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, (373 reviews)
"Best stop over before going to Key west. We enjoyed here a lot, parking our trailer was never a problem."
United States
Daisybel
The price is NZ$632
includes taxes & fees
1 Oct - 2 Oct
Old Wooden Bridge Resort and Marina

2. 🌴 TROPICAL RETREAT 🌴 RV In The Keys

🌴 TROPICAL RETREAT 🌴 RV In The Keys
Big Pine Key
8.6 out of 10, Excellent, (11 reviews)
"Its clean and plenty of room.Outdoor seating is wonderful. Could use a gas grill. But definitely a great place."
United States
DeeBrett
The price is NZ$597
includes taxes & fees
19 Oct - 20 Oct
🌴 TROPICAL RETREAT 🌴 RV In The Keys

3. 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 NZ$1,121
includes taxes & fees
1 Oct - 2 Oct
Charming 3-bedroom house in Big Pine Key near Beach and Key West

4. Star Room Barnacle Resort

Star Room Barnacle Resort
Long Beach Estates
8.0 out of 10, Very good, (7 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$618
includes taxes & fees
1 Oct - 2 Oct
Star Room Barnacle Resort

5. 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$667
includes taxes & fees
1 Oct - 2 Oct
LARGE LOT & RV Fisherman Camp

6. Beach View Room Dormitory Room Barnacle Resort

Beach View Room Dormitory Room Barnacle Resort
Long Beach Estates
The price is NZ$873
includes taxes & fees
1 Oct - 2 Oct
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$1,261
includes taxes & fees
1 Oct - 2 Oct
Treehouse Private Village Barnacle Resort

8. Ocean View Suite Barnacle Resort

Ocean View Suite Barnacle Resort
Long Beach Estates
The price is NZ$924
includes taxes & fees
6 Oct - 7 Oct
Ocean View Suite Barnacle Resort

9. Knight's Key Suites

Knight's Key Suites
3.0 star property
Marathon
9.0 out of 10, Wonderful, (1,236 reviews)
"Clean room with exceptional hospitality"
United States
chantal
The price is NZ$194
includes taxes & fees
12 Oct - 13 Oct
Knight's Key Suites

10. 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 NZ$324
includes taxes & fees
1 Oct - 2 Oct
Skipjack Resort & Marina

11. Yacht Haven Marina

Yacht Haven Marina
3.5 star property
Marathon
9.6 out of 10, Exceptional, (364 reviews)
"Clean Friendly staff Recommend for family"
United States
Yamei
The price is NZ$553
includes taxes & fees
19 Oct - 20 Oct
Yacht Haven Marina

12. Bluegreen Vacations Hammocks at Marathon, Ascend Collection Resort

Bluegreen Vacations Hammocks at Marathon, Ascend Collection Resort
2.5 star property
Marathon
9.2 out of 10, Wonderful, (145 reviews)
"It is an excellent place."
United States
Arianna
The price is NZ$385
includes taxes & fees
1 Oct - 2 Oct
Bluegreen Vacations Hammocks at Marathon, Ascend Collection Resort

13. 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
3 Oct - 4 Oct
Kelly's Kabin - Adorable Private Summerland Key Cottage

14. Aqua Lodge Rentals At Coconut Cay

Aqua Lodge Rentals At Coconut Cay
3.5 star property
Marathon
9.6 out of 10, Exceptional, (235 reviews)
"Never stayed in a houseboat before. It was a novel experience!"
United States
Susan
The price is NZ$518
includes taxes & fees
4 Oct - 5 Oct
Aqua Lodge Rentals At Coconut Cay

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

SAVE BIG $$$ SEPT/OCT. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
9.4 out of 10, Exceptional, (112 reviews)
"Our family had an amazing time staying here! Our hosts were quick to answer any questions we had and the house was clean and fully stocked with everything you might need. Our favorite part was being able to sit out on the deck by the canal and see all the marine wildlife. We even had a little family of manatees hang out for awhile. Definitely would recommend staying here!"
United States
Mckayla S.
The price is NZ$784
includes taxes & fees
4 Oct - 5 Oct
SAVE BIG $$$ SEPT/OCT. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

16. Tropical Cottages

Tropical Cottages
3.0 star property
Marathon
8.6 out of 10, Excellent, (1,002 reviews)
"Cute little cottage perfect for couples had an amazing stay and will definitely be back to tropical cottages again"
United States
Aaron
The price is NZ$157
includes taxes & fees
4 Oct - 5 Oct
Tropical Cottages

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

SAVE BIG $$$ SEPT/OCT. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
9.8 out of 10, Exceptional, (97 reviews)
"Great location, wonderful hosts!"
United States
Blue Mountain Footwear F.
The price is NZ$721
includes taxes & fees
1 Oct - 2 Oct
SAVE BIG $$$ SEPT/OCT. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

18. Florida Keys Canal-Front 2BR/2BA w/ 35' Seawall, Dock & Spacious Comfort

Florida Keys Canal-Front 2BR/2BA w/ 35' Seawall, Dock & Spacious Comfort
Cudjoe Key
9.6 out of 10, Exceptional, (5 reviews)
"Stayed with family and good location for family vacations. "
United States
Phani U.
The price is NZ$910
includes taxes & fees
7 Oct - 8 Oct
Florida Keys Canal-Front 2BR/2BA w/ 35' Seawall, Dock & Spacious Comfort

19. Oceanview Paradise AT Venture Out+4 Bikes & 2-2 Seat Kayaks! King & Queen Beds!

Oceanview Paradise AT Venture Out+4 Bikes & 2-2 Seat Kayaks! King & Queen Beds!
Cudjoe Key
8.0 out of 10, Very good, (21 reviews)
"Heated pool was very nice, and location of rental."
United States
Angela C.
The price is NZ$903
includes taxes & fees
1 Oct - 2 Oct
Oceanview Paradise AT Venture Out+4 Bikes & 2-2 Seat Kayaks! King & Queen Beds!

20. Waterfront 2BR/2BA | 35' Seawall for 32' Boat | Beautiful Sunrises on Cudjoe Key

Waterfront 2BR/2BA | 35' Seawall for 32' Boat | Beautiful Sunrises on Cudjoe Key
Cudjoe Key
10.0 out of 10, Exceptional, (4 reviews)
"Pool area was nice but only visited it once as so much to see and do!"
United States
Karen
The price is NZ$954
includes taxes & fees
1 Oct - 2 Oct
Waterfront 2BR/2BA | 35' Seawall for 32' Boat | Beautiful Sunrises on 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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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. Our travellers also rate Charming 3-bedroom house in Big Pine Key near Beach and Key West as a favourite home for rent in Big Pine Key.

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 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.