A calm river with boats, lush greenery, and a clear blue sky.

Big Pine Key Holiday Rentals

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Our top choices for Big Pine Key holiday rentals

1. Old Wooden Bridge Resort and Marina

Old Wooden Bridge Resort and Marina
2.5 star property
Punta Brisa
8.6 out of 10, Excellent, (365 reviews)
"We stayed in the 2 bedroom condo. It was spacious and clean. We enjoyed our time there."
United States
Kathy
The price is NZ$410
includes taxes & fees
1 Sept - 2 Sept
Old Wooden Bridge Resort and Marina

2. 🌴 TROPICAL RETREAT 🌴 RV In The Keys

🌴 TROPICAL RETREAT 🌴 RV In The Keys
Big Pine Key
8.4 out of 10, Very good, (10 reviews)
"The RV was well outfitted with the essentials needed for the 2 days we stayed. It was dated, with some upkeep needed on the shower door and sofa but it was comfortable and clean. Heather was a pleasure to deal with, was responsive and communicated very well."
Canada
Graham B.
The price is NZ$542
includes taxes & fees
20 Aug - 21 Aug
🌴 TROPICAL RETREAT 🌴 RV In The Keys

3. Star Room Barnacle Resort

Star Room Barnacle Resort
Long Beach Estates
8.8 out of 10, Excellent, (5 reviews)
"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 NZ$510
includes taxes & fees
19 Aug - 20 Aug
Star Room Barnacle Resort

4. LARGE LOT & RV Fisherman Camp

LARGE LOT & RV Fisherman Camp
Big Pine Key
6.4 out of 10, (6 reviews)
"Property was as described, very comfortable and close to family on Summerland Key. Deer walking through the park was a nice perk"
United States
Pauline A.
The price is NZ$648
includes taxes & fees
16 Aug - 17 Aug
LARGE LOT & RV Fisherman Camp

5. Cozy 2-bedroom house in charming Big Pine Key with canal view and relaxing pool

Cozy 2-bedroom house in charming Big Pine Key with canal view and relaxing pool
Big Pine Key
10.0 out of 10, Exceptional, (5 reviews)
"Loved the pool and the porch! Only issue was the bugs on the porch at night, but we enjoyed it all day long. Also, kayaking was very calm and pleasant."
United States
Gretchen W.
The price is NZ$963
includes taxes & fees
16 Aug - 17 Aug
Cozy 2-bedroom house in charming Big Pine Key with canal view and relaxing pool

6. Beach View Room Dormitory Room Barnacle Resort

Beach View Room Dormitory Room Barnacle Resort
Long Beach Estates
The price is NZ$822
includes taxes & fees
16 Aug - 17 Aug
Beach View Room Dormitory Room Barnacle Resort

7. Treehouse Private Village Barnacle Resort

Treehouse Private Village Barnacle Resort
Long Beach Estates
8.6 out of 10, Excellent, (4 reviews)
"Communication from host is great. They left a bottle of wine and snacks for us to enjoy the beautiful sunsets. This place is so peaceful and clean. I would stay at this place again."
United States
Tina S.
The price is NZ$1,201
includes taxes & fees
19 Aug - 20 Aug
Treehouse Private Village Barnacle Resort

8. Fishermen's Paradise | Pool, 220' Dock & Open-Water Views

Fishermen's Paradise | Pool, 220' Dock & Open-Water Views
Big Pine Key
10.0 out of 10, Exceptional, (32 reviews)
"A beautiful house with everything you need to have a great time"
United States
David T.
Fishermen's Paradise | Pool, 220' Dock & Open-Water Views

9. Ocean View Suite Barnacle Resort

Ocean View Suite Barnacle Resort
Long Beach Estates
The price is NZ$848
includes taxes & fees
18 Aug - 19 Aug
Ocean View Suite Barnacle Resort

10. Yacht Haven Marina

Yacht Haven Marina
3.5 star property
Marathon
9.8 out of 10, Exceptional, (349 reviews)
"Fantastic place! It was super clean and looked just like the photos. We would stay here again!"
United States
Clara
The price is NZ$407
includes taxes & fees
7 Sept - 8 Sept
Yacht Haven Marina

11. Aqua Lodge Rentals At Coconut Cay

Aqua Lodge Rentals At Coconut Cay
3.5 star property
Marathon
9.6 out of 10, Exceptional, (232 reviews)
"I never give 5 stars but it was as advertised and good pricing and fun little spot. Keep it up folks.."
Canada
Wesley
The price is NZ$476
includes taxes & fees
13 Sept - 14 Sept
Aqua Lodge Rentals At Coconut Cay

12. Affordable Dog Friendly Keys Retreat in Venture Out Near Key West

Affordable Dog Friendly Keys Retreat in Venture Out Near Key West
Cudjoe Key
The price is NZ$838
includes taxes & fees
4 Sept - 5 Sept
Affordable Dog Friendly Keys Retreat in Venture Out Near Key West

13. Knight's Key Suites

Knight's Key Suites
3.0 star property
Marathon
9.0 out of 10, Wonderful, (1,220 reviews)
"The rooms are always clean, no bugs, and walking distance to Sunset Grill."
United States
Cristina
The price is NZ$170
includes taxes & fees
3 Sept - 4 Sept
Knight's Key Suites

14. Skipjack Resort & Marina

Skipjack Resort & Marina
3.0 star property
Marathon
8.6 out of 10, Excellent, (1,287 reviews)
"We're very happy & please with the hotel"
United States
Barbara
The price is NZ$323
includes taxes & fees
1 Sept - 2 Sept
Skipjack Resort & Marina

15. Tropical Cottages

Tropical Cottages
3.0 star property
Marathon
8.6 out of 10, Excellent, (993 reviews)
"Very well kept-nice cottage! Would book again!"
United States
Susan
The price is NZ$172
includes taxes & fees
16 Aug - 17 Aug
Tropical Cottages

16. Kelly's Kabin - Adorable Private Summerland Key Cottage

Kelly's Kabin - Adorable Private Summerland Key Cottage
Summerland Key
9.8 out of 10, Exceptional, (128 reviews)
"Very nice place. Centrally located near good restaurants, markets, etc.. Pet friendly which worked for us. Nice long walking trail behind cottage."
United States
John B.
The price is NZ$894
includes taxes & fees
29 Aug - 30 Aug
Kelly's Kabin - Adorable Private Summerland Key Cottage

17. Bluegreen Vacations Hammocks at Marathon, Ascend Collection Resort

Bluegreen Vacations Hammocks at Marathon, Ascend Collection Resort
2.5 star property
Marathon
9.0 out of 10, Wonderful, (142 reviews)
"This was the perfect place, right on the ocean and a full kitchen so you can cook your own meals. The room was very clean, I loved that they had a laundry basket and laundry detergent in the room for you, came in handy seeing as we stayed for 7 days. Amazing place to watch the sunset from a hammock and we got lucky enough to see some nurse sharks at the docks right outside of our hotel."
United States
Andrew Jackson
The price is NZ$338
includes taxes & fees
10 Sept - 11 Sept
Bluegreen Vacations Hammocks at Marathon, Ascend Collection Resort

18. SAVE BIG $$$ AUG/SEPT. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

SAVE BIG $$$ AUG/SEPT. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
9.6 out of 10, Exceptional, (95 reviews)
"Great location, very clean, and a responsive host. We enjoyed our stay and highly recommended this spot!"
United States
David T.
The price is NZ$733
includes taxes & fees
20 Aug - 21 Aug
SAVE BIG $$$ AUG/SEPT. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

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

Charming 2-bedroom house with WiFi, AC in lovely Cudjoe Key
Cudjoe Key
10.0 out of 10, Exceptional, (5 reviews)
"Property was perfectly located and very clean and comfortable."
United States
Kiara
The price is NZ$976
includes taxes & fees
26 Aug - 27 Aug
Charming 2-bedroom house with WiFi, AC in lovely Cudjoe Key

20. Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access

Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access
Cudjoe Key
10.0 out of 10, Exceptional, (1 review)
"Excellent location - clean, quiet, well-kept community. Boat launch was key for us. Pool and beach looked very nice, but we didn't use. The unit is as described and has a nice patio out back that we used every day."
United States
Cheryl V.
The price is NZ$955
includes taxes & fees
16 Aug - 17 Aug
Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access
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

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Big Pine Key holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Big Pine Key. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Big Pine Key. Seeing all the best attractions is bound to make you fall in love with Big Pine Key. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Big Pine Key short-term rentals, that won’t be hard to do.

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?

Sugarloaf Key RV Resort & Cottages: This holiday home rental outside of Big Pine Key is located near a metro station, and offers an outdoor pool, air conditioning and free WiFi to help you feel perfectly comfortable in your new surroundings. This holiday rental also comes with free parking to give you added peace of mind.

How many holiday rentals are there in Big Pine Key?

With 143 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 Florida Keys Beaches and Calusa Beach 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.