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

Big Pine Key Vacation Rentals

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

Our top choices for Big Pine Key vacation rentals

A cozy room with a brown leather sofa, a white table, and a ceiling fan.

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, (380 reviews)
"Great view , clean room and excellent staff ( Mr. shaggy )"
United States
Jordan
$254 nightly
The price is $286
Nov 5 - Nov 6
Total with taxes and fees
Old Wooden Bridge Resort and Marina
A compact RV interior with a kitchenette, seating area, and a view of the outdoors.

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
$279 nightly
The price is $312
Nov 5 - Nov 6
Total with taxes and fees
🌴 TROPICAL RETREAT 🌴 RV In The Keys
A modern kitchen with a dishwasher, a dining area with a glass coffee table, and a ceiling fan.

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
8.0 out of 10, Very good, (17 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.
$511 nightly
The price is $571
Nov 9 - Nov 10
Total with taxes and fees
Charming 3-bedroom house in Big Pine Key near Beach and Key West
Terrace/patio

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.
$328 nightly
The price is $366
Nov 5 - Nov 6
Total with taxes and fees
LARGE LOT & RV Fisherman Camp
A hotel room with two beds, each with a wooden headboard, white bedding, and a bedside table with a lamp.

5. Knight's Key Suites

Knight's Key Suites
3.0 star property
Marathon
9.0 out of 10, Wonderful, (1,245 reviews)
"We had the pool view..Excellent!"
United States
Brandy
$112 nightly
The price is $123
Nov 29 - Nov 30
Total with taxes and fees
Knight's Key Suites
An outdoor seating area with wicker furniture and cushions, a thatched-roof structure, and lush greenery.

6. Tropical Cottages

Tropical Cottages
3.0 star property
Marathon
8.6 out of 10, Excellent, (1,013 reviews)
"The family running the food truck and tiki hut were great. Felt like we were guests in their home."
United States
Douglas
$119 nightly
The price is $134
Nov 10 - Nov 11
Total with taxes and fees
Tropical Cottages
A modern kitchen with white cabinets, a microwave, and a dining area with a table and chairs.

7. Yacht Haven Marina

Yacht Haven Marina
3.5 star property
Marathon
9.6 out of 10, Exceptional, (380 reviews)
"Loved staying in the aqua lodges, such a relaxing place."
United States
Lauren
$231 nightly
The price is $259
Nov 5 - Nov 6
Total with taxes and fees
Yacht Haven Marina
A pool area with multiple swimming pools, lounge chairs, and palm trees.

8. 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.
$342 nightly
The price is $382
Nov 5 - Nov 6
Total with taxes and fees
Affordable Dog Friendly Keys Retreat in Venture Out Near Key West
A covered outdoor area with wicker furniture and string lights.

9. 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
8.6 out of 10, Excellent, (4 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.
$389 nightly
The price is $434
Nov 11 - Nov 12
Total with taxes and fees
Updated 2BR/2BA Venture Out Home w/ Pool Access, Pet Friendly, Near Key West
A spacious living area with a gray sectional sofa, wooden beams, and a ceiling fan.

10. Aqua Lodge Rentals At Coconut Cay

Aqua Lodge Rentals At Coconut Cay
3.5 star property
Marathon
9.6 out of 10, Exceptional, (239 reviews)
"Never stayed in a houseboat before. It was a novel experience!"
United States
Susan
$228 nightly
The price is $256
Nov 5 - Nov 6
Total with taxes and fees
Aqua Lodge Rentals At Coconut Cay
A nighttime pool area with a clear view of the pool, surrounding palm trees, and a building with a sign.

11. Skipjack Resort & Marina

Skipjack Resort & Marina
3.0 star property
Marathon
8.6 out of 10, Excellent, (1,296 reviews)
"Great spot"
Canada
Justin
$199 nightly
The price is $224
Nov 15 - Nov 16
Total with taxes and fees
Skipjack Resort & Marina
A pool area with multiple swimming pools, lounge chairs, and palm trees.

12. 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.
$399 nightly
The price is $446
Nov 5 - Nov 6
Total with taxes and fees
Little Piece of Paradise #233 Waterfront Cottage with Dock, Pool & Canal Views
A kitchen with white cabinets, a stove, and a dining area with chairs and a table.

13. 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.
$374 nightly
The price is $417
Nov 10 - Nov 11
Total with taxes and fees
Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access
A waterfront property with a multi-story building featuring balconies, a dock, and a landscaped garden with palm trees.

14. SAVE BIG $$$ NOV./DEC. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

SAVE BIG $$$ NOV./DEC. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
9.6 out of 10, Exceptional, (99 reviews)
"Great location, wonderful hosts!"
United States
Blue Mountain Footwear F.
$443 nightly
The price is $492
Nov 21 - Nov 22
Total with taxes and fees
SAVE BIG $$$ NOV./DEC. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
A small, cozy room with a white lamp, a small table, and a bench. A sliding glass door leads to a kitchen area with wooden flooring and a yellow wall.

15. Breezy Point - Venture Out Unit 199

Breezy Point - Venture Out Unit 199
Cudjoe Key
Breezy Point - Venture Out Unit 199
A coastal property with a paved driveway leading to a building with a blue roof, surrounded by lush greenery and a view of the ocean.

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, (129 reviews)
"Great location and Host was very helpful and responsive."
United States
Dennis G.
$430 nightly
The price is $479
Nov 5 - Nov 6
Total with taxes and fees
Kelly's Kabin - Adorable Private Summerland Key Cottage
A pool area with multiple swimming pools, lounge chairs, and palm trees.

17. 2BR, 2BA Cudjoe Key Home with pool, hot tub, and patio.

2BR, 2BA Cudjoe Key Home with pool, hot tub, and patio.
Cudjoe Key
$449 nightly
The price is $501
Nov 13 - Nov 14
Total with taxes and fees
2BR, 2BA Cudjoe Key Home with pool, hot tub, and patio.
A pool area with multiple swimming pools, lounge chairs, and palm trees.

18. Waterfront 2BR/2BA with 35' Dock – Island Breeze Keys Escape

Waterfront 2BR/2BA with 35' Dock – Island Breeze Keys Escape
Cudjoe Key
8.8 out of 10, Excellent, (3 reviews)
"It was a short trip but we enjoyed our stay! "
United States
Jennifer S.
$425 nightly
The price is $474
Nov 9 - Nov 10
Total with taxes and fees
Waterfront 2BR/2BA with 35' Dock – Island Breeze Keys Escape
A waterfront property with a covered porch, a boat dock, and a clear sky.

19. SAVE BIG $$$ NOV./DEC. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

SAVE BIG $$$ NOV./DEC. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
9.4 out of 10, Exceptional, (113 reviews)
"Our family had an amazing time staying here! Our hosts were quick to answer any questions we had and the house was clean and fully stocked with everything you might need. Our favorite part was being able to sit out on the deck by the canal and see all the marine wildlife. We even had a little family of manatees hang out for awhile. Definitely would recommend staying here!"
United States
Mckayla S.
$388 nightly
The price is $431
Nov 9 - Nov 10
Total with taxes and fees
SAVE BIG $$$ NOV./DEC. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
A pool area with multiple swimming pools, lounge chairs, and palm trees.

20. Canal Front Retreat w/ Ocean Views, 35' Dock & Golf Cart Option

Canal Front Retreat w/ Ocean Views, 35' Dock & Golf Cart Option
Cudjoe Key
9.4 out of 10, Exceptional, (18 reviews)
"Perfect location, great price."
United States
Suzanne T.
$415 nightly
The price is $463
Nov 8 - Nov 9
Total with taxes and fees
Canal Front Retreat w/ Ocean Views, 35' Dock & Golf Cart Option
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

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
"Lindo hotel con un personal y servicio excelente."
Boris 2-night trip
Posted 11 hours ago
Faro Blanco Resort Marathon Florida Keys, Curio by Hilton

Find out more about Big Pine Key

Everything you need to know about Big Pine Key vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Big Pine Key vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Big Pine Key vacation 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 low season months. For more hustle and bustle, you may prefer to visit Big Pine Key in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $123 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Big Pine Key rentals

At Expedia, we put the best Big Pine Key vacation 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 vacation.

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.

Explore a world of travel with Expedia

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 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. Our travelers also rate Charming 3-bedroom house in Big Pine Key near Beach and Key West as a favorite home for rent in Big Pine Key.

How many vacation rentals are there in Big Pine Key?

With 148 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.