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

Big Pine Key Vacation Rentals

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Our top choices for Big Pine Key vacation 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 CA $125
CA $335 total
includes taxes & fees
Sep 1 - Sep 2
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 CA $206
CA $476 total
includes taxes & fees
Sep 22 - Sep 23
🌴 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 CA $277
CA $418 total
includes taxes & fees
Aug 27 - Aug 28
Star Room Barnacle Resort

4. 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 CA $285
CA $831 total
includes taxes & fees
Sep 8 - Sep 9
Charming 3-bedroom house in Big Pine Key near Beach and Key West

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 CA $248
CA $531 total
includes taxes & fees
Aug 27 - Aug 28
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 CA $455
CA $674 total
includes taxes & fees
Aug 27 - Aug 28
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 CA $556
CA $1,003 total
includes taxes & fees
Aug 27 - Aug 28
Treehouse Private Village Barnacle Resort

8. Ocean View Suite Barnacle Resort

Ocean View Suite Barnacle Resort
Long Beach Estates
The price is CA $476
CA $697 total
includes taxes & fees
Aug 27 - Aug 28
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 CA $122
CA $332 total
includes taxes & fees
Sep 1 - Sep 2
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 CA $157
CA $388 total
includes taxes & fees
Sep 13 - Sep 14
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 CA $173
CA $704 total
includes taxes & fees
Sep 4 - Sep 5
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, (1,225 reviews)
"The rooms are always clean, no bugs, and walking distance to Sunset Grill."
United States
Cristina
The price is CA $95
CA $137 total
includes taxes & fees
Sep 1 - Sep 2
Knight's Key Suites

13. Tropical Cottages

Tropical Cottages
3.0 star property
Marathon
8.6 out of 10, Excellent, (997 reviews)
"A/c was amazing, clean and beautiful cabins."
Canada
Natasha
The price is CA $125
CA $140 total
includes taxes & fees
Sep 2 - Sep 3
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 CA $178
CA $256 total
includes taxes & fees
Sep 9 - Sep 10
Skipjack Resort & Marina

15. 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 CA $183
CA $245 total
includes taxes & fees
Sep 16 - Sep 17
Bluegreen Vacations Hammocks at Marathon, Ascend Collection Resort

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 CA $268
CA $696 total
includes taxes & fees
Aug 31 - Sep 1
Kelly's Kabin - Adorable Private Summerland Key Cottage

17. 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 CA $232
CA $783 total
includes taxes & fees
Aug 27 - Aug 28
Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access

18. 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 CA $261
CA $811 total
includes taxes & fees
Aug 31 - Sep 1
Charming 2-bedroom house with WiFi, AC in lovely Cudjoe Key

19. 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 CA $138
CA $331 total
includes taxes & fees
Aug 31 - Sep 1
Venture Out RV lot 223

20. 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 CA $240
CA $787 total
includes taxes & fees
Sep 1 - Sep 2
Updated 2BR/2BA Venture Out Home w/ Pool Access, Pet Friendly, Near Key West
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 vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation 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 or room. 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 vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . 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 . 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 vacation rental 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 vacation 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 short-term rentals, that won’t be hard to do.

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Frequently asked questions

Can I find vacation rentals in Big Pine Key?

Yes, there are vacation rentals in Big Pine Key close to Blue Hole, or you can go with 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 vacation rentals that Big Pine Key has to offer?

Sugarloaf Key RV Resort & Cottages: This vacation home rental near 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 vacation rental also comes with free parking to give you added peace of mind.

How many vacation rentals are there in Big Pine Key?

With 143 Expedia vacation rentals, you're sure 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 vacation rentals like in Big Pine Key?

Vacation rentals are privately owned properties you can stay in for several days or more in Big Pine Key. Vacation rentals feature amenities like laundry facilities and kitchens so you'll have a home away from home. If you're concerned about a clean environment, a vacation rental can provide a sense of security away from shared hotel elevators and busy reception areas while still allowing you to travel. You'll also get more space in a vacation rental than in a standard hotel, which makes a vacation rental a popular option for family trips.