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1-50 of 77 Islamorada Rentals

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1 / 29

Islamorada Home
3 Bedrooms / 2 Bathrooms / Sleeps 6
Home / 3 Bedrooms / Sleeps 6

(5)“ Excellent ”5 Reviews

from

$415

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:6
Type:Home
Per night:$415 - $458
Per week:$2,900 - $3,200
Pets allowed:No
Internet:Yes

Location: Islamorada, Islamorada Area, Florida Keys, Florida, USA Accommodations: House, 3 Bedrooms, 2 Baths , Sleeps 6 122 Nautilus Drive, Islamorada, Florida Keys mile marker 74. 5 bay side, White Marlin Beach located 75 miles south of Miami and 75 miles North of...

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Villa Marlin

“ Excellent ”
March 27, 2015
We were looking for a quiet place to relax and snorkel. The villa is just as lovely as the pictures. Anything you would need is provided. The grounds are shady and comfortable and the location is quiet. We canoed in the canal and saw Manatee. We bicycled to the beach in the evening. We snorkeled all around Islamorada and out of Key largo, amazing corral and fish. The Villa owners were always available and helpful. We rent on trip advisor frequently and we can highly recommend Villa Marlin.
Stephanie Romm, Loveland, CO

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1 / 26

Islamorada Cottage
2 Bedrooms / 1 Bathroom / Sleeps 4
Cottage / 2 Bedrooms / Sleeps 4

from

$195

/ night

Email Owner
Bedrooms:2
Bathrooms:1
Sleeps:4
Type:Cottage
Per night:$195 - $350
Per month:$5,850 - $10,500
Pets allowed:No
Internet:Yes

CHARMING COTTAGE IN THE HEART OF ISLAMORADA, LOCATED IN MILE MARKER 87 IN THE HEART OF IT ALL, RIGHT ACROSS JUST 250 YARDS FROM "FOUNDERS PARK" WITH ONE OF THE MOST BEAUTIFUL BEACH IN THE KEYS, It's a 2 bedroom cottage very private corner house, with full kitchen including oven,...

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view of house from canal
1 / 21

Islamorada Home
2 Bedrooms / 2 Bathrooms / Sleeps 6
Home / 2 Bedrooms / Sleeps 6

(1)“ Excellent ”1 Review

from

$315

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:6
Type:Home
Per night:$315 - $372
Per week:$2,200 - $2,600
Pets allowed:Yes
Internet:Yes

Located on the peaceful, northern end of Islamorada, in the quite residential neighborhood of Venetian Shores. Just 75 miles from Miami Airport and 86 miles from Key West. Venetian Tropics boasts large rooms furnished in rattan and decorated with a tropical flair. Coconut palms,...

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Paradise in Islmorada

“ Excellent ”
July 6, 2010
Excellent location with a great view of the Canal. The Pool was the right size for our family and the Outside bar was Outstanding. The deck and dock were perfect for my 25' boat with ample room for my Grandson to fish for snapper. The Upstairs kitchen and living area with the high ceilings was fantastic. The downstairs bedroom was also great. The whole experience was truly enjoyable for my family.
BILL WHITE, STUART FLORIDA USA

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1 / 9

Islamorada Condo
2 Bedrooms / 2 Bathrooms / Sleeps 4
Condo / 2 Bedrooms / Sleeps 4

from

$136

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:4
Type:Condo
Per night:$136 - $186
Per week:$950 - $1,300
Pets allowed:No
Internet:Yes

Two oceanfront condominiums ranch style situated on floor 2 and 5 about 50 ft from the water . You can hear and see the fish break the water in the morning. There are a variety of large tropical birds to watch . We have a beautiful pool among lush tropical foliage on the ocean. We...

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Islamorada Florida Vacation Rentals - Home
1 / 20

Islamorada Home
4 Bedrooms / 3 Bathrooms / Sleeps 10
Home / 4 Bedrooms / Sleeps 10

Bedrooms:4
Bathrooms:3
Sleeps:10
Type:Home
No rental rates available - please contact the owner
 
Pets allowed:No
Internet:Yes

MINIMUM RENTAL: 28 NIGHTS (ONE MONTH) You'll love watching the fabulous sunsets over the tranquil waters in this semi- private lagoon setting. This is a three story single family home and offers two balconies overlooking the water and dock area. There's room to dock one 30' boat and...

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Islamorada Florida Vacation Rentals - Home
1 / 26

Islamorada Home
3 Bedrooms / 2 Bathrooms / Sleeps 6
Home / 3 Bedrooms / Sleeps 6

from

$140

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:6
Type:Home
Per night:$140 - $175
Per week:$980 - $1,225
Pets allowed:Yes
Internet:No

MINIMUM RENTAL: 1 MONTH BEAUTIFUL CANAL FRONT STILT HOME WITH HEATED POOL - For the guest who expects perfection this is it. This is a completely remodeled 3 bedroom/2 bath (2/1 up and 1/1 down) single family home - perfect for one couple or a smaller family. It is conveniently ...

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Sunset Deluxe
1 / 9

Islamorada Townhouse
2 Bedrooms / 2.5 Bathrooms / Sleeps 4
Townhouse / 2 Bedrooms / Sleeps 4

(4)“ Excellent ”4 Reviews

from

$158

/ night

Email Owner
Bedrooms:2
Bathrooms:2.5
Sleeps:4
Type:Townhouse
Per night:$158
Per week:$1,100
Pets allowed:Yes
Internet:Yes

Sunset view, tennis courts, heated pool, recently remodeled, fish from the dock, boat slip right in front of unit. quiet gated community, monthly $3250. 00 in season, $2450. 00 out of season This 2 bedroom townhome with built in bar is in a quiet, gated complex and has a...

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Best of islamorado

“ Excellent ”
October 6, 2014
We stayed at this Townhouse for the month of September. It was better than the pictures portrayed it. We enjoyed the view and the boat slip 20 ft from our front door. Very comfortable beds. Nice decor. We recommend this place for anyone enjoying the water. Also you can snorkel or swim in the newly finished heated pool. We hope to go again next year. Also 3 manatees entertained us almost everyday. One day 3 porpoises were jumping right in the middle of the bay. Many thanks David.
Betty Cameron, Daytona Beach, Florida

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1 / 9

Islamorada Condo
2 Bedrooms / 2 Bathrooms / Sleeps 6
Condo / 2 Bedrooms / Sleeps 6

(1)“ Excellent ”1 Review

from

$129

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:6
Type:Condo
Per night:$129 - $158
Per week:$900 - $1,100
Pets allowed:No
Internet:No

Enjoy the spacious ocean front beach condo . Two luxurious bedrooms and two baths . Luxurious master size bedroom offers a king size bed & trundle bed that comfortably sleeps 2 . Well appointed master size bath features double vanity and walk –in- closet & walk- in tile shower ....

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Wonderful!

“ Excellent ”
March 20, 2014
After searching for various hotels in the area in my price range (and determining that they were all pretty disgusting), I almost gave up my search until I stumbled upon this condo. The owner, Estelle, was incredibly easy to work with! The condo was absolutely awesome! Clean, well kept, lots of comforts of home. I loved the balcony where I started off each day basking in the sun. The pool area was very nice. I highly recommend this condo. I was tempted to keep this info to myself so that it's available for me next year, but it's too good to keep it a secret!
Nancy Ann Dalton, Sunnyvale, California, USA

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Relax and Enjoy
1 / 8

Islamorada Home
3 Bedrooms / 3 Bathrooms / Sleeps 8
Home / 3 Bedrooms / Sleeps 8

(14)“ Excellent ”14 Reviews

from

$358

/ night

Email Owner
Bedrooms:3
Bathrooms:3
Sleeps:8
Type:Home
Per night:$358 - $500
Per week:$2,500 - $3,500
Pets allowed:Yes
Internet:Yes

Oceanfront splendor on the Atlantic ocean. Has a 350' pier that can accomodate most any size boat. Just relax by the pool on those hot days or take a dip in the ocean. The pool is heated for the winter months. The house is extremely private. There is a wooden fence around ...

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satisfied.

“ Excellent ”
March 22, 2015
My husband and I went to Key West from Maine with our 2 daughters and their husbands, as a Xmas gift, so there were 6 of us, of varied ages. I did a lot of research to find the right part of town to stay in, and it paid off. This house was just right for us. I do believe that the camera that took the promo pix had some sort of lengthening lens on it - but the rooms were spacious and clean and the outdoor shower was GREAT. Not everything worked perfectly, but it was mostly very functional, and the few little annoyances (swollen door to the pool that wouldn't shut tight, for ex.), were tolerable enough that we didn't pursue calling for repairs. We were offered housekeeping services each day. Some days, if we were hanging around the place, we would just ask for towels and garbage emptying. If we were away, they also made the beds. We had an issue with the air conditioning not working at one point. I think that another renter was actually able to fix it, but I did leave a message with the rental agency and got a prompt reply the next morning that if there were further issues, to notify them immediately, and they would fix it within an hour. On the other hand, when we wanted to rent bikes (and we had been encouraged to just call the concierge service and they would do it for us), I didn't get a return call until the next day, well after we rented on our own. No problem, it was easy to do in Key West, on your own. The location was GREAT. Far enough from the craziness to feel relaxed, but within walking distance (or short taxi rides) to Duval and all the action. This is a good place for a group that may want to go off on their own at times or do things together at times - we had some fun BBQ's at home but also walked/taxi'ed to locations easily when we wanted to go out together. . . . .or separately as well. I would recommend the place, and would go back, if visiting Key West again. The pool was very warm. I was in it a LOT. The other renters (there are six rentals total, sharing the pool), were occasionally using the pool area, but not often. . . . .just enough to enjoy a little social interaction. Each rental was screened off from the pool enough to feel private, but still close to the pool. The place was well maintained, and secure and we had a great time overall.
Carol Thibodeau, South China, ME

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Islamorada Florida Vacation Rentals - Home
1 / 23

Islamorada Home
5 Bedrooms / 6.5 Bathrooms / Sleeps 12
Home / 5 Bedrooms / Sleeps 12

from

$484

/ night

Email Owner
Bedrooms:5
Bathrooms:6.5
Sleeps:12
Type:Home
Per night:$484 - $550
Per week:$3,384 - $3,850
Pets allowed:No
Internet:Yes

MINIMUM RENTAL 1 MONTH: 180 degree ocean views are yours from almost every room in this magnificent ocean front home. This home has over 5962 (not a typo) square feet of living area with 5 bedrooms, 6 and one half baths, and two full kitchens! This home comfortably sleeps 10 in...

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Islamorada Florida Vacation Rentals - Home
1 / 25

Islamorada Home
3 Bedrooms / 2 Bathrooms / Sleeps 4
Home / 3 Bedrooms / Sleeps 4

from

$140

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:4
Type:Home
Per night:$140 - $175
Per week:$980 - $1,225
Pets allowed:No
Internet:Yes

MINIMUM STAY 29 DAYS. BEAUTIFUL CANAL FRONT STILT HOME WITH HEATED POOL - For the guest who expects perfection this is it. This home was completely remodeled in 2013. There is 936 square feet of living area on the main level with 2 bedrooms, a full bath and an open living area. ...

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Islamorada Florida Vacation Rentals - Condo
1 / 12

Islamorada Condo
2 Bedrooms / 2 Bathrooms / Sleeps 4
Condo / 2 Bedrooms / Sleeps 4

from

$77

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:4
Type:Condo
Per night:$77 - $124
Per week:$537 - $864
Pets allowed:No
Internet:Yes

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....

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Islamorada Florida Vacation Rentals - Condo
1 / 17

Islamorada Condo
2 Bedrooms / 2 Bathrooms / Sleeps 4
Condo / 2 Bedrooms / Sleeps 4

from

$70

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:4
Type:Condo
Per night:$70 - $127
Per week:$490 - $887
Pets allowed:No
Internet:Yes

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...

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Islamorada Florida Vacation Rentals - Condo
1 / 12

Islamorada Condo
3 Bedrooms / 2 Bathrooms / Sleeps 6
Condo / 3 Bedrooms / Sleeps 6

from

$150

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:6
Type:Condo
Per night:$150 - $204
Per week:$1,050 - $1,425
Pets allowed:No
Internet:Yes

Welcome to our beautiful, private and secure gated community with all of the amenities to make your vacation as relaxing or exciting as you wish. Located on Plantation Key in Islamorada at mile marker 88. 5 on the bay side and boasting a great 60 slip marina, it provides quick access...

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Islamorada Florida Vacation Rentals - Condo
1 / 25

Islamorada Condo
2 Bedrooms / 2.5 Bathrooms / Sleeps 6
Condo / 2 Bedrooms / Sleeps 6

from

$179

/ night

Email Owner
Bedrooms:2
Bathrooms:2.5
Sleeps:6
Type:Condo
Per night:$179 - $257
Per week:$1,250 - $1,795
Pets allowed:No
Internet:Yes

MINIMUM STAY 7 NIGHTS, SATURDAY TO SATURDAY RENTAL ONLY 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....

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1 / 24

Islamorada Home
2 Bedrooms / 2 Bathrooms / Sleeps 6
Home / 2 Bedrooms / Sleeps 6

from

$358

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:6
Type:Home
Per night:$358
Per week:$2,500
Pets allowed:Yes
Internet:Yes

ower 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 - ...

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Pool and Jacuzzi on premises
1 / 7

Islamorada Home
3 Bedrooms / 2 Bathrooms / Sleeps 6
Home / 3 Bedrooms / Sleeps 6

(5)“ Excellent ”5 Reviews

from

$329

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:6
Type:Home
Per night:$329 - $429
Per week:$2,300 - $3,000
Pets allowed:No
Internet:No

Enjoy a beautiful solar heated pool with Jacuzzi on the premises. You also will have access to a private homeowner's sandy beach to swim and enjoy sunsets on the next street over. Come to paradise and enjoy this fabulous Islamorada bayside canal front 3/2. Located in a quiet neighborhood...

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Beautiful and Friendly

“ Excellent ”
January 22, 2014
This house was perfect. Great location, private beach, very clean, had everything you needed. Mark is very friendly and helpful. Can't wait to visit again:)
Kelly Seitzer Gee, Ocean city, md

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Islamorada Florida Vacation Rentals - Home
1 / 16

Islamorada Home
3 Bedrooms / 3 Bathrooms / Sleeps 6
Home / 3 Bedrooms / Sleeps 6

from

$543

/ night

Email Owner
Bedrooms:3
Bathrooms:3
Sleeps:6
Type:Home
Per night:$543
Per week:$3,800
Pets allowed:No
Internet:Yes

Ocean front retreat with overwhelming views of the Atlantic, large open verandahs, 100 feet of very private white sandy beach, and a gated entrance. The beach is very private on 3/4 of an acre loaded with palm trees. You can snorkel in the backyard on coral reefs within 1000 feet...

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Islamorada Florida Vacation Rentals - Home
1 / 15

Islamorada Home
3 Bedrooms / 3 Bathrooms / Sleeps 8
Home / 3 Bedrooms / Sleeps 8

(4)“ Excellent ”4 Reviews

from

$230

/ night

Email Owner
Bedrooms:3
Bathrooms:3
Sleeps:8
Type:Home
Per night:$230 - $430
Per week:$1,610 - $3,010
Pets allowed:No
Internet:Yes

Special vacation rental rates for off- season bookings and also for some last minute dates! Call us now for details. Located in Islamorada the fishing capitol of the world, this is a beautiful home decorated with Island style decor. Over 3, 000 square feet of living space. 100'...

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Escape

“ Excellent ”
February 21, 2015
The owner was very attentive to our needs. I sent him a text and he was " all over it". His house was decorated beautifully with a extremely well equipped kitchen. We cooked and grilled almost every night. Venetian shores is a nice community, nice to walk up and down the canals and enjoy looking at boats. About a mile from a very large park with walking trail, Olympic size swimming pool and sandy beach, even has a net to hit golf balls into for golfers to practice. I would recommend this home to anyone. If you have a disability make sure to tell the owner, as the house also has an elevator. enjoy the stay, we did!
Diane Sandoval, North Carolina, USA

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Islamorada Florida Vacation Rentals - Home
1 / 17

Islamorada Home
2 Bedrooms / 2 Bathrooms / Sleeps 4
Home / 2 Bedrooms / Sleeps 4

from

$147

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:4
Type:Home
Per night:$147 - $167
Per week:$1,027 - $1,167
Pets allowed:No
Internet:Yes

MINIMUM STAY 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...

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1 / 25

Islamorada Home
4 Bedrooms / 3 Bathrooms / Sleeps 12
Home / 4 Bedrooms / Sleeps 12

from

$117

/ night

Email Owner
Bedrooms:4
Bathrooms:3
Sleeps:12
Type:Home
Per night:$117 - $167
Per week:$817 - $1,167
Pets allowed:No
Internet:Yes

MINIMUM STAY 1 MONTH: Enjoy your stay in this gorgeous single family home. You’ll love the convenient location in the Ocean Shores area of Key Largo. There’s easy ocean access from this 90' concrete dock. Water, electricity, fish cleaning station and gas barbecue grill are all...

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Islamorada Florida Vacation Rentals - Home
1 / 9

Islamorada Home
4 Bedrooms / 4 Bathrooms / Sleeps 8
Home / 4 Bedrooms / Sleeps 8

(5)“ Excellent ”5 Reviews

from

$300

/ night

Email Owner
Bedrooms:4
Bathrooms:4
Sleeps:8
Type:Home
Per night:$300
Per week:$2,100
Pets allowed:No
Internet:Yes

This beautiful 4 bedroom/ 4 bathroom home has a 70' dock directly behind the home . Canal leads out to Snake Creek and has immediate Ocean and Bay access. The home is located in one of the finest neighborhoods of the Florida Keys- Venetian Shores. Upstairs there are 2 bedrooms/ 2...

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Islamorada, 110 El Capitan '15 Stay

“ Excellent ”
April 5, 2015
House was great, clean and well maintained. Neighborhood is very nice, I've stay there before. Location is perfect with close proximity to fishing marinas (Robbie's and Bud & Mary's) as well good dining locations (Islamorada Fish Company, Ma's Fish House, Chef Michael's and Lazy Days). Twenty minutes to Marathon. Will consider staying again in the future.
Dow Carter, Libertyville, IL

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1 / 16

Islamorada Townhouse
2 Bedrooms / 1.5 Bathrooms / Sleeps 6
Townhouse / 2 Bedrooms / Sleeps 6

(5)“ Excellent ”5 Reviews

from

$94

/ night

Email Owner
Bedrooms:2
Bathrooms:1.5
Sleeps:6
Type:Townhouse
Per night:$94
Per week:$654
Pets allowed:No
Internet:No

Vacation in beautiful peaceful Islamorada, in the Florida Keys. Islamorada, "Fishing Capital of the World". Bayside access Townhouse is a newly redone 2 bedroom, loft, 1 1/2 bath, comfortably sleeps 6 adults, patio with BBQ. Fully furnished and kitchen totally equipped. Washer/Dryer,...

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Florida Keys

“ Excellent ”
January 26, 2015
Had a wonderful time. The condo was perfect. I would definitely return next year.
Garrett Cox, Nov, MI USA

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Islamorada Florida Vacation Rentals - Home
1 / 23

Islamorada Home
3 Bedrooms / 2 Bathrooms / Sleeps 6
Home / 3 Bedrooms / Sleeps 6

from

$217

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:6
Type:Home
Per night:$217 - $284
Per week:$1,517 - $1,984
Pets allowed:No
Internet:Yes

MINIMUM STAY 1 MONTH: Oceanfront - Beach - Protected Dock and located in the Fishing Capital of the World - Islamorada. Realize your dreams - a beach home located on a swimmable beach and a place to dock your boat. This home is indeed a rare find in The Florida Keys. From the ...

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Islamorada Florida Vacation Rentals - Home
1 / 19

Islamorada Home
1 Bedroom / 1.5 Bathrooms / Sleeps 3
Home / 1 Bedroom / Sleeps 3

from

$149

/ night

Email Owner
Bedrooms:1
Bathrooms:1.5
Sleeps:3
Type:Home
Per night:$149 - $177
Per week:$1,040 - $1,235
Pets allowed:No
Internet:Yes

MINIMUM RENTAL 7 NIGHTS: You can have it all – privacy and convenience. The owners of this wonderful property called Sunshine Place are willing to share a portion of their piece of Paradise with you. The ground level living area of this home is perfect for one or two people who ...

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Islamorada Florida Vacation Rentals - Villa
1 / 22

Islamorada Villa
2 Bedrooms / 2 Bathrooms / Sleeps 4
Villa / 2 Bedrooms / Sleeps 4

from

$100

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:4
Type:Villa
Per night:$100 - $134
Per week:$700 - $933
Pets allowed:Yes
Internet:Yes

MINIMUM RENTAL 1 MONTH: 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...

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Islamorada Florida Vacation Rentals - Home
1 / 24

Islamorada Home
3 Bedrooms / 3 Bathrooms / Sleeps 6
Home / 3 Bedrooms / Sleeps 6

from

$358

/ night

Email Owner
Bedrooms:3
Bathrooms:3
Sleeps:6
Type:Home
Per night:$358
Per week:$2,500
Pets allowed:No
Internet:Yes

Venetian Shores 3/3 home with deep water boat slip, gorgeous custom pool with integrated hot tub and built- in seating. This beautifully updated tri- level home offers a 2/2 upstairs with soaring ceilings, wood floors and a wide porch off the living room overlooking the pool and...

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Islamorada Florida Vacation Rentals - Condo
1 / 22

Islamorada Condo
2 Bedrooms / 2 Bathrooms / Sleeps 4
Condo / 2 Bedrooms / Sleeps 4

from

$167

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:4
Type:Condo
Per night:$167 - $200
Per week:$1,167 - $1,400
Pets allowed:No
Internet:Yes

MINIMUM STAY 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);...

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Islamorada Florida Vacation Rentals - Home
1 / 20

Islamorada Home
2 Bedrooms / 2 Bathrooms / Sleeps 4
Home / 2 Bedrooms / Sleeps 4

from

$110

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:4
Type:Home
Per night:$110 - $164
Per week:$770 - $1,144
Pets allowed:No
Internet:Yes

MINIMUM STAY 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 ...

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Islamorada Florida Vacation Rentals - Home
1 / 15

Islamorada Home
3 Bedrooms / 2 Bathrooms / Sleeps 7
Home / 3 Bedrooms / Sleeps 7

from

$133

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:7
Type:Home
Per night:$133 - $158
Per week:$931 - $1,103
Pets allowed:No
Internet:Yes

MINIMUM RENTAL 1 MONTH: Charming vacation home located in the beautiful neighborhood of Port Antigua. You will love this home! There is a wonderful open concept floor plan with 3 nicely proportioned bedrooms. Sliding doors open from the dining area into the sunroom overlooking the...

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Islamorada Florida Vacation Rentals - Home
1 / 14

Islamorada Home
1 Bedroom / 2 Bathrooms / Sleeps 4
Home / 1 Bedroom / Sleeps 4

from

$379

/ night

Email Owner
Bedrooms:1
Bathrooms:2
Sleeps:4
Type:Home
Per night:$379
Per week:$2,650
Pets allowed:No
Internet:Yes

MINIMUM RENTAL 1 MONTH: Everything in this unit is exquisite - furnishings, linens, updated kitchen, appliances, and bathrooms. Great views of Florida Bay and our fabulous Keys sunsets. This complex is conveniently located just steps from a full service marina and 2 highly acclaimed...

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Waterfront II
1 / 17

Islamorada Home
4 Bedrooms / 3 Bathrooms / Sleeps 12
Home / 4 Bedrooms / Sleeps 12

(15)“ Excellent ”15 Reviews

from

$429

/ night

Email Owner
Bedrooms:4
Bathrooms:3
Sleeps:12
Type:Home
Per night:$429 - $458
Per week:$3,000 - $3,200
Pets allowed:No
Internet:Yes

The Great Islamorada Getaway features a spectacular canal front home on an over- sized property with 136 feet of dock space and an in ground pool (heater/chiller optional). Large outside patio with gas grill and upstairs screened in porch. Brand new kitchen and appliances enhance ...

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Great place

“ Excellent ”
October 11, 2013
Great place!
Pamela Fetters, St Louis MO

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Islamorada Florida Vacation Rentals - Condo
1 / 19

Islamorada Condo
3 Bedrooms / 2 Bathrooms / Sleeps 6
Condo / 3 Bedrooms / Sleeps 6

from

$124

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:6
Type:Condo
Per night:$124 - $157
Per week:$864 - $1,097
Pets allowed:No
Internet:Yes

MINIMUM RENTAL 1 MONTH: Enjoy unobstructed and panoramic views of the Atlantic Ocean from your own private balcony! This 3 bedroom/2 bath condo unit features direct ocean views from the living room, balcony and two of the three bedrooms. Tropical furnishings create a warm and inviting...

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Islamorada Florida Vacation Rentals - Cottage
1 / 19

Islamorada Cottage
2 Bedrooms / 2 Bathrooms / Sleeps 6
Cottage / 2 Bedrooms / Sleeps 6

from

$358

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:6
Type:Cottage
Per night:$358
Per week:$2,500
Pets allowed:No
Internet:Yes

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 a large bedroom with a king bed and full bath. The laundry area with a full size washer and dryer is also located in this room....

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water view
1 / 6

Islamorada Home
3 Bedrooms / 2 Bathrooms / Sleeps 7
Home / 3 Bedrooms / Sleeps 7

(3)“ Excellent ”3 Reviews

from

$250

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:7
Type:Home
Per night:$250
Per week:$1,750
Pets allowed:No
Internet:Yes

Choose between two seperate suites (2bed/lbath $950 or (1bed/1bath $850)or BOTH combined for $1750. The upstairs (The Lighhouse Suite) is on the second floor and will accommodate six people. There are two bedrooms and one bath, an eat- in kitchen with beautiful wood flooring ...

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most accomodating

“ Excellent ”
April 1, 2015
Fantastic find! Comfortable and quiet retreat with more than enough space for our family. Robert and Joan were a pleasure to work with and we couldn't have been happier with the location and amenities. Our next visit to Islamorada will begin with a call to these owners for availability. Deep water canal easily handled our 27' fishing boat and gear. Convenient to the marina and the supplies we needed. All around win for us! Thanks Joan and Robert! See you soon!
Brad Bergemann, Charlotte, NC

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PLANTATION BY THE SEA COMPLEX FRONT VIEW
1 / 20

Islamorada Condo
2 Bedrooms / 1.5 Bathrooms / Sleeps 6
Condo / 2 Bedrooms / Sleeps 6

from

$74

/ night

Email Owner
Bedrooms:2
Bathrooms:1.5
Sleeps:6
Type:Condo
Per night:$74 - $100
Per week:$514 - $700
Pets allowed:No
Internet:Yes

Picture Perfect Ocean Front Two Bedroom Duplex Condo Which Has Been Totally Renovated With Hi End Finishes. Attention To Detail Is Evident The Minute You Walk In. Designer Kitchen Offers Kensington Maple Cabinetry, Granite Counter Tops And Stainless Steel Appliances. Beautiful Tiled...

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Islamorada Florida Vacation Rentals - Condo
1 / 21

Islamorada Condo
2 Bedrooms / 2 Bathrooms / Sleeps 5
Condo / 2 Bedrooms / Sleeps 5

from

$77

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:5
Type:Condo
Per night:$77 - $130
Per week:$537 - $910
Pets allowed:No
Internet:Yes

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...

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Islamorada Florida Vacation Rentals - Townhouse
1 / 8

Islamorada Townhouse
2 Bedrooms / 2.5 Bathrooms / Sleeps 8
Townhouse / 2 Bedrooms / Sleeps 8

(2)“ Excellent ”2 Reviews

from

$315

/ night

Email Owner
Bedrooms:2
Bathrooms:2.5
Sleeps:8
Type:Townhouse
Per night:$315
Per week:$2,200
Pets allowed:No
Internet:No

Come enjoy a slice of paradise in this beautiful ocean front property settled in a private, gated and lushly landscaped community. Take it all in, from the breathtaking ocean views, to the serene swimming pool, it's like a tropical dream come true. In addition to the pool this...

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Fun, family vacation in the FL Keys

“ Excellent ”
April 5, 2015
We enjoyed a fun, warm week steps away from the Anglers Reef pool with our two kids ages, 4 and 6. About 1 hr 45 min drive from. Miami, depending on traffic. Upon arrival, the house was clean and well set-up. Good sized kitchen and downstairs living space (including 1/2 bath) and spacious 2 upstairs bedrooms each with their own bath. The upstairs washing machine was much appreciated and used hard! A few items to add to help with families with small kids include a step stool or two so kids can reach the sinks to wash hands and brush teeth without assistance and more melamine plates and cups which make dining al fresco (in particular) more feasible with little ones. Also would have loved to have access to kids' sized life vests to enjoy the owner's kayak. We did not end up using the kayak this trip. We enjoyed making most of our own meals in the kitchen and could have used a few more items to make that process a bit smoother, but great news was the blender worked well for frozen drinks :) Location is great and a mile or two down Overseas Highway from Theater of the Sea (a must see marine mammal park for families) and almost across the street from Smugglers Cove where we took a Family Fun Boat Tour, another great family experience. Note that the house sits close to the entry gate and is therefore not too far from the roadway. Not a safety issue due to the gated community but you are able to hear the Overseas Highway traffic. Two thumbs up for a fun family vacation! We were all sad to pack up and come back to cold PA.
Lori Hood Sanders, Garnet Valley, PA

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Islamorada Florida Vacation Rentals - Home
1 / 23

Islamorada Home
2 Bedrooms / 2 Bathrooms / Sleeps 4
Home / 2 Bedrooms / Sleeps 4

from

$107

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:4
Type:Home
Per night:$107 - $157
Per week:$747 - $1,097
Pets allowed:No
Internet:Yes

MINIMUM STAY 1 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, ...

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Islamorada Florida Vacation Rentals - Home
1 / 22

Islamorada Home
3 Bedrooms / 2 Bathrooms / Sleeps 6
Home / 3 Bedrooms / Sleeps 6

from

$358

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:6
Type:Home
Per night:$358
Per week:$2,500
Pets allowed:No
Internet:Yes

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...

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Islamorada Florida Vacation Rentals - Home
1 / 15

Islamorada Home
2 Bedrooms / 2 Bathrooms / Sleeps 4
Home / 2 Bedrooms / Sleeps 4

from

$64

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:4
Type:Home
Per night:$64 - $117
Per week:$444 - $817
Pets allowed:No
Internet:Yes

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 plenty of...

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Islamorada Florida Vacation Rentals - Condo
1 / 25

Islamorada Condo
2 Bedrooms / 2 Bathrooms / Sleeps 6
Condo / 2 Bedrooms / Sleeps 6

from

$97

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:6
Type:Condo
Per night:$97 - $134
Per week:$677 - $934
Pets allowed:No
Internet:Yes

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...

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Islamorada Florida Vacation Rentals - Home
1 / 25

Islamorada Home
3 Bedrooms / 2 Bathrooms / Sleeps 7
Home / 3 Bedrooms / Sleeps 7

from

$200

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:7
Type:Home
Per night:$200 - $267
Per week:$1,400 - $1,867
Pets allowed:No
Internet:Yes

MINIMUM STAY 1 MONTH: FABULOUS BEACH HOUSE with sea grape trees on three sides and the ocean on the other! This home is located directly on the Atlantic Ocean with a sandy beach big enough to take lovely morning walks. Wait for the tide to go out and take your chair and umbrella ...

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View from Balcony
1 / 8

Islamorada Condo
2 Bedrooms / 2 Bathrooms / Sleeps 5
Condo / 2 Bedrooms / Sleeps 5

(17)“ Excellent ”17 Reviews

from

$143

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:5
Type:Condo
Per night:$143 - $200
Per week:$1,000 - $1,400
Pets allowed:No
Internet:No

Located at Mile Marker 90 in the Florida Keys our 2 Bedroom/2 Bath Condo offers unobstructed views of the Atlantic Ocean. The complex offers a heated pool, tennis court, gym, water front beach, elevators, parking and secured entrances. Our condo has been recently updated with...

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Great Place!

“ Excellent ”
April 21, 2015
This was our first visit to the Keys and we could not have picked a better place to stay. The condo was clean, comfortable, had everything we needed, plus more. Shelly was super to work with and made it an easy process. We will definitely rent this place again.
Barb Smith, Shawnee, KS

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Islamorada Florida Vacation Rentals - Home
1 / 24

Islamorada Home
3 Bedrooms / 3 Bathrooms / Sleeps 8
Home / 3 Bedrooms / Sleeps 8

from

$175

/ night

Email Owner
Bedrooms:3
Bathrooms:3
Sleeps:8
Type:Home
Per night:$175 - $240
Per week:$1,225 - $1,680
Pets allowed:Yes
Internet:No

MINIMUM RENTAL 1 MONTH: Location, location, location! This home has it all - ocean side Lower Matecumbe location, totally remodeled in 2009. Relax by the cocktail pool or sunbathe in the private roof top sunning area. There are blue water ocean views from almost every room in...

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1 / 6

Islamorada Townhouse
3 Bedrooms / 2 Bathrooms / Sleeps 6
Townhouse / 3 Bedrooms / Sleeps 6

(5)“ Excellent ”5 Reviews

from

$100

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:6
Type:Townhouse
Per night:$100
Per week:$700
Pets allowed:No
Internet:Yes

Call Property Manager for Best Rate. Located on Windley Key this gated 5 unit complex has the best of the Keys with a private pool sandy Beachfront, fishing pier with flats boat dockage (drawing 24" or less) located directly on the ocean your views could NOT be any better. ...

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Awsome

“ Excellent ”
April 1, 2015
Great place to stay... This house exceeded my expectations.
Gary Atchison, Inverness, Fl

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Islamorada Florida Vacation Rentals - Home
1 / 20

Islamorada Home
2 Bedrooms / 1.5 Bathrooms / Sleeps 4
Home / 2 Bedrooms / Sleeps 4

from

$135

/ night

Email Owner
Bedrooms:2
Bathrooms:1.5
Sleeps:4
Type:Home
Per night:$135 - $158
Per week:$940 - $1,100
Pets allowed:No
Internet:No

MINIMUM STAY 1 MONTH: This 4th floor end unit in one of Key Largo's finest bay front condominium complexes offers a beautiful view of the Florida Bay and lots of natural light. You'll love the updated kitchen with granite counters, new cabinetry and appliances. New linens and fresh...

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Islamorada Florida Vacation Rentals - Home
1 / 1

Islamorada Home
1 Bedroom / 1 Bathroom / Sleeps 20
Home / 1 Bedroom / Sleeps 20

from

$536

/ night

Email Owner
Bedrooms:1
Bathrooms:1
Sleeps:20
Type:Home
Per night:$536
Per week:$3,750
Pets allowed:No
Internet:Yes

oooooooooooooooooooooooooooooo oooooooooooooooooooooooooooooo oooooooooooooooooooooooooooooo oooooooooooooooooooooooooooooo oooooooooooooooooooooooooooooo oooooooooooooooooooooooooooooo oooooooooooooooooooooooooooooo oooooooooooooooooooooooooooooo oooooooooooooooooooooooooooooo oooooooooooooooooooooooooooooo...

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Islamorada Florida Vacation Rentals - Home
1 / 17

Islamorada Home
3 Bedrooms / 2 Bathrooms / Sleeps 6
Home / 3 Bedrooms / Sleeps 6

Bedrooms:3
Bathrooms:2
Sleeps:6
Type:Home
No rental rates available - please contact the owner
 
Pets allowed:No
Internet:Yes

MINIMUM RENTAL 1 MONTH - You will love jewel of a home! Located in Lower Matecumbe, this charming canal front home offers a swimming pool, dockage, direct access to the ocean, covered fish cleaning station, a screened lanai, inviting décor and comfortable accommodations. ...

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About Islamorada

Islamorada, FL Travel Tips

Islamorada vacation rentals are a great choice for families visiting this tropical island. There are fun things to do, see, and explore. Activities are water-based and the family that loves fishing will have plenty of fun in the sun. Boating is a popular activity as well as snorkeling and scuba diving. Islamorada is in the Florida Keys and on the Atlantic Ocean and Florida Bay. Islamorada rentals enable families to enjoy their vacations while keeping the comforts of home. You will need a car to get around the island, so rent one if you are not driving from Miami or other surrounding cities.

Neighborhoods

You can find Islamorada vacation home rentals in each of the island’s three neighborhoods. Lower Matecumbe Beach, Matecumbe, and Plantation Key are popular neighborhoods for Islamorada rentals. Oceanfront Islamorada house rentals are easy to find online and are a perfect way to visit Florida. They provide easy access to water activities without giving up comfort. Traveling families enjoy the ease of staying in a rental home or condo. By-owner properties include necessities such as washers and dryers, kitchens, and full baths. For the family that wants to save on their vacation, rentals in Islamorada, FL, are an excellent choice.

Attractions

There are many attractions in Islamorada and the Florida Keys. One of the most popular attractions is the family-friendly park Theater of the Sea. Kids can swim with dolphins. There are opportunities for interacting with sea lions and turtles as well. Theater of the Sea also provides live snorkeling tours, ensuring fun for the entire family. Coral reef diving is an exciting adventure, and there are always chances for fishing. Rent a boat or join a fishing charter with an experienced tour guide.
San Pedro Underwater Archaeological Preserve State Park is a historical shipwreck site. The water is 18 feet deep and perfect for experienced divers. Another popular family-friendly attraction is the Windley Key Fossil Reef Geological State Park. The park includes hiking and nature trails and features fossilized coral. There are picnic tables and educational tours for kids. The park is home to a variety of birds, and wildlife viewing is a popular activity.
Anne’s Beach is a great place to bring the kids. There are many coves along the white sands, making it easy to find private spots for family fun. Mangroves surround the beach, making it the perfect location to observe ...

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