Top Winter Vacations - Vacation Rentals in Cook Island

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From US $223

         

10.0 (25 Reviews)

House

Your Best Fishing And Relaxing Experience! 2/2 Waterfront Home

• Air Conditioner
• Parking
• TV

• Florida
• Little Torch Key

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From US $7,000

         

New

Apartment

Florida Keys /Big Pine Key/ Dear Haven

• Air Conditioner
• Parking

• Florida
• Big Pine Key

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From US $309

         

|

8.2 (42 Reviews)

Bed & Breakfast

Barnacle Resort

• Air Conditioner
• Parking
• TV

• Big Pine Key
• Long Beach Estates

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From US $314

         

9.6 (4 Reviews)

House

7 Seas Bring your boat. This is a pet friendly home. A pet fee and approval of your pet is required.

• Air Conditioner
• Parking
• Pet Friendly

• Florida
• Little Torch Key

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From US $500

         

|

10.0 (2 Reviews)

Bed & Breakfast

Deer Run on the Atlantic

• Air Conditioner
• Parking
• Pet Friendly

• Big Pine Key
• Long Beach Estates

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From US $219

         

7.4 (1004 Reviews)

Hotel

Looe Key Reef Resort

• Air Conditioner
• Parking
• Pool

• Florida
• Ramrod Key

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From US $587

         

10.0 (61 Reviews)

Cottage

Waterfront Cozy Cottage with Boat Ramp & Dock!

• Air Conditioner
• Parking
• Pet Friendly

• Florida
• Little Torch Key

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From US $492

         

|

9.5 (7 Reviews)

Apartment

Ocean View Room at Barnacle Resort

• Air Conditioner
• Parking
• Pet Friendly

• Big Pine Key
• Long Beach Estates

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From US $205

         

|

9.2 (85 Reviews)

Bed & Breakfast

Barnacle Bed and Breakfast

• Big Pine Key
• Long Beach Estates

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From US $556

         

10.0 (15 Reviews)

House

Gorgeous Beachfront Home with a pool. Water views from every direction.

• Air Conditioner
• Parking
• Pet Friendly

• Big Pine Key
• Coupon Bight Aquatic Preserve

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From US $1,827

         

10.0 (77 Reviews)

House

Waterfront Beach Houses with Dock & Heated Pool!

• Air Conditioner
• Parking
• Pet Friendly

• Florida
• Little Torch Key

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From US $2,805

         

10.0 (39 Reviews)

House

A Tropical Luxury Getaway, Your own private resort!

• Air Conditioner
• Parking
• Pool

• Florida
• Little Torch Key

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From US $865

         

10.0 (38 Reviews)

House

Conch House - Ocean front with dock and pool

• Air Conditioner
• Parking
• Pool

• Florida
• Little Torch Key

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From US $340

         

10.0 (12 Reviews)

House

New pool & Huge master suite! Open water views , 2 stories of wrap around decks

• Air Conditioner
• Parking
• Pet Friendly

• Florida
• Little Torch Key

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From US $317

         

10.0 (9 Reviews)

House

Beautiful House on Canal - minutes to the Atlantic, no bridges

• Air Conditioner
• Parking
• Pet Friendly

• Florida
• Little Torch Key

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From US $576

         

10.0 (6 Reviews)

House

Beautiful Open-Water Property

• Air Conditioner
• Pet Friendly
• Pool

• Big Pine Key
• Pine Channel Estates

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From US $208

         

10.0 (6 Reviews)

House

Rising Sun: Unique, Round Canal Home on Big Pine Key, Offering Dock & Dog-Friendly Accommodations!

• Air Conditioner
• Pet Friendly
• TV

• Big Pine Key
• Pine Channel Estates

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From US $626

         

10.0 (5 Reviews)

House

Luxury and Lovely Water Front House

• Air Conditioner
• Parking
• TV

• Florida
• Big Pine Key

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From US $450

         

10.0 (5 Reviews)

House

Avail-Discount Feb 2026 -Keys cottage, oceanfront, dock, fenced backyard

• Air Conditioner
• Parking
• Pet Friendly

• Ramrod Key
• Breezeswept Beach Estates

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From US $322

         

10.0 (4 Reviews)

House

5 Pirate's - Pool & seawall for boat. This is a pet friendly home. A pet fee and approval of your pet is required.

• Air Conditioner
• Parking
• Pet Friendly

• Florida
• Little Torch Key

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From US $1,359

         

10.0 (2 Reviews)

House

300’ Private Beach, Pool & Rooftop w Panoramic Ocean Views

• Air Conditioner
• Parking
• Pet Friendly

• Big Pine Key
• Long Beach Estates

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From US $832

         

10.0 (2 Reviews)

House

Manatee Watch | 5 bedrooms, pool, ocean access

• Air Conditioner
• Pet Friendly
• Pool

• Florida
• Big Pine Key

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From US $576

         

10.0 (2 Reviews)

House

Keys To The Kingdom! Private Oceanfront Retreat with Beach and Pool

• Air Conditioner
• Parking
• Pool

• Big Pine Key
• Coupon Bight Aquatic Preserve

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From US $329

         

10.0 (2 Reviews)

RV Rental

🌴 TROPICAL RETREAT 🌴 RV in the Keys

• Air Conditioner
• Parking
• Pet Friendly

• Florida
• Big Pine Key

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★ Pro Tip: Topwintervacations makes it easy to compare the best listings on Topwintervacations homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Topwintervacations homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Cook Island.