Keys Holiday Rentals

(40 rentals)
Keys Holiday Rentals
19
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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6 BR | 6 BA | Sleeps 18 | Quick View

Distance to beach: 5 miles to Founder's Park

$1286

avg/night

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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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Key Amenities

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

About this property

Minimum Rental: 1 Month "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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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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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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Key Amenities

  • Air conditioning
  • 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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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

"Heaven on the Bay"

Our stay at A410 was absolutely perfect! We ventured out a few times but staying on Moon Bay property was what we enjoyed most. A one week stay was not enough, next visit will definitely be for longer.

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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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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

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly

About this property

MINIMUM RENTAL 1 MONTH: Delightful vacation home located in the popular Islamorada neighborhood of Port Antigua. You will love this charming and cozy home! There is a wonderful open concept floor plan with 3 nicely proportioned bedrooms. Sliding doors open into the sunroom extending the living area ...

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Property Type

Islamorada House

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4 BR | 3 BA | Sleeps 10 | Quick View

3

Distance to beach: 3 miles to Founders Park Beach

$390

avg/night

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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

"Wow - Beyond Amazing"

This was our first visit to the Keys so what we knew before coming to the area was learned through internet searches and friends. The website for Conch Bar South is nicely done, but certainly can’t convey ...

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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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2 BR | 2 BA | Sleeps 5 | Quick View

Distance to beach: 7 miles to Founders

$106

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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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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2 BR | 2 BA | Sleeps 4 | Quick View

1

Distance to beach: 7 miles to Founders

$122

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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Key Amenities

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

About this property

Minimum Rental: 28 Days"Beacon Reef 310" is located in one of the most desirable condominium complexes in the Upper Keys. New owners are in the process of remodeling the kitchen and adding new furnishings. NEW PHOTOS will be posted once the removations have been completed. This condo ...

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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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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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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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2 BR | 2 BA | Sleeps 6 | Quick View

Distance to beach: 5 miles to Founders

$429

avg/night

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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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2 BR | 2 BA | Sleeps 6 | Quick View

Distance to beach: 3 miles to Anne's Beach

$150

avg/night

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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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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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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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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

"Great time!"

We had a wonderful time at Sunshine Place. The accommodations were far above our expectations. I know this is crazy but you have clean comfortable white sheets, great pillows and a comfortable bed! The ...

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4 BR | 3 BA | Sleeps 8 | Quick View

1

Distance to beach: 5 miles to Founder's

$643

avg/night

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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 the bedding is: King, Queen/Queen in Tarpon and Queen, Twin/Twin in Bonefish. ...

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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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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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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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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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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

"a wonderful place."

beacon reef #503 was a great condo. We really enjoyed our month stay . The grounds were so well maintained and also the condo.We already booked for next year ! Cant wait till then. Lauren Mccrae

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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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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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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly

About this property

Minimum Rental: 28 nightsPelican 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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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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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

About this property

Minimum Rental: 1 Month This like-new 2 bedroom/2 bath condo has fabulous ocean views and was totally remodeled/updated very recently. You'll love the sparkling new natural stone counter-top kitchen with stainless steel appliances, induction cook top and microwave. The interior is bright, fresh and ...

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Property Type

Islamorada Condo

"Paradise"

We just loved staying in this beautiful condo for a month. This place has everything you need to enjoy your stay. Just bring clothes.

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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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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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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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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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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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Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Pool

About this property

MINIMUM STAY: 28 Nights. NEW OWNERS are in the process of making a number of renovations to this unit. Posted photos will be updated as soon as the renovations are completed – by August 2022. The anticipated date for completion is AUGUST 2022. Here is a partial list of planned improvements ...

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Property Type

Key Largo Townhome

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1 BR | 1 BA | Sleeps 4 | Quick View

1

Distance to beach: 7 miles to Founders

$72

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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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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