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, (366 reviews)
"Love being on the water in the houseboat. The dark skies were nice for stargazing"
United States
Lisa
The price is AU$337
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 AU$451
includes taxes & fees
25 Aug - 26 Aug
🌴 TROPICAL RETREAT 🌴 RV In The Keys

3. 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 AU$435
includes taxes & fees
25 Aug - 26 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 AU$525
includes taxes & fees
25 Aug - 26 Aug
LARGE LOT & RV Fisherman Camp

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 AU$787
includes taxes & fees
25 Aug - 26 Aug
Charming 3-bedroom house in Big Pine Key near Beach and Key West

6. Beach View Room Dormitory Room Barnacle Resort

Beach View Room Dormitory Room Barnacle Resort
Long Beach Estates
The price is AU$664
includes taxes & fees
25 Aug - 26 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 AU$1,012
includes taxes & fees
27 Aug - 28 Aug
Treehouse Private Village Barnacle Resort

8. Ocean View Suite Barnacle Resort

Ocean View Suite Barnacle Resort
Long Beach Estates
The price is AU$700
includes taxes & fees
25 Aug - 26 Aug
Ocean View Suite Barnacle Resort

9. Yacht Haven Marina

Yacht Haven Marina
3.5 star property
Marathon
9.8 out of 10, Exceptional, (353 reviews)
"Fantastic place! It was super clean and looked just like the photos. We would stay here again!"
United States
Clara
The price is AU$334
includes taxes & fees
1 Sept - 2 Sept
Yacht Haven Marina

10. 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 AU$391
includes taxes & fees
13 Sept - 14 Sept
Aqua Lodge Rentals At Coconut Cay

11. 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 AU$709
includes taxes & fees
4 Sept - 5 Sept
Affordable Dog Friendly Keys Retreat in Venture Out Near Key West

12. Knight's Key Suites

Knight's Key Suites
3.0 star property
Marathon
9.0 out of 10, Wonderful, (1,224 reviews)
"The rooms are always clean, no bugs, and walking distance to Sunset Grill."
United States
Cristina
The price is AU$138
includes taxes & fees
3 Sept - 4 Sept
Knight's Key Suites

13. Tropical Cottages

Tropical Cottages
3.0 star property
Marathon
8.6 out of 10, Excellent, (996 reviews)
"A/c was amazing, clean and beautiful cabins."
Canada
Natasha
The price is AU$141
includes taxes & fees
2 Sept - 3 Sept
Tropical Cottages

14. Skipjack Resort & Marina

Skipjack Resort & Marina
3.0 star property
Marathon
8.6 out of 10, Excellent, (1,289 reviews)
"Great spot"
Canada
Justin
The price is AU$261
includes taxes & fees
1 Sept - 2 Sept
Skipjack Resort & Marina

15. 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 AU$787
includes taxes & fees
25 Aug - 26 Aug
Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access

16. 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, (143 reviews)
"Amazing stay "
United States
Anthony
The price is AU$247
includes taxes & fees
15 Sept - 16 Sept
Bluegreen Vacations Hammocks at Marathon, Ascend Collection Resort

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

Charming 2-bedroom house with WiFi, AC in lovely Cudjoe Key
Cudjoe Key
9.8 out of 10, Exceptional, (6 reviews)
"Property was perfectly located and very clean and comfortable."
United States
Kiara
The price is AU$804
includes taxes & fees
25 Aug - 26 Aug
Charming 2-bedroom house with WiFi, AC in lovely Cudjoe Key

18. 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 AU$687
includes taxes & fees
31 Aug - 1 Sept
Kelly's Kabin - Adorable Private Summerland Key Cottage

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 AU$788
includes taxes & fees
1 Sept - 2 Sept
Updated 2BR/2BA Venture Out Home w/ Pool Access, Pet Friendly, Near Key West

20. Little Piece of Paradise #233 Waterfront Cottage with Dock, Pool & Canal Views

Little Piece of Paradise #233 Waterfront Cottage with Dock, Pool & Canal Views
Cudjoe Key
9.0 out of 10, Wonderful, (2 reviews)
"This was a sweet little modular home that gave us a clean and comfortable place to stay… away from the tourist scene."
United States
Nora Kay F.
The price is AU$797
includes taxes & fees
25 Aug - 26 Aug
Little Piece of Paradise #233 Waterfront Cottage with Dock, Pool & Canal Views
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

Everything you need to know about Big Pine Key holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Big Pine Key holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Big Pine Key holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Big Pine Key holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Big Pine Key. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Big Pine Key holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Big Pine Key holiday rentals we have selected for you start as low as AU$138 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Big Pine Key rentals

At Expedia, we put the best Big Pine Key holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Big Pine Key rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Big Pine Key holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Big Pine Key. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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.