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

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67 Best Family Vacation Rentals in Cook Island (Starting from $148)

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
Check Availability
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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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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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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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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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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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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Torchbearer - Lower
Torchbearer - Lower
House
Cook Island, Florida, USA
5.2k from Cook Island center

Guest Services, Parking, Sports/Activities, Laundry, Barbecue/Outdoor Cooking, Internet, Security/Safety

2 Bedrooms6 Guests
New to Booking
$148
Average price / night
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Beautiful 3 Bedroom Canal Home in Little Torch Key, FL w/ Great Boating Access
Beautiful 3 Bedroom Canal Home in Little Torch Key, FL w/ Great Boating Access
House
Little Torch Key, FL, 33042, United States
3.7k from Cook Island center

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

3 Bedrooms6 Guests
New to Booking
$415
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 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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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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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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Cayo Loco
Cayo Loco
House
Little Torch Key, FL, USA
5.3k from Cook Island center

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

3 Bedrooms6 Guests
New to Booking
$188
Average price / night
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Big Pine Key, Double Wide Canal w/ Super Quick Direct Access to Gulf & Atlantic
Big Pine Key, Double Wide Canal w/ Super Quick Direct Access to Gulf & Atlantic
House
Big Pine Key, FL, 33043, United States
4.0k from Cook Island center

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

3 Bedrooms6 Guests
9.6

Exceptional

13 reviews

$319
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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Beachfront 3B/3B Fishing Oasis
Beachfront 3B/3B Fishing Oasis
House
Ramrod Key, FL, 33042, United States
4.3k from Cook Island center

AC, Balcony, Barbecue, Crib, Dryer, Extra Bed, Free Parking, Heater, Internet

3 Bedrooms9 Guests
9.6

Exceptional

4 reviews

$538
Average price / night
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Love Shack
Love Shack
House
Summerland Key, FL, USA
6.9k from Cook Island center

Barbecue/Outdoor Cooking, Internet, Security/Safety, Laundry, Child Friendly

2 Bedrooms4 Guests
New to Booking
$150
Average price / night
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Cozy keys getaway
Cozy keys getaway
House
Ramrod Key, FL, 33042, United States
4.4k from Cook Island center

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

1 Bedroom1 Guest
New to Booking
$241
Average price / night
Check Availability
Keys Hideaway
Keys Hideaway
House
Summerland, FL, 33042, United States
4.4k from Cook Island center

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

3 Bedrooms1 Guest
New to Booking
$243
Average price / night
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BRILLIANT VIEWS OF OPEN WATERS- 75' DOCK - 250 ' TO OPEN CHANNEL\nBIG PINE KEY FL
BRILLIANT VIEWS OF OPEN WATERS- 75' DOCK - 250 ' TO OPEN CHANNEL\nBIG PINE KEY FL
House
Big Pine Key, FL, 33043, United States
4.6k from Cook Island center

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

3 Bedrooms8 Guests
9.8

Exceptional

20 reviews

$209
Average price / night
Check Availability
3-bedroom house in Lower Keys with Hot Tub, Sleeps 10+, Pet Freindly
3-bedroom house in Lower Keys with Hot Tub, Sleeps 10+, Pet Freindly
House
Big Pine Key, FL, 33043, United States
4.6k from Cook Island center

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

3 Bedrooms12 Guests
New to Booking
$407
Average price / night
Check Availability
A Tropical Luxury Getaway, Your own private resort!!
A Tropical Luxury Getaway, Your own private resort!!
House
Little Torch Key, FL, 33042, United States
4.6k from Cook Island center

AC, Arcade, Balcony, Barbecue, Dryer, Fireplace, Fitness Equipment, Free Parking, Heater

6 Bedrooms16 Guests
10.0

Exceptional

46 reviews

$2804
Average price / night
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Warm and relax 3-bed 2 bath home in charming Summerland Key minutes from K.West
Warm and relax 3-bed 2 bath home in charming Summerland Key minutes from K.West
House
Summerland Key, FL, 33042, United States
4.7k from Cook Island center

AC, Barbecue, Dryer, Heater, Internet, Laundry, Microwave, No Smoking, Outdoor Space

3 Bedrooms8 Guests
New to Booking
$300
Average price / night
Check Availability
New pool & Huge master suite! Open water views , 2 stories of wrap around decks
New pool & Huge master suite! Open water views , 2 stories of wrap around decks
House
Summerland Key, FL, 33042, United States
4.9k from Cook Island center

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

3 Bedrooms8 Guests
10.0

Exceptional

14 reviews

$341
Average price / night
Check Availability
Paradise in the lower KEYS!!!
Paradise in the lower KEYS!!!
House
Little Torch Key, FL, 33042, United States
5.0k from Cook Island center

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

3 Bedrooms7 Guests
10.0

Exceptional

15 reviews

$279
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 Family Vacation Rentals in Cook Island.

Where to stay in Cook Island? Best neighborhoods & areas

Cook Island Family Vacation Rentals on the Map

Frequently Asked Questions

You can explore 67 verified family-friendly vacation rentals in Cook Island. These include spacious homes, villas, and condos designed to accommodate families of different sizes.

Prices for family-friendly rentals in Cook Island vary depending on the season, number of bedrooms, and included amenities. Rates typically start from around $148 per night, with larger homes and peak travel periods often costing more.

Many family-friendly rentals in Cook Island offer baby-friendly items such as high chairs, cribs, or pack-and-play options. Availability can vary, so it’s helpful to check the listing details before booking.

Yes, some rentals in Cook Island are well suited for multi-generational stays, offering multiple bedrooms, separate living areas, and enough space for larger groups to stay comfortably together.

For busy travel periods such as school holidays or summer breaks, booking 90 to 120 days in advance is recommended to secure the best options. Availability may be more flexible during quieter times of the year.

Family-friendly rentals in Cook Island often include amenities such as Child Friendly, Laundry, and Internet. These features help make stays more convenient and enjoyable for both adults and children.

You can use search filters to find rentals that offer features like game rooms, playgrounds, or entertainment areas. Checking property descriptions can also help you identify homes that are well suited for families with children.