Vacation Rentals in Cook Island, FL: Compare 10+ Sites & Save

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304 Best Vacation Rentals in Cook Island (Starting from $178)

Ocean Depth Room at Barnacle Resort
Ocean Depth Room at Barnacle Resort
Apartment
Big Pine Key, FL, USA
2.6k from Cook Island center

Apartments, Cheap, Accommodations, Parking, Pet-friendly, Lodgings, Beach, Places to stay

1 Bedroom4 Guests
7.3

Good

3 reviews

$505
Average price / night
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Ocean Front Beach Home on Semi Private Island Only Accessible by Boat
Ocean Front Beach Home on Semi Private Island Only Accessible by Boat
House
Cook Island, FL, 33043, United States
0.4k from Cook Island center

AC, Extra Bed, Internet, No Smoking

3 Bedrooms8 Guests
New to Booking
$573
Average price / night
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Ocean View Room at Barnacle Resort
Ocean View Room at Barnacle Resort
Apartment
Big Pine Key, FL, USA
2.6k from Cook Island center

Apartments, Accommodations, Parking, Pet-friendly, Lodgings, Beach, Places to stay, Family

1 Bedroom4 Guests
9.5

Superb

4 reviews

$492
Average price / night
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300’ Private Beach, Pool & Rooftop w Panoramic Ocean Views
300’ Private Beach, Pool & Rooftop w Panoramic Ocean Views
House
Big Pine Key, FL, 33043, United States
1.6k from Cook Island center

AC, Balcony, Barbecue, Dryer, Free Parking, Internet, Kitchen, Laundry, Living Area

4 Bedrooms10 Guests
10.0

Exceptional

2 reviews

$1176
Average price / night
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Star Room at Barnacle Resort
Star Room at Barnacle Resort
Apartment
Big Pine Key, FL, USA
2.6k from Cook Island center

Apartments, Accommodations, Parking, Pet-friendly, Lodgings, Beach, Places to stay, Family

1 Bedroom2 Guests
9.0

Fabulous

2 reviews

$385
Average price / night
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Ocean View Suite Barnacle Resort
Ocean View Suite Barnacle Resort
Apartment
Big Pine Key, FL, 33043-3511, United States
2.6k from Cook Island center

AC, Balcony, Barbecue, Free Parking, Internet, Microwave, No Smoking, Outdoor Space, Patio

1 Bedroom4 Guests
New to Booking
$678
Average price / night
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Beach View Room at Barnacle Resort
Beach View Room at Barnacle Resort
Apartment
Big Pine Key, FL, USA
2.6k from Cook Island center

Apartments, Accommodations, Parking, Pet-friendly, Lodgings, Beach, Places to stay

1 Bedroom2 Guests
New to Booking
$499
Average price / night
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Star Room Barnacle Resort
Star Room Barnacle Resort
Apartment
Big Pine Key, FL, 33043-3511, United States
2.6k from Cook Island center

AC, Barbecue, Free Parking, Internet, Microwave, Outdoor Space, TV

1 Bedroom2 Guests
8.8

Fabulous

5 reviews

$369
Average price / night
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Treehouse Private Village at Barnacle Resort
Treehouse Private Village at Barnacle Resort
House
Big Pine Key, FL, USA
2.6k from Cook Island center

Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Places to stay

1 Bedroom4 Guests
7.7

Good

3 reviews

$560
Average price / night
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Treehouse Private Village Barnacle Resort
Treehouse Private Village Barnacle Resort
Cabin
Big Pine Key, FL, 33043-3511, United States
2.6k from Cook Island center

AC, Balcony, Barbecue, Free Parking, Internet, Kitchen, Microwave, No Smoking, Outdoor Space

1 Bedroom4 Guests
8.0

Good

3 reviews

$629
Average price / night
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Sunset Retreat
Sunset Retreat
House
Big Pine Key, FL, USA
3.3k from Cook Island center

Barbecue/Outdoor Cooking, Pool, Internet, Laundry, Child Friendly

3 Bedrooms6 Guests
New to Booking
$742
Average price / night
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Beach View Room Dormitory Room Barnacle Resort
Beach View Room Dormitory Room Barnacle Resort
Apartment
Big Pine Key, FL, 33043-3511, United States
2.6k from Cook Island center

AC, Balcony, Barbecue, Free Parking, Internet, Microwave, No Smoking, Outdoor Space, Patio

1 Bedroom2 Guests
New to Booking
$475
Average price / night
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Cayman Cottage
Cayman Cottage
House
Summerland Key, FL, USA
4.0k from Cook Island center

Accommodations, Villas, Vacation homes, Cottages, Lodgings, Places to stay

3 Bedrooms6 Guests
New to Booking
$247
Average price / night
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New 3BR Ocean-Side Home on Little Torch Key, hidden gem - 28 Miles from Key West
New 3BR Ocean-Side Home on Little Torch Key, hidden gem - 28 Miles from Key West
House
Summerland Key, FL, 33042, United States
2.8k from Cook Island center

AC, Dryer, Heater, Internet, Laundry, No Smoking, Washer

3 Bedrooms6 Guests
New to Booking
$511
Average price / night
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Experience Coastal Living at its Best Florida Keys
Experience Coastal Living at its Best Florida Keys
House
Summerland Key, FL, USA
4.5k from Cook Island center

Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Beach, Places to stay

1 Bedroom4 Guests
New to Booking
$293
Average price / night
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Keys To The Kingdom! Private Oceanfront Retreat with Beach and Pool
Keys To The Kingdom! Private Oceanfront Retreat with Beach and Pool
House
Big Pine Key, FL, 33043, United States
2.8k from Cook Island center

AC, Balcony, Barbecue, Crib, Dryer, Free Parking, Heater, Hot Tub, Internet

3 Bedrooms6 Guests
10.0

Exceptional

3 reviews

$576
Average price / night
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L`archipel
L`archipel
House
Key West, FL, USA
4.5k from Cook Island center

Accommodations, Villas, Vacation homes, Cottages, Lodgings, Places to stay

2 Bedrooms6 Guests
New to Booking
$185
Average price / night
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FLORIDA KEYS PARADISE! HEATED SWIMMING POOL
FLORIDA KEYS PARADISE! HEATED SWIMMING POOL
House
Little Torch Key, FL, 33042, United States
3.0k from Cook Island center

AC, Balcony, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry

3 Bedrooms8 Guests
9.8

Exceptional

9 reviews

$435
Average price / night
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RV In The Keys a Tropical Retreat
RV In The Keys a Tropical Retreat
House
Big Pine Key, FL, USA
4.5k from Cook Island center

Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Places to stay

1 Bedroom4 Guests
New to Booking
$178
Average price / night
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Luxury and Lovely Water Front House
Luxury and Lovely Water Front House
House
Big Pine Key, FL, 33043, United States
3.0k from Cook Island center

AC, Balcony, Barbecue, Dryer, Extra Bed, Free Parking, Internet, Kitchen, Laundry

3 Bedrooms4 Guests
10.0

Exceptional

5 reviews

$625
Average price / night
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Beautiful Keys Home w/ Open Water Views & 90' Dock
Beautiful Keys Home w/ Open Water Views & 90' Dock
House
Little Torch Key, FL, 33042, United States
3.0k from Cook Island center

AC, Balcony, Barbecue, Dryer, Elevator, Free Parking, Heater, Internet, Kitchen

3 Bedrooms8 Guests
10.0

Exceptional

6 reviews

$423
Average price / night
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Beautiful 2/2 Waterfront Designer Home for your family vacation
Beautiful 2/2 Waterfront Designer Home for your family vacation
House
Little Torch Key, FL, 33042, United States
3.1k from Cook Island center

AC, Balcony, Barbecue, Dryer, Free Parking, Heater, Hot Tub, Internet, Kitchen

2 Bedrooms6 Guests
9.8

Exceptional

38 reviews

$207
Average price / night
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SPECTACULAR SUNSETS-60' DOCK SO CLOSE TO OPEN WATER---\nLITTLE TORCH KEY
SPECTACULAR SUNSETS-60' DOCK SO CLOSE TO OPEN WATER---\nLITTLE TORCH KEY
House
Little Torch Key, FL, 33042, United States
3.1k from Cook Island center

AC, Balcony, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry

3 Bedrooms8 Guests
10.0

Exceptional

11 reviews

$227
Average price / night
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Keys Paradise 2-bedroom, 2-bath with heated pool & direct access to the Atlantic
Keys Paradise 2-bedroom, 2-bath with heated pool & direct access to the Atlantic
House
Little Torch Key, FL, 33042, United States
3.1k from Cook Island center

AC, Balcony, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry

2 Bedrooms6 Guests
10.0

Exceptional

4 reviews

$293
Average price / night
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5 Pirate's - Pool & seawall for boat.<br>This is a pet friendly home. A pet fee and approval of your pet is required.
5 Pirate's - Pool & seawall for boat.<br>This is a pet friendly home. A pet fee and approval of your pet is required.
House
Little Torch Key, FL, 33042, United States
3.2k from Cook Island center

AC, Balcony, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry

3 Bedrooms7 Guests
9.6

Exceptional

5 reviews

$322
Average price / night
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7 Seas Bring your boat.<br>This is a pet friendly home. A pet fee and approval of your pet is required.
7 Seas Bring your boat.<br>This is a pet friendly home. A pet fee and approval of your pet is required.
House
Little Torch Key, FL, 33042, United States
3.3k from Cook Island center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Microwave

3 Bedrooms8 Guests
9.6

Exceptional

4 reviews

$314
Average price / night
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Gorgeous Beachfront Home with a pool. Water views from every direction.
Gorgeous Beachfront Home with a pool. Water views from every direction.
House
Big Pine Key, FL, 33043, United States
3.3k from Cook Island center

AC, Balcony, Barbecue, Crib, Dryer, Free Parking, Heater, Internet, Kitchen

5 Bedrooms10 Guests
10.0

Exceptional

15 reviews

$556
Average price / night
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Pro Tip:
VacationByOwnerRentals aggregates the best inventory from leading travel sites, including Booking.com, Agoda.com, Expedia.com, Vrbo.com, and Airbnb.com. Use our Advanced Filters to compare verified homes, villas, cabins, condos, cottages, vacation rentals, hotels, and eco-friendly stays. Our goal is to help you find the absolute best Vacation Rentals in Cook Island.

Where to stay in Cook Island? Best neighborhoods & areas

Cook Island Vacation Rentals on the Map

Frequently Asked Questions

You can explore 304 verified vacation rentals in Cook Island. Our listings are sourced from a range of trusted providers, giving you access to a wide selection of private homes, apartments, and unique stays—all in one place.

Vacation rental prices in Cook Island vary depending on the season, property size, and location. Rates typically start from around $178 per night, with higher prices for larger homes or peak travel periods. Comparing available options can help you find a stay that matches both your budget and travel plans.

Most vacation rentals in Cook Island include fully equipped kitchens, making it easy to prepare meals and enjoy a more flexible stay. This is especially useful for families, longer stays, or travelers who prefer a home-like experience.

Yes, many vacation rentals in Cook Island welcome pets. Currently, 40 listings allow pets, although specific policies may vary by property. You can filter for pet-friendly options to quickly find suitable accommodations.

For popular travel periods such as holidays or peak seasons, it’s recommended to book your vacation rental 60 to 90 days in advance to secure the best options. During quieter times, you may still find good availability closer to your travel dates.

Vacation rentals in Cook Island often include amenities such as Internet, View, and Ocean View. These features provide added comfort and convenience, making them a popular choice for travelers seeking more space and privacy.

You can use filters to narrow down your search by criteria such as number of bedrooms, guest ratings, or specific amenities like private pools or beachfront access. This makes it easier to find a property that fits your exact needs and preferences.