
Cottage vacation rentals in Big Pine Key
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Top-rated cottage rentals in Big Pine Key
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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.

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

Floating 2 BD, 1 BATH Private Villa Pirates Lair
A houseboat stay was a new experience for us and it was remarkable. Some very friendly men customers insisted on unloading all our luggage from the car and taking it to the boat - they were so helpful. Everything you needed was right there. The bed and furniture was very comfortable and all was spotlessly clean. Watching the sun go down and drinking coffee in the morning on the deck was so peaceful and serene - I could have sat on that deck forever. A fantastic stay!

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.

Prime Location 1B/1B Home
We thoroughly enjoyed our stay! The cottage was very clean and comfortable with plenty of space for three adults. We especially loved the pool and proximity to the ocean - the views were stunning! Just a quick note about parking: the house rules state that parking for one vehicle is included with each reservation, but we were able to park both of our cars with no issue.
Private cottage rentals

Ann Street Tranquility
This charming unit exceeded our expectations and was wonderfully walkable yet totally private.

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.

Bali Hideaway: A studio cottage that's perfect
Loved our stay here. Close to everything yet did not hear the noise or sounds of the town. Great studio and fantastic little garden/yard. Loved the vibe and the privacy. Pool was great too!

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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