
Cottage vacation rentals in Big Pine Key
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Top-rated cottage rentals in Big Pine Key
Guests agree: these cottages are highly rated for location, cleanliness, and more.
Vacation rentals for every style
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Popular amenities for Big Pine Key cottage rentals
Cottage rentals with a hot tub

Turtle Cove Views at Venture Out
Enjoyed the stay - the cottage was cute and nicely decorated - met all of our needs. Great athletic facilities. Nice being on the water and watching the sun rise every morning.

OCEANIA... water front cottage retreat ~
If we could rate this 6+ stars out of 5, we would! Manuel was super easy to reach, he provided simple and clear instructions, the guards at the gate were easy to work with and available for 24/7 entry and check in.. the location is unbeatable for a boat owner! You dock right at your back door, clean your fish at the back door OR at the marina, immediate access to the Atlantic.. perfection. The home itself is extremely clean & beautiful. The kitchen and bathrooms were all stocked with anything you’d need as well as even the laundry room! We truly felt at home but twice as relaxed! Thanks Manuel!!

ATLANTIS...Ocean Front Cottage Retreat!
Manuel's home was clean, bright, quiet, and peaceful with a million dollar view. It sits directly on big open water which we enjoyed from the nice open porch. We ate meals on the porch while relaxing and savoring the amazing view of the blue water and the two islands beyond. We never tired of the view. The whole neighborhood is quiet and clean, and there is a small beach and a pool. The check in/check out process was simple and Manuel was responsive with all communications. We enjoyed exploring Key West (about a 30-35 minute drive) and walking the old train/then road Old Seven Mile Bridge from Marathon Key to Pigeon Key. The Bridge is a beautiful 4 mile round trip walk to small Pigeon Key where we swam and participated in a guided walking tour and shark feeding. If you're looking for a peaceful, relaxing, home with an amazing view to get away from it all, Manuel's home is the answer! It was perfect for my husband and me.

Darling of Duval at Old Town
What a great place to stay for a Key West trip! Perfect location, lots to do, super short walk to Duval St. Very easy check in, and Last Key were easily available for questions.

NAUTILUS...ocean front cottage retreat ~
Super responsive host! Place was great if you’re looking for a relaxed vibe. Close enough to key west but much less crowded relaxing vacation. My kids loved the pool and ocean being so close.

2BR dog-friendly water view stay, resort amenities
Perfect location for boaters and fishermen. Clean and mostly quiet canal with minimal low wake zone. House had all basics and very comfortable for my husband and I. Loved having the park nearby to take our dog, would recommend!
Pet-friendly cottage rentals

Colony Sunset- Bright and airy cottage
What a great find! Everything we needed was there! Quick walk to everywhere: beach, Duval street fun, restaurants and grocery store. So glad we went with this air bnb and not the hotel we normally go to. Saved so much money. Loved the privacy!

Floating 2 BD, 1 BATH Private Villa Pirates Lair
The place was awesome! So perfect! They helped with getting our jetskis in the water and let us tie them up to the doc. We'll definitely be back. Thank you Toni and Jay!

FLOATING 1BD 1BA PRIVATE COTTAGE - MAKO
We loved staying here for the two nights we were on the Keys. The patio outside was great for looking at the stars or sipping coffee and watching manatees. We would definitely return!

Osprey @ Colony
Perfect place for two. Awesome location, within walking distance of Duval but far enough away that it’s nice and quiet at night. Beautiful little pool. Will 100% stay here again next visit to Key West

Cute 1B/1B Lofted Cottage
What a beautiful, peaceful spot to stay! Family friendly and exceeded expectations. Great location to explore all of the Keys but always a nice, private and quiet place to come back to. Would absolutely stay here again!

Waterview 1B/1B Tiny Home
We absolutely loved it here and would've happily stayed for weeks! The tiny house was cute, clean and comfy with everything we needed. The location was perfect, would give it 110%. Beautiful sea view, amazing sunsets and the children enjoyed the games in the clubhouse and the pool. There are also lots of things to do nearby. Probably the best place we've ever stayed.

1 BD PRIVATE HOUSEBOAT/ COTTAGE TARPON
Toni was very nice. She went out of her way to make sure we were satisfied with everything. The bed was comfortable and we got a great night's sleep there on the water. Watching the fish jump and pelicans dive as we sat on the front deck was very relaxing.

Tropical Cottages - Cottage # 10
The Airbnb had a great location. My husband enjoyed the local fishing, which was a block away. The Airbnb was clean and very comfortable. We also enjoyed the taco truck and Tiki bar located on the premises. The most important thing was that we could bring our dog Chloe and felt comfortable and safe. We will come back again to the cottage.
Private cottage rentals

Colony Calypso - A quaint 1 Bedroom Cottage
Our stay was fantastic, the host was amazing and incredibly responsive. No issues at all, however, the Vacasa utility workers have a habit of entering the back patio areas unannounced. I think just a simple initial knock at the door, and a subsequent announcement of their entry would be satisfactory. This takes nothing away from the property or the hosts themselves, I believe Vacasa is a vendor. The stay itself was absolutely amazing, think rainforest escape to a beautiful place. The vibe was immaculate and I loved the pool. Stay here if you can, it is so worth it.

Waterfront 1B/1B Tiny Home
We had a great stay in their tiny house. The neighbor’s were all nice and friendly. The locals that live inside the campground are absolutely wonderful very nice and full of local information where to go and what to do.

Serene Cozy Cottage in Islamorada with Heated Pool
The place and location were perfect. We were looking for a no frills type of place so my kids would have to spend time without devices and just be outside. This little place is exactly what we needed, it’s just big enough to sleep, eat a quick breakfast and head out for the day on the keys. The pool area is really nice and everything was great. It does not come with any extras..like beach bike, beach chairs or extra beach towels so you may want to bring your own. We left a few behind for the next family to enjoy. Over all this was a very clean and nice place to stay in a good neighborhood located to almost everything.

Colony Poolside: A charming bungalow near Duval
We loved our time at Colony Poolside! We spent a long weekend at Colony Poolside (it was our second stay in this location). The rental was exactly like the pictures, clean and comfortable. The kitchen was well stocked, and there were even beach towels, sunblock and a workout mat. The pool was clean and quiet. Short walk to Duval and lots of great restaurants. We would highly recommend!

Pete's East Cottage: Cypress east cottage steps
Great location! Pool was great! We enjoyed our stay!

Luxurious Oasis: 2BR w/Pool, Tiki, Dock & Beach
Leeann’s place exceeded our expectations! She was incredibly responsive to any concerns or inquiries we had throughout our stay. The added perk of access to Glunz Beach Resort with its beach, pool, and gym made our experience even more delightful. The house was equipped with everything we needed for a comfortable stay. Thank you, Leeann!
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