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Big Pine Key Vacation Rentals

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Our top choices for Big Pine Key vacation rentals

Old Wooden Bridge Resort and Marina

Old Wooden Bridge Resort and Marina
2.5 star property
Punta Brisa
8.6 out of 10, Excellent, (281)
"Enjoyed the duplex, instead of a standard hotel room. Full kitchen, nice bathroom, and bedroom. "
United States
Alejandra
$236 nightly
The price is $266
Jan 8 - Jan 9, 2026
Total with taxes and fees
Old Wooden Bridge Resort and Marina

🌴 TROPICAL RETREAT 🌴 RV in the Keys

🌴 TROPICAL RETREAT 🌴 RV in the Keys
Big Pine Key
10.0 out of 10, Exceptional, (2)
"Its clean and plenty of room.Outdoor seating is wonderful. Could use a gas grill. But definitely a great place."
United States
DeeBrett
$314 nightly
The price is $350
Jan 3 - Jan 4, 2026
Total with taxes and fees
🌴 TROPICAL RETREAT 🌴 RV in the Keys

Star Room Barnacle Resort

Star Room Barnacle Resort
Long Beach Estates
9.4 out of 10, Exceptional, (3)
"We loved the location - quiet and secluded - away from everything but not so far away that you felt isolated. All very clean and amenities were as described."
United Kingdom
Robert
$294 nightly
The price is $320
Jan 13 - Jan 14, 2026
Total with taxes and fees
Star Room Barnacle Resort

🌴 TROPICAL RETREAT 🌴 RV IN THE KEYS 🌴

🌴 TROPICAL RETREAT 🌴 RV IN THE KEYS 🌴
Big Pine Key
$296 nightly
The price is $329
Dec 24 - Dec 25
Total with taxes and fees
🌴 TROPICAL RETREAT 🌴 RV IN THE KEYS 🌴

Fishermen's Paradise | Pool, dock, gorgeous home

Fishermen's Paradise | Pool, dock, gorgeous home
Big Pine Key
9.8 out of 10, Exceptional, (23)
"The location was very nice and secluded. The house was perfect for a family of five. The pool was great spent a lot of time in it. Lots to do in the area. The only complaint we had is the master bedroom bed mattress needs to be replaced. It seemed like it was very old possibly even broken communication with Karen was perfect. Everything about the trip was good :) "
United States
Michelle S.
$1,280 nightly
The price is $1,408
Jan 21 - Jan 22, 2026
Total with taxes and fees
Fishermen's Paradise | Pool, dock, gorgeous home

Treehouse Private Village Barnacle Resort

Treehouse Private Village Barnacle Resort
Long Beach Estates
8.0 out of 10, Very Good, (1)
"Great location, quiet with great views!"
United States
Lee A.
$540 nightly
The price is $588
Jan 13 - Jan 14, 2026
Total with taxes and fees
Treehouse Private Village Barnacle Resort

Charming 3-bedroom house in Big Pine Key near Beach and Key West

Charming 3-bedroom house in Big Pine Key near Beach and Key West
Sands
6.0 out of 10, (1)
"The house was not thoroughly cleaned. The cabinets and under the place mats were dirty. When we opened the pack and play it had an orange substance caked all over inside. We tried to watch tv and remote had no batteries, we tried the second remote and that didn’t work either. "
United States
Heather H.
$566 nightly
The price is $630
Jan 5 - Jan 6, 2026
Total with taxes and fees
Charming 3-bedroom house in Big Pine Key near Beach and Key West

Ocean Depth Room Barnacle Resort

Ocean Depth Room Barnacle Resort
Long Beach Estates
10.0 out of 10, Exceptional, (1)
"Enjoyed our short stay in the Ocean Depth Room. Utilized the shared kitchen to cook breakfast and eat on the beach each morning. Would def stay there again."
United States
Chrissy L.
$463 nightly
The price is $504
Jan 13 - Jan 14, 2026
Total with taxes and fees
Ocean Depth Room Barnacle Resort

Beach View Room Dormitory Room Barnacle Resort

Beach View Room Dormitory Room Barnacle Resort
Long Beach Estates
$412 nightly
The price is $448
Jan 13 - Jan 14, 2026
Total with taxes and fees
Beach View Room Dormitory Room Barnacle Resort

Ocean View Suite Barnacle Resort

Ocean View Suite Barnacle Resort
Long Beach Estates
$463 nightly
The price is $501
Jan 13 - Jan 14, 2026
Total with taxes and fees
Ocean View Suite Barnacle Resort

Yacht Haven Marina

Yacht Haven Marina
3.5 star property
Marathon
9.8 out of 10, Exceptional, (241)
"Friendly staff and extremely clean."
United States
Travis
$275 nightly
The price is $309
Jan 7 - Jan 8, 2026
Total with taxes and fees
Yacht Haven Marina

Aqua Lodge Rentals At Coconut Cay

Aqua Lodge Rentals At Coconut Cay
3.5 star property
Marathon
9.6 out of 10, Exceptional, (199)
"A unique and interesting place to vacation. Relaxing yet close enough to things to do. I highly recommend the Aqua Loge rentals as a place to stay."
United States
Keith
$345 nightly
The price is $388
Jan 11 - Jan 12, 2026
Total with taxes and fees
Aqua Lodge Rentals At Coconut Cay

Seabreeze Escape WF RV Lot 489

Seabreeze Escape WF RV Lot 489
Cudjoe Key
8.0 out of 10, Very Good, (1)
$277 nightly
The price is $298
Dec 27 - Dec 28
Total with taxes and fees
Seabreeze Escape WF RV Lot 489

Tropical Cottages

Tropical Cottages
3.0 star property
Marathon
8.6 out of 10, Excellent, (910)
"Decent stay, easy check in and contactless checkout. Very quiet and nice place! "
United States
Swastik
$135 nightly
The price is $152
Jan 8 - Jan 9, 2026
Total with taxes and fees
Tropical Cottages

Knight's Key Suites

Knight's Key Suites
3.0 star property
Marathon
9.0 out of 10, Wonderful, (1157)
"Very good location.. Clean room."
United States
Leonor
$147 nightly
The price is $162
Jan 15 - Jan 16, 2026
Total with taxes and fees
Knight's Key Suites

Skipjack Resort & Marina

Skipjack Resort & Marina
3.0 star property
Marathon
8.6 out of 10, Excellent, (1218)
"Beautiful location clean rooms friendly staff "
United States
Tiffany
$262 nightly
The price is $295
Jan 5 - Jan 6, 2026
Total with taxes and fees
Skipjack Resort & Marina

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
Cudjoe Key
8.6 out of 10, Excellent, (75)
"Place was everything we needed, would definitely stay again "
United States
James h.
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

Island Oasis ~ YOUR Paradise awaits in Venture Out Resort!

Island Oasis ~ YOUR Paradise awaits in Venture Out Resort!
Cudjoe Key
9.6 out of 10, Exceptional, (12)
"The owners were fantastic to deal with and the house was great. "
United States
Anonymous traveler
Island Oasis ~ YOUR Paradise awaits in Venture Out Resort!

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

Cottage with swimming pool and dockage, just minutes to Key West!
Cudjoe Key
9.0 out of 10, Wonderful, (160)
"Everything was there that I needed. Very nice area for my dog."
United States
Terry
Cottage with swimming pool and dockage, just minutes to Key West!

Private Oceanfront Cottage with dockage, pool just minutes to Key West!

Private Oceanfront Cottage with dockage, pool just minutes to Key West!
Cudjoe Key
8.6 out of 10, Excellent, (164)
"Beautiful serene, location, located close enough to Key West and also nice restaurants in the area and close to Bahia Honda State Park, which was beautiful and the key deer areas."
United States
Andrea S.
$341 nightly
The price is $379
Jan 19 - Jan 20, 2026
Total with taxes and fees
Private Oceanfront Cottage with dockage, pool just minutes to 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.
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Top Big Pine Key Hotel Reviews

Find out more about Big Pine Key

Everything you need to know about Big Pine Key vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Big Pine Key vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Big Pine Key vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Big Pine Key vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Big Pine Key. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Big Pine Key in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $152 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Big Pine Key rentals

At Expedia, we put the best Big Pine Key vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Big Pine Key rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Big Pine Key vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Big Pine Key. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently asked questions

Can I find vacation rentals in Big Pine Key?

Yes, there are vacation rentals in Big Pine Key close to Blue Hole, or you can go with a more secluded option if you're looking for a relaxing stay. Big Pine Key is known for its beaches.

What are some of the best vacation rentals that Big Pine Key has to offer?

The Hammocks at Marathon: This vacation home near Big Pine Key is located by the ocean and has an outdoor pool, a balcony, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities like a microwave and a coffee maker can make your vacation run smoothly. You and your friends and family can relax into your vacation with amenities like a hot tub.

How many vacation rentals are there in Big Pine Key?

With 149 Expedia vacation rentals, you're sure to find just the right place for your Big Pine Key stay.

What can I see and do in Big Pine Key?

Family-friendly attractions include Blue Hole and Big Munson Island, whereas Calusa Beach and Florida Keys Beaches are a couple of great spots to enjoy the outdoors. Other places in town to visit include Bahia Honda State Park and Big Pine Key Flea Market.

What are vacation rentals like in Big Pine Key?

Vacation rentals are privately owned properties you can stay in for several days or more in Big Pine Key. Vacation rentals feature amenities like laundry facilities and kitchens so you'll have a home away from home. If you're concerned about a clean environment, a vacation rental can provide a sense of security away from shared hotel elevators and busy reception areas while still allowing you to travel. You'll also get more space in a vacation rental than in a standard hotel, which makes a vacation rental a popular option for family trips.