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 homes

1. 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.
The price is CA $294
CA $821 total
includes taxes & fees
Nov 15 - Nov 16
Charming 3-bedroom house in Big Pine Key near Beach and Key West

2. 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 $202
CA $599 total
includes taxes & fees
Nov 14 - Nov 15
Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access

3. 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.
The price is CA $276
CA $688 total
includes taxes & fees
Nov 14 - Nov 15
Kelly's Kabin - Adorable Private Summerland Key Cottage

4. 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 CA $236
CA $640 total
includes taxes & fees
Nov 20 - Nov 21
Little Piece of Paradise #233 Waterfront Cottage with Dock, Pool & Canal Views

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

SAVE BIG $$$ NOV./DEC. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
9.6 out of 10, Exceptional, (99 reviews)
"Great location, wonderful hosts!"
United States
Blue Mountain Footwear F.
The price is CA $327
CA $767 total
includes taxes & fees
Nov 29 - Nov 30
SAVE BIG $$$ NOV./DEC. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

6. 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.
The price is CA $222
CA $623 total
includes taxes & fees
Nov 14 - Nov 15
Updated 2BR/2BA Venture Out Home w/ Pool Access, Pet Friendly, Near Key West

7. 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, (147 reviews)
"It is an excellent place."
United States
Arianna
The price is CA $233
CA $303 total
includes taxes & fees
Nov 18 - Nov 19
Bluegreen Vacations Hammocks at Marathon, Ascend Collection Resort

8. Canal-Front Retreat with Dock, Pool & Open Ocean Views

Canal-Front Retreat with Dock, Pool & Open Ocean Views
Cudjoe Key
9.0 out of 10, Wonderful, (13 reviews)
"This property is convenient to food and fun. It was very clean, comfortable and we felt safe to walk around the resort. We had a wonderful stay here."
United States
Catherine C.
The price is CA $263
CA $673 total
includes taxes & fees
Nov 14 - Nov 15
Canal-Front Retreat with Dock, Pool & Open Ocean Views

9. Blue Lobster Lodge #543 Open Coastal Retreat with Pool Near Key West

Blue Lobster Lodge #543 Open Coastal Retreat with Pool Near Key West
Cudjoe Key
8.8 out of 10, Excellent, (11 reviews)
"We loved our stayed and booked again for next year. Its in our price range, plenty of space and we were all so comfortable. Its our favorite house we have rented in the area and hope to be able to continue to enjoy it years to come. "
United States
Alisa M.
The price is CA $270
CA $681 total
includes taxes & fees
Nov 14 - Nov 15
Blue Lobster Lodge #543 Open Coastal Retreat with Pool Near Key West

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

SAVE BIG $$$ NOV./DEC. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
9.4 out of 10, Exceptional, (113 reviews)
"Our family had an amazing time staying here! Our hosts were quick to answer any questions we had and the house was clean and fully stocked with everything you might need. Our favorite part was being able to sit out on the deck by the canal and see all the marine wildlife. We even had a little family of manatees hang out for awhile. Definitely would recommend staying here!"
United States
Mckayla S.
The price is CA $255
CA $677 total
includes taxes & fees
Nov 19 - Nov 20
SAVE BIG $$$ NOV./DEC. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

11. 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.
The price is CA $256
CA $664 total
includes taxes & fees
Nov 14 - Nov 15
Canal Front Retreat w/ Ocean Views, 35' Dock & Golf Cart Option

12. 2BR, 2BA Cudjoe Key Home with pool, hot tub, and patio.

2BR, 2BA Cudjoe Key Home with pool, hot tub, and patio.
Cudjoe Key
The price is CA $303
CA $722 total
includes taxes & fees
Nov 14 - Nov 15
2BR, 2BA Cudjoe Key Home with pool, hot tub, and patio.

13. 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.
The price is CA $270
CA $681 total
includes taxes & fees
Nov 14 - Nov 15
Waterfront 2BR/2BA with 35' Dock – Island Breeze Keys Escape

14. 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, (6 reviews)
"Pool area was nice but only visited it once as so much to see and do!"
United States
Karen
The price is CA $290
CA $705 total
includes taxes & fees
Nov 16 - Nov 17
Waterfront 2BR/2BA | 35' Seawall for 32' Boat | Beautiful Sunrises on Cudjoe Key

15. Mahi House #440 Waterfront Retreat with Dock, Pool & Optional Golf Cart

Mahi House #440 Waterfront Retreat with Dock, Pool & Optional Golf Cart
Cudjoe Key
9.6 out of 10, Exceptional, (7 reviews)
"Clean and excellent water access"
United States
Chris P.
The price is CA $256
CA $664 total
includes taxes & fees
Nov 14 - Nov 15
Mahi House #440 Waterfront Retreat with Dock, Pool & Optional Golf Cart

16. Florida Keys Waterfront Escape - 2BR with 44' Seawall

Florida Keys Waterfront Escape - 2BR with 44' Seawall
Cudjoe Key
The price is CA $270
CA $665 total
includes taxes & fees
Nov 14 - Nov 15
Florida Keys Waterfront Escape - 2BR with 44' Seawall

17. 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 CA $270
CA $681 total
includes taxes & fees
Nov 14 - Nov 15
Florida Keys Canal-Front 2BR/2BA w/ 35' Seawall, Dock & Spacious Comfort

18. Sea La Vie #197 Oceanfront Home with 49' Dock, Heated Pool & Florida Keys Views

Sea La Vie #197 Oceanfront Home with 49' Dock, Heated Pool & Florida Keys Views
Cudjoe Key
9.6 out of 10, Exceptional, (18 reviews)
"It was great!"
United States
Jennifer B.
The price is CA $303
CA $722 total
includes taxes & fees
Nov 20 - Nov 21
Sea La Vie #197 Oceanfront Home with 49' Dock, Heated Pool & Florida Keys Views

19. Sailfish Haven #390 - Ocean Views, 35' seawall

Sailfish Haven #390 - Ocean Views, 35' seawall
Cudjoe Key
9.0 out of 10, Wonderful, (9 reviews)
"great House , and if you are a boater , venture out is great in cudjoe key FL"
United States
freddy c.
The price is CA $290
CA $705 total
includes taxes & fees
Nov 14 - Nov 15
Sailfish Haven #390 - Ocean Views, 35' seawall

20. Ground Level Waterfront 2BR in Venture Out - 23' Seawall, Pool, Marina & Pet Friendly

Ground Level Waterfront 2BR in Venture Out - 23' Seawall, Pool, Marina & Pet Friendly
Cudjoe Key
8.0 out of 10, Very good, (1 review)
The price is CA $270
CA $681 total
includes taxes & fees
Nov 14 - Nov 15
Ground Level Waterfront 2BR in Venture Out - 23' Seawall, Pool, Marina & Pet Friendly
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

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Big Pine Key Vacation Homes information

Number of reviews
418
Accommodation
1716 Vacation Homes
Lowest Price
CA $303
Highest Price
CA $821

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