Keys Holiday Rentals

(42 rentals)
Keys Holiday Rentals
Phone number: +1 (305) 664-8808
14
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.
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$330

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen

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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$177

avg/night

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Key Amenities

  • Air conditioning
  • Kitchen
  • Oceanfront

About this property

MINIMUM STAY: 28 DAYS “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 has all the comforts ...

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Property Type

Islamorada Condo

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4 BR | 3 BA | Sleeps 12 | Quick View

1

Distance to beach: 5 miles to Founder's

$543

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pet friendly

About this property

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

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Property Type

Islamorada House

"Awesome"

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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$100

avg/night

View Details

Key Amenities

  • Air conditioning
  • Beachfront

About this property

Minimum Rental: 1 Month Everything in this unit is lovely - furnishings, linens, updated kitchen, appliances, and bathrooms. Great views of Florida Bay and our fabulous Keys sunsets. This complex is conveniently located just steps from a full service marina and 2 highly acclaimed restaurants. Watch ...

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Property Type

Islamorada Condo

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$186

avg/night

View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • 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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1 BR | 1 BA | Sleeps 4 | Quick View

1

Distance to beach: 7 miles to Founders

$98

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Oceanfront
  • 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

"Great condo!"

This was a great location to watch beautiful sunrises. The facilities were as described. The condo was super clean and up to date.

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$133

avg/night

View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • 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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$240

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • 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!"

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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$315

avg/night

View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • 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 ...

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Property Type

Islamorada House

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6 BR | 6 BA | Sleeps 18 | Quick View

Distance to beach: 5 miles to Founder's Park

$1286

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • 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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$156

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen

About this property

Minimum Rental: 1 Month Enjoy a relaxing summer and fall here in the Keys at this immaculate and charming two bedroom and two bath condo with screened balcony overlooking views of the tropical complex and of course the beautiful ocean. While the owners attend to their other property "up north" ...

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Property Type

Islamorada Condo

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$282

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • 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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$263

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly

About this property

Minimum Rental: 3 MonthsPelican 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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$168

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • 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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$167

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • 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

"Lovely little home on a quiet street"

I rented this so I could have a quiet place to swim and relax before undergoing major surgery. The pool area is a perfect oasis with the occasional visiting birds and squirrels. The house is comfortable ...

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$292

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • 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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2 BR | 2 BA | Sleeps 5 | Quick View

Distance to beach: 0.3 miles to Port Antigua Neighborhood Beach

$200

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen

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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2 BR | 2 BA | Sleeps 6 | Quick View

Distance to beach: 3 miles to Anne's Beach

$173

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen

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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$187

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

About this property

Minimum Rental: 1 Month This 2 bedroom/2 bath condo with fabulous ocean views has been totally remodeled and updated. You'll love the sparkling new kitchen with stainless steel appliances and induction cook top. Store your beverages in the wine cooler. The interior is bright, spacious and clean. The ...

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Property Type

Islamorada Condo

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$173

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

About this property

MINIMUM STAY: ONE MONTH. Exceptional 5th floor (top floor) 2 bedroom 2 bath condo at Beacon Reef. Ocean views from the open air balcony. You’ll be so glad you have chosen to spend your holiday here. The kitchen was remodeled in 2013 – granite counters, stainless steel appliances, and ...

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Property Type

Islamorada Condo

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$135

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • 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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$429

avg/night

View Details

Key Amenities

  • Air conditioning
  • 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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$140

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • 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"

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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$300

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pool

About this property

MINIMUM STAY: One Month Gorgeous 3 bedroom ocean front condo with unobstructed ocean views from the screened balcony. Check out the photos! The kitchen was completely remodeled in 2021 with all new everything. Walls were moved to enhance the work flow. At the end of the kitchen there is a computer ...

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Property Type

Plantation Key Condo

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2 BR | 2 BA | Sleeps 6 | Quick View

Distance to beach: 7 miles to Founders

$137

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pool
  • Private pool

About this property

NEW LISTING 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 ...

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Property Type

Islamorada Condo

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$429

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pet friendly

About this property

Minimum Rental: 7 Days Little Bay's Upper Duplex is one of three rental units on this fabulous property. The Little Bay property is a one acre lush tropical setting in a gated compound located directly on Florida Bay. This is one of 3 separate units for rent by the week or month. Each unit sleeps ...

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Property Type

Islamorada House

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$283

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Private pool

About this property

Minimum Rental: 3 Months "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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$367

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • 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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$392

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Private pool

About this property

*25% OFF Rent for AUG, SEPT, OCT, and/or NOV 2021*BRAND NEW TO RENTAL MARKETMINIMUM STAY: 28 DAYS Exceptional single family home designed for tropical living - charming interior and extraordinary outdoor living areas. New owners have purchased all new linens and added many new amenities. ...

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Property Type

Tavernier House

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$133

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pool

About this property

Minimum Rental: 28 Days "The Palms #301" is an exceptional condo has been impeccably maintained and is located in one of the finest condo complexes in Islamorada. It features an updated kitchen, remodeled baths and is comfortably furnished. This unit is ready for your arrival. Be sure ...

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Property Type

Islamorada Condo

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$207

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • 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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$153

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pool

About this property

Minimum Rental: 28 Days "Beacon Reef 406" is an excellent choice for your vacation getaway, whether you're planning on staying a month or the entire season, this is a great unit. Beacon Reef is centrally located in the Heart of Islamorada making it convenient to everything - restaurants, ...

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Property Type

Islamorada Condo

Show less

2 BR | 2 BA | Sleeps 6 | Quick View

Distance to beach: 5 miles to Founders

$429

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pet friendly

About this property

Minimum Rental: 7 Days Little Bay's Lower Duplex is one of three rental units on this fabulous property. The Little Bay property is a one acre lush tropical setting in a gated compound located directly on Florida Bay. The units are available for rent by the week, or month. Each unit sleeps up ...

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Property Type

Islamorada Apartment

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4 BR | 3 BA | Sleeps 10 | Quick View

2

Distance to beach: 3 miles to Founders Park Beach

$417

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Private pool

About this property

Minimum Rental: 1 Month"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

"The view is incredible!!"

We stayed at Conch Bar South the month of January and It was amazing! Chantree and Courtney were so helpful. Any questions or concerns that we had were taken care of immediately. The kitchen is fully stocked ...

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2 BR | 2 BA | Sleeps 4 | Quick View

1

Distance to beach: 7 miles to Founders

$150

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pool
  • Private pool

About this property

MINIMUM STAY: 1 Month 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 ...

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Property Type

Islamorada Condo

"Stunning"

My stay at the Palms has been one of my best vacations. The views, the fishing, the pool and great people. The condo was simply gorgeous , fully stocked and the people were oh so nice. I cant wait to ...

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$147

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pool

About this property

MINIMUM STAY: 30 DAYS This condo offers breathtaking oceanfront views. Imagine watching the sun rise as you lay comfortably in your bed or have your morning beverage on the balcony and enjoy watching the fishing boats leave for their day's adventure. You'll be able to see cruise ships as they ...

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Property Type

Key Largo Condo

"Beautiful location stunning home."

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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$175

avg/night

View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • 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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$320

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • 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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$218

avg/night

View Details

Key Amenities

  • Air conditioning
  • 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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$325

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • 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

Islamorada House

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$180

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Private pool

About this property

MINIMUM STAY: 28 DAYS 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 preference. Dine in the ...

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Property Type

Islamorada Condo

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$167

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • 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

"Great stay."

Clean, well equipped, phenomenal views, and friendly residents. Realty staff was very helpful and responsive to any issues that came up. Great spot for kids as well, and very close to many top restaurants.

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