Vacation Rentals

28 properties  

$300-450/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.

Photos Details Inquire

$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.

Photos Details Inquire

$239-313/night

Buttonwood Bay H6

2 Bedrooms • 3 Baths • 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.

Photos Details Inquire

$175-202/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.

Photos Details Inquire

$737-920/night

Fish House

3 Bedrooms • 2 Baths • Sleeps 3-6
Internet Near Ocean Private Pool Hot Tub
This jaw-dropping 3-bedroom, 3-bath Islamorada gem is where luxury meets laid-back island vibes. Inside, you’ll find three cozy bedrooms, two tranquil bathrooms, a stunning open concept living and dining area, and expansive sliding glass doors leading out to spacious balconies overlooking your backyard oasis. Outside, the good life awaits: 70 ft. of dockage with a front-row seat to the Atlantic Ocean, a custom pool and hot tub, a fun yet cozy fire pit, swinging chairs and tropical landscape.

Photos Details Inquire

$285-313/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.

Photos Details Inquire

$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.

Photos Details Inquire

$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.

Photos Details Inquire

$166-184/night

Keys Cottage

2 Bedrooms • 1 Bath • Sleeps 2-4
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.

Photos Details Inquire

$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.

Photos Details Inquire

$1,329-1,330/night

MarchettiVille

5 Bedrooms • 3 Baths • Sleeps 8-12
Beachfront Private Pool
Welcome to Marchettiville - a waterfront vacation home offering the ultimate escape, combining luxury and comfort with stunning views. This estate offers five spacious bedrooms, a heated pool, a tiki hut, two margarita machines, and a private dock with a beach, making this the perfect place to unwind and recharge.

Photos Details Inquire

$1,288-2,575/night

Morada Shores

5 Bedrooms • 6 Baths (5 full, 1 half) • Sleeps 5-12
Allows pets Internet Oceanfront Private Pool

Welcome to Morada Shores, an exquisite estate where every detail has been carefully crafted for the ultimate vacation experience.

Morada Shores is a thoughtfully designed home boasting 5 spacious suites and 5.5 elegant bathrooms, providing a spacious haven for friends and family.

The custom-built pool provides a refreshing oasis, while the indoor/outdoor porch is ideal for entertaining, and the private sandy beach invites you to soak up the sun and enjoy the tranquil surroundings.

Photos Details Inquire

1 – 12 of 28 places to stay