Keys Holiday Rentals

(39 rentals)
Keys Holiday Rentals
Phone number: +1 (305) 664-8808
8
We manage privately owned single family homes and condos. Established in 2007 we have grown due to our reputation for guest satisfaction and enjoy repeat business. The properties we represent are clean and offer a variety of amenities in a variety of price ranges.
Manatee Manor - Opportunity to experience The Florida Keys at its best.

$198

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pet Friendly
  • Private Pool

About this property

Minimum Rental: 28 Days"Manatee Manor" is a 3 Bedrooms and 2 ½ Baths home with POOL, Dock, and all new furnishings make this your opportunity to experience The Florida Keys at its best. Conveniently located on a deep and wide canal with easy access to the Bay or a short ride to Tavernier ...

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Property Type

Tavernier House

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Pelican Landing - Waterfront Home With Dock and Access to Community Beach

$263

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pet Friendly

About this property

Minimum Rental: 1 MonthPelican Landing is located in the prestigious neighborhood of Port Antigua on a deep and wide canal. The main floor offers 3 bedrooms and an open concept with ample seating for the entire family. The large balcony overlooks a canal where pelicans are usually seen diving into ...

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Property Type

Islamorada House

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Palms #309 - Exceptional condo with panoramic views of the Atlantic Ocean.

$82

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Oceanfront
  • Pool

About this property

Minimum Rental: 28 Days "The Palms #309" is an exceptional condo with panoramic views of the Atlantic Ocean. This condo is in one of the most popular condo complexes in Islamorada - The Palms of Islamorada. Comfortably furnished and ready for your arrival this unit offers an updated kitchen ...

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Property Type

Islamorada Condo

"Great place to relax"
Reviewed August 3, 2019

Condo is in great location and in nice condition Everything was as was promised Loved the pool and walking in the ocean Great dining just walking distance Only thing I would ask is better kitchen ...

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Moon Bay A410 - End Unit in one of Key Largo's finest bay front condo complexes

$168

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Private Pool

About this property

Minimum Rental: 7 Nights Saturday to Saturday"Moon Bay #A410" is a 4th floor end unit in one of Key Largo's finest bay front condominium complexes offers a beautiful view of the Florida Bay and lots of natural light. You'll love the updated kitchen with granite counters, new cabinetry ...

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Property Type

Key Largo Condo

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Moon Bay A206 - Totally Remodeled Condo with Pool in Key Largo

$189

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

Minimum Rental: 7 Nights"Moon Bay A206" is calling all fishermen and divers... Whether you plan to fish or dive on your next visit to the Keys, you will find these exceptional accommodations first class and affordable. World famous dive sites are minutes away and phenomenal fishing is ...

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Property Type

Key Largo Condo

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Sunrise on Sunset

3 BR | 3 BA | Sleeps 12 | Quick View

$300

per night

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Key Amenities

  • Air Conditioning
  • Beachfront
  • Full Kitchen
  • Kid Friendly
  • Oceanfront
  • Pet Friendly

About this property

MINIMUM STAY: 28 DAYS “Sunrise on Sunset” is the ULTIMATE BEACH FRONT HOME. There are BREATH TAKING OCEAN VIEWS from almost every room in this house! Play in the sand, walk into the ocean or sit under the covered ground level area. This spacious 3BR/3BA single family home offers many ...

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Property Type

Islamorada House

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Flamingo Cottage - Adorable 2 bedroom, 2 bath cozy cottage with pool.

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pet Friendly
  • Private Pool

About this property

Minimum Rental: 28 DaysFlamingo Cottage is an adorable 3 bedroom stilt home nestled among tropical foliage. There are two bedrooms and one bath on the main living level of this home plus a private studio type apartment with a private bath on the ground level. This home has a cozy cottage like feeling ...

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Property Type

Islamorada House

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Beacon Reef #310 - Beautiful condo with lovely views of the ocean.

$113

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Oceanfront
  • Pool

About this property

Minimum Rental: 28 Days"Beacon Reef 310" is one of the most desirable condominium complexes in the Upper Keys. Located in Islamorada it is convenient to everything - restaurants, fishing, diving, snorkeling, swim with the dolphin programs and much more. Picture yourself relaxing on your ...

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Property Type

Islamorada Condo

"PERFECT VACATION GETAWAY!"
Reviewed June 9, 2019

This beautiful condo was beautifully decorated for the island appeal. Very clean, and conveniently located. Everything we needed for a PERFECT vacation. Pool and Grounds were also immaculate, with a ...

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Bay Therapy - 3 Bedroom Waterfront Home with Hot Tub and Boat Dock

$160

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pet Friendly

About this property

Minimum Rental: 28 DaysHappy vacationing starts here! The owners call their special getaway “Bay Therapy” for many reasons. It is located in a great neighborhood in Key Largo. It is convenient to the mainland and is the gateway to the Keys. Since purchasing this home the owners have ...

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Property Type

Islamorada House

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Palm Harbor - Fabulous Home with Privacy Gate, Pool, Dock and Outdoor Enter

$333

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pet Friendly
  • Private Pool

About this property

Minimum Rental: 28 Days "Palm Harbor" is a spacious elegant home with pool and dock. Gently swaying palm trees greet you at the gated entrance to this wonderful home. The ground level entry features a billiard/game room, bedroom and full bath. An open curved staircase leads to the 2nd ...

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Property Type

Plantation Key House

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Beba's Reef House - Capture your imagination the moment you enter this home .

$150

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Private Pool

About this property

Minimum Rental: 28 Days"Beba's Reef House" will capture your imagination the moment you enter the home and rise to the main living level through the reef painted on the walls of the stair well and the photos of fish captured by the owner during numerous dives here in the Keys. This is a ...

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Property Type

Tavernier House

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Bayside Breeze - Beautiful Home with Open Living, Gourmet Kitchen and Boat Lift

$125

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly

About this property

BEST PRICED WATERFRONT HOME IN AREA *********ALL NEW MONTHLY RATES********Minimum Rental: 28 Days "Bayside Breeze" is a wonderful 2013 built stilt home centrally located in the Islamorada/Tavernier area. The open concept living area - kitchen, dining, and living - invites family togetherness. ...

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Property Type

Plantation Key House

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My Paradise - Oceanfront beach house with protected dockage.

$227

per night

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Key Amenities

  • Air Conditioning
  • Beachfront
  • Full Kitchen
  • Kid Friendly
  • Oceanfront
  • Pet Friendly

About this property

Minimum Rental: 28 Days "My Paradise" is an oceanfront beach house with protected dockage and located in the Fishing Capital of the World - Islamorada. Realize your dreams - a beach home located on a swimmable beach and a place to dock your boat. This home is indeed a rare find in The Florida ...

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Property Type

Islamorada House

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PALMS #317

1 BR | 1 BA | Sleeps 4 | Quick View

$63

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool
  • Private Pool

About this property

MINIMUM RENTAL: 1 Month The Palms of Islamorada is a condo complex consisting of 84 units and is located directly on the Atlantic Ocean. The complex features separate his and hers mini-gyms, heated pool, hot tub, tiki for gatherings and lots of lounge chairs so soaking up the wonderful sunshine. ...

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Property Type

Islamorada Condo

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Lyons Landing - Large Spacious 4/3 Home on Wide Canal with Pool, Dock & Boatlift

$262

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pet Friendly
  • Private Pool

About this property

MINIMUM STAY: 28 NIGHTS Lyons Landing is an exceptional single family home with pool, dock, boat lift and outdoor living area located in the prestigious neighborhood of Venetian Shores in Islamorada. Everything you need for a spectacular vacation awaits you in this extraordinary home. 3 bedrooms ...

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Property Type

Key Largo House

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Sunshine Place - Ground Level Unit with Ocean Views.

$180

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Oceanfront
  • Pet Friendly

About this property

Minimum Rental: 7 Days"Sunshine Place" is setup perfectly for privacy and convenience. The owners of this wonderful property called Sunshine Place are willing to share a portion of their piece of Paradise with you. The ground level living area of this home is perfect for one or two people ...

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Property Type

Islamorada House

"Wonderful!"
Reviewed April 23, 2019

Beautiful view; lots of privacy; an exceptional experience! The home was immaculate and had a “well-supplied” kitchen. We genuinely enjoyed our stay, We loved getting up in the morning and having ...

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Villa Riolo - Updated home and perfect for your next holiday in Islamorada

$117

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pet Friendly

About this property

Minimum Rental: 28 Days"Villa Riolo" is an updated single family stilt home and perfect for your next holiday in Islamorada! It comfortably sleeps 6 in two bedrooms. This home has been meticulously cared for over the years and for the first time the owners are offering you an opportunity ...

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Property Type

Islamorada House

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West Plaza del Lago - Gorgeous Waterfront Home with Boat Lift and Beach Access!

2 BR | 2 BA | Sleeps 5 | Quick View

Distance to beach: 0.3 miles to Port Antigua Neighborhood Beach

$133

per night

View Details

Key Amenities

  • Air Conditioning
  • Kid Friendly

About this property

Minimum Rental: 28 Days"West Plaza Del Lago" promises to be a favorite. Beautifully remodeled roomy single family stilt home with vaulted ceilings and located in prestigious Port Antigua on a deep and wide canal. You will love the interior of this home as much as the exterior! As you enter ...

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Property Type

Islamorada House

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Little Bay - Entire Compound Islamorada FL 33036

$1179

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pet Friendly

About this property

MINIMUM RENTAL: 7 NIGHTS This is a lush tropical setting in a gated compound located directly on Florida Bay. Protected dockage in the "Little Bay" will keep your 30' boat (or smaller) safe. There’s a “sunning” area with lounge chairs on the peninsula so you can capture ...

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Property Type

Islamorada Estate

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BEACON REEF 301 - ISCBEAC301

2 BR | 2 BA | Sleeps 4 | Quick View

$117

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Oceanfront

About this property

MINIMUM STAY: 28 DAYS NEW TO RENTAL MARKET "Beacon Reef 301" is a fully renovated condo that offers inspiring tropical views including the ocean from the open-air balcony accessed from the main living area and the master bedroom suite. This charming, clean, spacious 2 bedroom 2 bath condo ...

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Property Type

Islamorada Condo

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Key Largo Yacht Club #8 - 3 BR Townhouse Oceanside with 30' Dock and Boat Lift

$117

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool

About this property

Minimum Rental: 28 Days"Key Largo Yacht Club #8" is an exceptional 3 story townhouse located in a quiet oceanfront complex with heated pool and marina. Inspiring ocean views from two balconies and a ground level patio to BBQ. Protected marina and deeded boat slip easily accommodates a ...

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Property Type

Key Largo Townhome

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HARBOR BREEZE

1 BR | 1 BA | Sleeps 4 | Quick View

$60

per night

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Key Amenities

  • Air Conditioning
  • Kid Friendly
  • Pool
  • Private Pool

About this property

MINIMUM STAY: 28 DAYS Looking for a place to hang your hat while you are fishing? Don't want or need a big place? This is it. Harbor Breeze is a spacious one room accommodation with a full bath. There are two queen beds, and a small sitting area with a leather sofa and wall hung flat screen TV. A ...

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Property Type

Tavernier Condo

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BEACON REEF #503

2 BR | 2 BA | Sleeps 4 | Quick View

$143

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool
  • Private Pool

About this property

MINIMUM STAY: 28 DAYS FIRST TIME ON RENTAL MARKET. This exquisite condo has been TOTALLY remodeled and updated from top to bottom. This is a 5th floor unit with ocean views from the balcony and master bedroom suite. The furnishings are all brand new. There are three TV's - one to suit everyone's ...

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Property Type

Islamorada Condo

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Conch Bar South - 4 Bedroom Waterfront Home with Swimming Pool

4 BR | 3 BA | Sleeps 10 | Quick View

1

Distance to beach: 3 miles to Founders Park Beach

$367

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pet Friendly
  • Private Pool

About this property

Minimum Rental: 28 Days"Conch Bar South" is a magnificent home is located at the mouth of a wide canal in Plantation Key and offers phenomenal open water views. The furnishings are new and provide a comfortable and extremely inviting living environment. This 4 bedroom 3 bath single family ...

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Property Type

Tavernier House

"I have rented in the Keys for 53 years; I would rate this property number 1,"
Reviewed August 6, 2019

The picture is worth 100 characters, We enjoyed the month, too many good restaurants to list, convenient access to ocean and back country; we brought our boat, dock user friendly with adequate bumpers, ...

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Brock Haus - Bayfront Weekly Townhome with Boat Slip, Pool, Beach.

$211

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool

About this property

Minimum Rental: 7 Days (Saturday to Saturday)"Brock Haus on the Gulf" is an end unit townhouse on the water's edge with water views on 3 sides! The main living area faces the Florida Bay, one side faces the inlet leading to the marina basin and the back faces the marina. The panoramic open ...

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Property Type

Plantation Key Condo

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Beacon Reef #522 - Oceanfront 5th floor (top floor) condo at Beacon Reef.

$147

per night

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Key Amenities

  • Air Conditioning
  • Beachfront
  • Full Kitchen
  • Kid Friendly
  • Oceanfront
  • Pool

About this property

Minimum Rental: 28 Days NEW ON THE RENTAL MARKET. PHOTO UPDATES COMING SOON. "Beacon Reef 522" offers magnificent 180 degree oceanfront views. Enjoy the sea breezes as your relax on your private balcony and gaze at the water. Whether staying one month or more you will be more than happy ...

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Property Type

Islamorada Condo

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Martin Family Fish Camp - Private Bayfront Peninsula with 2 Cottages & Dockage

4 BR | 3 BA | Sleeps 12 | Quick View

1

Distance to beach: 5 miles to Founder's

$543

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Oceanfront
  • Pet Friendly

About this property

MINIMUM STAY: 7 Nights The Martin Family Fish Camp is located on a private peninsula and offers two cottages named Bonefish and Tarpon. Each cottage offers two private bedrooms. Between the two cottages there is sleeping for 10 in beds plus an additional 2 on the sleeper sofa for an occasional ...

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Property Type

Islamorada Cottage

"Awesome"
Reviewed July 11, 2019

We stayed for a month at Blue Water Retreat and had an awesome time with family and friends. The ocean views were magnificent. The pool was a big hit with the kids. We even had our dog with us. Hope to ...

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Little Bay Cottage- Gated Bayfront Property Shared with 2 Other Rental Units

$393

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen

About this property

Minimum Rental: 7 Days"Little Bay's Cottage" is one of three rental units on this property. The cottage is a ground level dwelling separate from two duplex units. It offers a unique floor plan with the main living area in the center of the house with kitchen, dining area, sitting area ...

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Property Type

Islamorada Cottage

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Antigua Place - Charming vacation home located in Port Antigua.

$187

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pet Friendly

About this property

MINIMUM RENTAL 1 MONTH: Charming vacation home located in the beautiful neighborhood of Port Antigua. You will love this home! There is a wonderful open concept floor plan with 3 nicely proportioned bedrooms. Sliding doors open from the dining area into the sunroom overlooking the canal. You’ll ...

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Property Type

Islamorada House

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Twice the Charm - Canal Home with Pool, Dock and Fish Cleaning Station

$183

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pet Friendly
  • Private Pool

About this property

Minimum Rental: 28 Days "Twice the Charm" is a gorgeous newly remodeled single family home. You’ll love the convenient location in the Ocean Shores area of Key Largo. There’s easy ocean access from the dock which accommodates a boat up to 30' and includes davits, water, electricity, ...

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Property Type

Key Largo House

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PALMS #404

2 BR | 2 BA | Sleeps 6 | Quick View

$77

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool
  • Private Pool

About this property

Minimum Rental 1 month. This is an exceptional 2 bedroom and 2 bath condo located in one of the most popular Islamorada condo complexes - The Palms of Islamorada. The balcony is large enough to dine or recline and offers fabulous open water views. While sipping coffee in the morning you can watch ...

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Property Type

Islamorada Condo

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Tropical Oasis - Exceptional single family home designed for tropical living.

$292

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pet Friendly
  • Private Pool

About this property

Minimum Rental: 28 Days "Tropical Oasis" is an exceptional single family home designed for tropical living - charming interior and extraordinary outdoor living areas. Open concept living area on the middle level of the home offers a formal dining with 8 chairs and 3 bar stools at the kitchen ...

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Property Type

Key Largo House

"Beautiful location stunning home."
Reviewed January 11, 2020

Beautifully decorated and fabulous location! I highly recommend this home. We had a great time and wonderful experience here in Key Largo FL.

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BEACON REEF 306 - ISCBEAC306

2 BR | 2 BA | Sleeps 4 | Quick View

$100

per night

View Details

Key Amenities

  • Air Conditioning
  • Beachfront
  • Full Kitchen

About this property

Minimum Rental: 1 Month Enjoy a relaxing stay here in the Keys at this immaculate and charming two bedroom and two bath condo. While the owners attend to their other property "up north" you can relish all the delightful amenities of their condo. This unit is beautifully appointed and ...

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Property Type

Islamorada Condo

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Beacon Reef #222 - Gorgeous condo with panoramic views of the Atlantic Ocean.

$147

per night

View Details

Key Amenities

  • Air Conditioning
  • Beachfront
  • Full Kitchen
  • Kid Friendly
  • Oceanfront

About this property

Minimum Rental: 28 Days"Beacon Reef 222" is an extraordinary ocean front condo with panoramic views of the Atlantic Ocean. Relax on your own balcony or use the spiral stairs to access the sandy beach below. This condo is located in one of the most prestigious condo complexes in Islamorada. ...

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Property Type

Islamorada Condo

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RHCP8 - Bayfront townhouse located in a lush tropical setting.

$100

per night

View Details

Key Amenities

  • Air Conditioning
  • Beachfront
  • Full Kitchen
  • Kid Friendly
  • Pool

About this property

MINIMUM STAY: 28 Nights. Bayfront townhouse located in the lush tropical setting of Rock Harbor Club in Key Largo. You'll love the open water views from the two oversized screened balconies - one off the main living area and the other off the master suite. There's something for everyone at Rock Harbor ...

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Property Type

Key Largo Townhome

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FISH WHISTLE - ISH137BAYV

4 BR | 3 BA | Sleeps 10 | Quick View

$500

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen

About this property

MINIMUM STAY: 28 DAYS Fish Whistle is an amazing privately owned estate located directly on Snake Creek in Islamorada. It offers spectacular views and easy access to the Atlantic Ocean or Florida Bay for either sport fishing or diving/snorkeling activities. This home comfortably sleeps 8 people in ...

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Property Type

Islamorada House

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PALMS #313

2 BR | 2 BA | Sleeps 4 | Quick View

$73

per night

View Details

Key Amenities

  • Air Conditioning
  • Beachfront
  • Full Kitchen
  • Kid Friendly
  • Pool
  • Private Pool

About this property

Spectacular oceanfront views are yours from both the master bedroom and the balcony of this beautifully appointed condo. Alligator Reef Lighthouse is easily visible from your master suite or the balcony and you'll be able to watch cruise ships as they pass by the reef and adventure seekers as they ...

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Property Type

Islamorada Condo

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Plantation Adventure - Sensational remodeled home awaits your arrival.

$217

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pet Friendly
  • Private Pool

About this property

Minimum Rental: 28 Days "Plantation Adventure" is a sensational remodeled single family home on Plantation Key awaits your arrival. The gorgeous POOL, HOT TUB, and TIKI BAR are ready and waiting. Imagine fun filled days and evenings relaxing in the patio and yard area! The patio is spacious ...

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Property Type

Plantation Key House

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Palms #407 - Beautiful condo with panoramic views of the Atlantic Ocean.

$97

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Oceanfront

About this property

Minimum Rental: 28 Days"The Palms #407" is a charming 2 bedroom, 2 bath condo with updated kitchen and baths. Walk out onto your balcony and enjoy the sea breezes and ever changing ocean views. The comfortable furnishings and convenient floor plan provide an inviting place to call home. ...

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Property Type

Islamorada Condo

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