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$99

2 BR / 2 BA / Sleeps 8

1 Reviews

$99

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Newly Renovated Executive Bay Townhouse**Discounts Available**

2 BR / 2 BA / Sleeps 8 | Quick view
“ Excellent ” 1 Reviews

Details

Reviews

(1)

Beautiful two bedroom townhouse on the Bay side with private beach access in sunny Islamorada (near Key Largo). Welcome to our little slice of paradise! Come and relax at our beautiful, newly renovated townhome in the Florida Keys. The Executive Bay Club is located in Islamorada, the Sport Fishing Capital of the World…
  • 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

(1)

Great condo, perfect location!

Left on Jan 02, 2015 for a stay in December 2014

I have two small children and the condo was perfect and comfortable for the entire family. It was nicely remodeled. The pool and dock area were very nice. Security was visible and very friendly. The location was close to everything. The property management service was excellent. We had a wonderful family vacation and will definitely be returning next year!

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$110

2 BR / 1 BA / Sleeps 4

75651 Overseas Hwy Islamorada Fla Keys Oceanfront - Islamorada vacation rentals
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$110

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75651 Overseas Hwy Islamorada Fla Keys Oceanfront

2 BR / 1 BA / Sleeps 4 | Quick view

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Directly on your private oceanfront beach. Ocean views from every room of your two bedroom one bath Keys style duplex villa. You will experience the true 'old Keys' charm of bird watching on the wraparound deck to fishing on the beach...or perhaps just relaxing on the sand. With over a half acre of tropical landscape…
  • Private Beach
  • Ocean or water views
  • Internet Access
  • Housekeeping Optional
  • Washing Machine
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask

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$77

2 BR / 2 BA / Sleeps 4

Executive Bay Club A-1 - Islamorada vacation rentals
1 / 21

$77

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Executive Bay Club A-1

2 BR / 2 BA / Sleeps 4 | Quick view

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N/A
  • Shared outdoor pool (unheated)
  • A/C or climate control
  • Dishwasher
  • Microwave
  • Toaster
  • Suitable for children - ask
  • Suitable for the elderly - ask

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$83

2 BR / 0 BA / Sleeps 4

135 Gulfview Dr - Islamorada vacation rentals
1 / 19

$83

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135 Gulfview Dr

2 BR / Sleeps 4 | Quick view

Details

Click here to view photos on a mobile device.
  • Ocean or water views
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • A/C or climate control
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$258

2 BR / 3 BA / Sleeps 6

3 Reviews

$258

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Islamorada Luxury Waterfront Condo with Boat Slip

2 BR / 3 BA / Sleeps 6 | Quick view
“ Excellent ” 3 Reviews

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Reviews

(3)

Escape to Islamorada in the Florida Keys and enjoy the breathtaking gulf and ocean views from your top floor balcony in this decorator furnished, two bedroom luxurious condo. This unit located in the complex of Bay Harbour offers a private 50' boat slip, heated swimming pool, hot tub, club house, fitness center, …
  • Waterfront
  • Ocean or water views
  • Hot Tub/Jacuzzi
  • Internet Access
  • Washing Machine
  • Suitable for children
  • Suitable for the elderly - elevator access
  • Wheelchair accessible

Details

Reviews

(3)

Wonderful stay at Bay Harbour

Left on Jan 24, 2014 for a stay in January 2014

This condo exceeded our expectations. It was truly a home away from home. It has all the amenities you will need to have a great vacation. The kitchen is fully furnished, the condo is spacious, and the little extras like bikes, tennis rackets, and baseball gloves are an added bonus.

Our family was happy to see a manatee and calf in the water right outside the condo!

Pool was very …

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$149

2 BR / 2 BA / Sleeps 4

Moon Bay Condo A-206 - Islamorada vacation rentals
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$149

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Moon Bay Condo A-206

2 BR / 2 BA / Sleeps 4 | Quick view

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A beautifully decorated condo located at mm 104. This unit has 2 bedrooms and 1.5 baths and its own deeded boat slip. This condo in conveniently located close to the main land. This is a perfect condo for fishermen, divers, or just a Key's getaway. Amenities include heated pool, jacuzzi, tennis courts, sauna, and game…
  • Shared outdoor pool (unheated)
  • Sauna
  • Internet Access
  • A/C or climate control
  • Dishwasher
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$100

2 BR / 2 BA / Sleeps 4

2 Reviews

$100

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157 Ojibway Ave - 28 NIGHT MINIMUM

2 BR / 2 BA / Sleeps 4 | Quick view
“ Very Good ” 2 Reviews

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Reviews

(2)

This 2Bed/2Bath stilt home is located at mile marker 89 at the very end of Indian Waterways subdivision. Located on a canal with approximately 30' of dockage, you'll have almost immediate access to the Florida Bay and just a 7 minute boat ride to Tavernier Creek, which takes right over to the Atlantic Ocean. The yard …
  • Ocean or water views
  • Internet Access
  • A/C or climate control
  • Grill
  • Dishwasher
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(2)

Very nice and relaxing...

Left on Feb 23, 2011 for a stay in January 2011

Very nice...my 3rd time renting the house...no problems...excellent service...great location...I would recommend to others...hope to be back soon...

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$190

2 BR / 3 BA / Sleeps 4

1 Reviews

$190

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Futura Townhome 731

2 BR / 3 BA / Sleeps 4 | Quick view
“ Excellent ” 1 Reviews

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Reviews

(1)

Enjoy the spectacular view of the Florida Bay from this beautiful townhome. There are tons of things to keep you and your family busy without having to leave the Futura Condo complex. There are tennis courts and a swimming pool located on the property. Make your self at home in our home away from home. Boat dockage …
  • Waterfront
  • Ocean or water views
  • Shared outdoor pool (unheated)
  • A/C or climate control
  • Grill
  • Suitable for children - ask
  • 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 …

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$208

2 BR / 2 BA / Sleeps 4

2 Reviews

$208

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75130 Overseas Highway

2 BR / 2 BA / Sleeps 4 | Quick view
“ Excellent ” 2 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
  • Smoking allowed - ask
  • Suitable for children - ask
  • 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.

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$117

2 BR / 2 BA / Sleeps 4

2 Reviews

$117

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75190 Overseas Hwy - 28 NIGHT MINIMUM!!!!!!!

2 BR / 2 BA / Sleeps 4 | Quick view
“ Excellent ” 2 Reviews

Details

Reviews

(2)

Great home with an even better view ... come and stay for a month and enjoy the Incredible endless views from the patio. Home is located in the perfect spot for snorkeling, fishing, and diving, and has a protected & private boat basin! Come once and you will see why so many people come back year after year to …
  • Ocean or water views
  • Internet Access
  • A/C or climate control
  • Grill
  • Dishwasher
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(2)

Relaxing

Left on Aug 18, 2011 for a stay in July 2011

The location was great.Mad Dog's & Ziggy's was fabulous! Love shopping at Morada Bay Gallery. The kitchen was ill equipped, who ever heard of a house in the Keys w/o a blender??? Nasty grill. The beach at the house was great. The gate to the house was locked and we were not supplied the key and had to wait for 45 minutes for someone to bring us one.

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$107

2 BR / 0 BA / Sleeps 4

1 / 20

$107

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114 Plantation Ave

2 BR / Sleeps 4 | Quick view

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This charming 2 bedroom, 2 bathroom home is located at the 90 mile marker. This home is centrally located to shopping, restaurants, and grocery store.
  • Ocean or water views
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • A/C or climate control
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$100

2 BR / 3 BA / Sleeps 4

1 / 1

$100

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Executive Bay Club Unit G-5 - 28 NIGHT MINIMUM

2 BR / 3 BA / Sleeps 4 | Quick view

Details

Click here to view this photo slideshow on a mobile device.
  • Ocean or water views
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • A/C or climate control
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$100

2 BR / 2 BA / Sleeps 6

2 Reviews

$100

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Summer Sea #418 - 28 Night Minimum

2 BR / 2 BA / Sleeps 6 | Quick view
“ Excellent ” 2 Reviews

Details

Reviews

(2)

This 2 bedroom, 2 bathroom condo located directly on the Florida Bay is the perfect sunny getaway! Situation with perfect views of the community pool, community marina, and open bay, you'll enjoy coffee in the morning while watching the boaters head out for their perfect catch and enjoy a sunset cocktail in the …
  • Ocean or water views
  • Shared outdoor pool (unheated)
  • A/C or climate control
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(2)

Heaven in Islamorada, Florida

Left on Aug 23, 2011 for a stay in July 2011

Rented a 2/2 condo for the month of July 2011.
Great location, nice amenities,clean,wonderful view, friendly staff and condo owners.
Excellent price.
I will definitely do this again soon.

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$214

2 BR / 3 BA / Sleeps 6

1 / 24

$214

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LUXURY KEYS HOME IN PARADISE-106 ANGLERS REEF

2 BR / 3 BA / Sleeps 6 | Quick view

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This beautiful villa has all new furnishings and is located in the exclusive oceanfront gated community of Angler's Reef in Islamorada at Mile Marker 84. Angler's reef is a luxury retreat resort framed by mangroves and the clear waters of the Atlantic ocean with 52 colonial detached villas set along quaint streets …
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Suitable for children
  • Suitable for the elderly

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$250

2 BR / 3 BA / Sleeps 6

1 / 7

$250

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Angler's Reef Coastal Conch Style Vacation Home

2 BR / 3 BA / Sleeps 6 | Quick view

Details

This Coastal Conch Style Cottage has been recently updated to accommodate vacation renters and their families. The cottage has all new furnishings and accessories that offers a "home away from home" feel. The Coastal style conch cottage is located in the gated community, ocean front resort development of Angler's Reef…
  • Suitable for children
  • Suitable for the elderly

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$129

2 BR / 2 BA / Sleeps 4

1 Reviews

$129

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Futura Condo 205

2 BR / 2 BA / Sleeps 4 | Quick view
“ Excellent ” 1 Reviews

Details

Reviews

(1)

This charming condo is located in the Futura Yacht Club community, located at mile marker 88.5 on the bay side in Islamorada. The unit comes fully furnished with a full kitchen, dining room, large living room with sleeper sofa, expansive balcony with great views of the Florida Bay and the community's two tennis courts…
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • A/C or climate control
  • Central heating
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(1)

This condo has everything and more

Left on May 17, 2013 for a stay in March 2013

This condo was perfect for our vacation. While there was only 2 of us a family of 4 could definitely fit. The kitchen was incredibly well stocked with everything you could possibly need as well as extra towels and linens in the closet. Living room had a huge comfortable couch and TV. There was also a deck with chairs overlooking the tennis courts and pool.

The washer and dryer were outside …

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$200

2 BR / 1 BA / Sleeps 4

2 Reviews

$200

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83261 Old Highway

2 BR / 1 BA / Sleeps 4 | Quick view
“ Excellent ” 2 Reviews

Details

Reviews

(2)

A quaint bungalow on a not-so-quaint piece of oceanfront land right in the Heart of Islamorada! This home has two bedrooms, two bathrooms, and a lot of Keysy charm. During your stay, you will enjoy such amenities as a fishing dock with Chickee hut (1ft draft), cable television, a kayak, and a white picket fence …
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(2)

House with privats beach and fishing pier

Left on Mar 27, 2014 for a stay in March 2014

Great house; really stocked well. Huge property with a grass yard in the front, side and about half grass and sandy beach in the back. Saw a shark, stingrays, spuffer fish and baracuda from the fishing pier. Also a great location; close to everything. May be better for a couple since there is only 1 bathroom; a little tight for a family of four. Really my only complaint is they should put down…

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$100

2 BR / 1 BA / Sleeps 1

1 / 1

$100

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241 Tollgate Blvd - 28 NIGHT MINIMUM!!!!!!!!!!!!!!

2 BR / 1 BA / Sleeps 1 | Quick view

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"Cute & Keysy" perfectly describe this Conch home! Located in the Tollgate Shores subdivision of Lower Matecumbe (south Islamorada), this delightfully quaint home has lots of character, charm, and is well-maintained. You'll enjoy sea breezes and the smell of salty air coming through the windows of the sunroom, or …
  • Ocean or water views
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • A/C or climate control
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$190

2 BR / 3 BA / Sleeps 4

2 Reviews

$190

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Futura Townhome 708

2 BR / 3 BA / Sleeps 4 | Quick view
“ Poor ” 2 Reviews

Details

Reviews

(2)

This unit's kitchen, bathrooms, windows, and doors received a facelift in January 2014! Enjoy the spectacular view of the Florida Bay from either one of the TWO balconies in this 2 story townhome, located off the master bedroom or the living room. Amenities include Wi-Fi, flat panel TV's in the living room and master …
  • Waterfront
  • Shared outdoor pool (unheated)
  • Grill
  • Dishwasher
  • Microwave
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(2)

i need of update and repiar

Left on Mar 11, 2011 for a stay in February 2011

In need of repair pant and up date . They ants all over contertops paint was peeling from walls and trim.

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$215

2 BR / 2 BA / Sleeps 4

16 Reviews

$215

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132 Columbus Drive

2 BR / 2 BA / Sleeps 4 | Quick view
“ Excellent ” 16 Reviews

Details

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".

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$243

2 BR / 3 BA / Sleeps 6

1 / 25

$243

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Anglers Reef Islamorada Florida Sleeps 6

2 BR / 3 BA / Sleeps 6 | Quick view

Details

2 bedrooms, 2 full bathrooms, 1 half bathroom, sleeps 6 This magnificent oceanfront home is at Mile Marker 85 in exclusive Angler's Reef - 52 homes . Quaint streets & walking paths wind through this village-styled retreat. Enjoy a drink in the lushly landscaped pool area overlooking the ocean or on the 500' of …
  • 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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$397

2 BR / 3 BA / Sleeps 5

1 / 14

$397

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Islamorada getaway home with private boat dock.

2 BR / 3 BA / Sleeps 5 | Quick view

Details

This property is a single family home with a boat dock included in the price. Not a condo. Note: we only offer 7 day minimum stays with 4PM Saturday check ins and 10 AM checkouts. Maximum number of guests is 5. No pets, No smoking and maximum guests is strictly enforced. Rates start at $2,775 per week plus tax and …
  • Wireless Internet
  • Washing Machine
  • Clothes Dryer
  • A/C or climate control
  • Central heating
  • Suitable for children

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$300

2 BR / 2 BA / Sleeps 6

1 Reviews

$300

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Islamorada Florida Keys Beautiful 2B 2B Townhouse

2 BR / 2 BA / Sleeps 6 | Quick view
“ Excellent ” 1 Reviews

Details

Reviews

(1)

We also have monthly and 3 day weekend rates! Vacation in Paradise!!... you will love this fun filled, relaxing townhouse in the beautiful Florida Keys. The Executive Bay Club is located in Islamorada, the Sport Fishing Capital of the World. It is a private, gated community and the grounds have 2 tennis courts, a …
  • Waterfront
  • Wireless Internet
  • Washing Machine
  • Clothes Dryer
  • A/C or climate control
  • Suitable for children

Details

Reviews

(1)

Marvelous Property- First Class All the Way!

Left on Jan 16, 2015 for a stay in December 2014

The Daniels' property was an outstanding vacation rental. It is centrally located in the middle of Islamorada. This is a two story end unit condo that is in perfect, (yes, perfect) condition. There is a roomy master bedroom, 2nd bedroom and a loft (accessible through the master). The living room is expansive, the kitchen is modern, ultra well equipped and easy to use.

I would love …

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$133

2 BR / 2 BA / Sleeps 4

1 / 17

$133

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BEACON REEF 222

2 BR / 2 BA / Sleeps 4 | Quick view

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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

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$77

2 BR / 2 BA / Sleeps 4

1 / 14

$77

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THE PALMS 402

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
  • Balcony or terrace
  • Fitness Room
  • Suitable for children - ask
  • Suitable for the elderly - ask

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$107

2 BR / 2 BA / Sleeps 4

1 / 23

$107

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BEACON REEF 501

2 BR / 2 BA / Sleeps 4 | Quick view

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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

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$110

2 BR / 2 BA / Sleeps 4

1 / 20

$110

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BEACON REEF 314

2 BR / 2 BA / Sleeps 4 | Quick view

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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

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$358

2 BR / 2 BA / Sleeps 6

3 Reviews

$358

Inquire

LITTLE BAY - Upper Duplex

2 BR / 2 BA / Sleeps 6 | Quick view
“ Excellent ” 3 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
  • Patio
  • 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 …

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$358

2 BR / 2 BA / Sleeps 6

4 Reviews

$358

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LITTLE BAY - Lower Duplex

2 BR / 2 BA / Sleeps 6 | Quick view
“ Excellent ” 4 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 …

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$97

2 BR / 2 BA / Sleeps 6

1 / 26

$97

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THE PALMS 405 - 93

2 BR / 2 BA / Sleeps 6 | Quick view

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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

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$63

2 BR / 2 BA / Sleeps 4

1 / 15

$63

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THE PALMS 506

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
  • Balcony or terrace
  • Suitable for children - ask
  • Suitable for the elderly - ask

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$167

2 BR / 2 BA / Sleeps 4

1 / 24

$167

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OCEAN HARBOUR K4

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

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$67

2 BR / 2 BA / Sleeps 6

1 / 16

$67

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BOATER'S DELIGHT

2 BR / 2 BA / Sleeps 6 | Quick view

Details

Minimum Rental: 1 Year Beautifully furnished, this almost new single family stilt home sits on an ocean side canal front lot. Bring your boat and your swim suit! This 2 bedroom, 2 bath home has everything you need, including a laundry room with a clothes washer and dryer and a fully equipped kitchen. Enjoy your …
  • Hot Tub/Jacuzzi
  • Patio
  • Parking
  • Grill
  • Refrigerator
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask

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$100

2 BR / 1 BA / Sleeps 6

2 Reviews

$100

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122 Leoni Dr - 28 night Minimum!!!

2 BR / 1 BA / Sleeps 6 | Quick view
“ Very Good ” 2 Reviews

Details

Reviews

(2)

Modest home in great subdivision. Excellent, deep dockage on a wide canal with easy ocean and bay access via Snake Creek. Cool tropical breezes can be enjoyed on the screened in porch. Minimum Stay for this home is 28 night minimum. Wirelss internet. Click Here for Map! CLICK HERE to view photos on a mobile device…
  • Waterfront
  • Ocean or water views
  • Wireless Internet
  • Washing Machine
  • Clothes Dryer
  • Pet friendly - ask
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(2)

Very good service from Freewheeler

Left on Jun 22, 2010 for a stay in May 2010

Only thing missed was internet access. Otherwise a good stay.

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$67

2 BR / 2 BA / Sleeps 4

1 / 14

$67

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THE PALMS 408

2 BR / 2 BA / Sleeps 4 | Quick view

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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

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$179

2 BR / 2 BA / Sleeps 6

4 Reviews

$179

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BROCK HAUS ON THE GULF

2 BR / 2 BA / Sleeps 6 | Quick view
“ Excellent ” 4 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…

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$133

2 BR / 2 BA / Sleeps 4

1 / 18

$133

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BEACON REEF 211

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
  • Patio
  • Suitable for children - ask
  • Suitable for the elderly - ask

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$70

2 BR / 2 BA / Sleeps 4

1 / 18

$70

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THE PALMS 214

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
  • Balcony or terrace
  • Suitable for children - ask
  • Suitable for the elderly - ask

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$70

2 BR / 2 BA / Sleeps 6

1 / 16

$70

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THE PALMS 301

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

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$80

2 BR / 2 BA / Sleeps 4

1 / 20

$80

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THE PALMS 403

2 BR / 2 BA / Sleeps 4 | Quick view

Details

Minimum Rental: 1 Month This exceptional 2 bedroom and 2 bath condo is located in one of the most popular Islamorada condo complexes - The Palms. The balcony is large enough to dine or recline and offers fabulous open water ocean views. Watching the sunrise over the Atlantic Ocean as you sip your morning …
  • Shared outdoor pool (unheated)
  • Hot Tub/Jacuzzi
  • Internet Access
  • Balcony or terrace
  • Fitness Room
  • Suitable for children - ask
  • Suitable for the elderly - ask

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$100

2 BR / 2 BA / Sleeps 4

1 Reviews

$100

Inquire

VILLA RIOLO

2 BR / 2 BA / Sleeps 4 | Quick view
“ Excellent ” 1 Reviews

Details

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.

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$77

2 BR / 2 BA / Sleeps 5

1 / 21

$77

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THE PALMS 314

2 BR / 2 BA / Sleeps 5 | Quick view

Details

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

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$358

2 BR / 2 BA / Sleeps 6

1 Reviews

$358

Inquire

LITTLE BAY - Cottage

2 BR / 2 BA / Sleeps 6 | Quick view
“ Excellent ” 1 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.

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$172

2 BR / 2 BA / Sleeps 4

3 Reviews

$172

Inquire

Sea Gulls Condo - Unit 406

2 BR / 2 BA / Sleeps 4 | Quick view
“ Excellent ” 3 Reviews

Details

Reviews

(3)

This newly remodeled & renovated (in 2012), two bedroom, Sea Gulls Condo unit, located on the oceanside of Plantation Key at Mile Marker 90, has an awesome view! Unit is comfortably and stylishly furnished, has TVs in the living room, two queen beds and a sleeper sofa. The Sea Gulls community features a fish cleaning …
  • Waterfront
  • Ocean or water views
  • Shared outdoor pool (unheated)
  • Sauna
  • Internet Access
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(3)

Adequate

Left on May 24, 2012 for a stay in April 2012

The condo provided plenty of space for two couples. The complex is quiet. The pool is nice and the meditation beach(tiny) was relaxing. The condo itself was very dated. The beds were comfortable. The living room furniture was stained. The entire condo had an odor but tolerable. Possibly it had not been used for some time, not sure. Smelled musky. The balcony is large and was enjoyable for…

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$500

2 BR / 2 BA / Sleeps 6

1 Reviews

$500

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Islamorada Waterfront Paradise 2

2 BR / 2 BA / Sleeps 6 | Quick view
“ Very Good ” 1 Reviews

Details

Reviews

(1)

Dive right into paradise while staying at Casa Rio. With a beautiful view of a sleepy natural waterway in the Florida Keys you can quickly relax and transform into 'island time.' This exclusive bayside home is situated in a secluded location on Islamorada with quick access to the Florida Bay and Atlantic Ocean. Your …
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Fireplace
  • Housekeeping Optional
  • Suitable for children
  • Suitable for the elderly - ask

Details

Reviews

(1)

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.

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$315

2 BR / 3 BA / Sleeps 4

1 / 1

$315

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Angler's Reef | 130 Anglers Way

2 BR / 3 BA / Sleeps 4 | Quick view

Details

Add some Caribbean spice to your next visit to the Florida Keys. This two-bedroom/two-and-half bath villa sits within Angler's Reef, a charming community of detached town homes that take their inspiration from the architecture of the British West Indies. Located at mile marker 85, on Windley Key, it's the perfect …
  • Ocean or water views
  • Internet Access
  • Clothes Dryer
  • A/C or climate control
  • Central heating
  • Suitable for children - ask
  • Suitable for the elderly - ask

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$3,000

2 BR / 2 BA / Sleeps 4

3 Reviews

$3,000

Inquire

2-bed,1.5-bath Condos On The Bay, Islamorada

2 BR / 2 BA / Sleeps 4 | Quick view
“ Average ” 3 Reviews

Details

Reviews

(3)

Complex Amenities - MM 88.5 - Building has five floors - Large swimming pool & children's pool - Exercise room with sauna - Laundry room on each floor - Billiard and Ping-Pong room - Adult party lounge - Cookout facilities - Direct access to Florida Bay and then ocean - Minutes from Islamorada, “sport fishing …
  • Waterfront
  • Ocean or water views
  • Sauna
  • Washing Machine
  • Clothes Dryer
  • Suitable for children
  • Suitable for the elderly
  • Wheelchair accessible

Details

Reviews

(3)

Beautiful Vacation Spot- Great for families!

Left on Apr 18, 2013 for a stay in April 2013

The condo in Islamorada was clean, updated, and nicely furnished, perfect for our family of 4. The kitchen is updated with granite counters & stainless steel appliances. The view from the living area in the condo is simply gorgeous-crystal clear water. There is a cozy little deck for drinking coffee in the morning and watching sunsets in the evening. The master bedroom has a king size bed, …

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$250

2 BR / 2 BA / Sleeps 4

1 / 20

$250

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Oceanfrontparadise: 209

2 BR / 2 BA / Sleeps 4 | Quick view

Details

Welcome to beautiful Islamorada located in the Florida Keys. Islamorada is known as the "Sport Fishing Capital of the World". Our ocean contains the world's most sought-after gamefish including tuna, dolphin, Marlin, permit, tarpon and bonefish. In addition to fishing, Islamorada is a favorite of divers too. Our …
  • Balcony or terrace
  • Linens Provided
  • Towels Provided
  • Freezer
  • Microwave
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$300

2 BR / 3 BA / Sleeps 5

22 Reviews

$300

Book

Luxurious Anglers Reef with Boat Slip, Pool, Ocean

2 BR / 3 BA / Sleeps 5 | Quick view
“ Excellent ” 22 Reviews

Details

Reviews

(22)

House, 2 Bedrooms + Convertible Bed(s), 2.5 Baths (Sleeps 5) Islamorada home set in OceanFront gated community with swimming pool and private boat dock This charming home has 2 Bedrooms, 2.5 Bathrooms, A/C, Granite work tops, modern stainless steel appliances. Open porches and balconies, rich hard wood floors, …
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Housekeeping Optional
  • Washing Machine
  • Suitable for children
  • Suitable for the elderly - ask

Details

Reviews

(22)

Beautiful luxury and an absolute great stay in Keys! No hesitati

Left on Oct 18, 2012 for a stay in October 2012

This beautiful condo in Islamorada is pristine clean, has all the updates needed and is centrally and perfectly located if staying in the Keys! Jo (the owner) made us feel like family, gave us wonderful recommendations of who to take us snorkeling, diving, kayak rental, where to eat and even went out of her way to purchase a charcoal grill so we could cook out if we wanted to stay "home". I was …

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$250

2 BR / 2 BA / Sleeps 4

1 Reviews

$250

Book

Oceanfrontparadise: 509

2 BR / 2 BA / Sleeps 4 | Quick view
“ Excellent ” 1 Reviews

Details

Reviews

(1)

Welcome to beautiful Islamorada located in the Florida Keys. Islamorada is known as the "Sport Fishing Capital of the World". Our ocean contains the world's most sought-after gamefish including tuna, dolphin, Marlin, permit, tarpon and bonefish. In addition to fishing, Islamorada is a favorite of divers too. Our …
  • Waterfront
  • Internet Access
  • Housekeeping Optional
  • Washing Machine
  • Clothes Dryer
  • Smoking allowed - ask
  • Suitable for children
  • Suitable for the elderly
  • Wheelchair accessible

Details

Reviews

(1)

We had fun

Left on Nov 16, 2014 for a stay in November 2014

my husband and 2 friends stayed in this unit for 4 days and 3 nights. they found the condo to be clean, plenty of space and conveniently located.

they would definitely stay here again!!

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