Holiday Homes in Big Pine Key

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

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
8.8 out of 10, Excellent, (3 reviews)
"Great property, surrounded by key deer and wild roosters. "
United States
Scott B.
The price is €532
includes taxes & fees
20 Jan - 21 Jan
Charming 3-bedroom house in Big Pine Key near Beach and Key West

Fishermen's Paradise | Pool, dock, gorgeous home

Fishermen's Paradise | Pool, dock, gorgeous home
Big Pine Key
9.8 out of 10, Exceptional, (25 reviews)
"this home slept 6 adults and 2 children more than comfortable. Would highly recommend! "
United States
karin p.
The price is €1,252
includes taxes & fees
21 Jan - 22 Jan
Fishermen's Paradise | Pool, dock, gorgeous home

Blue Lobster Lodge - Venture Out #543 - Cudjoe Key

Blue Lobster Lodge - Venture Out #543 - Cudjoe Key
2.5 star property
Cudjoe Key
9.2 out of 10, Wonderful, (7 reviews)
"Close to Key West. Would stay there again!!"
United States
elisa b.
The price is €532
includes taxes & fees
19 Jan - 20 Jan
Blue Lobster Lodge - Venture Out #543 - Cudjoe Key

Charming 2-bedroom house in Marathon with pool

Charming 2-bedroom house in Marathon with pool
Marathon
8.0 out of 10, Very good, (2 reviews)
"Great Home & Location & Enjoyable Stay! Thanks!"
United States
James J.
The price is €649
includes taxes & fees
26 Jan - 27 Jan
Charming 2-bedroom house in Marathon with pool

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
The price is €528
includes taxes & fees
18 Jan - 19 Jan
Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access

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
7.6 out of 10, Good, (13 reviews)
"Good experience. The property is well place and the Venture is really nice and quiet."
United States
Primeau J.
The price is €472
includes taxes & fees
4 Feb - 5 Feb
Oceanview Paradise AT Venture Out+4 Bikes & 2-2 Seat Kayaks! King & Queen Beds!

Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West

Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West
Cudjoe Key
8.8 out of 10, Excellent, (157 reviews)
"Great location , clear communications and listing accuracy. Will be coming back again "
United States
Kirk D.
The price is €525
includes taxes & fees
28 Jan - 29 Jan
Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West

SAVE BIG $$$ JANUARY! WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

SAVE BIG $$$ JANUARY! WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
9.4 out of 10, Exceptional, (101 reviews)
"Great location. "
United States
Davian k.
The price is €548
includes taxes & fees
22 Jan - 23 Jan
SAVE BIG $$$ JANUARY! WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

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

SAVE BIG $$ JANUARY! OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!
Cudjoe Key
9.8 out of 10, Exceptional, (82 reviews)
"The place is clean and convenient for anyone wanting to spend time on the water in the keys"
United States
Ubaldo G.
The price is €532
includes taxes & fees
18 Jan - 19 Jan
SAVE BIG $$ JANUARY! OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!

Palm - Beach Houses Key West

Palm - Beach Houses Key West
Upper Sugarloaf Key
10.0 out of 10, Exceptional, (14 reviews)
"Beautiful! Pool was amazing!"
United States
Jennifer B.
Palm - Beach Houses Key West

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

Waterfront Getaway with 23' Seawall, Boat Access, Outdoor Dining & Cozy Interiors
2.0 star property
Cudjoe Key
The price is €583
includes taxes & fees
28 Jan - 29 Jan
Waterfront Getaway with 23' Seawall, Boat Access, Outdoor Dining & Cozy Interiors

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
2.0 star property
Cudjoe Key
The price is €593
includes taxes & fees
19 Jan - 20 Jan
Updated 2BR/2BA Venture Out Home w/ Pool Access, Pet Friendly, Near Key West

One of the very few beach houses with a daily, rental license in the Keys.

One of the very few beach houses with a daily, rental license in the Keys.
Summerland Key
8.8 out of 10, Excellent, (65 reviews)
"Excellent secluded location but near everything Thanks!!!!!"
United States
Gary D.
The price is €1,059
includes taxes & fees
25 Jan - 26 Jan
One of the very few beach houses with a daily, rental license in the Keys.

Starlight Serenity - Hideaway w Stunning Views

Starlight Serenity - Hideaway w Stunning Views
2.0 star property
Summerland Key
The price is €653
includes taxes & fees
28 Jan - 29 Jan
Starlight Serenity - Hideaway w Stunning Views

Cudjoe Cottages, swimming pool, just 20 miles from Key West

Cudjoe Cottages, swimming pool, just 20 miles from Key West
Cudjoe Key
8.8 out of 10, Excellent, (150 reviews)
"Boat access and docking spaces could be improved but overall not terrible. Spent a week here and enjoyed the stay. Quiet decent location. "
United States
bryan c.
The price is €582
includes taxes & fees
19 Jan - 20 Jan
Cudjoe Cottages, swimming pool, just 20 miles from Key West

Just 20 miles from Key West! Oceanfront, dockage, swimming pool

Just 20 miles from Key West! Oceanfront, dockage, swimming pool
Cutthroat Harbor Estates
8.4 out of 10, Very good, (120 reviews)
"Great experience "
United States
Peyton S.
The price is €558
includes taxes & fees
18 Jan - 19 Jan
Just 20 miles from Key West! Oceanfront, dockage, swimming pool

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

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

Oceanfront Cudjoe Key Home - 35' Seawall, Sunrise Views, Pool & Pet-Friendly

Oceanfront Cudjoe Key Home - 35' Seawall, Sunrise Views, Pool & Pet-Friendly
Cudjoe Key
10.0 out of 10, Exceptional, (4 reviews)
"Beautiful "
United States
Lisa P.
The price is €899
includes taxes & fees
28 Jan - 29 Jan
Oceanfront Cudjoe Key Home - 35' Seawall, Sunrise Views, Pool & Pet-Friendly

Starlight Serenity - Hideaway with Stunning Views

Starlight Serenity - Hideaway with Stunning Views
Summerland Key
The price is €619
includes taxes & fees
28 Jan - 29 Jan
Starlight Serenity - Hideaway with Stunning Views

Open-water home with stunning views, 42' seawall for 40' boat, modern updates, large balcony

Open-water home with stunning views, 42' seawall for 40' boat, modern updates, large balcony
2.0 star property
Cudjoe Key
Open-water home with stunning views, 42' seawall for 40' boat, modern updates, large balcony
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Big Pine Key Hotel Reviews

Find out more about Big Pine Key

Big Pine Key Holiday Homes information

Number of reviews
732
Accommodation
1759 Holiday Homes
Lowest Price
€472
Highest Price
€1,252