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

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  2. Vacation Rentals with Pool
  3.  USA

  4.  Florida
  5.  Cook Island

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127 Best Vacation Rentals with Pool in Cook Island (Starting from $160)

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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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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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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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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Parmer's Resort
Parmer's Resort
Resort
Little Torch Key, FL, USA
5.1k from Cook Island center

Accommodations, Pools, Resorts, Parking, Romantic, Pet-friendly, Lodgings, Beach, Places to stay

29 Bedrooms37 Guests
8.6

Fabulous

440 reviews

$215
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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Fishermen`s Paradise
Fishermen`s Paradise
House
Big Pine Key, FL, USA
5.3k from Cook Island center

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

3 Bedrooms8 Guests
9.0

Fabulous

1 reviews

$1127
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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Tiki Beach - Big Pine Key
Tiki Beach - Big Pine Key
House
Big Pine Key, FL, USA
5.3k from Cook Island center

Pool, Parking, Security/Safety, View, Sports/Activities, Spa, Barbecue/Outdoor Cooking

4 Bedrooms10 Guests
New to Booking
$831
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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Salty Air Retreat
Salty Air Retreat
House
Little Torch Key, FL, USA
5.5k from Cook Island center

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

3 Bedrooms8 Guests
New to Booking
$656
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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Hellenga Haven
Hellenga Haven
House
Big Pine Key, FL, USA
7.7k from Cook Island center

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

3 Bedrooms8 Guests
New to Booking
$411
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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Old Wooden Bridge Resort & Marina
Old Wooden Bridge Resort & Marina
Cabin
Big Pine Key, FL, USA
7.9k from Cook Island center

Accommodations, Pools, Parking, Lodges, Cabins, Pet-friendly, Lodgings, Places to stay

43 Bedrooms138 Guests
8.4

Very Good

241 reviews

$257
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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Skyway Living
Skyway Living
House
Summerland Key, FL, USA
8.1k from Cook Island center

Accommodations, Pools, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Places to stay, Accessible hotels

2 Bedrooms6 Guests
New to Booking
$237
Average price / night
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Ocean front paradise in Little Torch Key
Ocean front paradise in Little Torch Key
House
Little Torch Key, FL, 33042, United States
3.4k from Cook Island center

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

3 Bedrooms8 Guests
10.0

Exceptional

1 reviews

$569
Average price / night
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Summerland Canal
Summerland Canal
House
Summerland Key, FL, USA
8.3k from Cook Island center

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

2 Bedrooms5 Guests
New to Booking
$160
Average price / night
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Waterfront Canal Home w/ Dock & Pool 27+ Days
Waterfront Canal Home w/ Dock & Pool 27+ Days
House
Little Torch Key, FL, 33042, United States
3.4k from Cook Island center

AC, Balcony, Barbecue, Dryer, Fitness Equipment, Free Parking, Heater, Internet, Kitchen

4 Bedrooms8 Guests
10.0

Exceptional

1 reviews

$429
Average price / night
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Newer Construction Private Luxury Waterfront Home w/ Heated Pool
Newer Construction Private Luxury Waterfront Home w/ Heated Pool
House
Little Torch Key, FL, 33042, United States
3.5k from Cook Island center

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

4 Bedrooms8 Guests
10.0

Exceptional

3 reviews

$478
Average price / night
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Lower Keys PARADISE 200 Ft of Dockage, Heated Pool, Quick Atlantic Access
Lower Keys PARADISE 200 Ft of Dockage, Heated Pool, Quick Atlantic Access
House
Little Torch Key, FL, 33042, United States
3.5k from Cook Island center

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

5 Bedrooms8 Guests
10.0

Exceptional

3 reviews

$444
Average price / night
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Beautiful Oceanfront Home on Ramrod Key - Three Lots, Dock & Poolside Tiki Bar
Beautiful Oceanfront Home on Ramrod Key - Three Lots, Dock & Poolside Tiki Bar
House
Ramrod Key, FL, 33065, United States
3.8k from Cook Island center

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

3 Bedrooms6 Guests
10.0

Exceptional

80 reviews

$808
Average price / night
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Private House Facing the Ocean with Heated Pool/Spa
Private House Facing the Ocean with Heated Pool/Spa
House
RAMROD KEY, FL, 33042, United States
3.8k from Cook Island center

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

4 Bedrooms8 Guests
10.0

Exceptional

5 reviews

$347
Average price / night
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Manatee Watch | 5 bedrooms, pool, ocean access
Manatee Watch | 5 bedrooms, pool, ocean access
House
Big Pine Key, FL, 33043, United States
3.9k from Cook Island center

AC, Balcony, Barbecue, Dryer, Extra Bed, Heater, Hot Tub, Internet, Kitchen

5 Bedrooms12 Guests
10.0

Exceptional

2 reviews

$574
Average price / night
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5-4 house with canal and pool
5-4 house with canal and pool
House
Little Torch Key, FL, 33042, United States
4.0k from Cook Island center

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

5 Bedrooms6 Guests
New to Booking
$379
Average price / night
Check Availability
Unique Waterfront Dome Home with Dock & Pool – Little Torch Key
Unique Waterfront Dome Home with Dock & Pool – Little Torch Key
House
Summerland Key, FL, 33042, United States
4.0k from Cook Island center

AC, Barbecue, Dryer, Free Parking, Internet, Laundry, Microwave, No Smoking, Pool

2 Bedrooms6 Guests
New to Booking
$218
Average price / night
Check Availability

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 with Pool in Cook Island.

Where to stay in Cook Island? Best neighborhoods & areas

Cook Island Vacation Rentals with Pool on the Map

Frequently Asked Questions

You can explore 127 verified vacation rentals with a pool in Cook Island. These include a wide range of private homes, villas, and condos that offer on-site swimming facilities for a more relaxing stay.

Prices for vacation rentals with a pool in Cook Island vary depending on the season, property size, and whether the pool is private or shared. Rates typically start from around $160 per night, with private pool homes and peak travel periods often costing more.

Many rentals in Cook Island offer private pools for exclusive use, while others provide access to shared or community pools. You can use filters to specifically find properties with private pools if that is your preference.

Yes, some vacation rentals with pools in Cook Island welcome pets. Currently, 34 listings allow pets, although policies may vary by property. It’s a good idea to review any rules related to pets around pool areas before booking.

Properties with pools are often in high demand, especially during warmer months and holidays, so booking 90 to 120 days in advance is recommended for the best selection. During off-peak seasons, you may still find availability closer to your travel dates.

Vacation rentals with pools in Cook Island often include additional outdoor features such as Pool, Laundry, and Fireplace/Heating. These amenities enhance comfort and make it easier to enjoy outdoor living during your stay.

Some vacation rentals in Cook Island offer heated pools, which can be especially useful during cooler months. In certain cases, pool heating may be available for an additional fee, so it’s best to check the property details before booking.