Vacation Rentals

15 properties  

$283-412/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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$313-367/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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$258/night

Key Largo Yacht Club 20

3 Bedrooms • 3 Baths • Sleeps 4-6
Internet Ocean View Hot Tub
The perfect “Keys” retreat awaits. This modern, coastal townhome is located in one of the most desirable hidden gems in Key Largo and has everything you need for the ultimate Florida Keys getaway. With a community pool, hot tub and stunning ocean views, you’ll never want to leave Key Largo Yacht Club. This exquisite 3 story townhome features 3 bedrooms and 3 bathrooms, balconies off every room, and as much charm as you can squeeze in. Located in the heart of Key Largo.

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$221-258/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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$258-309/night

Ocean Pointe 1414

2 Bedrooms • 2 Baths • Sleeps 2-4
Internet Oceanfront Hot Tub
Escape to this Keys Retreat. Enjoy the ocean breeze from this island inspired oceanfront condo in Ocean Pointe.
This charming 2 bedroom, 2 bath top floor condo offers a great open concept living area, spacious master suite, comfortable guest room and two private balconies overlooking the marina, protected mangrove preserve and Atlantic Ocean. Enjoy all the amenities of Ocean Pointe including an Olympic sized pool, 12 person jacuzzi, poolside cabana bar, sandy beach, fishing pier, marina with dockage and boat ramp, tennis courts, and so much more.Located on 60 acres in Tavernier, Ocean Pointe is perfectly centered between Key Largo, the Dive Capital of the World, and Islamorada, the Sportfishing Capital of the World.

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$205-309/night

Ocean Pointe 5414

2 Bedrooms • 2 Baths • Sleeps 2-6
Internet Ocean View Hot Tub

This island inspired 2 bedroom, 2 bath oceanfront condo in the gated resort of Ocean Pointe Suites. Enjoy all the amenities of the resort including pool, sandy beach, marina and so much more. Located in Tavernier, Ocean Pointe is perfectly centered between Key Largo and Islamorada.

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$423-481/night

Palm Harbor

4 Bedrooms • 3 Baths • Sleeps 4-8
Allows pets Internet Near Ocean Private Pool
A Tropical Oasis with a Pool and Dockage on Plantation Key.
This luxurious 4 bedroom, 3 bath pool home has everything you’re looking for and more. This luxurious 4 bedroom, 3 bath pool home has everything you’re looking for and more. With 100 feet of deep-water dockage, a delightful beach area, your own private pool and multiple lounge areas to soak up the sun, this is island living at its finest. Located in Kahiki Harbor, you are seconds away from the famous Tavernier Creek, an avenue that guides you to the Everglades National Park and Atlantic Ocean.

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$363-431/night

Peacock Shores

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

This modern, luxurious oceanfront townhome offers 2 bedrooms, 2.5 baths, two screened in porches and a roof top deck. Port of Call offers the ultimate vacation amenities including a pool, beach area and more. Unique to only Port of Call, the grounds are home to a family of friendly peacocks. Located on Plantation Key in Islamorada. 

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$1,219-3,090/night

Pirate's Point

5 Bedrooms • 4 Baths • Sleeps 6-10
Internet Oceanfront Private Pool Hot Tub

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$294-313/night

Sandy Pointe 101

3 Bedrooms • 3 Baths (2 full, 1 half) • Sleeps 4-6
Internet Oceanfront

Enjoy all the wonders Sandy Pointe Townhome has to offer. With breathtaking bay views, deep water dockage and a private beach, this townhome is the perfect Islamorada retreat. This bayfront home features 3 bedrooms and 2.5 bathrooms, townhome style. Located on prestigious Lower Matecumbe, close to downtown Islamorada and only minutes away from the most wonderful fishing spots in the world.

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