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

Big Pine Key Holiday Rentals

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Check prices for these dates

In two weeks
18 Sept - 20 Sept
In two months
30 Oct - 1 Nov
In three months
27 Nov - 29 Nov
In four months
25 Dec - 27 Dec

Our top choices for Big Pine Key holiday rentals

Living area

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, (367 reviews)
"Love being on the water in the houseboat. The dark skies were nice for stargazing"
United States
Lisa
The price is HK$706
HK$1,896 total
includes taxes & fees
7 Sept - 8 Sept
Old Wooden Bridge Resort and Marina
Interior

2. 🌴 TROPICAL RETREAT 🌴 RV In The Keys

🌴 TROPICAL RETREAT 🌴 RV In The Keys
Big Pine Key
8.6 out of 10, Excellent, (11 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 HK$1,168
HK$2,691 total
includes taxes & fees
22 Sept - 23 Sept
🌴 TROPICAL RETREAT 🌴 RV In The Keys
Terrace/patio

3. 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 HK$1,404
HK$2,988 total
includes taxes & fees
7 Sept - 8 Sept
LARGE LOT & RV Fisherman Camp
Interior

4. Star Room Barnacle Resort

Star Room Barnacle Resort
Long Beach Estates
9.0 out of 10, Wonderful, (6 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 HK$1,639
HK$2,439 total
includes taxes & fees
9 Sept - 10 Sept
Star Room Barnacle Resort
Interior

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

Charming 3-bedroom house in Big Pine Key near Beach and Key West
Sands
8.4 out of 10, Very good, (15 reviews)
"This place was perfect for our family. Just the right distance between Marathon and Key West. Would definitely recommend it to anyone looking for a place to stay"
United States
Robert C.
The price is HK$2,109
HK$5,286 total
includes taxes & fees
14 Sept - 15 Sept
Charming 3-bedroom house in Big Pine Key near Beach and Key West
Interior

6. Beach View Room Dormitory Room Barnacle Resort

Beach View Room Dormitory Room Barnacle Resort
Long Beach Estates
The price is HK$2,580
HK$3,791 total
includes taxes & fees
9 Sept - 10 Sept
Beach View Room Dormitory Room Barnacle Resort
Interior

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 HK$3,152
HK$5,612 total
includes taxes & fees
9 Sept - 10 Sept
Treehouse Private Village Barnacle Resort
Interior

8. Ocean View Suite Barnacle Resort

Ocean View Suite Barnacle Resort
Long Beach Estates
The price is HK$2,697
HK$3,911 total
includes taxes & fees
9 Sept - 10 Sept
Ocean View Suite Barnacle Resort
Premium bedding, soundproofing, iron/ironing board, free WiFi

9. Knight's Key Suites

Knight's Key Suites
3.0 star property
Marathon
9.0 out of 10, Wonderful, (1,229 reviews)
"It was absolutely amazing.We'll definitely stay there again"
United States
Jessica
The price is HK$540
HK$776 total
includes taxes & fees
10 Sept - 11 Sept
Knight's Key Suites
Exterior

10. Yacht Haven Marina

Yacht Haven Marina
3.5 star property
Marathon
9.8 out of 10, Exceptional, (356 reviews)
"Fantastic place! It was super clean and looked just like the photos. We would stay here again!"
United States
Clara
The price is HK$706
HK$1,896 total
includes taxes & fees
13 Sept - 14 Sept
Yacht Haven Marina
Exterior

11. Tropical Cottages

Tropical Cottages
3.0 star property
Marathon
8.6 out of 10, Excellent, (998 reviews)
"A/c was amazing, clean and beautiful cabins."
Canada
Natasha
The price is HK$706
HK$794 total
includes taxes & fees
8 Sept - 9 Sept
Tropical Cottages
Outdoor pool, pool loungers

12. Skipjack Resort & Marina

Skipjack Resort & Marina
3.0 star property
Marathon
8.6 out of 10, Excellent, (1,290 reviews)
"Great spot"
Canada
Justin
The price is HK$1,122
HK$1,580 total
includes taxes & fees
8 Sept - 9 Sept
Skipjack Resort & Marina
BBQ/picnic Area

13. 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)
"Cleanness relaxing location, nice views, good air conditioning"
United States
Hakan
The price is HK$781
HK$2,069 total
includes taxes & fees
7 Sept - 8 Sept
Aqua Lodge Rentals At Coconut Cay
Beach

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

Affordable Dog Friendly Keys Retreat in Venture Out Near Key West
Cudjoe Key
10.0 out of 10, Exceptional, (1 review)
"This property was meticulously clean and perfect for us. The property was decorated well-very home-like feel. The communication with the host was prompt and they answered all questions asked. In addition, we loved that we could bring our fur-babies (dogs) to the property with us. We highly recommend this property!"
United States
Elena S.
The price is HK$980
HK$4,003 total
includes taxes & fees
11 Sept - 12 Sept
Affordable Dog Friendly Keys Retreat in Venture Out Near Key West
Exterior

15. SAVE BIG $$$ SEPT/OCT. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

SAVE BIG $$$ SEPT/OCT. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
9.4 out of 10, Exceptional, (111 reviews)
"$125.00 extra charge when arriving. Almost all the remotes needed batteries. Furniture was all shoved up against walls, everything needed to be set back up. Kayaks were under house buried under a massive amount of junk and covered with sand and debris. A/C worked on and off. A/c window unit drain poured water on steps down to sea wall making them very slippery all the time. May have been a very nice place years ago but really shows its age and poor maintenance. Did not feel like calling the...
United States
Ken
The price is HK$1,011
HK$3,179 total
includes taxes & fees
8 Sept - 9 Sept
SAVE BIG $$$ SEPT/OCT. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Coffee/tea maker, fridge, microwave, oven

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 HK$1,552
HK$3,986 total
includes taxes & fees
8 Sept - 9 Sept
Kelly's Kabin - Adorable Private Summerland Key Cottage
Exterior

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

SAVE BIG $$$ SEPT/OCT. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
9.8 out of 10, Exceptional, (96 reviews)
"Great location, wonderful hosts!"
United States
Blue Mountain Footwear F.
The price is HK$1,168
HK$3,379 total
includes taxes & fees
7 Sept - 8 Sept
SAVE BIG $$$ SEPT/OCT. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Property grounds

18. Venture Out RV lot 223

Venture Out RV lot 223
Cudjoe key
7.4 out of 10, Good, (3 reviews)
"We really like the location."
United States
Zunen C.
The price is HK$784
HK$1,886 total
includes taxes & fees
7 Sept - 8 Sept
Venture Out RV lot 223
A heated pool

19. Updated 2BR/2BA Venture Out Home w/ Pool Access, Pet Friendly, Near Key West

Updated 2BR/2BA Venture Out Home w/ Pool Access, Pet Friendly, Near Key West
Cudjoe Key
8.0 out of 10, Very good, (3 reviews)
" Great 2 bedroom home in a lovely vacation community . We enjoyed the 2 recliners to relax after a full day of exploring as well as in the morning with our coffee. The screened in patio was a nice perk as well . At check in , a calendar of events was provided and the staff were friendly and helpful. FYI : We enjoyed a gorgeous sunrise right by the beach near the pool ."
United States
jim b.
The price is HK$1,358
HK$4,445 total
includes taxes & fees
8 Sept - 9 Sept
Updated 2BR/2BA Venture Out Home w/ Pool Access, Pet Friendly, Near Key West
Terrace/patio

20. Canal Front home with easy Ocean access

Canal Front home with easy Ocean access
Cudjoe Key
8.6 out of 10, Excellent, (188 reviews)
"Very nice property, as advertised. Great location for boating and fishing. "
United States
Lawrence L.
The price is HK$1,294
HK$2,968 total
includes taxes & fees
9 Sept - 10 Sept
Canal Front home with easy Ocean 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

Faro Blanco Resort Marathon Florida Keys, Curio by Hilton

Faro Blanco Resort Marathon Florida Keys, Curio by Hilton

10/10 Excellent
"Very nice pools. Staff was great. We will be returning."
Gregory 3-night trip
Posted 12 hours ago
Faro Blanco Resort Marathon Florida Keys, Curio by Hilton

Find out more about Big Pine Key

Search for holiday rentals in Big Pine Key on Expedia! You can easily find your home rentals, villas, holiday apartments in Big Pine Key using one of the methods below:

  • View our selection of featured holiday rentals in Big Pine Key
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  • Enter your travel dates to view the best deals on holiday rentals in Big Pine Key while they last

Look no further and take a look at our great range of rental properties in Big Pine Key!

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 145 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.