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Top Holiday Rentals in Big Pine Key

🌴 TROPICAL RETREAT 🌴 RV in the Keys

The price is £247
includes taxes & fees
13 Jul - 14 Jul
🌴 TROPICAL RETREAT 🌴 RV in the Keys

Keys 3 Bedroom Corner Home near Beach & Key West

9.6 out of 10, Exceptional, (8)
"Great location, right in the middle keys, easy access to everything. "
The price is £494
includes taxes & fees
11 Jul - 12 Jul
Keys 3 Bedroom Corner Home near Beach & Key West

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

The price is £554
includes taxes & fees
29 Jul - 30 Jul
Charming 3-bedroom house in Big Pine Key near Beach and Key West

Ocean View Suite Barnacle Resort

The price is £470
includes taxes & fees
6 Aug - 7 Aug
Ocean View Suite Barnacle Resort

Beautiful Home in Key Colony Beach! Private Pool. Dock. Tiki Hut

8.8 out of 10, Excellent, (90)
"We enjoyed the property."
The price is £1,072
includes taxes & fees
19 Jul - 20 Jul
Beautiful Home in Key Colony Beach! Private Pool. Dock. Tiki Hut

Old Florida Style, wrap around porch, boat basin for dockage, open water

9.6 out of 10, Exceptional, (76)
"Very nice place to stay. Quick and efficient communication with host! Seemless check in and check out process. "
The price is £666
includes taxes & fees
2 Aug - 3 Aug
Old Florida Style, wrap around porch, boat basin for dockage, open water

One of the very few beach houses with a daily, rental license in the Keys.

8.8 out of 10, Excellent, (62)
"The house is special, it transmits a lot of peace next to that spectacular dock where the fishing is fabulous, everything is very clean and well equipped with cauldrons etc.I will be back 100%"
The price is £990
includes taxes & fees
18 Jul - 19 Jul
One of the very few beach houses with a daily, rental license in the Keys.

Kelly's Kabin - Adorable Private Summerland Key Cottage

9.8 out of 10, Exceptional, (117)
"This was our second time staying here. Feels very secluded although it's right off the highway. We saw many Key deer on our way to No Name Pub , including babies who thougt we should feed them) (We did not feed them). Highly recommend!"
The price is £371
includes taxes & fees
11 Jul - 12 Jul
Kelly's Kabin - Adorable Private Summerland Key Cottage

Stunning Ocean Views! 2BR Waterfront Home w/ Dock in Gated Keys Community

9.8 out of 10, Exceptional, (8)
"Venture Out is a gated community in Cudjoe Key. The house was very clean and had everything you need to make yourself comfortable. We visited Key West which is about 30 minutes by car. Great place to stay"
The price is £691
includes taxes & fees
11 Jul - 12 Jul
Stunning Ocean Views! 2BR Waterfront Home w/ Dock in Gated Keys Community

Keys to Paradise #95 - 56' Dock & Ocean Views!

9.8 out of 10, Exceptional, (141)
"Very clean cottage right on the corner of the harbor and the canal. Wonderful views!"
The price is £720
includes taxes & fees
24 Jul - 25 Jul
Keys to Paradise #95 - 56' Dock & Ocean Views!

Salty Breeze #161 - Canal Front Venture Out Home on Cudjoe Key

2.0 star property
9.0 out of 10, Wonderful, (4)
"Place was perfect for our trip. Staff was super nice and helpful as well. "
The price is £642
includes taxes & fees
12 Jul - 13 Jul
Salty Breeze #161 - Canal Front Venture Out Home on Cudjoe Key

Sailfish Haven #390 - Ocean Views, 35' seawall

8.8 out of 10, Excellent, (6)
"We really enjoyed our stay. The home was exactly as advertised which we definitely appreciated. It was nice to have the kitchen with a wine opener and decent dishes. Being on the water was a plus for our cousin specifically but enjoyed by all. We sat on the back deck morning and night. It was fun to watch the pelicans and boats. Definitely highly recommend. "
The price is £489
includes taxes & fees
15 Jul - 16 Jul
Sailfish Haven #390 - Ocean Views, 35' seawall

Post Card Point #319 - Ocean Views!

10.0 out of 10, Exceptional, (47)
"Really nice super clean & modern house with a great view. Lots of space. The community it’s in was very nice and quiet."
The price is £625
includes taxes & fees
22 Jul - 23 Jul
Post Card Point #319 - Ocean Views!

Reel Island Retreat #273 at Venture Out in the Florida Keys

9.4 out of 10, Exceptional, (6)
"The staff at Venture one was absolutely amazing. The home we stayed in was also a great location. Dated but clean. Definitely will stay at Venture again !"
The price is £482
includes taxes & fees
10 Jul - 11 Jul
Reel Island Retreat #273 at Venture Out in the Florida Keys

Oceanfront 2BR in Venture Out | 35' Dock, Sunrise Views, Coastal Charm

The price is £868
includes taxes & fees
10 Jul - 11 Jul
Oceanfront 2BR in Venture Out | 35' Dock, Sunrise Views, Coastal Charm

WATERFRONT PARADISE AT VENTURE OUT+4 BIKES & 2-2 SEAT KAYAKS! KING & QUEEN BEDS

9.6 out of 10, Exceptional, (95)
"Really great, friendly community with lots of activities and a great view of the beach. Would definitely be on my list for another visit soon."
The price is £399
includes taxes & fees
23 Jul - 24 Jul
WATERFRONT PARADISE AT VENTURE OUT+4 BIKES & 2-2 SEAT KAYAKS! KING & QUEEN BEDS

Blue Lobster Lodge - Venture Out #543 - Cudjoe Key

2.5 star property
9.6 out of 10, Exceptional, (5)
"A cozy, clean, and great stay in Cudjoe! Only 30 mins from Key West."
The price is £467
includes taxes & fees
10 Jul - 11 Jul
Blue Lobster Lodge - Venture Out #543 - Cudjoe Key

Little Piece of Paradise #233 - 35' Seawall - Cudjoe Key

The price is £467
includes taxes & fees
10 Jul - 11 Jul
Little Piece of Paradise #233 - 35' Seawall - Cudjoe Key

Spanish Queen @Venture Out, Cudjoe Key

9.4 out of 10, Exceptional, (18)
"This is our second time staying at this property and everything was just as good as the first time!"
The price is £510
includes taxes & fees
14 Jul - 15 Jul
Spanish Queen @Venture Out, Cudjoe Key

OCEAN PARADISE AT VENTURE OUT + 4 BIKES & 2-2 PERSON KAYAKS! KING & QUEEN BEDS!

9.8 out of 10, Exceptional, (80)
"Great atmosphere, right on a canal. A perfect and comfortable home!"
The price is £375
includes taxes & fees
11 Jul - 12 Jul
OCEAN PARADISE AT VENTURE OUT + 4 BIKES & 2-2 PERSON KAYAKS! KING & QUEEN BEDS!
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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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 148 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.