Dockage, Sunset Views and Pool

Bayside Home w/Shared Pool, Rooftop Terrace, Free WiFi, Gas Grill, and Views

9.0 out of 10, Wonderful, (90)
"Wonderful property in a great central location in the Keys. Loved it and would stay again! Included extras like dish soap, toilet paper, and bathroom toiletries were unexpected. Only thing we would have liked would’ve been an umbrella for the rooftop, but it appeared to us there probably was one there at one time. There were umbrella stands on the roof and umbrella instructions in the instruction book. Looked everywhere and couldn’t find an umbrella so we’re assuming someone before us must have...
Bayside Home w/Shared Pool, Rooftop Terrace, Free WiFi, Gas Grill, and Views

Charming 2-bedroom villa in a great location in fantastic Marathon

10.0 out of 10, Exceptional, (1)
"We stayed here 5 of a 17 day trip to the Keys. This home was cute, very clean, which is extremely important to us as it shows the owners take care of their home and it was cozy. The location was in a good spot, as it was close to a lot of attractions and places to go out for a meal. The owners were very helpful and quick to respond. Something for the host to consider would be to put a book together of some suggestions of places you recommend to eat and nearby attractions. That would be very...
Charming 2-bedroom villa in a great location in fantastic Marathon

Absolutely Perfect! Reel Vacation Villa w/Pool, Dock, Close to Beach w/Extras!

10.0 out of 10, Exceptional, (56)
"We loved staying here. It was the perfect location to see the Keys!"
Absolutely Perfect! Reel Vacation Villa w/Pool, Dock, Close to Beach w/Extras!

Dock/Private Pool! Elevator! Walk to Sombrero Beach! NEW Villa! 5/5

10.0 out of 10, Exceptional, (32)
"This was such a lovely home to visit. The three floors with 5 spacious bedrooms gave everyone their own space, and there was plenty of spots to gather for meals and pool time. The view of the canal at sunset was beautiful. The location was great; the market is down the road, you can walk or bike to the beach, and there are many excellent restaurants just a couple of miles away. Our hostess was gracious and always available. My elderly father used the elevator and enjoyed the suite on the first...
Dock/Private Pool! Elevator! Walk to Sombrero Beach! NEW Villa! 5/5

Florida Keys, private wellness enjoyment with two private hot tubs

8.6 out of 10, Excellent, (7)
" The bones of this property are excellent. Two relaxing outside areas with hot tubs - one roof top and one covered on the ground floor -plus two decks. The space was spacious and perfect for our needs. "
Florida Keys, private wellness enjoyment with two private hot tubs
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other property types in Big Pine Key

Old Wooden Bridge Resort and Marina

2.5 star property
8.6 out of 10, Excellent, (201)
"It was a little off the beaten path, but staff were super friendly and communicative. Full kitchen was definitely a perk for family travel. An easy drive to Key West, though not much to do locally (unless you fish!). Lovely sunrise, and we saw key deer."
The price is SAR 559
SAR 1,004 total
includes taxes & fees
24 Mar - 25 Mar
Old Wooden Bridge Resort and Marina

Sunshine Key RV Resort & Marina

2.0 star property
8.8 out of 10, Excellent, (145)
"We enjoyed the stay so much. Great pool area and very friendly staff!!"
Sunshine Key RV Resort & Marina

Keys 3 Bedroom Corner Home near Beach & Key West

9.6 out of 10, Exceptional, (5)
"We stayed for four nights. They have ample beds, a nice tv, a large kitchen, and many parking spots. There are not many walkable beaches but there is a couple of good restaurants nearby. We had a great time, everything was nice, and everything was as listed. I would rent again. "
The price is SAR 1,234
SAR 2,809 total
includes taxes & fees
31 Mar - 1 Apr
Keys 3 Bedroom Corner Home near Beach & Key West
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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