Holiday Rentals in Big Pine Key

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Our top choices for Big Pine Key holiday 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, (280)
"Enjoyed the duplex, instead of a standard hotel room. Full kitchen, nice bathroom, and bedroom. "
United States
Alejandra
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
The price is €332
includes taxes & fees
21 Jan - 22 Jan 2026
🌴 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
The price is €273
includes taxes & fees
13 Jan - 14 Jan 2026
Star Room Barnacle Resort

🌴 TROPICAL RETREAT 🌴 RV IN THE KEYS 🌴

🌴 TROPICAL RETREAT 🌴 RV IN THE KEYS 🌴
Big Pine Key
The price is €288
includes taxes & fees
23 Dec - 24 Dec
🌴 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.
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.
The price is €513
includes taxes & fees
13 Jan - 14 Jan 2026
Treehouse Private Village Barnacle Resort

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.
The price is €440
includes taxes & fees
13 Jan - 14 Jan 2026
Ocean Depth Room Barnacle Resort

Beach View Room Dormitory Room Barnacle Resort

Beach View Room Dormitory Room Barnacle Resort
Long Beach Estates
The price is €391
includes taxes & fees
13 Jan - 14 Jan 2026
Beach View Room Dormitory Room Barnacle Resort

Ocean View Suite Barnacle Resort

Ocean View Suite Barnacle Resort
Long Beach Estates
The price is €437
includes taxes & fees
13 Jan - 14 Jan 2026
Ocean View Suite Barnacle Resort

Yacht Haven Marina

Yacht Haven Marina
3.5 star property
Marathon
9.8 out of 10, Exceptional, (240)
"Friendly staff and extremely clean."
United States
Travis
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
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)
The price is €261
includes taxes & fees
27 Dec - 28 Dec
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
The price is €130
includes taxes & fees
8 Jan - 9 Jan 2026
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
The price is €126
includes taxes & fees
23 Dec - 24 Dec
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
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.
The price is €303
includes taxes & fees
23 Dec - 24 Dec
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 traveller
The price is €338
includes taxes & fees
23 Dec - 24 Dec
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
The price is €306
includes taxes & fees
27 Dec - 28 Dec
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)
"Bad need of repair....rust....no boat ramp......shallow water....screened in porch was aweful with holes in the screens and lots of mosquitos and rusted grill."
United States
Debra M.
The price is €250
includes taxes & fees
23 Dec - 24 Dec
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 holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Big Pine Key holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Big Pine Key holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Big Pine Key holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Big Pine Key holiday rentals we have selected for you start as low as €126 per night. Entering your travel dates in the search wizard 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 holiday 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 holiday.

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 holiday rentals in Big Pine Key?

Yes, there are holiday rentals in Big Pine Key close to Blue Hole, or you can select 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 holiday rentals that Big Pine Key has to offer?

The Hammocks at Marathon: This holiday home rental outside of Big Pine Key is located by the ocean, and has an outdoor pool, a balcony and a BBQ to put you at ease in your new surroundings. Kitchen amenities such as a microwave and a coffee maker can make your holiday run smoothly. You and your friends and family can relax into your holiday with amenities such as 1 hot tub.

How many holiday rentals are there in Big Pine Key?

With 149 Expedia holiday rentals, you're guaranteed 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 holiday rentals like in Big Pine Key?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Big Pine Key. Holiday rentals feature extras like laundry facilities and kitchens so you'll have all the conveniences of home. If you're concerned about a sanitised environment, holiday rentals can offer a sense of security away from shared hotel lifts and busy reception areas while still allowing you to travel. You'll also get more space in a holiday rental than in a standard hotel, which makes a holiday rental a popular choice for a family trip.