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Three story home 100 feet deep water dock big pool - Islamorada vacation rentals
1 / 9

$250

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Three story home 100 feet deep water dock big pool

Islamorada house
3 BR / 3 BA / Sleeps 8 | Quick view

Details

Please contact us if you have any policy questions since we do not agree with this website forcing us to choose policies they dictate. We have our own polices so please ignore what's posted in the policies section on this website. Also please visit our website at www.KeysRentalHouse.com Beautiful three story luxury …
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Housekeeping Optional
  • Washing Machine
  • Suitable for children
  • Suitable for the elderly

$643

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Aguazul

Islamorada house
4 BR / 3 BA / Sleeps 8 | Quick view
Very Good1 Reviews

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Reviews

(1)

Village Permit #VR-09-82 You can not rent this property for less than one week. Ahhhh...Ocean Front...Pool...Dockage...It's all hear at Aguazul. Aguazul is located at Mile Marker 89, in beautiful Islamorada. This gorgeous four bedroom,three bath home will sleep 8 people very comfortably. Aguazul has everything you …
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Housekeeping Optional
  • Washing Machine
  • Pet friendly - ask
  • Suitable for children
  • Suitable for the elderly

Details

Reviews

(1)

The perfect getaway

Left on Sep 26, 2011 for a stay in August 2011

My family had a fantastic vacation. This home is located really close to some great restaurants. It was so nice to sit back and relax all day while the kids played in the ocean and pool.

$250

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The Cottage (28 DAY MINIMUM)

Islamorada house
3 BR / 1 BA / Sleeps 6 | Quick view
Excellent1 Reviews

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Reviews

(1)

****DUE TO A COUNTY ORDINANCE THIS PROPERTY CANNOT RENT FOR LESS THAN 28 DAYS**** You fall in love with The Cottage at first sight. Built in 1935, this once Red Cross building serves as a true historical reflection of the Florida Keys. Both bedrooms overlook the ocean, which is a mere 30 feet from the wrap around …
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Pet friendly - ask
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(1)

COTTAGE @ SCHOONER BAY - ABSOLUTE SOLITUDE AND SUPERB LOCATION

Left on Dec 02, 2013 for a stay in November 2013

We were so lucky to have visited this home during November. We had the whole private gated compound to ourselves and even though we only leased the Cottage, the owners were so gracious to allow us total use of the pool at the Palm house next door. I cannot say enough good things about our entire experience here. It was quiet, our main bedroom was literally 30 feet from the water, it was …

$715

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The Palms

Islamorada house
3 BR / 4 BA / Sleeps 6 | Quick view
Average1 Reviews

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Reviews

(1)

VR-203 You can not rent this property for less than one week. Relax and rejuvenate at The Palms. Features are a plantation-style home and beautiful wrap around porch, 3 bedrooms/3.5 baths, a beach entry pool, and abundant coquina decking. The natural landscaping enhances the amazing grounds and ocean blue pool. Also …
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(1)

Pretty nice place....the pool was a bummer.

Left on Apr 08, 2013 for a stay in March 2013

The site was beautiful. Nice sized house, clean, beautiful view, well kept grounds. Really nice covered porch all around the house where you could get out of the sun and enjoy the views and palm trees. There are houses on either side, but privacy was maintained.

The big let down was the pool. We rented the house exclusively for our kids to have free run of a private pool....but discovered …

CASA THORN SECRET GARDEN ROOM - Islamorada vacation rentals
1 / 4

$139

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CASA THORN SECRET GARDEN ROOM

Islamorada B&B
1 BR / 1 BA / Sleeps 2 | Quick view

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Enter through a private garden with a tropical atmosphere to a quiet and secluded room with a queen size bed and a private bath. The room is completely private and features a coffee maker, microwave, refrigerator, TV and free WiFi. Full breakfast. LOCATED IN A QUIET,SECLUDED , TROPICAL SETTING YET MINUTES TO FISHING…
  • Shared outdoor pool (unheated)
  • Wireless Internet
  • A/C or climate control
  • Balcony or terrace
  • Parking
  • Pet friendly
  • Smoking allowed - ask
  • Suitable for children
  • Wheelchair accessible - ask
Casa Thorn Bombay Room - Islamorada vacation rentals
1 / 9

$129

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Casa Thorn Bombay Room

Islamorada B&B
1 BR / 1 BA / Sleeps 2 | Quick view

Details

This wonderful room opens up into a garden with a water pond. It includes a/c, coffee maker, TV, free WiFi, heat, microwave, refrigerator, shared bath with one other couple. Pool on premises. Close proximity to the beach. Includes full breakfast. LOCATED IN A QUIET, SECLUDED, TROPICAL SETTING YET MINUTES TO …
  • Shared outdoor pool (unheated)
  • Internet Access
  • Housekeeping Optional
  • Outdoor Dining Area
  • A/C or climate control
  • Pet friendly
  • Smoking allowed - ask
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask
1 / 7

$89

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Casa Thorn Tiki Hut Room

Islamorada B&B
1 BR / 1 BA / Sleeps 2 | Quick view

Details

A small stand alone room in the corner of the garden. Features a/c, coffee maker, free WiFi, grill on premises, heat, microwave, refrigerator, shared bathroom with one other couple, TV and includes full breakfast. LOCATED IN A QUIET, SECLUDED, TROPICAL SETTING YET MINUTES TO FISHING, DIVING, SNORKELING. VISIT JOHN …
  • Shared outdoor pool (unheated)
  • Internet Access
  • Housekeeping Optional
  • Outdoor Dining Area
  • A/C or climate control
  • Pet friendly
  • Smoking allowed - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask
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$1,279

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Kara-Pan

Islamorada house
5 BR / 7 BA / Sleeps 10 | Quick view

Details

You can not rent this property for less than one week. The ultimate island experience awaits you at Kara-Pan I. This exquisite, private, two story, Plantation Style home is located on a pristine natural white sand beach with oceanviews that inspire relaxation. The 5 bedroom 7 bath home with a wrap around porch, is …
  • Waterfront
  • Ocean or water views
  • Hot Tub/Jacuzzi
  • Internet Access
  • Housekeeping Optional
  • Suitable for children
  • Suitable for the elderly
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$858

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Southern Comfort

Islamorada house
5 BR / 6 BA / Sleeps 10 | Quick view

Details

Village Permit # VR-204 You can not rent this property for less than one week. Sit back, relax, a light breeze, gaze the blue waters of the Atlantic Ocean….and be lost. Southern Comfort is the perfect vacation home in the Florida Keys, located at MM 77. This very private Estate sits on 3+ acres offering 5 bedrooms…
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Pet friendly - ask
  • Suitable for children
  • Suitable for the elderly
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$786

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The Gardens

Islamorada house
4 BR / 4 BA / Sleeps 8 | Quick view

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VR-202 You can not rent this property for less than one week. The Gardens is a 4/4 private home surrounded by impeccably landscaped grounds. This property has over 50 types of palms, abundant orchids, and bougainvilleas. At your doorstep is a breathtaking view of the Atlantic Ocean where you can experience endless …
  • Waterfront
  • Ocean or water views
  • Hot Tub/Jacuzzi
  • Internet Access
  • Housekeeping Optional
  • Pet friendly - ask
  • Suitable for children
  • Suitable for the elderly - ask
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$663

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Pineapple Plantation (28 Day Minimum)

Islamorada house
5 BR / 6 BA / Sleeps 10 | Quick view

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****This house cannot rent for less than 28 days, per County Ordinance**** Breathtaking Sunset's, Breathtaking Home. Pineapple Plantation is an unbelievable gated, New Bay Front home. It is perfectly located a Mile Marker 89, Islamorada. Boasting 5 Bedroom Suite's, Gourmet kitchen with an ocean view, Dining Room that…
  • Waterfront
  • Ocean or water views
  • Shared outdoor pool (unheated)
  • Hot Tub/Jacuzzi
  • Internet Access
  • Pet friendly - ask
  • Suitable for children
  • Suitable for the elderly - ask
1 / 12

$358

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Blue Harbour

Islamorada house
4 BR / 3 BA / Sleeps 8 | Quick view

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Village Permit #VR-09-82 You can not rent this property for less than one week. Ahhhh...Ocean Front....Protected Dockage... Blue Harbor is located at Mile Marker 85, in beautiful Islamorada. This Ocean Front four bedroom,three bath home will sleep 8 people very comfortably. (One of the bedrooms is on the ground level…
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Housekeeping Optional
  • Washing Machine
  • Pet friendly - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
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$500

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Beach House

Islamorada house
4 BR / 3 BA / Sleeps 10 | Quick view

Details

Village Permit #VR-138 You can not rent this property for less than one week. An affordable ocean front, beach, pool and hot tub home.   This popular home is located in south Islamorada.  Three bedrooms, two baths, living kitchen and dining area are upstairs. Downstairs is a separate area with a private …
  • Waterfront
  • Ocean or water views
  • Hot Tub/Jacuzzi
  • Internet Access
  • Washing Machine
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask

$175

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BLUE WATER RETREAT

Islamorada house
3 BR / 3 BA / Sleeps 8 | Quick view
Excellent1 Reviews

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Reviews

(1)

Minimum Rental: 1 Month Location, location, location! This home has it all - ocean side Lower Matecumbe location, totally remodeled in 2009. Relax by the cocktail pool or sunbathe in the private roof top sunning area. There are blue water ocean views from almost every room in this home. It is located on a canal …
  • Shared outdoor pool (unheated)
  • Internet Access
  • Patio
  • Parking
  • Grill
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask

Details

Reviews

(1)

Blue Water = Everything that you want

Left on Jul 15, 2013 for a stay in July 2013

This place delivers.

You never really know what you are going to get from looking at a website and photos. I just stayed there July/2013 and this place is great, everything is new and clean. Most of all the house is on a peninsula that looks at the ocean from all sides and is just a few miles south of most of that main attractions in Islamorada giving the home a calm but close feel. Also working…

$133

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MATECUMBE JEWEL

Islamorada house
3 BR / 2 BA / Sleeps 6 | Quick view
Excellent1 Reviews

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Reviews

(1)

Minimum Rental: 1 Month You will love jewel of a home! Located in Lower Matecumbe, this charming canal front home offers a swimming pool, dockage, direct access to the ocean, covered fish cleaning station, a screened lanai, inviting décor and comfortable accommodations. It is located on a dead-end street in a …
  • Internet Access
  • Patio
  • Parking
  • Grill
  • Refrigerator
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask

Details

Reviews

(1)

Our Lobster Trip to the Keys

Left on Aug 24, 2013 for a stay in August 2013

My family and I stayed at the Matecumbe Jewel in the month of august for Lobster season. The home shows even better than the photos, was clean, well furnished and kept. We could not have asked for better accomodations while on our first Lobstering vacation! The service by Keys Holiday Rental was a+++! We will certainly be back! Thanks again to everyone at Keys Rental and the owners of the …

$100

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VILLA RIOLO

Islamorada house
2 BR / 2 BA / Sleeps 6 | Quick view
Excellent1 Reviews

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Reviews

(1)

MINIMUM STAY: 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 to share their vacation …
  • Internet Access
  • Balcony or terrace
  • Parking
  • Refrigerator
  • Satellite or cable TV
  • Suitable for children - ask
  • Suitable for the elderly - ask

Details

Reviews

(1)

Fishing Vacation

Left on Aug 13, 2014 for a stay in July 2014

Was a very clean house with all the amenities. I would stay again. Easy access to the Ocean for fishing and plenty of dock for your boat.

$179

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BROCK HAUS ON THE GULF

Islamorada condo
2 BR / 2 BA / Sleeps 6 | Quick view
Excellent4 Reviews

Details

Reviews

(4)

Minimum Rental: 7 Nights (Saturday to Saturday) BROCKHAUS 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 water views from this unit …
  • Ocean or water views
  • Shared outdoor pool (unheated)
  • Internet Access
  • Balcony or terrace
  • Parking
  • Suitable for children - ask
  • Suitable for the elderly - ask

Details

Reviews

(4)

Great week on Islamorada

Left on Aug 21, 2013 for a stay in August 2013

Just returned from a week at Brockhaus. This was our 4th time staying at this property (although the last time was in 2009) and everything felt very familiar and comfortable. The location is perfect,the views are spectacular, and the convenience of the boat slip right out the door is a huge plus! The 2 bedrooms are comfortable but the town home could use a bit of updating (it hasn't changed a bit…

$217

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MY PARADISE

Islamorada house
3 BR / 2 BA / Sleeps 6 | Quick view
Excellent1 Reviews

Details

Reviews

(1)

Minimum Rental: 1 Month Oceanfront - Beach - Protected Dock 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 Keys. From the moment you arrive, you'll know …
  • Ocean or water views
  • Internet Access
  • Balcony or terrace
  • Parking
  • Grill
  • Pet friendly - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask

Details

Reviews

(1)

My Paradise from architect's perspective

Left on Jan 23, 2013 for a stay in April 2012

My wife and I spend a month at My Paradise and, as an architect, there are certain aspects that bear mention. First, if the weather is mild, you can open the wall of folding glass doors and unite the main interior room (dining, den and kitchen) with the oversize teak deck. The deck itself is a marvel. A covered sitting area gets you out of the sun, with six teak sun loungers for warming up and …

$358

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LITTLE BAY - Upper Duplex

Islamorada villa
2 BR / 2 BA / Sleeps 6 | Quick view
Excellent3 Reviews

Details

Reviews

(3)

Minimum Rental: 7 Nights Upper Duplex - This 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 up to 6 people - …
  • Ocean or water views
  • Internet Access
  • Balcony or terrace
  • Parking
  • Grill
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask

Details

Reviews

(3)

Iguanas, sunshine and the sea in your backyard.......

Left on Nov 05, 2012 for a stay in October 2012

We found Little Bay after our previously planned accomodation had been damaged in a fire so Andi & Katy at Keys Holiday Rentals literally saved us from camping on the beach! The apartment couldn't have been nicer, 2 bed, 2 bath with the second bedroom having twin beds so was perfect for the children (6 & 12). The apartment was well laid out with a HUGE deck overlooking the garden (iguanas!) and …

$358

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LITTLE BAY - Lower Duplex

Islamorada villa
2 BR / 2 BA / Sleeps 6 | Quick view
Excellent4 Reviews

Details

Reviews

(4)

Minimum Rental: 7 Nights Lower Duplex - This 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 to 6 people - rent …
  • Ocean or water views
  • Internet Access
  • Patio
  • Parking
  • Grill
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask

Details

Reviews

(4)

Paradise!

Left on Jun 03, 2013 for a stay in May 2013

My family and I spent Memorial Day Weekend at this gorgeous property and it was like paradise! Not only was it beautiful inside and out it had a sophisticated charm and inviting ora from the moment you entered the property and opened the door! This place screams class while still giving you the feeling of total relaxation. The beds are amazing!!! The grounds are clean and beautiful and we even …

$358

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LITTLE BAY - Cottage

Islamorada villa
2 BR / 2 BA / Sleeps 6 | Quick view
Excellent1 Reviews

Details

Reviews

(1)

Minimum Rental: 7 Nights Cottage - This 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 and a full bath. To the right is …
  • Ocean or water views
  • Internet Access
  • Parking
  • Grill
  • Refrigerator
  • Suitable for children - ask
  • Suitable for the elderly - ask

Details

Reviews

(1)

A place where memories are made.....

Left on May 28, 2013 for a stay in May 2013

The pictures really don't do this place justice, there are so many comforts that it feels more like a home. It is in a great location and since it is gated, it was safe enough for my 9 year old twins to go exploring on their own. It truly has something for everyone. We cooked, laid out, watched the sunset, even took a dip in the bay. It was really lovely. We will definitely be returning.

$77

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THE PALMS 314

Islamorada condo
2 BR / 2 BA / Sleeps 5 | Quick view
Excellent1 Reviews

Details

Reviews

(1)

Minimum Rental: 1 Month Sensational oceanfront views are yours from both the master bedroom and the balcony of this beautifully appointed condo. Watch the fishing charter boats as they come and go from Bud and Mary's Marina. You'll be able to see cruise ships as they pass by Alligator Reef and Light House or …
  • Ocean or water views
  • Shared outdoor pool (unheated)
  • Hot Tub/Jacuzzi
  • Internet Access
  • Patio
  • Suitable for children - ask
  • Suitable for the elderly - ask

Details

Reviews

(1)

Wow, what a beautiful view

Left on Feb 13, 2015 for a stay in January 2015

This condo was clean, nicely furnished and had a view to die for. We really appreciated the washer and dryer in the unit, which most did not have. Also, being on the end we had "the window" in the master bedroom and in the daytime the view would take your breath. However, at night the lights from the parking lot would shine into our bedroom. Alas, with the flip of a switch an outside shutter …

1 / 16

$133

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TURTLE TIME

Islamorada house
3 BR / 2 BA / Sleeps 7 | Quick view

Details

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 find this …
  • Internet Access
  • Patio
  • Parking
  • Grill
  • Refrigerator
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask
1 / 18

$70

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THE PALMS 214

Islamorada condo
2 BR / 2 BA / Sleeps 4 | Quick view

Details

Minimum Rental: 1 Month Gorgeous 2 bedroom, 2 bath condo. This is a gated complex located directly on the Atlantic Ocean. This unit has unobstructed views of the ocean from the master suite and the balcony. Wake up every morning, open the curtains and view a panorama of the Atlantic Ocean directly in front of you…
  • Ocean or water views
  • Shared outdoor pool (unheated)
  • Hot Tub/Jacuzzi
  • Internet Access
  • Patio
  • Suitable for children - ask
  • Suitable for the elderly - ask
1 / 16

$70

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THE PALMS 301

Islamorada condo
2 BR / 2 BA / Sleeps 6 | Quick view

Details

Minimum Rental: 1 Month This 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 to look at the Visual Tour to see just how …
  • Ocean or water views
  • Shared outdoor pool (unheated)
  • Hot Tub/Jacuzzi
  • Internet Access
  • Balcony or terrace
  • Suitable for children - ask
  • Suitable for the elderly - ask
1 / 24

$167

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OCEAN HARBOUR K4

Islamorada condo
2 BR / 2 BA / Sleeps 4 | Quick view

Details

Minimum Rental: 1 Month New on the rental market. This is your opportunity to secure your winter getaway at a luxurious oceanfront condo in one of Islamorada's most prestigious condominium communities. Ocean front dockage is available for boats up to 28' in length (separate rental); heated free-form swimming pool, …
  • Shared outdoor pool (unheated)
  • Hot Tub/Jacuzzi
  • Internet Access
  • Balcony or terrace
  • Fitness Room
  • Suitable for children - ask
  • Suitable for the elderly - ask
1 / 17

$147

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BEACON REEF 222

Islamorada condo
2 BR / 2 BA / Sleeps 4 | Quick view

Details

Minimum Rental: 1 Month 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. It offers 2 spacious bedrooms, 2 full baths…
  • Ocean or water views
  • Shared outdoor pool (unheated)
  • Hot Tub/Jacuzzi
  • Internet Access
  • Patio
  • Suitable for children - ask
  • Suitable for the elderly - ask
1 / 18

$133

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BEACON REEF 211

Islamorada condo
2 BR / 2 BA / Sleeps 4 | Quick view

Details

Minimum Rental: 1 Month This is a very special unit in a premier condominium complex located directly on the Atlantic Ocean and in the heart of Islamorada. This unit provides spectacular ocean views. It is one of the few units that offer spiral stairs to the ground level directly from your private balcony. The …
  • Ocean or water views
  • Shared outdoor pool (unheated)
  • Hot Tub/Jacuzzi
  • Internet Access
  • Balcony or terrace
  • Suitable for children - ask
  • Suitable for the elderly - ask
1 / 23

$107

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BEACON REEF 501

Islamorada condo
2 BR / 2 BA / Sleeps 4 | Quick view

Details

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 tray ceiling with …
  • Ocean or water views
  • Shared outdoor pool (unheated)
  • Hot Tub/Jacuzzi
  • Internet Access
  • Fitness Room
  • Suitable for children - ask
  • Suitable for the elderly - ask
1 / 26

$97

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THE PALMS 405 - 93

Islamorada condo
2 BR / 2 BA / Sleeps 6 | Quick view

Details

Minimum Rental: 1 Month A Diamond! Be among the first to rent this gorgeous two bedroom condo. It has been completely renovated from floor to ceiling. The floors have been replaced with tile and the old popcorn ceilings are gone. You'll adore the comfortable living room furnishings and the flat screen TV, not …
  • Shared outdoor pool (unheated)
  • Hot Tub/Jacuzzi
  • Internet Access
  • Balcony or terrace
  • Fitness Room
  • Suitable for children - ask
  • Suitable for the elderly - ask
1 / 21

$123

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THE PALMS 316

Islamorada condo
3 BR / 2 BA / Sleeps 6 | Quick view

Details

MINIMUM STAY: 29 DAYS Enjoy unobstructed and panoramic views of the Atlantic Ocean from your own private balcony! This 3 bedroom/2 bath condo unit features direct ocean views from the living room, balcony and two of the three bedrooms. Tropical furnishings create a warm and inviting atmosphere. You'll really…
  • Shared outdoor pool (unheated)
  • Hot Tub/Jacuzzi
  • Internet Access
  • Balcony or terrace
  • Fitness Room
  • Suitable for children - ask
  • Suitable for the elderly - ask
1 / 14

$77

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THE PALMS 402

Islamorada condo
2 BR / 2 BA / Sleeps 4 | Quick view

Details

Minimum Rental: 1 Month Pure pleasure will be yours in this beautifully remodeled and immaculate condo. You'll love the uncluttered and modern décor along with the recent renovations. Enjoy the picturesque views of Alligator Reef and the Atlantic Ocean from this 4th floor balcony. Watch the fishing boats …
  • Shared outdoor pool (unheated)
  • Hot Tub/Jacuzzi
  • Internet Access
  • Patio
  • Fitness Room
  • Suitable for children - ask
  • Suitable for the elderly - ask
1 / 20

$110

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BEACON REEF 314

Islamorada condo
2 BR / 2 BA / Sleeps 4 | Quick view

Details

Minimum Rental: 1 Month Beacon Reef 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 own private balcony …
  • Ocean or water views
  • Shared outdoor pool (unheated)
  • Hot Tub/Jacuzzi
  • Internet Access
  • Balcony or terrace
  • Suitable for children - ask
  • Suitable for the elderly - ask
1 / 14

$67

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THE PALMS 408

Islamorada condo
2 BR / 2 BA / Sleeps 4 | Quick view

Details

Minimum Rental: 1 Month Comfortably furnished and ready for you. Conveniently located just steps from a full service marina and 2 highly acclaimed restaurants. Watch the sun rise over the ocean as fishing boats leave on their daily charters, or watch the spectacular sunsets over the bay. Exercise in the men's or…
  • Ocean or water views
  • Shared outdoor pool (unheated)
  • Hot Tub/Jacuzzi
  • Patio
  • Fitness Room
  • Suitable for children - ask
  • Suitable for the elderly - ask
1 / 15

$63

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THE PALMS 506

Islamorada condo
2 BR / 2 BA / Sleeps 4 | Quick view

Details

Description….. MINIMUM STAY: Minimum Rental: 1 Month 5th Floor unit at one of Islamorada's favorite condo complexes. This unit was recently sold and the new owners are beginning to update some of the décor. You'll love the fantastic panoramic ocean views as you relax or dine on the balcony. There's …
  • Ocean or water views
  • Shared outdoor pool (unheated)
  • Hot Tub/Jacuzzi
  • Internet Access
  • Patio
  • Suitable for children - ask
  • Suitable for the elderly - ask
1 / 20

$183

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EMERALD COVE

Islamorada house
4 BR / 3 BA / Sleeps 10 | Quick view

Details

MINIMUM RENTAL: 28 NIGHTS (ONE MONTH) You'll love watching the fabulous sunsets over the tranquil waters in this semi-private lagoon setting. This is a three story single family home and offers two balconies overlooking the water and dock area. There's room to dock one 30' boat and a fish cleaning station conveniently…
  • Ocean or water views
  • Hot Tub/Jacuzzi
  • Internet Access
  • Balcony or terrace
  • Parking
  • Suitable for children - ask
  • Suitable for the elderly - ask
1 / 26

$140

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OCEAN BREEZE

Islamorada house
3 BR / 2 BA / Sleeps 4 | Quick view

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MINIMUM STAY 29 DAYS. BEAUTIFUL CANAL FRONT STILT HOME WITH HEATED POOL - For the guest who expects perfection this is it. This home was completely remodeled in 2013. There is 936 square feet of living area on the main level with 2 bedrooms, a full bath and an open living area. On the ground level there is a …
  • Shared outdoor pool (unheated)
  • Balcony or terrace
  • Parking
  • Grill
  • Refrigerator
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask

$215

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132 Columbus Drive

Islamorada house
2 BR / 2 BA / Sleeps 4 | Quick view
Excellent16 Reviews

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Reviews

(16)

This is a neat house! It sits right on the ocean with a large yard (by keys standards!). Very nicely landscaped (hibiscus, palm trees, tall pine trees, green grass)with statues from all over the world. Very private with a big gate. The house is decorated with pictures taken from all over the world and different keys …
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Suitable for children
  • Suitable for the elderly - ask

Details

Reviews

(16)

Exactly what we were looking for

Left on Jul 14, 2010 for a stay in June 2010

We were looking for a waterfront rental to give us more room than a reg hotel or bungalow. We were not looking for a pool and wanted something laid back. This was exactly what we were looking for and suited us, a fmily of 4 to the proverbial T. Not for a larger group/family or for folks looking for "Island Luxe".

$286

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76300 Overseas Highway

Islamorada house
3 BR / 2 BA / Sleeps 6 | Quick view
Excellent6 Reviews

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Reviews

(6)

Enjoy this Bayfront home with a spectacular sunset view, fenced yard and tile throughout the house. Also has great dockage and clean swimming area. Secured wi-fi, local telephone, & cable television (basic) included. VACATION RENTAL LICENSE: VR-039 CLICK HERE to view photos on a mobile device. Additional amenities …
  • Waterfront
  • Internet Access
  • Porch
  • Grill
  • Dishwasher
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(6)

Great views and convenient to the entire Keys chain

Left on Feb 09, 2011 for a stay in December 2010

Great location, fantastic views, great access to the Bay and atlantic. Older home but clean and well maintained. Nicely situated in the Keys for access to Key West to Key Largo. Home had only basic cable and the dish washer did not work but overall would recommend the home. If your looking for luxury, this is not your place but if you want to just experience the keys and all they offer it's …

$208

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75130 Overseas Highway

Matecumbe Key house
2 BR / 2 BA / Sleeps 4 | Quick view
Excellent2 Reviews

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Reviews

(2)

Great house in Lower Matecumbe (south side of Islamorada) at the 75 mile marker on the bayside. This house has fabulous sunset views in a nice quiet part of town. There is a small beach area in the back with palm trees giving you a little more privacy. A screened in porch with tables and chairs makes for a great …
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Television
  • Pet friendly - ask
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(2)

The view and location was excellent.

Left on May 06, 2011 for a stay in April 2011

The house had most of the amenities I would expect at a beach location. You can't beat the sunsets over the bay!
We snorkeled at Key Largo and took a day trip into key West, so the location was perfect. The area had the best restaurants. We tried them all.
Only complaints were: no outdoor grill, no wine glasses, sheets kept pulling off the bed and rusted beach chairs.

$929

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75731 Overseas Highway

Matecumbe Key house
4 BR / 4 BA / Sleeps 10 | Quick view
Excellent13 Reviews

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Reviews

(13)

Islamorada is the Spiritual Center of the Keys, the Sportfishing Capital of the World, and home to the largest fleet of charter boats in the Keys. Fish deep water or the back bay. Snorkeling and SCUBA sites abound. Restaurants, art galleries, and other shopping are plentiful in Islamorada. Pass through a private …
  • Waterfront
  • Ocean or water views
  • Internet Access
  • A/C or climate control
  • Grill
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(13)

Paradise!!!

Left on Jul 14, 2010 for a stay in May 2010

Michelle Sorell was a great help and everything was just perfect. I hated to leave. the property is well maintained and Randy was also nice with all our grandboys that came in to visit while we were there. Thanks again for making our vacation so wonderful.

$300

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Islamorada Waterfront Paradise 2

Matecumbe Key house
2 BR / 2 BA / Sleeps 6 | Quick view
Excellent3 Reviews

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Reviews

(3)

**We do not use the optional calendar feature on this listing. ** ***For holiday weeks, lobster opening week, and lobster mini season week rates will be higher.*** This is a very popular rental, so book your preferred week well in advance of peak season! I reply to EVERY inquiry. If you do not receive a reply, …
  • Waterfront
  • Ocean or water views
  • Wireless Internet
  • Washing Machine
  • Clothes Dryer
  • Suitable for children

Details

Reviews

(3)

A little paradise

Left on Feb 18, 2015 for a stay in January 2015

We had a great family time in this house.

It's perfectly located in the Keys. It's clean, well equiped, quiet and peaceful.

$350

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Enjoy stunning views of the sunrise from this beautiful Keys condo

Islamorada condo
3 BR / 3 BA / Sleeps 8 | Quick view
Excellent3 Reviews

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Reviews

(3)

Revel in the beauty of the morning sunrise as you relax on your own, private lanai while sipping your morning coffee, or enjoy a meal al fresco to the sound of the waves and gulls. This piece of paradise is sure to become your favorite home away from home. This beautifully furnished and spacious condo offers all the …
  • Ocean or water views
  • Shared outdoor pool (unheated)
  • Hot Tub/Jacuzzi
  • Internet Access
  • Washing Machine
  • Pet friendly
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(3)

Great Vacation!

Left on Dec 22, 2014 for a stay in October 2014

We have stayed at Bay Harbor several times in this condo and love it. The condo feels like home and has everything you would ever need during your stay The complex is very well maintained and the pool area is great for relaxing, the slip for your boat is also a plus. Everything from the great fishing, snorkeling and great restaurants, there is something for everyone in the family. This will …

$92

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Family Friendly Executive Bay**Discounts Available**

Islamorada house
3 BR / 2 BA / Sleeps 8 | Quick view
Excellent7 Reviews

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Reviews

(7)

Beautiful three bedroom bay side townhouse with private beach access in sunny Islamorada (near Key Largo). Welcome to our little slice of paradise! Come and relax at our beautiful townhome in the Florida Keys. The Executive Bay Club is located in Islamorada, the Sport Fishing Capital of the World. It is a private, …
  • Shared outdoor pool (unheated)
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • A/C or climate control
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(7)

Wonderful

Left on Jul 20, 2013 for a stay in June 2013

This rental by far was one of the best rentals we have stayed at. The location and the house were perfect! The house is very large and everything you can imagine has been supplied. The pool, community center, tennis courts and complex in general were beautiful and well maintained. Really good experience!

$150

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200 Plantation Shores Drive

Islamorada house
3 BR / 3 BA / Sleeps 6 | Quick view
Excellent4 Reviews

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Reviews

(4)

A very charming and immaculate 3 bedroom home in Plantation Key. This home has excellent protected deep water dockage. Ocean views from balcony. Easy bay access via Tavernier Creek. Close to resturants and store. CLICK HERE to view photos on a mobile device. Additional amenities include: dock/boat-slip, coffee maker…
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Grill
  • Dishwasher
  • Pet friendly - ask
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(4)

Islamorada Getaway

Left on Sep 06, 2012 for a stay in July 2012

The service from Freewheeler Vacations, Inc was above & beyond! Our family rented the Islamorada home for the month of July 2012. The ocean breezes were fantastic! There were only two things I wish would have been better. One, the quality of the cookware and second, the aC cooling of the downstairs bedroom. If these items were to be updated/corrected then this truly would be a perfect vacation …

$600

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76190 Overseas Highway - Casa Dorado

Islamorada house
4 BR / 4 BA / Sleeps 8 | Quick view
Very Good1 Reviews

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Reviews

(1)

Casa Dorado is a premier rental vacation home on Lower Matecumbe Key in Islamorada, Florida. Completely renovated in 2014, the spacious living and dining areas, four bedrooms, and three and a half bathrooms will make for a very comfortable stay during your visit to the Florida Keys. The house is located on the Florida…
  • Ocean or water views
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • A/C or climate control
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(1)

Casa Dorado delivers!

Left on Dec 26, 2014 for a stay in December 2014

The house is newly remodeled and in great condition. Very clean- which was a must for me! The views are wonderful. We thouroghly enjoyed the week we spent there (myself, my husband, our 24yr old daughter and her friend). It was a great location for biking, walking, kayaking and paddle boarding. The home has a pool, but we did not use it because it was not heated. We highly recommend Casa Dorado.

$190

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Futura Condos and Townhomes

Islamorada condo
2 BR / Sleeps 4 | Quick view
Excellent1 Reviews

Details

Reviews

(1)

Please send us an inquiry or call us for availability. We have condos and townhomes. Prices vary on the units. Your own tropical paradise overlooking the fabulous Florida Bay in Islamorada. Futura Yacht Club is a 70 unit community with a 53 slip marina and accommodations available for that tranquil tropical …
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(1)

Most awesome vacation in Islamorda Florida!!

Left on Jul 14, 2010 for a stay in June 2010

Futura - The price is right. The location is perfect. The townhouse is very comfortable, beautifuly decorated, with a most awesome view of Florida Bay. The marina, dock, and boat ramp are all at the same location and are well maintained. The pool, tennis courts, basketball, and volley ball court are an added bonus.
In addition, Freewheeler Realty has been providing our vacation services for over …

$472

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Maison Matecumbe 304

Islamorada condo
3 BR / 3 BA / Sleeps 6 | Quick view
Excellent1 Reviews

Details

Reviews

(1)

This three bedroom, three bathroom condominium sits on a lushly landscaped property, offering the Florida Keys you've always imagined. Enjoy beautiful oceanfront vistas from one of two balconies. Take a dip in the spacious pool that sits right at the foot of the condo staircase. Or journey a few yards further to the …
  • Ocean or water views
  • Shared outdoor pool (unheated)
  • Internet Access
  • A/C or climate control
  • Porch
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(1)

Relaxing in Islamorada

Left on Jul 14, 2010 for a stay in June 2010

Everything was beautiful. Very nice property. Private but very close to fishing charters.

Toaster did not work and upstairs a/C quit working the night before we left. Other than that the condo was great.

$400

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74920 Overseas Hwy

Islamorada house
4 BR / 5 BA / Sleeps 8 | Quick view
Excellent2 Reviews

Details

Reviews

(2)

One of a kind bay front estate! This is an absolutely gorgeous estate home offering a gated entrance paved brick driveway, 3,500 sf, 3 bedrooms, 3.5 bathrooms upstars and a bonus 1 bedroom, 1 bathroom apartment downstairs. Enjoy ocean & lagoon views, deep water protected dockage, 2 Great rooms, private master suite, …
  • Waterfront
  • Ocean or water views
  • Hot Tub/Jacuzzi
  • A/C or climate control
  • Telephone
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(2)

The Best

Left on May 29, 2012 for a stay in April 2012

Everything about this property was exactly as represented by Freewheeler. It was spotless and completely ready for our group despite last minute changes to the schedule. We will certainly consider this property and Freewheeler for our future visits to the Keys.

$1,715

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Alligator Reef Luxury Estate

Islamorada house
10 BR / 10 BA / Sleeps 20 | Quick view
Excellent13 Reviews

Details

Reviews

(13)

Got a large group that wants to "get away from it all"? Or do you need lots of space for a family reunion or wedding? This is the perfect solution! Terrific location, beautiful view, two private pools for you to enjoy... And since it's 4 separate homes, you aren't right on top of each other. Wide decks let you enjoy …
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Pet friendly - ask
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(13)

Island Perfection

Left on Jul 01, 2010 for a stay in May 2010

Perfect house for a island getaway. Hammocks, wildlife, marinelife, pool, kayaks, near "the infamous islamorada sandbar", ping pong table, boat rentals nearby, the place couldn't be better for kicking back soaking up everything that makes the Florida Keys special.

Real friendly and easy to deal with reservation systems and staff. A++ all the way. We will use Freewheeler again and again.

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