
Holiday houses in Big Pine Key
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Top-rated holiday rentals in Big Pine Key
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Other great holiday rentals in Big Pine Key

Home in Summerland Key
4.82 out of 5 average rating, 57 reviewsKelly’s Kabin - Private FL Keys Cottage
LadyRating, 5 stars2 weeks ago
The cabin was cozy and super cute. It was impeccably clean. I only stayed one night but wish I stayed longer. She had all the necessary amenities. I didn’t get to use the patio since I mostly stayed out on the boat but wish I had more time to do so. Kristin had board games, shampoo, conditioner, body wash, blow dryer, washer, dryer and everything you would want in an AirBNB. There are plenty of restaurants nearby and the supermarket wasn’t too far. I felt safe in the neighborhood. I hope to come back and stay here again!

Campervan/RV in Big Pine Key
4.6 out of 5 average rating, 25 reviewsTiny home in RV park with pool
HermesRating, 5 stars3 weeks ago
everything was good and I recommend

Campervan/RV in Big Pine Key
4.8 out of 5 average rating, 5 reviewsGlamping in the Keys
JeffreyRating, 5 stars4 days ago
A1 place to stay! Ms Donna is a great host!

Condo in Key West
4.91 out of 5 average rating, 82 reviewsOcean Front Suite with Direct Beach Access
TerrenceRating, 5 stars1 week ago
It was a wonderful experience and the amenities and staff were great! Will 100% recommend the on site restaurants dinner menus (PRIME RIB!!). The 24 hr pool and hot tub access were also a nice touch. Allowed us to enjoy water activities during the day, and some cooler experiences in the evening away from the sun!

Holiday home in Big Pine Key
5 out of 5 average rating, 5 reviewsBoater dream home 75ft wide crystal clear canal
KathyRating, 5 stars14 months ago
My husband and I, along with some friends, stayed the month of March. The description of the house is accurate; clean, homey, comfortable beds, nice furnishings and decorated nicely. A few minor issues came up while we were there and Kelly & Walter responded very quickly to resolve! We kayaked/paddle board with manatees in the canal right outside our front door, to include different kinds of fish. I enjoyed my morning runs on the bike/walking trail at the end of our street. Also, met many nice neighbors as well while walking our dog. The weather was beautiful, only rained 3 days the entire time we were there. The boat lift and pool were a plus, after a day of boating we would come back and cool off in the pool. We enjoyed our stay so much, we have already booked March of next year!!! Thank you Kelly & Walter for sharing your home with us!

Townhouse in Little Torch Key
4.77 out of 5 average rating, 91 reviewsWaterfront 2BD / 2.5BTH Luxury Townhome
AlexRating, 5 stars1 month ago
Wonderful place to stay and great location for multiple key adventures throughout your stay. My family and I enjoyed the stay. We will definitely stay with little torch cottages again!
Top Guest favourite

Home in Big Pine Key
5 out of 5 average rating, 10 reviewsHibiscus House
ReginaRating, 5 stars2 weeks ago
We love to travel and have stayed in quite a few airbnbs now but this one has gotten 5 stars from all the adults and the kids! This spot is so unique we all loved it! It’s beautiful inside and out. The wildlife comes right up into the yard. Every evening we have a family of deer show up. I think this was everyone’s favorite part but the loved the pool and the deck and the space the home has. Plenty of seating to separate or spend some time as a family. We are definitely coming back to this unit when we come back to the keys and we’ve been telling all our friends and family about it for their next trip! The host was great and very responsive!

Guesthouse in Big Pine Key
4.79 out of 5 average rating, 19 reviewsCaptain's Hideout
StasiaRating, 5 stars3 weeks ago
Great place to stay for a quiet waterfront vacation What we liked: Absolutely unmatched waterfront views Privacy Very quiet Close to the No Name Pub Boat dock What we didn’t like: Lack of a stove The location is awesome. Waterfront to saltwater with a wide channel that is not too close. Able to watch boats go by without much noise. The area itself is very quiet, being a dead end, and having a lot of distance to nearby houses. The house was clean and comfortable. The house includes a dock on a small canal across the street. The dock itself is of good size and full concrete construction. It would probably fit a 20-22 foot boat easily. The water depth at the dock is 6-8 feet. We were able to launch about 2 miles away for $20 ($10 in, $10 out). There is a narrow channel into the canal, and we had no issues getting in and out of the dock area. Definitely a beautiful site. Probably unmatched for privacy and solitude on the entire island. We plan to stay again. Highly recommend!
Quick stats about holiday rentals in Big Pine Key
Total rentals
260 properties
Nightly prices starting at
$77 AUD before taxes and fees
Total number of reviews
4.9K reviews
Family-friendly rentals
190 properties are a good fit for families
Pet-friendly rentals
120 properties allow pets
Rentals with a pool
130 properties have a pool
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