
Cottage vacation rentals in Big Pine Key
Find and book unique cottages on Airbnb
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
Get the amount of space that is right for you
Popular amenities for Big Pine Key cottage rentals
Cottage rentals with a hot tub

OCEANIA... water front cottage retreat ~
Place was great. We loved the kayaks and Bikes that were there. Very clean and spacious. Beautiful view being on the canal. my negative I would say, which has nothing to do with the host, We were aware of the $125 resort fee, And our fee was increased to $145 cause my son’s large pickup. Curious as to what that fee actually pays for. We would definitely stay again.

ATLANTIS...Ocean Front Cottage Retreat!
We had an amazing 6-night stay at this waterfront Airbnb! The location is perfect—right on the water with gorgeous sunrise views. We used the provided kayaks every day, and my husband loved fishing off the deck while I relaxed in the sun. The house is super cute, clean, and beachy. The bed was very comfortable, and the kitchen was well-stocked with basics like spices and oil, making it easy to cook most of our meals. We also appreciated the strong, hot shower and provided toiletries. Extras like beach towels, umbrellas, fishing gear, and a washer/dryer made our stay even better. The area is peaceful, clean, and friendly—plus, Key West is just a short drive away. We’d definitely stay here again!

Tidewater Views at Venture Out
Great location, and a very practical and cute little house. The neighbor who resides on the ocean side was wonderful and inviting, which made the stay so much better. Well stocked kitchen. Lots of clean towels and name brand starter essentials. The down side, there was a bag of (assumed??) dirty bedding left by the door, which I contacted our concierge about when we arrived, and it went ignored until I brought it up at check out again. It worked out fine though, my kids brought their own blankets and used them instead. Everything else was great though!

Cozy, Perfect Conch Cottage! - VO315
Loved our stay! Clean place, great location and the community at VO is so nice. Great place to stay. Clean and cozy spot. Had everything we needed. Would definitely stay here again!

NAUTILUS...ocean front cottage retreat ~
Manuel was so kind and responsive! This place was sooo cute and perfect to stay in! The community felt super safe with the constant security, and he had so many amenities for us such as kayaks, fishing poles, bikes, kitchen supplies, hair dryer, etc. We had a slight issue with the wifi and he accommodated us to an extra day! It was soo sweet of him to do that and it made our stay extra fun:) Overall, I recommend 100% for anyone to stay here! It’s awesome. The pool and hot tub are so nice as well!

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
The location was great. We parked our car and walked to everything. The condo was very nice and we loved the pool!

Hidden Oasis @ the Colony ~ Great location
We had an amazing stay! Beautiful hideaway, felt like we were at home! Very clean and had everything we needed and more! The grounds were well kept and the pool was perfect! This is DEFINITELY a gem!! And we will 100% rebook in the future! We had a small issue with the mini split and it was handled quickly and never gave us another issue!

Floating 2 BD, 1 BATH Private Villa Pirates Lair
We are definitely planning on coming back to stay. We only spent 2 nights here and I’m disappointed we booked another spot in the lower keys for the rest of our trip. The guys at the front desk were very friendly and helpful! We grabbed some local shrimp and bbq’d on the grill. Totally a comfortable, peaceful, and relaxing place to stay, but very close to everything

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!

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.

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.

Cute 1B/1B Lofted Cottage
Our stay in the cottage at Sun Outdoors was excellent! The neighborhood is very peaceful and friendly. It is also located right on the gulf side so the sunsets were gorgeous!!! The pictures matched the cottage perfectly and the employees are very helpful and available when needed. My family and I would stay here again!

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.
Private cottage rentals

Colony Calypso - A quaint 1 Bedroom Cottage
Nice little space for 2. Spacious rooms, great location. Privacy, quiet street Easy to walk or bike to many restaurants, museums, shops Nice little pool, there are beach towels available to use We would definitely recommend and stay again if in the area b

Serene Cozy Cottage in Islamorada with Heated Pool
Great choice! Very close to everything, central. Pool was so nice & our own mostly. Cottage is modern clean & comfortable. Perfect for a girls trip!

Colony Poolside: A charming bungalow near Duval
GREAT location. Our poolside location was fantastic and the staff were very helpful. My only complaint would be the bed. Rather thin mattress and the frame felt a little on the cheap side. This is the only bad thing I can say about our stay. Highly recommend

Tropical Cottages - Cottage # 03
The cottage was cute, comfortable and made a great central location for all our excursions. Loved having a tiki bar and taco truck waiting for us after a long day. We loved our stay.

Luxurious Oasis: 2BR w/Pool, Tiki, Dock & Beach
What a fantastic place to stay in Marathon! LeeAnn really makes sure you feel right at home. Forgot a toothbrush? Didn't pack or want to buy shampoo? No problem, it's there! The pool is amazing, house is spotless, and the Key Colony Beach community is the best. It is quiet and relaxing while also being in the heart of everything to do in the Florida Keys. LeeAnn is so nice and responsive, she got back to us quickly with any questions that we had. Overall, this was one of the nicest places that my family and I have ever stayed on a vacation. 10/10 would recommend to anyone!
Destinations to explore
- Key West Vacation rentals
- Florida Keys Vacation rentals
- Miami Vacation rentals
- Gold Coast Vacation rentals
- Miami Beach Vacation rentals
- Havana Vacation rentals
- Fort Lauderdale Vacation rentals
- Tampa Bay Vacation rentals
- St Petersburg Vacation rentals
- Central Florida Vacation rentals
- Seminole Vacation rentals
- Tampa Vacation rentals
- Rentals with a kayak Big Pine Key
- Rentals with beach access Big Pine Key
- Kid-friendly rentals Big Pine Key
- Rentals with pools Big Pine Key
- Waterfront rentals Big Pine Key
- House rentals Big Pine Key
- Smoking-friendly rentals Big Pine Key
- Rentals with a patio Big Pine Key
- Rentals with outdoor seating Big Pine Key
- Apartment rentals Big Pine Key
- Rentals with a hot tub Big Pine Key
- Beachfront rentals Big Pine Key
- Rentals with a fire pit Big Pine Key
- Pet-friendly rentals Big Pine Key
- Rentals with a washer and dryer Big Pine Key
- Family-friendly rentals Big Pine Key
- Fitness-friendly rentals Big Pine Key
- Villa rentals Big Pine Key
- Cottage rentals Monroe County
- Cottage rentals Florida
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom