Showing

PreviousNext property

$99

3 BR / 2 BA / Sleeps 8

7 Reviews

$99

Inquire

Family Friendly Executive Bay**Discounts Available**

3 BR / 2 BA / Sleeps 8 | Quick view
“ Excellent ” 7 Reviews

Details

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!

PreviousNext property

$99

2 BR / 2 BA / Sleeps 8

1 Reviews

$99

Inquire

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!

PreviousNext property

$110

2 BR / 1 BA / Sleeps 4

75651 Overseas Hwy Islamorada Fla Keys Oceanfront - Islamorada vacation rentals
1 / 17

$110

Book

75651 Overseas Hwy Islamorada Fla Keys Oceanfront

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

$215

3 BR / 2 BA / Sleeps 7

2 Reviews

$215

Inquire

Gorgeous Keys Water Front Home with Private Dock and Ramp

3 BR / 2 BA / Sleeps 7 | Quick view
“ Excellent ” 2 Reviews

Details

Reviews

(2)

Water Front home, located Oceanside in Lower Matecumbe key, Islamorada mile marker 73, (The Sport Fishing Capital of the World). 40' dock and 12’ wide ramp, so bring your own boat and enjoy the sun!! Easy canal access to the ocean. There is covered fish clean area. Minutes away from Anne's Beach with it's white …
  • Ocean or water views
  • Wireless Internet
  • Washing Machine
  • Clothes Dryer
  • A/C or climate control
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(2)

Great Getaway!

Left on Dec 09, 2014 for a stay in June 2014

This property was great! It was nicely stocked, very comfortable beds. I loved being on the water! Excellent place to stay! I will return again next summer.

PreviousNext property

$500

4 BR / 3 BA / Sleeps 8

9 Reviews

$500

Book

Private Beachfront Paradise

4 BR / 3 BA / Sleeps 8 | Quick view
“ Excellent ” 9 Reviews

Details

Reviews

(9)

Beautiful two story home ......four bedroom three baths.....on your private white sandy Beachfront property with large pool facing the ocean. First floor is independent with a very large one bedroom, bar with wine cooler full bath, living, dinning and new kitchen. The covered patio is huge at 60X15. The second floor…
  • Waterfront
  • Ocean or water views
  • Hot Tub/Jacuzzi
  • Sauna
  • Internet Access
  • Pet friendly - ask
  • Suitable for children
  • Suitable for the elderly
  • Wheelchair accessible

Details

Reviews

(9)

Great House and Great Property Owner

Left on Dec 06, 2013 for a stay in November 2013

My family and I had the pleasure of staying at this home during Thanksgiving week. Not only did the house beat our expectations, but the communication with the owner was also fantastic. She was so helpful with every inquiry we had and went well above what we expected to make sure our time in Islamorada was as well as it could be.

The house itself was extremely clean, beautiful and very …

PreviousNext property

$149

2 BR / 2 BA / Sleeps 4

Moon Bay Condo A-206 - Islamorada vacation rentals
1 / 1

$149

Inquire

Moon Bay Condo A-206

2 BR / 2 BA / Sleeps 4 | Quick view

Details

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

PreviousNext property

$77

2 BR / 2 BA / Sleeps 4

1 / 21

$77

Inquire

Executive Bay Club A-1

2 BR / 2 BA / Sleeps 4 | Quick view

Details

N/A
  • Shared outdoor pool (unheated)
  • A/C or climate control
  • Dishwasher
  • Microwave
  • Toaster
  • 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

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 …
  • 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...

PreviousNext property

$258

2 BR / 3 BA / Sleeps 6

3 Reviews

$258

Book

Islamorada Luxury Waterfront Condo with Boat Slip

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

$83

2 BR / 0 BA / Sleeps 4

1 / 19

$83

Inquire

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

PreviousNext property

$190

2 BR / 3 BA / Sleeps 4

1 Reviews

$190

Inquire

Futura Townhome 731

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

Details

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 …

PreviousNext property

$214

2 BR / 3 BA / Sleeps 6

1 / 24

$214

Book

LUXURY KEYS HOME IN PARADISE-106 ANGLERS REEF

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

$350

3 BR / 3 BA / Sleeps 8

2 Reviews

$350

Inquire

Bay Harbour Waterfront Condo

3 BR / 3 BA / Sleeps 8 | Quick view
“ Excellent ” 2 Reviews

Details

Reviews

(2)

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

(2)

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 …

PreviousNext property

$100

2 BR / 2 BA / Sleeps 6

2 Reviews

$100

Inquire

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.

PreviousNext property

$107

2 BR / 0 BA / Sleeps 4

1 / 20

$107

Inquire

114 Plantation Ave

2 BR / Sleeps 4 | Quick view

Details

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

PreviousNext property

$217

4 BR / 4 BA / Sleeps 9

1 / 26

$217

Inquire

152 Valencia Drive - 28 Night Minimum

4 BR / 4 BA / Sleeps 9 | Quick view

Details

This is a beautiful Venetian Shores home... It truly is a must see! The interior is clean and nicely decorated. The large porch on the back allows you to see the famous Florida Keys sunsets from your own home! Located a few houses down from Snake Creek, you'll have quick ocean and bay access. Deep water dockage, tiki …
  • Waterfront
  • Ocean or water views
  • A/C or climate control
  • Grill
  • Dishwasher
  • Pet friendly - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

PreviousNext property

$208

2 BR / 2 BA / Sleeps 4

2 Reviews

$208

Inquire

75130 Overseas Highway

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
  • 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.

PreviousNext property

$117

2 BR / 2 BA / Sleeps 4

2 Reviews

$117

Inquire

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.

PreviousNext property

$250

2 BR / 3 BA / Sleeps 6

1 / 7

$250

Book

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

PreviousNext property

$150

3 BR / 1 BA / Sleeps 1

4 Reviews

$150

Inquire

200 Plantation Shores Drive

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

Details

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 - ask
  • 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 …

PreviousNext property

$100

2 BR / 3 BA / Sleeps 4

1 / 1

$100

Inquire

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

PreviousNext property

$117

3 BR / 2 BA / Sleeps 6

1 / 1

$117

Inquire

258 Mohawk St - 28 Night Minimum!!!!!!!

3 BR / 2 BA / Sleeps 6 | Quick view

Details

Looking for an extended stay in the Upper Keys that won't bust the bank? If so, you need not search any farther than this cozy, modern home on Islamorada's Plantation Key. Located in the popular Indian Waterways neighborhood, this three-bedroom/two-bath house is a great value at just $3,500 per month. The residence …
  • Waterfront
  • Internet Access
  • A/C or climate control
  • Porch
  • Grill
  • Pet friendly - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

PreviousNext property

$643

4 BR / 3 BA / Sleeps 8

1 / 1

$643

Inquire

50 Schooner Bay Rd - Aguazul

4 BR / 3 BA / Sleeps 8 | Quick view

Details

How about sipping coffee and watching the sun come up as you fish off the end of your very own 300 foot pier? Sounds good, right? Well, that's just one reason to stage your upcoming vacation at this lovely, hacienda-style home on a quaint and private oceanfront street in Islamorada. CLICK HERE to view photos on a …
  • 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

PreviousNext property

$129

2 BR / 2 BA / Sleeps 4

1 Reviews

$129

Inquire

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 …

PreviousNext property

$286

3 BR / 3 BA / Sleeps 6

4 Reviews

$286

Inquire

130 Bayview Isle Dr

3 BR / 3 BA / Sleeps 6 | Quick view
“ Excellent ” 4 Reviews

Details

Reviews

(4)

Great neighborhood located on Snake Creek. 2 bedroom/2 bath upstairs with a bunkroom and bath downstairs. An outdoor hot tub and sundeck complement the excellent deep water dockage and easy bay or ocean access. There is room for about a 36 foot boat or less. Mile Marker 86, Bayside. VACATION RENTAL LICENSE: VR-069 …
  • Waterfront
  • Ocean or water views
  • Hot Tub/Jacuzzi
  • Internet Access
  • Washing Machine
  • Pet friendly - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(4)

I loved this place!

Left on Nov 02, 2010 for a stay in October 2010

Both the home and the location in Islamorada were perfect! I spent a week at 130 Bayview Isle and it was exactly what I hoped it to be. It was incredibly quiet and felt like home. If the home is for rent next year, I will absolutely rent it again. Awesome place!

PreviousNext property

$140

1 BR / 1 BA / Sleeps 4

1 / 11

$140

Book

Seagulls Condominiums, Enjoy the Florida Keys!

1 BR / 1 BA / Sleeps 4 | Quick view

Details

Come enjoy our home away from home. Perfect for a couples retreat. Enjoy your own fully equipped condo. Sip coffee on the balcony and watch the beautiful sunrise. Read one of our Jimmy Buffett books and dream of running away for a life on sea. Once this salt air gets in you you will never want to go home. Please…
  • Waterfront
  • Sauna
  • A/C or climate control
  • Central heating
  • Balcony or terrace

PreviousNext property

$380

3 BR / 3 BA / Sleeps 6

3 Reviews

$380

Inquire

75333 Overseas Hwy

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

Details

Reviews

(3)

Exceptional oceanfront home equipped with a sandy beach and forever views! Exquisite design and rich appointments compliment this oceanfront home in Lower Matecumbe, (mile marker 75, South Islamorada). You will enjoy private terraces from each bedroom overlooking picturesque sunrises and panoramic views of the open …
  • Internet Access
  • Microwave
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(3)

Heaven on Earth

Left on Jan 30, 2013 for a stay in December 2012

My husband and I rented this home for the week of Christmas. We also invited our respective parents. This is the most peaceful home in Islamorada. Centrally located to the upper and lower keys.

There home is well appointed with everything you need except for the groceries and tolietries that you will need. All appliances work well and the home is in excellent condition.

Freewheeler realty…

PreviousNext property

$236

3 BR / 2 BA / Sleeps 6

2 Reviews

$236

Inquire

155 Azalea Street

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

Details

Reviews

(2)

Plantation Key canal home. Nice new home with screened porch and pool table! Delightfully furnished for a comfortable stay. Excellent outdoor entertaining space, great for soaking in the hot tub, gazing at fish in the canal, having cocktails under the Chickee, or for the kids to run around and play. Great dockage with…
  • Waterfront
  • Hot Tub/Jacuzzi
  • Internet Access
  • A/C or climate control
  • Porch
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(2)

Loved the place and location!!

Left on Aug 11, 2013 for a stay in July 2013

We completely enjoyed our stay. Plenty of room for 6 ppl to sleep. Nice sized kitchen and dining area. We stayed with two young children and they loved it. Great location for both gulf access and on land access to grocery, dining and all. We can't wait to go back.

PreviousNext property

$150

3 BR / 2 BA / Sleeps 6

1 / 1

$150

Inquire

127 Tequesta - 28 Night Minimum

3 BR / 2 BA / Sleeps 6 | Quick view

Details

N/A
  • 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

PreviousNext property

$190

2 BR / 3 BA / Sleeps 4

2 Reviews

$190

Inquire

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.

PreviousNext property

$600

4 BR / 0 BA / Sleeps 8

1 Reviews

$600

Inquire

76190 Overseas Highway - Casa Dorado

4 BR / Sleeps 8 | Quick view
“ Very Good ” 1 Reviews

Details

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 - ask
  • 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.

PreviousNext property

$329

3 BR / 3 BA / Sleeps 6

6 Reviews

$329

Inquire

138 Bayview Isle

3 BR / 3 BA / Sleeps 6 | Quick view
“ Very Good ” 6 Reviews

Details

Reviews

(6)

Modern canal home with views of Snake Creek. The property is completely fenced in. Third level master suite with private master balcony. Well furnished with all the extras. Easy ocean or bay access and dockage up to 50 feet. Open floor plan with regulation pool table and screened in porch. This home's entertainment …
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Pet friendly
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(6)

Perfect location

Left on May 27, 2011 for a stay in May 2011

Other then having to Clean-up the bug's it was great.

PreviousNext property

$243

3 BR / 2 BA / Sleeps 6

2 Reviews

$243

Book

Islamorada PARADISE FOUND 3 bedroom/2 bath

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

Details

Reviews

(2)

BEAUTIFUL NEWLY REMODELED 3 BEDROOM, 2 FULL BATHROOM VACATION RENTAL IS LOCATED IN THE EXECUTIVE BAY CLUB. BREATHTAKING BAY VIEW FROM YOUR OWN BACK YARD! UNIT HAS BRAND NEW CUTOME KITCHEN CABINETS WITH GRANITE COUNTER TOPS. ALL STAINLESS STEEL APPLIANCES, DOUBLE DOOR REFRIGERATOR, DISHWASHER, GLASS STOVE COUNTER …
  • Ocean or water views
  • Wireless Internet
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • Suitable for children

Details

Reviews

(2)

Beautiful, relaxing and comfortable!

Left on Feb 23, 2015 for a stay in December 2014

When we first contacted the owner regarding the rental, she responded immediately and was very nice and helpful. The unit was impeccable when we arrived and the location in the complex was excellent! We were right in front of the pool, and the beach area was very close. One of my favorite things to do during our stay was to sit out in the terrace of the unit and relax while looking at the ocean. …

PreviousNext property

$500

4 BR / 3 BA / Sleeps 8

4 Reviews

$500

Inquire

101 Palo de Oro

4 BR / 3 BA / Sleeps 8 | Quick view
“ Excellent ” 4 Reviews

Details

Reviews

(4)

Great pool home in desirable Venetian Shores. This 4 bedroom/3 bath home is roomy and has great porches overlooking the wide, clean canal. Lovely master suite on the top floor with it's own balcony. Comfortably furnished pool home with 90 feet of excellent deep water dockage on a wide canal leading directly to Snake …
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(4)

Wonderful

Left on Jul 15, 2010 for a stay in June 2010

We have stayed at this house 2 years in a row. The house is comfortable and a great location. The area has wonderful restaurants and fishing is great. We plan on staying next year for 2 weeks.

PreviousNext property

$429

5 BR / 4 BA / Sleeps 10

8 Reviews

$429

Inquire

140 Atlantic Lane

5 BR / 4 BA / Sleeps 10 | Quick view
“ Excellent ” 8 Reviews

Details

Reviews

(8)

Amazing ocean views can be enjoyed from this beautiful stilt home with seperate mother-in-law cottage. You'll fall in love with this little piece of Heaven. Enjoy fishing, diving, and catching lobster with all the comforts of home. Best ocean views in town! Interior photos are available! Mile Marker 76.5, Oceanside. …
  • Ocean or water views
  • A/C or climate control
  • Grill
  • Dishwasher
  • Microwave
  • Pet friendly
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(8)

Summer vacation 2010

Left on Sep 13, 2010 for a stay in August 2010

Overall nice place, kitchen items were not very organized, and place could use a deep cleaning

PreviousNext property

$100

2 BR / 1 BA / Sleeps 1

1 / 1

$100

Inquire

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

2 BR / 1 BA / Sleeps 1 | 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 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

PreviousNext property

$200

2 BR / 1 BA / Sleeps 4

2 Reviews

$200

Inquire

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…

PreviousNext property

$286

3 BR / 2 BA / Sleeps 7

6 Reviews

$286

Inquire

76300 Overseas Highway

3 BR / 2 BA / Sleeps 7 | Quick view
“ Excellent ” 6 Reviews

Details

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 - ask
  • 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 …

PreviousNext property

$175

4 BR / 4 BA / Sleeps 8

1 / 36

$175

Inquire

164 Plantation Shores Drive - 28 NIGHT MINIMUM

4 BR / 4 BA / Sleeps 8 | Quick view

Details

This is a very spacious and very well-maintained 4 bedroom, 3 bathroom home toward the mouth of the canal on a quiet street in Plantation Key (Tavernier). You and your group will enjoy stunning views from the main level, master suite, & rooftop sundeck. There is approximately 20ft concrete dockage. The home sits on a …
  • Ocean or water views
  • Internet Access
  • A/C or climate control
  • Grill
  • Dishwasher
  • Pet friendly - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

PreviousNext property

$115

1 BR / 1 BA / Sleeps 3

2 Reviews

$115

Book

Serenity Waterfront-Dock, View, Tiki Hut, spa/hot

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

Details

Reviews

(2)

Located in beautiful Plantation Key, the first Island of Islamorada. An area of all waterfront homes Wifi, boat dock, trailer parking, and all amenities are included also, Lovely Tiki Hut overlooking the water. Plus a huge covered entertainment area complete with dining areas, settee and gas BBQ. Dockage for …
  • Waterfront
  • Hot Tub/Jacuzzi
  • Internet Access
  • Outdoor Dining Area
  • A/C or climate control
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children
  • Suitable for the elderly
  • Wheelchair accessible

Details

Reviews

(2)

Great owners-average accommodations

Left on Apr 25, 2014 for a stay in April 2014

You've got to like Key Islamarada because it's strictly for boaters and this place has a slip for yours. We booked it because it was one of the few rentals with handicapped access. You will spend most of your time in the covered recreation area, which is a large shaded area and always had a nice breeze while we were there. Some things in the unit could use owner's attention, such as the glued …

PreviousNext property

$643

4 BR / 3 BA / Sleeps 8

1 Reviews

$643

Inquire

Aguazul

4 BR / 3 BA / Sleeps 8 | Quick view
“ Very Good ” 1 Reviews

Details

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.

PreviousNext property

$329

3 BR / 3 BA / Sleeps 6

6 Reviews

$329

Inquire

137 Leserra Lane

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

Details

Reviews

(6)

Beautiful designer appointed Oceanside canal home located at the Mile Marker 76.5 in Lower Matecumbe (South part of Islamorada). This home is the second one in on a point and has a great ocean view. Fully loaded kitchen with dishwasher, microwave, coffee maker, toaster, and blender. There are two flat panel TV's in …
  • 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

(6)

We had a very relaxing and fun-filled vacation

Left on Jul 15, 2010 for a stay in June 2010

The house is in a great location in Lower Matecumbe. Robbie's restaurant is only one mile away which we went to three times (twice by car, once by boat). We also went to anne's Beach twice with our dogs. The house is great for pets, the yard is fenced in and there is plenty of room for the dogs to run around.

PreviousNext property

$929

4 BR / 4 BA / Sleeps 10

13 Reviews

$929

Inquire

75731 Overseas Highway

4 BR / 4 BA / Sleeps 10 | Quick view
“ Excellent ” 13 Reviews

Details

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 - ask
  • 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.

PreviousNext property

$215

2 BR / 2 BA / Sleeps 4

16 Reviews

$215

Inquire

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".

PreviousNext property

$397

2 BR / 3 BA / Sleeps 5

1 / 14

$397

Book

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

PreviousNext property

$179

1 BR / 1 BA / Sleeps 2

1 / 4

$179

Book

CASA THORN

1 BR / 1 BA / Sleeps 2 | Quick view

Details

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
  • Suitable for children

PreviousNext property

$243

2 BR / 3 BA / Sleeps 6

1 / 25

$243

Book

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

PreviousNext property

$215

3 BR / 2 BA / Sleeps 6

15 Reviews

$215

Inquire

Windy Cove Townhome #1

3 BR / 2 BA / Sleeps 6 | Quick view
“ Excellent ” 15 Reviews

Details

Reviews

(15)

Relax in this great townhouse style condo, which overlooks the sparkling Atlantic Ocean. This condo features 3 bedrooms and 2 bathrooms, a balcony off the living room, a private balcony off the master bedroom, and the quaintness of only 4 other units in the complex. Enjoy a drink by the pool, soak up the sun on the …
  • Ocean or water views
  • Shared outdoor pool (unheated)
  • A/C or climate control
  • Television
  • Telephone
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(15)

Absolutely awesome

Left on Jun 21, 2010 for a stay in June 2010

Windy Cove was a wonderful place.
The view was amazing. The location was perfect. We will be staying here again!

PreviousNext property

$117

3 BR / 3 BA / Sleeps 6

1 / 1

$117

Inquire

157 Caloosa St - 28 Night Minimum

3 BR / 3 BA / Sleeps 6 | Quick view

Details

This is a beautifully, modern home with two separate quarters. The main living area is located on the ground level with 2 bedrooms & 1 bathroom. It is equipped with full kitchen (blender & toaster included), DirectV, wireless internet, Netflix, and washer & dryer. Click here to view this photo slideshow on a mobile …
  • Ocean or water views
  • A/C or climate control
  • Grill
  • Dishwasher
  • Microwave
  • Pet friendly - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

PreviousNext property

$358

4 BR / 3 BA / Sleeps 8

4 Reviews

$358

Inquire

76004 Overseas Highway

4 BR / 3 BA / Sleeps 8 | Quick view
“ Excellent ” 4 Reviews

Details

Reviews

(4)

Enjoy spectacular sunsets while drinking margaritas on the observation deck of this stunning home nestled back behind swaying palm trees. Large sandy beach and great dock. Interior photos available! Mile Marker 76, Bayside. Home has 2 bedrooms & 2 bathrooms upstairs, and a separate 2 bedroom, 2 bathroom apartment …
  • A/C or climate control
  • Garage
  • Grill
  • Dishwasher
  • Microwave
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(4)

A Week in a Tropical Paradise.

Left on Aug 03, 2010 for a stay in July 2010

We had a fantastic time. Incredible home on the water with boat dock. Plenty of room and privacy. Accommodations were five star. We highly recommend it.

1 23
page 1 of 3
Load more