Search Cottages in Big Pine Key

  • Plan, book, stay with confidence

    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Next weekend
14 Feb - 16 Feb
In two weeks
21 Feb - 23 Feb
In one month
7 Mar - 9 Mar
In two months
4 Apr - 6 Apr

Compare 56 Cottages in Big Pine Key with updated reviews, rates, and availability.

Old Wooden Bridge Resort and Marina
Exterior

Old Wooden Bridge Resort and Marina

2.5 star property
8.4 out of 10, Very Good, (188)
"Nice quiet area Everyone is so friendly and the little deer , are just adorable "
The price is AED 511
AED 942 total
includes taxes & fees
5 Feb - 6 Feb
Old Wooden Bridge Resort and Marina
Tropical Cottages
Exterior

Tropical Cottages

3.0 star property
8.4 out of 10, Very Good, (776)
"From the moment we opened the door, we felt welcomed. The room was spacious and had touches of hospitality from the bedding to the bureau with a coffee area. The roosters woke us early! We saw a manatee from the the dock outside. "
The price is AED 731
AED 822 total
includes taxes & fees
4 Feb - 5 Feb
Tropical Cottages
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Exterior

Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

9.0 out of 10, Wonderful, (40)
"This is our second year at one of these cottages. We love the complex and the location is great to get to many things. The cottage has everything you would need and is very clean. The host has been great to work with."
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Exterior detail

Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

8.8 out of 10, Excellent, (59)
"Very nice location. Clean and we love the pool. Good communication with owner "
The price is AED 1,010
AED 1,817 total
includes taxes & fees
19 Feb - 20 Feb
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Cottage with Pool and Boat Dockage just minutes to Key West!
Pool

Cottage with Pool and Boat Dockage just minutes to Key West!

8.6 out of 10, Excellent, (132)
"Perfect location for us 23 miles to key west. Restaurants near by, pool, fishing pier. Can't wait to come back and do it all over again!"
Cottage with Pool and Boat Dockage just minutes to Key West!
Quaint cottage, pool, dockage just minutes to Key West!
Exterior

Quaint cottage, pool, dockage just minutes to Key West!

9.0 out of 10, Wonderful, (132)
"It is what it is, only wish the furniture was not worn out. "
The price is AED 1,010
AED 1,740 total
includes taxes & fees
8 Feb - 9 Feb
Quaint cottage, pool, dockage just minutes to Key West!
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Exterior

Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

9.2 out of 10, Wonderful, (67)
"My family and I enjoyed our stay. It was very convenient to everything we wanted to do. Would definitely stay again."
The price is AED 1,010
AED 1,817 total
includes taxes & fees
26 Feb - 27 Feb
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Wonderful Chalet, with Terrace & Private Patio – 20 miles from Key West.
Property grounds

Wonderful Chalet, with Terrace & Private Patio – 20 miles from Key West.

10.0 out of 10, Exceptional, (17)
"We really enjoyed the mini vacation in the Florida Keys."
Wonderful Chalet, with Terrace & Private Patio – 20 miles from Key West.
Waterfront Cozy Cottage with Boat Ramp & Dock!
Cozy Cottage dock for fishing, snorkeling, and relaxing.

Waterfront Cozy Cottage with Boat Ramp & Dock!

10.0 out of 10, Exceptional, (54)
"Brother-in-law and I stayed for 3 nights for a quick fishing getaway. The property was perfect for our needs. The property manager was proactive and communicative. He even reached out the day of check-in to let us know an early check-in was available. The property was in a nice quiet area, but just close enough to Kiki's to hear the evening live music from the fantastic pier. Also, within walking distance to Kiki's for a quick bite and a drink after fishing.The property was extremely clean...
Waterfront Cozy Cottage with Boat Ramp & Dock!
Waterfront Home
View from the porch

Waterfront Home

8.8 out of 10, Excellent, (154)
"I wasn't expecting a 140 resort fee due before proceeding past the gate guard. The gate guard's response to my puzzled look was, "You were aware of the resort fee, right?" The fee is likely (at least I hope) embedded in the TOS. Moving on. The property permits pets but walking one's dog is prohibited. The properties are so small that one must walk a dog. Knowing this property was on a canal with open water access, I was not surprised that it needed some TLC. I think, most folks rent this type...
The price is AED 918
AED 1,785 total
includes taxes & fees
21 Feb - 22 Feb
Waterfront Home
Lakefront Bungalow - Pet-Friendly - Sugarloaf Key - Great Amenities (22)
Aerial view

Lakefront Bungalow - Pet-Friendly - Sugarloaf Key - Great Amenities (22)

10.0 out of 10, Exceptional, (11)
"Super cute bungalow surrounded by a beautiful lake. The location was perfect for us and super convenient to Key West! The staff was very friendly and very helpful. After hours check-in was very smooth. We will stay there again when we are in the area!"
Lakefront Bungalow - Pet-Friendly - Sugarloaf Key - Great Amenities (22)
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Drive to cottages

Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

8.6 out of 10, Excellent, (38)
"Well located to visit Key West as well as other Keys both East and West. House needs some attention. "
The price is AED 643
AED 1,345 total
includes taxes & fees
22 Feb - 23 Feb
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Canal front, dockage, 2 bedroom, 2 bath
Exterior

Canal front, dockage, 2 bedroom, 2 bath

9.0 out of 10, Wonderful, (74)
"My husband loved fishing everyday and I enjoyed reading.The place was in a perfect location and had most of the comforts of home. There was no cleaning table for the fish big inconvenience and no light available. My issue is the lack of shade on the porch on the comfortable couch. It’s way too hot"
Canal front, dockage, 2 bedroom, 2 bath
Escape to the Keys! Pet-Friendly Sugarloaf Key Bungalow - Great Amenities (84)
Miscellaneous

Escape to the Keys! Pet-Friendly Sugarloaf Key Bungalow - Great Amenities (84)

9.8 out of 10, Exceptional, (9)
"We arrived to a spotless cabana! The bed was perfect! Just awesome accommodations that I would definitely book again!!! Highly recommend- it was close to Key West but quiet and relaxing. And our pet stayed with us."
Escape to the Keys! Pet-Friendly Sugarloaf Key Bungalow - Great Amenities (84)
Riley's Retreat - Venture Out 107

Riley's Retreat - Venture Out 107

8.6 out of 10, Excellent, (7)
"We would stay here again. Very clean. Kitchen well supplied. The beds could be more comfortable, but that could be a preference of bed type. The blinds in the bedrooms did not close completly so if you sleep late the light could be an issue. Itwasnt for us."
Riley's Retreat - Venture Out 107
Direct Oceanfront Cottage-Sunrise View- #2,
Wouldn't you love to start your morning with a beautiful sunrise like this?

Direct Oceanfront Cottage-Sunrise View- #2,

8.6 out of 10, Excellent, (169)
"It was kind of exciting. the cops showed up on the property and on the next door property to the North, there was a tree of stolen bouys and a stolen crab trap. It was quiet. there was a bit of a flood when it rained but within a day or 2 the water was gone. we had trouble opening the slider on the deck and I think there was moisture in the door. Hopefully we left it pretty clean. we had to be at the airport by 6:30. thank you, it was a wonderful stay. Patty "
Direct Oceanfront Cottage-Sunrise View- #2,
Cottage with swimming pool and dockage, just minutes to Key West!
Property grounds

Cottage with swimming pool and dockage, just minutes to Key West!

9.0 out of 10, Wonderful, (137)
"We had a wonderful stay in a small cottage in Cudjoe Key. It was a fun little place stay. Location was great for visiting the other Keys. I would seriously look at staying in one of the bigger cottages if I brought my family down. Thank you very much!"
The price is AED 551
AED 1,040 total
includes taxes & fees
16 Feb - 17 Feb
Cottage with swimming pool and dockage, just minutes to Key West!
Cottage with Pool and Dockage, just minutes to Key West
Exterior

Cottage with Pool and Dockage, just minutes to Key West

9.2 out of 10, Wonderful, (130)
"If your thrifty and dont mind thrift store funishings and buildings, then this is your place. Great location, small pool, small boat dock. Nice view if you walk down to the shared waters edge. Very "old keys vibe"."
Cottage with Pool and Dockage, just minutes to Key West
Pet-Friendly Bungalow in Sugarloaf Key, FL - Fantastic Amenities (83)
Exterior

Pet-Friendly Bungalow in Sugarloaf Key, FL - Fantastic Amenities (83)

9.8 out of 10, Exceptional, (12)
"Great spot. Very quiet and clean. "
Pet-Friendly Bungalow in Sugarloaf Key, FL - Fantastic Amenities (83)
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Exterior detail

Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

8.0 out of 10, Very Good, (33)
"This property is clean and adequate. Close to the lower keys, and easy to get to the upper keys and back. The listing indicates that there is a washer and dryer; however, these are coin-operated and in a different part of the compound, not in the unit. There has been road work done in the area, so the driveway was not easy to find by using the directions listed. All-in-all, not bad!"
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Don't see what you're looking for?
See all available properties in Big Pine Key
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other property types in Big Pine Key

Old Wooden Bridge Resort and Marina
Exterior

Old Wooden Bridge Resort and Marina

2.5 star property
8.4 out of 10, Very Good, (188)
"Nice quiet area Everyone is so friendly and the little deer , are just adorable "
The price is AED 511
AED 942 total
includes taxes & fees
5 Feb - 6 Feb
Old Wooden Bridge Resort and Marina
Keys 3 Bedroom Corner Home near Beach & Key West
Living area

Keys 3 Bedroom Corner Home near Beach & Key West

9.6 out of 10, Exceptional, (4)
"Great location, right in the middle keys, easy access to everything. "
The price is AED 1,388
AED 2,989 total
includes taxes & fees
6 Feb - 7 Feb
Keys 3 Bedroom Corner Home near Beach & Key West
Skipjack Resort & Marina
Pool

Skipjack Resort & Marina

3.0 star property
8.6 out of 10, Excellent, (1149)
"Rooms are dated, could use a few more things in the very small kitchen, building is showing it’s age, decent place to stay."
The price is AED 1,319
AED 1,616 total
includes taxes & fees
4 Feb - 5 Feb
Skipjack Resort & Marina
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Frequently asked questions

Why book your cottage in Big Pine Key with Expedia?
Reserving a cottage in Big Pine Key is as simple as deciding on your travel dates and selecting an ideal place for a vacation in the outdoors. From ritzy retreats to budget-friendly properties and cottages that come with amenities like laundry facilities, Expedia has something for all styles. As for the best deals around? We’ve got your back!
How can I find cheap cottages in Big Pine Key?
Expedia can help you track down cheap cottages in Big Pine Key. To book your ideal stay in a matter of clicks, use the filter tool to tailor your search results by budget, amenities and star rating.