Big Pine Key Holiday Rentals

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Holiday Rentals in Big Pine Key

🌴 TROPICAL RETREAT 🌴 RV in the Keys

The price is NZ$525
includes taxes & fees
28 June - 29 June
🌴 TROPICAL RETREAT 🌴 RV in the Keys

Keys 3 Bedroom Corner Home near Beach & Key West

9.8 out of 10, Exceptional, (7)
"We stayed for four nights. They have ample beds, a nice tv, a large kitchen, and many parking spots. There are not many walkable beaches but there is a couple of good restaurants nearby. We had a great time, everything was nice, and everything was as listed. I would rent again. "
The price is NZ$1,138
includes taxes & fees
28 June - 29 June
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 NZ$1,221
includes taxes & fees
8 July - 9 July
Charming 3-bedroom house in Big Pine Key near Beach and Key West

Ocean View Suite Barnacle Resort

The price is NZ$1,280
includes taxes & fees
1 July - 2 July
Ocean View Suite Barnacle Resort

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

8.8 out of 10, Excellent, (89)
"We enjoyed the property."
The price is NZ$2,344
includes taxes & fees
19 July - 20 July
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, (75)
"Very nice place to stay. Quick and efficient communication with host! Seemless check in and check out process. "
The price is NZ$1,465
includes taxes & fees
28 June - 29 June
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 NZ$2,295
includes taxes & fees
18 July - 19 July
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, (116)
"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 NZ$803
includes taxes & fees
28 June - 29 June
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 NZ$1,519
includes taxes & fees
9 July - 10 July
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 NZ$1,689
includes taxes & fees
28 June - 29 June
Keys to Paradise #95 - 56' Dock & Ocean Views!

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

2.0 star property
9.4 out of 10, Exceptional, (3)
"Place was perfect for our trip. Staff was super nice and helpful as well. "
The price is NZ$1,395
includes taxes & fees
22 July - 23 July
Salty Breeze #161 - Canal Front Venture Out Home on Cudjoe Key

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 NZ$1,304
includes taxes & fees
1 July - 2 July
Post Card Point #319 - Ocean Views!

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

9.2 out of 10, Wonderful, (5)
"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 NZ$1,058
includes taxes & fees
10 July - 11 July
Reel Island Retreat #273 at Venture Out in the Florida Keys

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

9.6 out of 10, Exceptional, (93)
"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 NZ$773
includes taxes & fees
29 June - 30 June
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
9.4 out of 10, Exceptional, (3)
"The Blue Lobster is a gem. Clean, cute, enough room to spread out and every extra provided to make your stay comfortable. Community is friendly and has a nice pool, hot tubs and pickle ball courts. Loved it here. "
The price is NZ$1,005
includes taxes & fees
30 June - 1 July
Blue Lobster Lodge - Venture Out #543 - Cudjoe Key

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

The price is NZ$989
includes taxes & fees
28 June - 29 June
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 NZ$1,133
includes taxes & fees
14 July - 15 July
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 NZ$821
includes taxes & fees
11 July - 12 July
OCEAN PARADISE AT VENTURE OUT + 4 BIKES & 2-2 PERSON KAYAKS! KING & QUEEN BEDS!

Charming 2-bedroom house with WiFi, AC in lovely Cudjoe Key

The price is NZ$608
includes taxes & fees
29 June - 30 June
Charming 2-bedroom house with WiFi, AC in lovely Cudjoe Key

Island Time #110 Ocean Views - Cudjoe Key

2.5 star property
9.4 out of 10, Exceptional, (3)
"The house was lovely and the view outstanding. We had fun fishing, swimming, and talking to neighbors. Thank you for your hospitality. "
The price is NZ$1,026
includes taxes & fees
10 July - 11 July
Island Time #110 Ocean Views - Cudjoe Key
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 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.