Castle In Hawaii - Vacation Rentals in Jimmy Johnson's Big Chill

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From US $232

         

9.6 (152 Reviews)

Villa

Tastefully Remodeled Island Villa in Key Largo, 2 Bedrooms, 2 Bathrooms.

• Air Conditioner
• Parking
• Pool

• Florida
• Key Largo

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From US $474

         

|

10.0 (7 Reviews)

Apartment

Villa Valbuena Aqua Vista Key Largo Marina Pickleball Remodeled 2025

• Air Conditioner
• Parking
• Pool

• Florida
• Key Largo

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From US $441

         

|

8.8 (1003 Reviews)

Resort

Playa Largo Resort & Spa, Autograph Collection

• Air Conditioner
• Parking
• Pool

• Key Largo
• Rock Harbor

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From US $709

         

10.0 (90 Reviews)

Villa

Beautiful Oceanside Mariner`s 3 Bedroom Townhome

• Air Conditioner
• Parking
• Pool

• Key Largo
• Rock Harbor

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From US $278

         

|

10.0 (4 Reviews)

Apartment

Port Largo Villas Escape 5A

• Air Conditioner
• Parking
• Pool

• Florida
• Key Largo

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From US $340

         

|

8.6 (1004 Reviews)

Resort

Baker's Cay Resort Key Largo, Curio Collection by Hilton

• Air Conditioner
• Parking
• Pool

• Florida
• Key Largo

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From US $480

         

10.0 (81 Reviews)

Villa

Newly upgraded Key Largo Villa W/Boat Slip

• Air Conditioner
• Parking
• Pet Friendly

• Florida
• Key Largo

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From US $270

         

|

10.0 (2 Reviews)

Villa

New Lagoon-front townhouse with Marina Day Dreams Key Largo

• Air Conditioner
• Parking
• Pet Friendly

• Florida
• Key Largo

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From US $657

         

10.0 (60 Reviews)

Villa

Oceanview Marinaview Free Golf Cart Pool Pickleball

• Air Conditioner
• Parking
• Pet Friendly

• Florida
• Key Largo

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From US $280

         

10.0 (25 Reviews)

Villa

Tropical Retreat Villa on Lush Acre

• Air Conditioner
• Parking
• TV

• Florida
• Key Largo

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From US $392

         

10.0 (24 Reviews)

Villa

Sunset Villas: Bayfront Beach Compound *28 Night Min*

• Air Conditioner
• Parking
• Pet Friendly

• Key Largo
• Rock Harbor

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From US $1,618

         

10.0 (8 Reviews)

Villa

Villa in Key Largo – Pool & Beach Club

• Air Conditioner
• Parking
• Pet Friendly

• Key Largo
• Rock Harbor

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From US $280

         

10.0 (8 Reviews)

Villa

Tropical bayfront villa with sandy beach

• Air Conditioner
• Parking
• TV

• Florida
• Key Largo

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From US $2,168

         

10.0 (3 Reviews)

Villa

Villa in Key Largo – Gym, Pool + Beach

• Air Conditioner
• Parking
• Pet Friendly

• Key Largo
• Rock Harbor

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From US $1,673

         

9.8 (7 Reviews)

Villa

Luxury Villa by the Ocean | Pool & Resort

• Air Conditioner
• Parking
• Pet Friendly

• Key Largo
• Rock Harbor

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From US $537

         

9.6 (87 Reviews)

Villa

Free Golf Cart Free Kayaks Steps to Pool Pickleball

• Air Conditioner
• Parking
• Pool

• Florida
• Key Largo

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From US $584

         

9.6 (52 Reviews)

Villa

Our place overlooks the Atlantic. Our marina is less than 50 ft from our patio

• Air Conditioner
• Parking
• Pool

• Florida
• Key Largo

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From US $1,958

         

9.6 (25 Reviews)

Villa

4BR Key Largo Villa w/Beach & Marriott Perks

• Air Conditioner
• Parking
• Pet Friendly

• Key Largo
• Rock Harbor

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From US $663

         

9.6 (20 Reviews)

Villa

Oceanview - Pool Indoor/Outdoor Pickleball September Deals

• Air Conditioner
• Parking
• Pool

• Key Largo
• Rock Harbor

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From US $1,831

         

9.6 (18 Reviews)

Villa

Key Largo 3BR Villa | Pool, Kayaks & Resort Perks

• Air Conditioner
• Parking
• Pet Friendly

• Key Largo
• Rock Harbor

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From US $2,274

         

9.6 (14 Reviews)

Villa

4BR Key Largo Stay – Pool, Parking + Beach Club

• Air Conditioner
• Parking
• Pet Friendly

• Key Largo
• Rock Harbor

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From US $511

         

9.6 (5 Reviews)

Villa

Waterfront Lagoon Retreat | Kayaks Paddleboard Golf Cart

• Air Conditioner
• Parking
• Pet Friendly

• Florida
• Key Largo

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From US $1,932

         

9.4 (10 Reviews)

Villa

4BR Villa w/Private Pool & Gym Access

• Air Conditioner
• Parking
• Pet Friendly

• Key Largo
• Rock Harbor

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From US $2,051

         

9.4 (6 Reviews)

Villa

Key Largo 4BR Villa | Partial Ocean View + Marriott

• Air Conditioner
• Parking
• Pet Friendly

• Key Largo
• Rock Harbor

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★ Pro Tip: Castleinhawaii makes it easy to compare the best listings on Castleinhawaii homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Castleinhawaii 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 Jimmy Johnson's Big Chill.