
Vacation rentals in Pine Key
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Top-rated vacation rentals in Pine Key
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Other great vacation rentals in 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!

Vacation 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!

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!
Top guest favorite

Home in Marathon
5 out of 5 average rating, 51 reviewsLuxury Boating Paradise+Pool+Sailing Kayaks
RickRating, 5 stars1 week ago
We had an amazing family weekend here! The home was spotlessly clean, beautifully maintained, and incredibly well equipped with everything we needed. The ping pong table, video games, and sail kayaks were huge hits with the whole family. We also rented a boat, and having a private dock made that experience seamless and unforgettable. The location was quiet, safe, and perfect for quality time—cozy enough to relax, yet close to everything we needed. It truly felt like a home away from home. For all the amenities and the exceptional condition of the property, the price was a fantastic value. We’ve stayed in many vacation rentals, but this one stands out as one of the best. We’re already looking forward to coming back. Highly recommended!
Top guest favorite

Home in Key Colony Beach
5 out of 5 average rating, 18 reviewsBohemian Beach Bungalow
AnnaRating, 5 stars6 days ago
I can’t say enough great things about this beach bungalow! From the moment we arrived, we were welcomed with warm hospitality and thoughtful touches that made our stay truly special. The bungalow itself is cozy, clean, and beautifully decorated with a laid-back coastal vibe—exactly what you want for a beach getaway. Whether you’re looking for a romantic escape, a solo retreat, or a peaceful base for beach adventures, this place is a gem. We left feeling refreshed and recharged, and we’re already dreaming of coming back!
Top guest favorite

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 stars2 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!
Guest favorite

Home in Big Pine Key
5 out of 5 average rating, 6 reviewsCozy Waterfront Key Deer Retreat
KatherineRating, 5 stars1 month ago
Beautiful, Beautiful Beautiful did I say Beautiful. you won't be disappointed if you rent this house, so private and quiet. yes the neighbors are close but they weren't home our entire stay and we wouldn't have noticed if they were there, there was to much to do and see. So easy and close to a marina to put your boat in the water for 10$ each day In and Out. The Rooster was perfect for many dinners. Boondocks 10 minutes away for a little competitive putt putt, live music,and great food. Shopping galore Key West just 30 minutes away. Oh yes and the house was Beautiful, the beds were comfy, extremely clean and everything to make your vacation great is right here. The Key Deer are a bonus. Thank you Estrella we will be back.
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