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$500

4 BR / 3 BA / Sleeps 8

9 Reviews

$500

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Private Beachfront Paradise

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

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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 …

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$350

3 BR / 3 BA / Sleeps 8

2 Reviews

$350

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Bay Harbour Waterfront Condo

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

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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 …

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$110

1 BR / 1 BA / Sleeps 3

3 Reviews

$110

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

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

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Reviews

(3)

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

(3)

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 …

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$229

1 BR / 1 BA / Sleeps 2

Casa Thorn Moroccan Room - Islamorada vacation rentals
1 / 4

$229

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Casa Thorn Moroccan Room

1 BR / 1 BA / Sleeps 2 | Quick view

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The Moroccan room is a fabulous honeymoon destination with king size canopy bed. Room features a/c, coffee maker, heat, microwave, refrigerator, TV, WiFi. Enormous bathroom with sunken tub and terrycloth robes to lounge in includes full breakfast. LOCATED IN A QUIET, SECLUDED, TROPICAL SETTING YET MINUTES TO …
  • Shared outdoor pool (unheated)
  • Hot Tub/Jacuzzi
  • Internet Access
  • A/C or climate control
  • Central heating
  • Pet friendly
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$1,279

5 BR / 7 BA / Sleeps 10

Kara-Pan - Islamorada vacation rentals
1 / 13

$1,279

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Kara-Pan

5 BR / 7 BA / Sleeps 10 | Quick view

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

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$236

3 BR / 2 BA / Sleeps 6

2 Reviews

$236

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155 Azalea Street

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

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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.

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$286

3 BR / 3 BA / Sleeps 6

4 Reviews

$286

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130 Bayview Isle Dr

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

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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!

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$400

3 BR / 3 BA / Sleeps 5

6 Reviews

$400

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You will never want to leave

3 BR / 3 BA / Sleeps 5 | Quick view
“ Excellent ” 6 Reviews

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Reviews

(6)

3 bedroom, 2.5 bath home at the end of a quiet private road in Islamorada. Queen bed in the master with a fantastic view of the ocean from your pillow. Two queen beds in the second bedroom with en suite bath The third bedroom is used as an office. From the moment you open the front door you have a view of the ocean …
  • Waterfront
  • Ocean or water views
  • Hot Tub/Jacuzzi
  • Internet Access
  • Washing Machine
  • Pet friendly - ask
  • Suitable for the elderly - ask

Details

Reviews

(6)

Really Super great place. Have stayed here twice and this place

Left on Dec 09, 2013 for a stay in December 2013

We have stayed here twice. Could not ask for a more peaceful and scenic view. Super great place and all of the things that you need. Very clean and very nice. Beautiful inside and out and the owners as nice as the place. Fantastic restaurants within a few miles north or south. One of the nicest little Bass Pro Shops around just a few miles up the road. The sunsets are amazing the mornings are …

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$715

4 BR / 3 BA / Sleeps 10

1 / 38

$715

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82754 Overseas Highway

4 BR / 3 BA / Sleeps 10 | Quick view

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OSPREY BAY VILLA! Wonderful bayfront home in the heart of Islamorada in the fabulous Florida Keys for rent by the week or monthly. Offering 5 bedrooms and 3 full baths on 2 living levels overlooking the Florida Bay with its incredible sunset views. Sleeps 10 people comfortably. Spacious fully equiped kitchen with the …
  • Waterfront
  • Ocean or water views
  • Hot Tub/Jacuzzi
  • Internet Access
  • Fireplace
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$663

5 BR / 6 BA / Sleeps 10

1 / 15

$663

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Pineapple Plantation (28 Day Minimum)

5 BR / 6 BA / Sleeps 10 | Quick view

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

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$500

4 BR / 4 BA / Sleeps 10

3 Reviews

$500

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SANCTUARY IN PARADISE

4 BR / 4 BA / Sleeps 10 | Quick view
“ Excellent ” 3 Reviews

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Reviews

(3)

WWW.SCHOONERHAMMOCK.COM This unique property offers : -master suite -apartment -cottage -3 full kitchens On Atlantic Ocean. Simple, sweet, and serene sanctuary. Please contact Andy Cancela 828 808 1693 We love The Lord and look forward to sharing our home with you.
  • Waterfront
  • Ocean or water views
  • Hot Tub/Jacuzzi
  • Internet Access
  • Housekeeping Optional
  • Pet friendly
  • Suitable for children
  • Suitable for the elderly

Details

Reviews

(3)

Amazing Experience and even more Amazing Hosts

Left on Aug 20, 2014 for a stay in May 2014

This was the best family vacation! The home was beautiful and comfortable. Definitely something you would call home away from home.The property was perfect for each person in our family to find bliss. Just minutes away from grocery stores, bate shops and restaurants. Fishing (plenty of mangroves and tarpon) and snorkeling right off the dock, laziness in the hammocks, a relaxing hot tub and plenty…

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$858

4 BR / 4 BA / Sleeps 8

1 / 14

$858

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The Gardens @ Schooner Bay Estate

4 BR / 4 BA / Sleeps 8 | Quick view

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

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$500

4 BR / 3 BA / Sleeps 10

1 / 14

$500

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Beach House

4 BR / 3 BA / Sleeps 10 | Quick view

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

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$167

2 BR / 2 BA / Sleeps 4

1 / 10

$167

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One of the best views in Islamorada

2 BR / 2 BA / Sleeps 4 | Quick view

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Imagine waking to the beauty of a sunrise brimming over the aqua seas. Linger in your master suite and watch the ocean shift through a prism of aqua, blues and emerald greens. Gentle breezes waft through this two bedroom, two bath condo with comfortable appointments and an elegant sea glass tiled kitchen. …
  • Waterfront
  • Ocean or water views
  • Hot Tub/Jacuzzi
  • Sauna
  • Internet Access
  • Suitable for children - ask
  • Suitable for the elderly
  • Wheelchair accessible - ask

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$428

3 BR / 3 BA / Sleeps 6

1 / 21

$428

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Elegant Bay Harbour Condo with 50 Foot Boat Slip

3 BR / 3 BA / Sleeps 6 | Quick view

Details

Lower Matecumbe Key condo description Welcome to paradise! This beautiful three bedroom, two and a half bath end unit condominium sleeps 6 people. Master bedroom has a king bed with direct access to the water front balcony. Second bedroom has a queen bed and the third has two twin beds. Brand new flat screen HD TVs in…
  • Waterfront
  • Ocean or water views
  • Hot Tub/Jacuzzi
  • Internet Access
  • Washing Machine
  • Suitable for children
  • Suitable for the elderly - elevator access
  • Wheelchair accessible

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$155

2 BR / 2 BA / Sleeps 4

1 / 9

$155

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Islamorada, Florida Keys (Beacon Reef MM87)

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

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$429

4 BR / 3 BA / Sleeps 10

2 Reviews

$429

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The Perfect Getaway

4 BR / 3 BA / Sleeps 10 | Quick view
“ Very Good ” 2 Reviews

Details

Reviews

(2)

This pretty, four-bedroom, three-bath house is conveniently located in the heart of Islamorada, the fishing capital of the world. Situated in a pretty upscale neighborhood of all waterfront homes, the house is equipped with all the comforts of home. It is additional tidy and modernly furnished. Upstairs there are …
  • Hot Tub/Jacuzzi
  • Internet Access
  • Washing Machine
  • A/C or climate control
  • Patio
  • Suitable for children
  • Suitable for the elderly - ask

Details

Reviews

(2)

House had everything we needed for a Keys vacation!

Left on Jul 14, 2013 for a stay in July 2013

The Perfect Getaway is an appropriate name for this house; it had everything needed for a perfect vacation getaway in the Keys. The pool and hot tub were great to cool off from the afternoon sun. The dock was large enough to fit our kayak, wave runner and 21' boat. The house was clean and had all the amenities/accessories needed for a house stay.

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$300

2 BR / 2 BA / Sleeps 4

1 Reviews

$300

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Ocenfront condo with pool and Huge T dock

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

Details

Reviews

(1)

This remodeled 2 bedroom 2 bath condo is directly on the Atlantic Ocean with ground access via a spiral staircase. Stunning views from the Master bedroom and balcony. Wake up to the sunrise and enjoy your leisurely day on the boat, at the nearby sand bar, or lounge in the zero entry pool. There is even a work out …
  • Waterfront
  • Ocean or water views
  • Hot Tub/Jacuzzi
  • Internet Access
  • Housekeeping Optional
  • Suitable for children
  • Suitable for the elderly - elevator access
  • Wheelchair accessible

Details

Reviews

(1)

Clean, comfortable, and beautiful condo

Left on Jan 06, 2012 for a stay in December 2011

My husband and I stayed here for almost 2 weeks for our honeymoon/vacation over the Christmas holiday. We were nervous about renting something over the internet that we had never visited in person. We had been to Islamorada, but not this particular condo complex. We looked at many different vacation rentals online, and this one had all the things we wanted: budget friendly, private beach access, …


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