Search Vacation Homes in Big Pine Key

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Our top choices for Big Pine Key vacation homes

9.8 out of 10, Exceptional, (23)
"The location was very nice and secluded. The house was perfect for a family of five. The pool was great spent a lot of time in it. Lots to do in the area. The only complaint we had is the master bedroom bed mattress needs to be replaced. It seemed like it was very old possibly even broken communication with Karen was perfect. Everything about the trip was good :) "
United States
Michelle S.
$1,536 nightly
The price is $1,691
Jan 11 - Jan 12, 2026
Total with taxes and fees
Fishermen's Paradise | Pool, dock, gorgeous home
8.0 out of 10, Very Good, (2)
"Great Home & Location & Enjoyable Stay! Thanks!"
United States
James J.
$606 nightly
The price is $672
Dec 21 - Dec 22
Total with taxes and fees
Charming 2-bedroom house in Marathon with pool
9.8 out of 10, Exceptional, (122)
"We enjoyed our stay! Great little house and location. "
United States
Lisa K.
$465 nightly
The price is $515
Dec 20 - Dec 21
Total with taxes and fees
Kelly's Kabin - Adorable Private Summerland Key Cottage
$534 nightly
The price is $593
Dec 20 - Dec 21
Total with taxes and fees
Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access
9.4 out of 10, Exceptional, (101)
"Great location. "
United States
Davian k.
$551 nightly
The price is $613
Jan 10 - Jan 11, 2026
Total with taxes and fees
DECEMBER SAVE 60% OFF! WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
$560 nightly
The price is $621
Dec 20 - Dec 21
Total with taxes and fees
Updated 2BR/2BA Venture Out Home w/ Pool Access, Pet Friendly, Near Key West
9.8 out of 10, Exceptional, (82)
"The place is clean and convenient for anyone wanting to spend time on the water in the keys"
United States
Ubaldo G.
$551 nightly
The price is $613
Jan 15 - Jan 16, 2026
Total with taxes and fees
DECEMBER SAVE 60% OFF OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!
$552 nightly
The price is $612
Dec 20 - Dec 21
Total with taxes and fees
Galleon Getaway #533- Oceanfront Community
$558 nightly
The price is $619
Dec 20 - Dec 21
Total with taxes and fees
Florida Keys Canal-Front 2BR/2BA w/ 35' Seawall, Dock & Spacious Comfort

Vacation Home in Cudjoe Key

Spanish Queen @Venture Out, Cudjoe Key
9.4 out of 10, Exceptional, (19)
"This is our third time staying here. It is a great property and works perfectly for a three-person family."
United States
Kimberly G.
$636 nightly
The price is $707
Dec 20 - Dec 21
Total with taxes and fees
Spanish Queen @Venture Out, Cudjoe Key

Vacation Home in Summerland Key

Starlight Serenity - Hideaway w Stunning Views
2.0 star property
$728 nightly
The price is $819
Dec 22 - Dec 23
Total with taxes and fees
Starlight Serenity - Hideaway w Stunning Views
8.6 out of 10, Excellent, (89)
"We had a great time and will be back. "
United States
Michelle K.
$629 nightly
The price is $698
Dec 20 - Dec 21
Total with taxes and fees
Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West
$605 nightly
The price is $672
Jan 4 - Jan 5, 2026
Total with taxes and fees
Waterfront Getaway with 23' Seawall, Boat Access, Outdoor Dining & Cozy Interiors
8.8 out of 10, Excellent, (65)
"Excellent secluded location but near everything Thanks!!!!!"
United States
Gary D.
$1,254 nightly
The price is $1,391
Jan 7 - Jan 8, 2026
Total with taxes and fees
One of the very few beach houses with a daily, rental license in the Keys.
9.6 out of 10, Exceptional, (7)
"We really enjoyed our stay here. We really loved sitting on the back porch by the water and the closeness to the community pool and courts. "
United States
Lindsay C.
$619 nightly
The price is $690
Dec 20 - Dec 21
Total with taxes and fees
Reel Island Retreat #273 at Venture Out in the Florida Keys
9.6 out of 10, Exceptional, (88)
"This place really had it all , one of my best stays yet anywhere. "
United States
Charles M.
$739 nightly
The price is $821
Jan 1 - Jan 2, 2026
Total with taxes and fees
Old Florida Style, wrap around porch, boat basin for dockage, open water
$653 nightly
The price is $726
Dec 22 - Dec 23
Total with taxes and fees
Starlight Serenity - Hideaway with Stunning Views

Vacation Home in Cudjoe Key

Mahi House #440 - 35' seawall
10.0 out of 10, Exceptional, (2)
"Clean and excellent water access"
United States
Chris P.
$647 nightly
The price is $718
Dec 20 - Dec 21
Total with taxes and fees
Mahi House #440 - 35' seawall

Vacation Home in Upper Sugarloaf Key

The Lighthouse - Beach Houses Key West
9.6 out of 10, Exceptional, (11)
"Thank you for our wonderful stay at this beautiful property - everything was perfect - Peter"
United States
Peter Q.
$1,205 nightly
The price is $1,334
Dec 20 - Dec 21
Total with taxes and fees
The Lighthouse - Beach Houses Key West

Vacation Home in Upper Sugarloaf Key

The Hemingway - Beach Houses Key West
9.6 out of 10, Exceptional, (8)
"Perfect location way off the path if you like seclusion."
United States
Jonathan L.
$2,063 nightly
The price is $2,284
Jan 3 - Jan 4, 2026
Total with taxes and fees
The Hemingway - Beach Houses 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

Big Pine Key Vacation Homes information

Number of reviews
612
Accommodation
1759 Vacation Homes
Lowest Price
$515
Highest Price
$2,284

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