Vacation Rentals

29 properties  

$300-415/night

Angler's Reef 105

2 Bedrooms • 3 Baths (2 full, 1 half) • Sleeps 3-6
Internet Near Ocean

Escape to Islamorada’s Finest Oceanfront Gated Community

Soak up the sun and enjoy the ocean breeze from this charming 2 bedroom, 2 bath Key West style villa located in the exclusive community of Angler’s Reef. Accommodating up to six people, this exquisite home makes it easy to both entertain and relax with its open floor plan, private balconies, and abundance of on-site amenities. Enjoy all the wonders of this highly sought after community including a heated oceanfront pool, private marina with deep-water dockage and two white sandy beaches with kayaks for your own use.

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$88-110/night

Aquamarine Apartment

1 Bedroom • 1 Bath • Sleeps 2
Allows pets Internet Near Ocean
Welcome to your little home away from home. This canal front 1 bedroom, 1 bath downstairs apartment is recently renovated, charmingly decorated, and fully furnished. Aquamarine Apartment offers a great outdoor space, spacious back porch overlooking the canal and dockage for you to bring your kayak or paddleboards. Centrally located in Tavernier, between Key Largo and Islamorada, this rental is near restaurants, shopping, grocery stores and more.

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$322-368/night

Bluewater Escape

4 Bedrooms • 3 Baths • Sleeps 4-8
Allows pets Internet Waterfront
Step into luxury as you enter this brand new home, featuring coastal-inspired furniture that creates a serene atmosphere. Upstairs you are greeted with a tranquil, yet spacious living area that offers 3 bedrooms & 2 bathrooms. Downstairs offers a cozy living area with one bedroom, perfect for guests. The highlight of this waterfront haven is the 40 feet of dockage with a boat lift and jet ski dock. Located in Tavernier, this home is in between Key Largo and Islamorada.

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$276-313/night

Buttonwood Bay H6

2 Bedrooms • 3 Baths (2 full, 1 half) • Sleeps 2-4
Internet Oceanfront

Key Largo Townhome with Stunning Views, Modern Comforts, and Resort-Style Amenities

This modern yet cozy retreat is a meticulously remodeled townhome with high-end finishes, two bedrooms, two full baths, and a half guest bath downstairs. Step outside to enjoy resort-style amenities, including three heated swimming pools, a marina with dockage, a fully equipped gym, five tennis and pickleball courts, saunas, basketball, a sandy beach and various observation docks overlooking the Florida Bay.

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$184-202/night

Camelot Cove

3 Bedrooms • 2 Baths • Sleeps 3-5
Allows pets Internet Ocean View
Enjoy the coastal charm and comfort of delightful Hammer Point home. This charming canal front retreat offers 2 bedrooms, 2 bathrooms, and a great den with a pull-out couch perfect for guests. Whether you are looking to soak up some sun, adventure the neighborhood, or take a sunset cruise, Camelot Cove checks all the boxes. Featuring 20 feet of dockage with a boat lift, a large fenced in yard, BBQ grill, canoes, and bikes, you’ll have everything you need for the perfect vacation.

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$441-515/night

Casa del Sol

5 Bedrooms • 3 Baths • Sleeps 5-10
Allows pets Internet Near Ocean
This splendid 5-bedroom, 3-bath canal front home is a boater’s paradise. Casa del Sol offers 35 feet of dockage, a filet table, and is located in popular Port Antigua, with direct bay & ocean access only minutes from some of the best fishing spots in the Keys. Adding an extra layer of excitement to your vacation experience, this neighborhood also features an amazing white sandy beachfront homeowner's park, boat ramp, and spectacular sunsets.

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$147-184/night

Executive Bay Club F1

2 Bedrooms • 2 Baths (1 full, 1 half) • Sleeps 5-6
Internet
Escape to paradise in this delightful 2-bedroom townhouse, nestled in the peaceful compound of Executive Bay Club. At Executive Bay Club, there's no shortage of activities to enjoy! Unwind on the secluded private beach, cool off with a refreshing swim in the pool, engage in a friendly game of tennis, or take a leisurely sunset stroll amidst the peaceful grounds of EBC. Located on Plantation Key, Executive Bay Club is close to great local attractions, restaurants, shopping, and more.

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$294-313/night

Hammer Point Hideaway

2 Bedrooms • 2 Baths • Sleeps 3-6
Allows pets Internet
Nestled in the heart of paradise, this 2-bedroom, 2-bath canal front home offers a perfect blend of comfort and style. Bring your boat and enjoy the convenience of your own private dock complete with a fish cleaning station, or use one of the kayaks or paddle boards and explore the Florida Bay. Spend your morning sipping coffee on the cozy screened in front porch or have dinner and drinks on the spacious back deck with a gas firepit, dining table, and lounge seating complete with stunning bay views. Centrally located between Key Largo and Islamorada, you are near local attractions, dining, and shopping.

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$397-434/night

Islamorada Reef Home

3 Bedrooms • 2 Baths • Sleeps 3-5
Allows pets Internet Near Ocean Private Pool

Welcome to Islamorada Reef Home, a light and bright Islamorada pool home with dockage.

You’ll feel right at home in this newly renovated 3 bedroom, 2 bath canal front gem offering a spacious loft, a great open living area, updated kitchen and a balcony overlooking the canal. Complete with vaulted ceilings, charming Keys décor, and water views, this is the perfect Florida Keys retreat.

Islamorada Reef Home is a boater’s paradise with 65 feet of dockage and fish cleaning station. Located right off Tavernier Creek you are only minutes away from the Florida Bay and seconds from some of the best fishing and diving spots in the Atlantic. With brand-new pool, completed in December 2022, a BBG grill, outdoor shower, and great canal views, you’ll never have to leave this inviting backyard.

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$129-184/night

Kawama Yacht Club 408

2 Bedrooms • 2 Baths • Sleeps 3-6
Internet Near Ocean
Enjoy Kawama Yacht Club, an oceanside oasis with an abundance of amenities.

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$166-184/night

Keys Cottage

2 Bedrooms • 1 Bath • Sleeps
Allows pets Internet Near Ocean
Escape to this quaint 2-bedroom, 1-bathroom conch-style cottage in the heart of Islamorada. The fully equipped kitchen and cozy living space invite you to feel right at home, while the Keys-style Florida room offers a breezy spot to soak up the beautiful winter weather. With a spacious, fenced-in yard featuring a hot tub, multiple outdoor lounge areas, and spacious green grass yard, this cozy retreat is perfect for those seeking relaxation and tranquility. Located in Downtown Islamorada at MM81.

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$182-258/night

Long Key Oasis

3 Bedrooms • 2 Baths • Sleeps 5-10
Internet Near Ocean Hot Tub
Enjoy the sun and the sea at this charming canal front home in Layton. This canal front home with two separate living areas can easily accommodate 10 guests and all their toys. Enjoy the natural wonders of Long Key State Park located just down the canal. Bring your boat, or use one of the kayaks or paddle boards on a nice sunny day, then come home and relax in the hot tub. Located on Long Key, this property is the midway point between Islamorada and Marathon.

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