Big Pine Key Holiday Rentals

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Holiday Rentals in Big Pine Key

Old Wooden Bridge Resort and Marina

2.5 star property
8.4 out of 10, Very good, (161)
"The houseboat was a delight. Super comfortable and a full kitchen. Very dog-friendly. The woman who checked us in was super nice, and the salt-water pool felt great!"
The price is AU$377
includes taxes & fees
25 Nov - 26 Nov
Old Wooden Bridge Resort and Marina

Tropical Caribbean Wonderland

9.2 out of 10, Wonderful, (77)
"The camper was clean and easy to find. There’s a bath/shower house 2campsites away. We enjoyed our stay."
Tropical Caribbean Wonderland

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 AU$1,093
includes taxes & fees
5 Dec - 6 Dec
Keys 3 Bedroom Corner Home near Beach & Key West

Ocean Front Beach Home on Semi Private Island Only Accessible by Boat

Ocean Front Beach Home on Semi Private Island Only Accessible by Boat

Aqua Lodge Rentals At Coconut Cay

3.5 star property
9.6 out of 10, Exceptional, (124)
"Clean, quiet. Balcony to the sea was a big plus. Everything was excellent."
The price is AU$514
includes taxes & fees
1 Dec - 2 Dec
Aqua Lodge Rentals At Coconut Cay

Skipjack Resort & Marina

3.0 star property
8.6 out of 10, Excellent, (1133)
"Large rooms, clean, quiet."
The price is AU$272
includes taxes & fees
26 Nov - 27 Nov
Skipjack Resort & Marina

Yacht Haven Marina

3.5 star property
9.8 out of 10, Exceptional, (92)
"Spent most of a week in one of the houseboats, it was super clean and comfortable. It was a real nice alternative to a hotel room, fun to watch the fish and manatee from the balcony and the view was awesome too, we will return!"
Yacht Haven Marina

Knight's Key Suites

3.0 star property
9.0 out of 10, Wonderful, (1064)
"I liked full kitchen. Balcony door dos not close, but it’s not a big deal. Location is central to Fla Keys. "
The price is AU$196
includes taxes & fees
9 Dec - 10 Dec
Knight's Key Suites

Tropical Cottages

3.0 star property
8.4 out of 10, Very good, (745)
"Great place. Clean rooms and great staff. Thanks for the hospitality. Highly recommended "
The price is AU$147
includes taxes & fees
5 Dec - 6 Dec
Tropical Cottages

Ocean Perch, Dock, Open Water Views, 80' Heated Pool, Tennis, 20 Min to Key West

9.0 out of 10, Wonderful, (184)
"Loved this ocean view property! Very nice location and very comfortable home!"
Ocean Perch, Dock, Open Water Views, 80' Heated Pool, Tennis, 20 Min to Key West

Cabins at Bonefish Bay

3.0 star property
10.0 out of 10, Exceptional, (22)
"Very quiet easy access,on the water free kayak and bike use will definitely stay here again only hour drive to key west but way more reasonable."
Cabins at Bonefish Bay

TA Beach, Pool, Marina, family friendly, Kitchen, Jacuzzi

9.4 out of 10, Exceptional, (184)
"Beautiful beach view. Turquoise blue water. Close to a lot of fun things to see, like the Dolphin Research Center and the Sea Turtle Hospital. "
TA Beach, Pool, Marina, family friendly, Kitchen, Jacuzzi

34’ Catamaran Sailboat

9.6 out of 10, Exceptional, (27)
"Overall it was a great experience."
34’ Catamaran Sailboat

Gated Community on Open Water with Dock, Heated Pool, Kayaks, Bikes

9.8 out of 10, Exceptional, (216)
"Property was clean and had everything to have an enjoyable stay."
The price is AU$1,115
includes taxes & fees
25 Nov - 26 Nov
Gated Community on Open Water with Dock, Heated Pool, Kayaks, Bikes

PF Pool Beach Kitchen Sleep 6, Hot Tub W&D Marina WiFi Parking

9.6 out of 10, Exceptional, (38)
"The property is right on a beach, although the beach is not great. Small and it was muddy and weedy when we were there, but it might have been due to the waves. The bungalow was clean and spacious. The only draw back is that the bathrooms are located upstairs and you have to climb circular stairs."
PF Pool Beach Kitchen Sleep 6, Hot Tub W&D Marina WiFi Parking

TJ1 Beach, Pool, Kitchen, Sleep 6, HotTub, W&D, Dock, BBQ, WiFi, Parking, Tennis

9.6 out of 10, Exceptional, (17)
"We enjoyed our stay at the keys. The pool was amazing! My favorite spot was sitting under the coconut tree gazing out over the ocean and watching the sunset."
TJ1 Beach, Pool, Kitchen, Sleep 6, HotTub, W&D, Dock, BBQ, WiFi, Parking, Tennis

Oceanside Paradise in the FL Keys Free Kayaks Bikes Wifi Outdoor BBQ Grill

9.8 out of 10, Exceptional, (198)
"The location was perfect and the unit was clean and comfortable. The key lime pie from the hosts was a nice touch."
Oceanside Paradise in the FL Keys Free Kayaks Bikes Wifi Outdoor BBQ Grill

Just 20 miles from Key West! Oceanfront, dockage, swimming pool

8.4 out of 10, Very good, (95)
"Great property. Brought our boat and had a great time. Quick drive to Key Wedt."
The price is AU$829
includes taxes & fees
22 Dec - 23 Dec
Just 20 miles from Key West! Oceanfront, dockage, swimming pool

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

9.0 out of 10, Wonderful, (54)
"Our trip was supposed to be a boys fishing trip but that was derailed by the hurricane. We were not able to reschedule the trip so my wife and I decided to come down for a private retreat. The house is much more than two people need but we had a great time. The morning views are spectacular. The only thing I would change would be the addition of a full size oven for those who like to cook at the house. "
The price is AU$2,066
includes taxes & fees
8 Dec - 9 Dec
One of the very few beach houses with a daily, rental license in the Keys.

Beautiful Coral Lagoon #12 - Waterfront - Boat Slips Available at the Marina

10.0 out of 10, Exceptional, (126)
"We enjoyed our stay at Coral Lagoon #12. The property was everything advertised. The townhome had comfortable beds, plenty of seating, and a nice kitchen with all the right pots and pans. We were able to keep the boat we rented right in front of the condo at no extra charge. There were good places to eat near by and it was a short drive to Key West. All in all a good trip."
Beautiful Coral Lagoon #12 - Waterfront - Boat Slips Available at the 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.
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Other types of properties in Big Pine Key you may be interested in

Old Wooden Bridge Resort and Marina

2.5 star property
8.4 out of 10, Very good, (161)
"The houseboat was a delight. Super comfortable and a full kitchen. Very dog-friendly. The woman who checked us in was super nice, and the salt-water pool felt great!"
The price is AU$377
includes taxes & fees
25 Nov - 26 Nov
Old Wooden Bridge Resort and Marina

Barnacle Bed and Breakfast

3.0 star property
8.2 out of 10, Very good, (16)
"The location of the property was great and we saw the key deer on property and nearby. The room and bathroom were very nicely decorated and clean. The bed was comfortable. The beach front area had some trash that needed to be picked up and the home could use some landscaping. We did not stay for the continental breakfast so can not speak to that. Check in was a little challenging; I did not receive the e-mail day before check-in that I was expecting but did receive a phone call. However,...
The price is AU$481
includes taxes & fees
17 Dec - 18 Dec
Barnacle Bed and Breakfast

Tropical Caribbean Wonderland

9.2 out of 10, Wonderful, (77)
"The camper was clean and easy to find. There’s a bath/shower house 2campsites away. We enjoyed our stay."
Tropical Caribbean Wonderland
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.
Beautiful view of the beach with palm trees

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Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.

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?

Aqua Lodge Rentals At Coconut Cay: This holiday home rental outside of Big Pine Key is located near the beach, and offers an outdoor pool, air conditioning and daily housekeeping to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a full-sized fridge, a stovetop and a microwave. Our travellers also rate Tropical Caribbean Wonderland as a favourite home for rent in Big Pine Key.

How many holiday rentals are there in Big Pine Key?

With 141 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 Bahia Honda State Park are a couple of great spots to enjoy the outdoors. Other places in town to visit include Florida Keys Beaches 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.