Islamorada Condo Rentals

(29 rentals)
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Islamorada Condo
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2 bathrooms

$205

avg/night

$205
avg per night
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Key Amenities

  • Air conditioning
  • Hot tub
  • Oceanfront
  • Pool
  • Rentals by owner
  • WiFi

About this property

Popular Beacon Reef Condo Oceanfront Islamorada, Florida (Max 4 Persons / **MONTHLY RENTALS ONLY!!) Come and enjoy our Paradise Found 2nd home. FREE BOAT DOCKAGE (with proof of insurance) In the fishing capital of the world, Islamorada. If you have never experienced summer in the Keys, you might be surprised! ...

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Property Type

Islamorada Condo

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Islamorada Condo
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2 bathrooms
3 reviews

Distance to beach: 1 miles to Anne's Beach State Park

$333

avg/night

$333
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

This Condo sleeps 4 and comes with a 30' Boat slip, Tennis courts, pool, club house, undercover parking and elevators for easy access. Located on quiet Lower Matecumbe Key, Bay Harbour is just 7 miles from Islamorada's center with nearby beaches and parks. Newly refurnished and refurbished, ...

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Property Type

Islamorada Condo

Featured review

"A great two weeks in beautiful Islamorada."

This two bedroom apartment in the beautiful Bay Harbour condominium was special. The views of the ocean and the apartment complexes marina were exceptional. The apartment was well stocked with all the cooking ...

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Islamorada Condo
3 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2 bathrooms
8 reviews

Distance to beach: 5 miles to Anne's Beach

$329

avg/night

$329
avg per night
View Details

Key Amenities

  • Air conditioning
  • Oceanfront
  • Pool
  • WiFi

About this property

Enjoy the sunrise from the balcony or from the condo through 50' of glass sliding doors. You can also view the sunset from our walkway on bayside. We have a full kitchen, dishwasher to microwave, washer/dryer, even beach towels. We have wifi,cable TV in living area and all bedrooms, master bath ...

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Property Type

Islamorada Condo

Featured review

"Keys Condo"

Awesome peaceful location,clean and perfect amenities lots of birds and fish at marina manatee, sand sharks ,etc

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Islamorada Condo
2 BR | 2 BA | Sleeps 5 | Quick View
Sleeps 5, 2 bedrooms, 2 bathrooms
6 reviews

$124

avg/night

$124
avg per night
View Details

Key Amenities

  • Air conditioning
  • Oceanfront
  • Pool
  • Rentals by owner
  • WiFi

About this property

Luxurious and large 2 bedroom 2 bath condo with balcony, large heated swimming pool, stainless steel appliances, flat screen televisions in every room in the beautiful Florida Keys.Huge ocean front dock with plenty of room for fishing! Wifi, deluxe cable, and restaurants within walking distance.2 ...

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Property Type

Islamorada Condo

Featured review

"We had a great stay at Tony & Nancy’s condo at Plantation by the Sea!"

The condo was neat and well furnished. Great location and a beautiful property! Founders park across Rt 1 is a great take with a nice beach and very helpful staff at the visitors center.

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Islamorada Condo
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2 bathrooms
5 reviews

$358

avg/night

$358
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

This Condo is located on Lower Matecumbe Key, close to restaurants, shopping and Tiki bars. With pool, tennis courts and a protected marina, Bay Harbour is a preferred residence for repeat visitors to the Keys. Elevators for easy access and a second floor location make it easy to enjoy your stunning view ...

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Property Type

Islamorada Condo

Featured review

"Feels like home"

We have rented a condo at Bay Harbour for many years now. We love the location and the complex amenities. I fish a lot so my husband is happy with the workout room, pool, safe bike paths, hot tub and ...

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Islamorada Condo
1 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 1 bedroom, 2 bathrooms

$200

avg/night

$200
avg per night
View Details

Key Amenities

  • Air conditioning
  • Oceanfront
  • Pool
  • WiFi

About this property

A beautiful piece of serenity and paradise can be yours, available for seasonal rental from January through April. Islamorada the fishing dream of all sport and causal fishing enthusiast. But if you don't fish (that is a shame) you can enjoy the wonderful dining, the historic parks, diving and ...

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Property Type

Islamorada Condo

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Islamorada Condo
3 BR | 2.5 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2.5 bathrooms

$557

avg/night

$557
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Oceanfront
  • Pool
  • Rentals by owner
  • WiFi

About this property

Beautiful views from this condo!Bay Harbour is a gated community located at MM 77.5 bayside in Islamorada, FL.We are new owners of this condo that has never been in the rental pool. (that is why few reviews)Complete remodel with no expense spared!The location is quiet with the most beautiful ...

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Property Type

Islamorada Condo

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Islamorada Condo
3 BR | 2.5 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2.5 bathrooms
3 reviews

$379

avg/night

$379
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • Rentals by owner
  • WiFi

About this property

1st I want to thank all our past guests for their great reviews. Bay Harbour Starfish is a luxury condo overlooking a large boat basin with views of the Atlantic Ocean. Situated in Lower Matecumbe Key, Islamorada, the Sport Fishing Capital of the World. This very spacious 3 bedroom, 2 and half bath condo ...

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Property Type

Islamorada Condo

Featured review

"warm retreat"

Bay Harbor was delightful, from the condo unit to the grounds and amenities. We used the hot tub, exercise room and swimming pool, When we left there was 76 degrees, returned to 20 degrees in Pennsylvania.

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Islamorada Condo
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2 bathrooms

$200

avg/night

$200
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Hot tub
  • Pool
  • WiFi

About this property

Beautiful oceanfront apartment with easy access to pool, spa, and beach. Dock with boat slips and tiki hut overlooking the Atlantic Ocean. Community exercise room Master Bedroom overlooking the ocean Two bedrooms, two full baths. Gourmet equipped kitchen Laundry room Balcony with spiral stairs ...

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Property Type

Islamorada Condo

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Islamorada Condo
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2 bathrooms
3 reviews

Distance to beach: 100 feet to Front door

$163

avg/night

$163
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Hot tub
  • Oceanfront
  • Pool
  • Rentals by owner
  • WiFi

About this property

MINIMUM STAY: 30 daysSpacious and beautiful 2 bedroom/2 bath ocean front condo unit with unobstructed ocean views. BOAT SLIP is available upon request for up to a 46 foot boat, low tide draw is 30 inches. There is an additional fee for boat slip.Walk out your front door and go boating.You’ll ...

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Property Type

Islamorada Condo

Featured review

"Pure serenity"

So clean, so quiet, so beautiful! My wife and I loved our stay at Ocean Harbour. Looking forward to next year!

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Islamorada Condo
3 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2 bathrooms

$468

avg/night

$468
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Pool
  • WiFi

About this property

Welcome to Mother Ocean!This stunning ocean view condo boasts three bedrooms and two full bathrooms, making it perfect for a family or group of friends. It features modern amenities and coastal decor throughout, providing a comfortable and inviting atmosphere for your stay. The spacious living room ...

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Property Type

Islamorada Condo

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Islamorada Condo
3 BR | 3 BA | Sleeps 7 | Quick View
Sleeps 7, 3 bedrooms, 3 bathrooms
5 reviews

$582

avg/night

$582
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Escape to Paradise at Peaceful Palms in Islamorada!Welcome to your luxurious condo with ocean views, in the heart of the Florida Keys! Located in the exclusive, gated community of Peaceful Palms, this spacious and beautifully appointed property is perfect for families, couples, or groups seeking a ...

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Property Type

Islamorada Condo

Featured review

"Perfect retreat"

Outstanding location close to everything Islamorada. The accommodations are absolutely beautiful and thoughtfully designed. The hosts thought of everything and were very personable and communicative. You ...

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Islamorada Condo
3 BR | 2.5 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2.5 bathrooms

$486

avg/night

$486
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

This Condo comes with a 30' Boat slip, Tennis courts, pool, club house, undercover parking and elevators for easy access. Located on quiet Lower Matecumbe Key Bay Harbour is just 7 miles from Islamorada's center with nearby beaches and parks.

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Property Type

Islamorada Condo

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Islamorada Condo
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2 bathrooms
3 reviews

$185

avg/night

$185
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

Tropically furnished condominium with amazing views of the Gulf of Mexico, located at the Futura Yacht Club in the Village of Islamorada. Futura Yacht Club is a gated community located on the Gulf of Mexico and consisting of 70 units. It is centrally located, with easy access to Restaurants, shopping ...

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Property Type

Islamorada Condo

Featured review

"Beautiful Views"

We really enjoyed our stay. It had everything we needed for a great week. It was spotless when we arrived. We absolutely had every convenience you could ever need. Susan was a great host. She answered us ...

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Islamorada Condo
3 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2 bathrooms
3 reviews

$200

avg/night

$200
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Pool
  • Rentals by owner
  • WiFi

About this property

This condo is located in a tropical paradise overlooking the fabulous Florida Bay in idyllic Islamorada in Futura Yacht Club. FYC is a private 70-unit, gated community with a 53-slip marina and accommodations available for that tranquil tropical getaway you've always imagined. This condo offers ...

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Property Type

Islamorada Condo

Featured review

"Location"

We have been searching for a unit in this area and found this. Islamorada has many restaurants, from fast food to white tablecloths, from waterfront dining to sports bars.

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Islamorada Condo
3 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2 bathrooms
12 reviews

Distance to beach: 4 miles to Anne's Beach

$329

avg/night

$329
avg per night
View Details

Key Amenities

  • Air conditioning
  • Oceanfront
  • Pool
  • Rentals by owner
  • WiFi

About this property

Enjoy the sunrise from the balcony or from in the condo through 50 ft of glass sliding doors. You can also see the sunset from our walkway on bayside. We have a full kitchen from dishwasher to microwave, washer/dryer, even beach towels. We have wifi, cable TV, and a Master Bath with whirlpool tub, ...

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Property Type

Islamorada Condo

Featured review

"EXCELLENT CONDO"

We had a fabulous time at this condo. Spectacular views, great fishing. Close to EVERYTHING. The condo was spacious and VERY CLEAN. EVERYTHING you would need for a fun time was here.. will be back again ...

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Islamorada Condo
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2 bathrooms
3 reviews

$126

avg/night

$126
avg per night
View Details

Key Amenities

  • Air conditioning
  • Oceanfront
  • Pool
  • Rentals by owner
  • WiFi

About this property

Gorgeous updated 2 bedroom, 2 bathroom condo with large modern kitchen in an oceanfront gated building with oceanfront pool, fishing dock, gym, sauna, barbecue grills and so much more, and the best part is YOU'RE IN THE FLORIDA KEYS!

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Property Type

Islamorada Condo

Featured review

"Jan Feb 2023"

Great condo, pool, and neighbors. Highly recommend. The pool is heated. Ocean view is great. Community room. Has exercise room and sauna.

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Islamorada Condo
3 BR | 4 BA | Sleeps 8 | Quick View
Sleeps 8, 3 bedrooms, 4 bathrooms

$733

avg/night

$733
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Private pool
  • WiFi

About this property

Mile Marker 83 – BayfrontWelcome to your dream waterfront rental home in Islamorada, located in the heart of the Florida Keys. This stunning 4 bedroom, 4 bathroom home sits on the bay and offers breathtaking views of the water and world class sunsets.As you enter the home, you’ll ...

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Property Type

Islamorada Condo

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Islamorada Condo
2 BR | 2.5 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 2.5 bathrooms

$417

avg/night

$417
avg per night
View Details

Key Amenities

  • Air conditioning
  • Oceanfront
  • Private pool
  • WiFi

About this property

Green Coconut – Mile Marker 80, Heart of IslamoradaTucked away on the quiet stretch of Old Highway at Mile Marker 80, Green Coconut is a private island sanctuary in the heart of Islamorada. This beautifully designed property offers two fully separate living spaces—perfect for extended ...

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Property Type

Islamorada Condo

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Islamorada Condo
3 BR | 3 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 3 bathrooms
1 review

$470

avg/night

$470
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Private pool
  • WiFi

About this property

Sunrise is a spectacular unit within the Maison Matecumbe gated community. Maison Matecumbe is a small 9 unit condo located just off the old road in Islamorada at mile marker 81. Newly done pool and hot tub! 3 bedrooms, 3 baths, sleeps 6, pool, sandy beach.Dockage can be obtainable through Islamorada ...

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Property Type

Islamorada Condo

Featured review

"Thrilled"

I was under contract on neighboring unit. I had absolute affirmation after staying one week in this unit.

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Islamorada Condo
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2 bathrooms
9 reviews

Distance to beach: 0.9 miles to Founders Park

$99

avg/night

$99
avg per night
View Details

Key Amenities

  • Air conditioning
  • Oceanfront
  • Pool
  • Rentals by owner
  • WiFi

About this property

Oceanfront gated community. Offers pool overlooking the ocean, pier which you can fish off of, clubhouse, sauna, exercise room, and very clean bathrooms by the pool. 2 Bed, 2 Bath. Master bedroom offers queen bed, sitting room, coffee, 50 inch smart tv, storage, master bath separate toilet. 2nd Bedroom ...

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Property Type

Islamorada Condo

Featured review

"Super comfortable condo - amazing location - wonderful host!"

We spent a month in Sharon's condo (January 2025). Upon arrival we had everything we needed for the month! She goes above and beyond stocking the kitchen, cleaning supplies, pantry etc. The bedrooms are ...

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Islamorada Condo
3 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2 bathrooms
22 reviews

$196

avg/night

$196
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

Escape to paradise in the fabulous Florida Keys at Futura Yacht Club. This property is a private gated community with a 65 slip deep water marina. This tropical waterfront community offers world class fishing and diving, 2 lighted tennis courts, pickleball, heated pool, private beach, and dockage for ...

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Property Type

Islamorada Condo

Featured review

"Great Stay/Location"

Excellent stay. Owner is super nice and helpful. Great location, beautiful sunsets. Easy access to both the bay and the ocean. Place was very clean when we arrived. Would stay again.

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Islamorada Condo
3 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2 bathrooms

Distance to beach: 2 miles to Founders Park

$165

avg/night

$165
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

Experience high-end coastal luxury while staying at “Sea Breeze 41” in the highly sought-after Coral Harbour Club Condominium (CHC) . Your spacious 3 Bedroom / 2 Bathroom island getaway exudes luxury tropical vibes and is professionally decorated in Tropical Modern style. A 30' Boat Slip ...

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Property Type

Islamorada Condo

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Islamorada Condo
3 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

3 Beds/2 bath townhouse in Islamorada, Florida Keys. Ground Floor features a full kitchen, full bath, living room with large tv, dining room with views of the tennis court, outdoor patio with BBQ and additional dining table. Second Floor features a large full bath, 1 king size bed, 1 queen size bed, 2 ...

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Property Type

Islamorada Condo

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Islamorada Condo
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2 bathrooms
1 review

$298

avg/night

$298
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pool
  • Rentals by owner
  • WiFi

About this property

We have owned and rented this property for 20 years and have been coming to Seagulls Condominiums for over 40 years. The condo bathrooms and bedrooms have just been updated and the entire building has just finished a major upgrading and painting. If my pics don't import from vrbo 49422, then you ...

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Property Type

Islamorada Condo

Featured review

"Outstanding view and amenities. Will return soon!"

Classic art deco style building which was fully remodeled both inside and out. The owners are very responsible and have been doing this a long time.

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Islamorada Condo
1 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 1 bedroom, 2 bathrooms

Distance to beach: 4 miles to Founders Park

$290

avg/night

$290
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Bayside is a first floor apartment overlooking the water. Bayside is located on a small resort property nestled in a native hammock on Florida Bay. An easy 90 minute drive from Miami International Airport, this property is located in the heart of Islamorada, directly on Florida Bay. Bayside is fully air ...

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Property Type

Islamorada Condo

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Islamorada Condo
2 BR | 1.5 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 1.5 bathrooms

$97

avg/night

$97
avg per night
View Details

Key Amenities

  • Air conditioning
  • Oceanfront
  • Pool
  • WiFi

About this property

Beautiful area of island on ocean

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Property Type

Islamorada Condo

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Islamorada Condo
5 BR | 3 BA | Sleeps 12 | Quick View
Sleeps 12, 5 bedrooms, 3 bathrooms

$525

avg/night

$525
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • WiFi

About this property

PROPERTY NAME: Sandglass 4 74980 Overseas Highway #4, Islamorada, FLLOCATION: Bayside Town House Located in Lower MatecumbeMINIMUM STAY: 7 DaysMILE MARKER: 74.9DETAILS: ONE OF A KIND!!! Magnificent two story townhouse with 5 bedrooms and 3 baths located on Lower Matecumbe in Islamorada. ...

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Property Type

Islamorada Condo

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Islamorada Condo
3 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2 bathrooms
2 reviews

$131

avg/night

$131
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

Welcome to our beautiful, private and secure gated community with all of the amenities to make your vacation as relaxing or exciting as you wish. Located on Plantation Key in Islamorada at mile marker 88.5 on the bay side and boasting a great 60 slip marina, it provides quick access to the ocean via Snake ...

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Property Type

Islamorada Condo

Featured review

"Wonderful"

I highly recommend this vacation spot. Not only is the condo very nice the whole property is set up for your every need. The owner and property manager are very nice and accommodating. I was amazed by the ...

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Islamorada Vacation Rentals