Showing

PreviousNext property

$99

2 BR / 2 BA / Sleeps 8

2 Reviews

$99

Inquire

Newly Renovated Townhouse in Beautiful Executive Bay **Discounts Available**

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

Details

Reviews

(2)

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

(2)

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!

PreviousNext property

$358

2 BR / 2 BA / Sleeps 6

1 Reviews

$358

Inquire

LITTLE BAY - Cottage

Islamorada villa
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.

PreviousNext property

$133

2 BR / 2 BA / Sleeps 4

BEACON REEF 211 - Islamorada vacation rentals
1 / 18

$133

Inquire

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

PreviousNext property

$315

2 BR / 3 BA / Sleeps 4

Angler's Reef | 130 Anglers Way - Islamorada vacation rentals
1 / 1

$315

Inquire

Angler's Reef | 130 Anglers Way

Islamorada house
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
  • Suitable for the elderly - ask

PreviousNext property

$67

2 BR / 2 BA / Sleeps 4

THE PALMS 408 - Islamorada vacation rentals
1 / 14

$67

Inquire

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

PreviousNext property

$179

2 BR / 2 BA / Sleeps 6

4 Reviews

$179

Inquire

BROCK HAUS ON THE GULF

Islamorada condo
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…

PreviousNext property

$100

2 BR / 1 BA / Sleeps 4

1 / 1

$100

Inquire

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

Islamorada house
2 BR / 1 BA / Sleeps 4 | Quick view

Details

"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 …
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

PreviousNext property

$70

2 BR / 2 BA / Sleeps 6

1 / 16

$70

Inquire

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

PreviousNext property

$70

2 BR / 2 BA / Sleeps 4

1 / 18

$70

Inquire

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

PreviousNext property

$358

2 BR / 2 BA / Sleeps 6

3 Reviews

$358

Inquire

LITTLE BAY - Upper Duplex

Islamorada villa
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 …

PreviousNext property

$358

2 BR / 2 BA / Sleeps 6

4 Reviews

$358

Inquire

LITTLE BAY - Lower Duplex

Islamorada villa
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 …

PreviousNext property

$200

2 BR / 1 BA / Sleeps 4

2 Reviews

$200

Inquire

83261 Old Highway

Islamorada house
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…

PreviousNext property

$100

2 BR / 2 BA / Sleeps 4

1 Reviews

$100

Inquire

VILLA RIOLO

Islamorada house
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.

PreviousNext property

$243

2 BR / 3 BA / Sleeps 6

1 / 25

$243

Book

Anglers Reef Islamorada Florida Sleeps 6

Islamorada house
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

PreviousNext property

$167

2 BR / 2 BA / Sleeps 4

1 / 24

$167

Inquire

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

PreviousNext property

$190

2 BR / 0 BA / Sleeps 4

1 Reviews

$190

Inquire

Futura Condos and Townhomes

Islamorada condo
2 BR / Sleeps 4 | Quick view
“ Excellent ” 1 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 - over five
  • 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 …

PreviousNext property

$215

2 BR / 2 BA / Sleeps 4

16 Reviews

$215

Inquire

132 Columbus Drive

Islamorada house
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".

PreviousNext property

$100

2 BR / 2 BA / Sleeps 4

1 / 7

$100

Inquire

Executive Bay Club

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

Details

Please send us an inquiry or call us for availability. Prices vary on the units. 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 swimming pool, a clubhouse, a private beach and a fishing/boat dock. Next …
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

PreviousNext property

$143

2 BR / 0 BA / Sleeps 4

3 Reviews

$143

Inquire

Sea Gulls Condominium Complex

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

Details

Reviews

(3)

Please send us an inquiry or call us for availability. Prices vary on the units. Sea Gulls Condominiums, on the shores of the Atlantic Ocean provides vacationers the splendor of the Atlantic waters with luxury living at an affordable price. This perfect family vacation destination offers something to do in, under, …
  • Waterfront
  • Ocean or water views
  • Sauna
  • Internet Access
  • A/C or climate control
  • Suitable for children
  • 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…

PreviousNext property

$77

2 BR / 2 BA / Sleeps 5

1 Reviews

$77

Inquire

THE PALMS 314

Islamorada condo
2 BR / 2 BA / Sleeps 5 | Quick view
“ Excellent ” 1 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 …

PreviousNext property

$107

2 BR / 2 BA / Sleeps 4

1 / 20

$107

Inquire

114 Plantation Ave - 28 NIGHT MINIMUM!!!

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

Details

This charming 2 bedroom and 2 bathroom home is located at the 90 mile marker. This home is centrally located to shopping, restaurants, and grocery store. This home offers deep water dockage and easy access to the Atlantic Ocean via Tavernier Creek. Great outdoor space whether you are sitting on the porch or sitting …
  • 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

PreviousNext property

$110

2 BR / 2 BA / Sleeps 4

1 / 20

$110

Inquire

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

PreviousNext property

$300

2 BR / 2 BA / Sleeps 6

3 Reviews

$300

Book

Florida Keys Beautiful 2B 2B Townhouse

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

Details

Reviews

(3)

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 swimming pool, a clubhouse, a private beach and a …
  • Waterfront
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • A/C or climate control
  • Suitable for children

Details

Reviews

(3)

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 …

PreviousNext property

$100

2 BR / 2 BA / Sleeps 4

2 Reviews

$100

Inquire

Summer Sea Condominium Complex

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

Details

Reviews

(2)

Summer Seas is located directly on the Florida Bay is the perfect sunny getaway! The complex is centrally located at mm 88. There is also on-site community laundry, a pool, hot tub, and clubhouse. Islamorada, the "Village of Islands," is widely known as the sportfishing capital of the world. Its islands …
  • Waterfront
  • Ocean or water views
  • Shared outdoor pool (unheated)
  • A/C or climate control
  • Parking
  • Suitable for children
  • 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.

PreviousNext property

$83

2 BR / 2 BA / Sleeps 4

1 / 19

$83

Inquire

135 Gulfview Dr - 28 Night Minimum!!!!

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

Details

This delightful 2 bedroom, 2 bathroom home is located in Port Antigua (south Islamorada) at the 74 mile marker. While not located directly on the bay, you'll still be able enjoy the homeowners park that has a beach and beautiful sunsets. The home comes equipped with Wi-Fi internet. Click here to view photos on a …
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

PreviousNext property

$110

2 BR / 1 BA / Sleeps 4

1 / 17

$110

Book

75651 Overseas Hwy Islamorada Fla Keys Oceanfront

Matecumbe Key condo
2 BR / 1 BA / Sleeps 4 | Quick view

Details

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

PreviousNext property

$63

2 BR / 2 BA / Sleeps 4

1 / 15

$63

Inquire

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

PreviousNext property

$107

2 BR / 2 BA / Sleeps 4

1 / 23

$107

Inquire

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

PreviousNext property

$97

2 BR / 2 BA / Sleeps 6

1 / 26

$97

Inquire

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

PreviousNext property

$100

2 BR / 2 BA / Sleeps 4

2 Reviews

$100

Inquire

157 Ojibway Ave - 28 NIGHT MINIMUM

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

Details

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 …
  • 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

(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...

PreviousNext property

$147

2 BR / 2 BA / Sleeps 4

1 / 17

$147

Inquire

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

PreviousNext property

$250

2 BR / 2 BA / Sleeps 4

1 / 20

$250

Book

Oceanfrontparadise: 209

Islamorada condo
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

PreviousNext property

$67

2 BR / 2 BA / Sleeps 6

1 / 16

$67

Inquire

BOATER'S DELIGHT

Islamorada house
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

PreviousNext property

$208

2 BR / 2 BA / Sleeps 4

2 Reviews

$208

Inquire

75130 Overseas Highway

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

Details

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.

PreviousNext property

$117

2 BR / 3 BA / Sleeps 4

2 Reviews

$117

Inquire

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

Matecumbe Key house
2 BR / 3 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
  • Suitable for children
  • 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.

PreviousNext property

$77

2 BR / 2 BA / Sleeps 4

1 / 14

$77

Inquire

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

PreviousNext property

$300

2 BR / 3 BA / Sleeps 5

22 Reviews

$300

Book

Luxurious Anglers Reef with Boat Slip, Pool, Ocean

Islamorada house
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 …

PreviousNext property

$100

2 BR / 2 BA / Sleeps 4

2 Reviews

$100

Inquire

122 Leoni Dr - 28 night Minimum!!!

Islamorada house
2 BR / 2 BA / Sleeps 4 | 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
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • 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.

PreviousNext property

$250

2 BR / 2 BA / Sleeps 4

1 Reviews

$250

Book

Oceanfrontparadise: 509

Islamorada condo
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!!

PreviousNext property

$107

2 BR / 2 BA / Sleeps 6

11 Reviews

$107

Inquire

Islamorada Tropical Escape! Clean, Affordable & Li

Islamorada condo
2 BR / 2 BA / Sleeps 6 | Quick view
“ Excellent ” 11 Reviews

Details

Reviews

(11)

Escape from the world in this beautiful island paradise.Plenty of room to spread out in a two bedroom condo. Relax by the heated pool overlooking the turqoise bay; fish from the dock, snorkel in the protected cove. Kids can play in the game room or playground. Enjoy the clear, turquoise waters, breathtaking views, …
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(11)

Great vacation!

Left on Jan 17, 2012 for a stay in January 2012

The condo was very convienient, well equipped, comfortable and clean. With a four year old and a five month old, we had plenty of room, pack and play available, and some Disney/Sprout for the rainy afternoon was great! Had lots to do in the area and had a great time!

PreviousNext property

$3,000

2 BR / 2 BA / Sleeps 4

3 Reviews

$3,000

Inquire

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

Islamorada condo
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, …

PreviousNext property

$258

2 BR / 3 BA / Sleeps 6

3 Reviews

$258

Book

Islamorada Luxury Waterfront Condo with Boat Slip

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

Details

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 …

PreviousNext property

$185

2 BR / 2 BA / Sleeps 6

4 Reviews

$185

Inquire

Islamorada 2-bedroom Condo

Islamorada condo
2 BR / 2 BA / Sleeps 6 | Quick view
“ Very Good ” 4 Reviews

Details

Reviews

(4)

If you’ve been to Islamorada you know it as the sportfishing capital of the world, a place where you’ll find every water-related activity imaginable, with fine restaurants to crab shacks serving local fare, and plenty of nightlife for both the young and young at heart. If you’ve never been here, a tropical …
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Housekeeping Optional
  • Washing Machine
  • Suitable for children
  • Suitable for the elderly
  • Wheelchair accessible

Details

Reviews

(4)

Fantastic Views

Left on Jun 06, 2012 for a stay in February 2011

This 6th floor unit has all you need for a relaxing vacation. Close proximity to local attractions and fantastic Seafood Restaurants. The Hospital is one mile from the condo and has an excellent rehab and emergency. The complex has a private heated poool, work out room and sauna. The grounds are cleaned every morning and the manager responds to needs promptly. We will again stay here in …

PreviousNext property

$500

2 BR / 2 BA / Sleeps 6

2 Reviews

$500

Book

Islamorada Waterfront Paradise 2

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

Details

Reviews

(2)

**We do not use the optional calendar feature on this listing. ** 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, please contact me again! Email me for additional pictures of this wonderful hideaway. EVERY RENTER IS…
  • Waterfront
  • Ocean or water views
  • Wireless Internet
  • Washing Machine
  • Clothes Dryer
  • Suitable for children

Details

Reviews

(2)

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.

PreviousNext property

$397

2 BR / 3 BA / Sleeps 5

1 / 14

$397

Book

Islamorada getaway home with private boat dock.

Islamorada house
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

PreviousNext property

$279

2 BR / 3 BA / Sleeps 6

1 / 24

$279

Book

LUXURY KEYS HOME IN PARADISE-106 ANGLERS REEF

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

Details

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

PreviousNext property

$143

2 BR / 4 BA / Sleeps 4

1 / 9

$143

Book

Oceanview Islamorada Florida Keys

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

Details

This oceanfront condo in Islamorada Florida (Keys) is located at mile marker 90. It is the best ocean view from everyroom and is on the 4th floor. IT IS A ONE WEEK MINIMUM AND 4 PERSON MAXIMUM BY LICENSE. ..It has all tiled floors, newly painted, new AC, and has all the conveniences of home. There is a full kitchen…
  • Wireless Internet
  • A/C or climate control
  • Central heating
  • Balcony or terrace
  • Parking
  • Suitable for children
  • Suitable for the elderly - elevator access
  • Wheelchair accessible

PreviousNext property

$250

2 BR / 3 BA / Sleeps 6

1 / 7

$250

Book

Angler's Reef Coastal Conch Style Vacation Home

Islamorada cottage
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

PreviousNext property

$158

2 BR / 2 BA / Sleeps 6

1 Reviews

$158

Inquire

FYC -updated condo - excellent location -Marina

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

Details

Reviews

(1)

This magnificent two bedroom, two bath Condo, sleeps six comfortably. Newly decorated & tastefully furnished with wood floors throughout. Fully-equipped kitchen with new appliances. Flat Screen TV with Digital sound, DVD, stereo and CD player. WIFI included !!! Outside patio and laundry just steps away.. We have …
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Suitable for children
  • Suitable for the elderly

Details

Reviews

(1)

Beautiful, comfortable condo

Left on Jan 06, 2014 for a stay in December 2013

I traveled with my partner and another couple. We enjoyed the comfortable roomy accomodations. Loved the convenience of cooking meals. The grounds are beautiful. We enjoyed the pool that is newly refreshed. Easy access to the beach area to watch New Year's fireworks was great. The owner was available by phone to answer any questions we had. We plan on renting again.

PreviousNext property

$155

2 BR / 2 BA / Sleeps 4

1 / 9

$155

Book

Islamorada, Florida Keys (Beacon Reef MM87)

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

Details

Provisionally not available February through April, 2016. I will notify all who inquire if it becomes available. Available: September/October: $4600 November/December/January: $4900 single month, two or more months $4800 KINDLY NOTE: MONTHLY RENTAL. To maintain the beauty of Beacon Reef, rental contracts …
  • Waterfront
  • Ocean or water views
  • Hot Tub/Jacuzzi
  • Housekeeping Optional
  • Washing Machine
  • Pet friendly - ask
  • Suitable for children
  • Suitable for the elderly - elevator access
  • Wheelchair accessible - ask
1 2
page 1 of 2
Load more