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

Holiday Homes in Big Pine Key

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Check prices for these dates

In two weeks
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

Our top choices for Big Pine Key holiday homes

A modern kitchen with a dishwasher, a dining area with a glass coffee table, and a ceiling fan.

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 NZ$1,063
includes taxes & fees
22 Oct - 23 Oct
Charming 3-bedroom house in Big Pine Key near Beach and Key West
A modern kitchen with granite countertops, stainless steel appliances, and light-colored cabinetry.

2. 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 NZ$896
includes taxes & fees
17 Oct - 18 Oct
Kelly's Kabin - Adorable Private Summerland Key Cottage
A waterfront property with a multi-story building featuring balconies, a dock, and a landscaped garden with palm trees.

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

SAVE BIG $$$ OCT./NOV. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
9.6 out of 10, Exceptional, (98 reviews)
"Great location, wonderful hosts!"
United States
Blue Mountain Footwear F.
The price is NZ$754
includes taxes & fees
21 Oct - 22 Oct
SAVE BIG $$$ OCT./NOV. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
A resort with a pool area, lounge chairs, and a small island with thatched umbrellas.

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 NZ$846
includes taxes & fees
17 Oct - 18 Oct
Little Piece of Paradise #233 Waterfront Cottage with Dock, Pool & Canal Views
A resort with a pool area, lounge chairs, and a small island with thatched umbrellas.

5. 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 NZ$957
includes taxes & fees
17 Oct - 18 Oct
2BR, 2BA Cudjoe Key Home with pool, hot tub, and patio.
Pool

6. 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 NZ$816
includes taxes & fees
2 Nov - 3 Nov
Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access
A resort with a pool area, lounge chairs, and a small island with thatched umbrellas.

7. 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 NZ$899
includes taxes & fees
17 Oct - 18 Oct
Mahi House #440 Waterfront Retreat with Dock, Pool & Optional Golf Cart
A resort with a pool area, lounge chairs, and a small island with thatched umbrellas.

8. 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$922
includes taxes & fees
17 Oct - 18 Oct
Florida Keys Canal-Front 2BR/2BA w/ 35' Seawall, Dock & Spacious Comfort
A waterfront property with a covered porch, a boat dock, and a clear sky.

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

SAVE BIG $$$ OCT./NOV. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
9.4 out of 10, Exceptional, (113 reviews)
"Our family had an amazing time staying here! Our hosts were quick to answer any questions we had and the house was clean and fully stocked with everything you might need. Our favorite part was being able to sit out on the deck by the canal and see all the marine wildlife. We even had a little family of manatees hang out for awhile. Definitely would recommend staying here!"
United States
Mckayla S.
The price is NZ$776
includes taxes & fees
19 Oct - 20 Oct
SAVE BIG $$$ OCT./NOV. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Pool

10. 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 NZ$828
includes taxes & fees
20 Oct - 21 Oct
Updated 2BR/2BA Venture Out Home w/ Pool Access, Pet Friendly, Near Key West
Pool

11. 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 NZ$899
includes taxes & fees
17 Oct - 18 Oct
Ground Level Waterfront 2BR in Venture Out - 23' Seawall, Pool, Marina & Pet Friendly
Pool

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

Sailfish Haven #390 - Ocean Views, 35' seawall
Cudjoe Key
9.0 out of 10, Wonderful, (8 reviews)
"great House , and if you are a boater , venture out is great in cudjoe key FL"
United States
freddy c.
The price is NZ$934
includes taxes & fees
17 Oct - 18 Oct
Sailfish Haven #390 - Ocean Views, 35' seawall
A resort with a pool area, lounge chairs, and a small island with thatched umbrellas.

13. 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)
"Our family had an amazing vacation! We love the house and hope to come back!! "
United States
Tammy G.
The price is NZ$906
includes taxes & fees
21 Oct - 22 Oct
Canal Front Retreat w/ Ocean Views, 35' Dock & Golf Cart Option
A resort with a pool area, lounge chairs, and a small island with thatched umbrellas.

14. 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 NZ$906
includes taxes & fees
22 Oct - 23 Oct
Canal-Front Retreat with Dock, Pool & Open Ocean Views
A swimming pool with a tiled edge, surrounded by lounge chairs and umbrellas, under a cloudy sky.

15. 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$905
includes taxes & fees
17 Oct - 18 Oct
Oceanview Paradise AT Venture Out+4 Bikes & 2-2 Seat Kayaks! King & Queen Beds!
A bench by the water with palm trees and a clear sky.

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

Florida Keys Waterfront Escape - 2BR with 44' Seawall
Cudjoe Key
The price is NZ$962
includes taxes & fees
17 Oct - 18 Oct
Florida Keys Waterfront Escape - 2BR with 44' Seawall
Pool

17. 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 NZ$922
includes taxes & fees
18 Oct - 19 Oct
Blue Lobster Lodge #543 Open Coastal Retreat with Pool Near Key West
A resort with a pool area, lounge chairs, and a small island with thatched umbrellas.

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, (17 reviews)
"Great water view and comfortable for four adults "
United States
Kyle F.
The price is NZ$958
includes taxes & fees
26 Oct - 27 Oct
Sea La Vie #197 Oceanfront Home with 49' Dock, Heated Pool & Florida Keys Views
Pool

19. 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$939
includes taxes & fees
9 Nov - 10 Nov
Waterfront 2BR/2BA | 35' Seawall for 32' Boat | Beautiful Sunrises on Cudjoe Key
A resort with a pool area, lounge chairs, and a small island with thatched umbrellas.

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

Waterfront 2BR/2BA with 35' Dock – Island Breeze Keys Escape
Cudjoe Key
8.0 out of 10, Very good, (2 reviews)
"It was a short trip but we enjoyed our stay! "
United States
Jennifer S.
The price is NZ$922
includes taxes & fees
18 Oct - 19 Oct
Waterfront 2BR/2BA with 35' Dock – Island Breeze Keys Escape
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

Isla Bella Beach Resort & Spa

Isla Bella Beach Resort & Spa

10/10 Excellent
"We had a great visit! Amazing property, welcoming and kind staff and comfortable room."
Michelle 2-night trip
Posted 1 hour ago
Isla Bella Beach Resort & Spa

Find out more about Big Pine Key

Big Pine Key Holiday Homes information

Number of reviews
433
Accommodation
1716 Holiday Homes
Lowest Price
NZ$754
Highest Price
NZ$1,063