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

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Our top choices for Big Pine Key holiday homes

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, (12 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 £564
includes taxes & fees
20 Jul - 21 Jul
Charming 3-bedroom house in Big Pine Key near Beach and Key West

Fishermen's Paradise | Pool, 220' Dock & Open-Water Views

Fishermen's Paradise | Pool, 220' Dock & Open-Water Views
Big Pine Key
9.8 out of 10, Exceptional, (30 reviews)
"A beautiful house with everything you need to have a great time"
United States
David T.
The price is £1,409
includes taxes & fees
12 Jul - 13 Jul
Fishermen's Paradise | Pool, 220' Dock & Open-Water Views

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, (140 reviews)
"This was the perfect place, right on the ocean and a full kitchen so you can cook your own meals. The room was very clean, I loved that they had a laundry basket and laundry detergent in the room for you, came in handy seeing as we stayed for 7 days. Amazing place to watch the sunset from a hammock and we got lucky enough to see some nurse sharks at the docks right outside of our hotel."
United States
Andrew Jackson
The price is £196
includes taxes & fees
7 Jul - 8 Jul
Bluegreen Vacations Hammocks at Marathon, Ascend Collection Resort

Kelly's Kabin - Adorable Private Summerland Key Cottage

Kelly's Kabin - Adorable Private Summerland Key Cottage
Summerland Key
9.8 out of 10, Exceptional, (124 reviews)
"House was very clean and in close proximity to Key West, Marathon, and Big Pine Key."
United States
Sharon L.
The price is £411
includes taxes & fees
12 Jul - 13 Jul
Kelly's Kabin - Adorable Private Summerland Key Cottage

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
7.8 out of 10, Good, (20 reviews)
"Everything was perfect location house amenities Really enjoyed our time there"
United States
Matt S.
The price is £351
includes taxes & fees
6 Jul - 7 Jul
Oceanview Paradise AT Venture Out+4 Bikes & 2-2 Seat Kayaks! King & Queen Beds!

Bright 2BR 2BA in Cudjoe Key| Sleeps 6 | WiFi | Washer Dryer | Near Water & Key West

Bright 2BR 2BA in Cudjoe Key| Sleeps 6 | WiFi | Washer Dryer | Near Water & Key West
Cudjoe Key
The price is £279
includes taxes & fees
18 Jul - 19 Jul
Bright 2BR 2BA in Cudjoe Key| Sleeps 6 | WiFi | Washer Dryer | Near Water & Key West

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 £429
includes taxes & fees
14 Jul - 15 Jul
Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access

SAVE BIG $$ JUNE/JULY! OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

SAVE BIG $$ JUNE/JULY! OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
9.8 out of 10, Exceptional, (91 reviews)
"Great location, very clean, and a responsive host. We enjoyed our stay and highly recommended this spot!"
United States
David T.
The price is £416
includes taxes & fees
14 Jul - 15 Jul
SAVE BIG $$ JUNE/JULY! OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

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, (3 reviews)
"Pool area was nice but only visited it once as so much to see and do!"
United States
Karen
The price is £491
includes taxes & fees
1 Jul - 2 Jul
Waterfront 2BR/2BA | 35' Seawall for 32' Boat | Beautiful Sunrises on Cudjoe Key

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
9.4 out of 10, Exceptional, (3 reviews)
"Stayed with family and good location for family vacations. "
United States
Phani U.
The price is £469
includes taxes & fees
1 Jul - 2 Jul
Florida Keys Canal-Front 2BR/2BA w/ 35' Seawall, Dock & Spacious Comfort

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

Charming 2-bedroom house with WiFi, AC in lovely Cudjoe Key
Cudjoe Key
10.0 out of 10, Exceptional, (5 reviews)
"Absolutely love it here… Randy is great to work with and always available. "
United States
Jeannine R.
The price is £485
includes taxes & fees
1 Jul - 2 Jul
Charming 2-bedroom house with WiFi, AC in lovely Cudjoe Key

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, (10 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 £440
includes taxes & fees
6 Jul - 7 Jul
Blue Lobster Lodge #543 Open Coastal Retreat with Pool Near Key West

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

Canal Front Retreat w/ Ocean Views, 35' Dock & Golf Cart Option
Cudjoe Key
9.2 out of 10, Wonderful, (15 reviews)
"Our family had an amazing vacation! We love the house and hope to come back!! "
United States
Tammy G.
The price is £449
includes taxes & fees
1 Jul - 2 Jul
Canal Front Retreat w/ Ocean Views, 35' Dock & Golf Cart Option

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
8.0 out of 10, Very good, (1 review)
"The unit was very old and tired. As such, several windows did not open, the cook top light was not working, the shower surround was cracked and the joint caulking was bad to name some examples. However, the place was spotless when we arrived and with (needed) working AC. The kitchen is WELL appointed with cooking items, some spices, and baking supplies. The washer/dryer was a treat as we travel light. The waterfront deck/patio area was great for morning coffee and evening cocktails. Venture out...
United States
Pauline Y.
The price is £441
includes taxes & fees
5 Jul - 6 Jul
Little Piece of Paradise #233 Waterfront Cottage with Dock, Pool & Canal Views

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 £443
includes taxes & fees
14 Jul - 15 Jul
Updated 2BR/2BA Venture Out Home w/ Pool Access, Pet Friendly, Near Key West

Waterfront Getaway with 23' Seawall, Boat Access, Outdoor Dining & Cozy Interiors

Waterfront Getaway with 23' Seawall, Boat Access, Outdoor Dining & Cozy Interiors
Cudjoe Key
8.0 out of 10, Very good, (1 review)
The price is £469
includes taxes & fees
10 Jul - 11 Jul
Waterfront Getaway with 23' Seawall, Boat Access, Outdoor Dining & Cozy Interiors

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
9.4 out of 10, Exceptional, (13 reviews)
"Fishing off the back was amazing. Close to really good food. Family had a great time !"
United States
Ashley D.
The price is £494
includes taxes & fees
5 Jul - 6 Jul
Sea La Vie #197 Oceanfront Home with 49' Dock, Heated Pool & Florida Keys Views

Waterfront 2BR/2BA with 35' Dock, Bikes & Kayaks – Island Breeze Keys Escape

Waterfront 2BR/2BA with 35' Dock, Bikes & Kayaks – Island Breeze Keys Escape
Cudjoe Key
8.0 out of 10, Very good, (1 review)
"It was a short trip but we enjoyed our stay! "
United States
Jennifer S.
The price is £469
includes taxes & fees
1 Jul - 2 Jul
Waterfront 2BR/2BA with 35' Dock, Bikes & Kayaks – Island Breeze Keys Escape

Sailfish Haven #390 - Ocean Views, 35' seawall

Sailfish Haven #390 - Ocean Views, 35' seawall
Cudjoe Key
8.8 out of 10, Excellent, (6 reviews)
"It was a perfect home to stay in cudokey"
United States
Patricia H.
The price is £449
includes taxes & fees
14 Jul - 15 Jul
Sailfish Haven #390 - Ocean Views, 35' seawall

Spanish Queen @Venture Out, Cudjoe Key

Spanish Queen @Venture Out, Cudjoe Key
Cudjoe Key
9.4 out of 10, Exceptional, (26 reviews)
"Everything about our stay was simply wonderful. It was very Clean and quiet. It is in a very nice neighborhood and pet friendly. We loved the pool and the privacy. I will be back!"
United States
Marie
The price is £512
includes taxes & fees
1 Jul - 2 Jul
Spanish Queen @Venture Out, Cudjoe Key
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

Big Pine Key Holiday Homes information

Number of reviews
489
Accommodation
1762 Holiday Homes
Lowest Price
£196
Highest Price
£1,409