Islamorada Vacation Rentals, Homes, & More

1-50 of 76 Islamorada Rentals

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Islamorada Florida Vacation Rentals - Condo
1 / 9

Islamorada Condo
2 Bedrooms / 2 Bathrooms / 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 - Condo
1 / 8

Islamorada Condo
3 Bedrooms / 2 Bathrooms / Sleeps 6

from

$150

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:6
Type:Condo
Per night:$150 - $200
Per week:$1,050 - $1,400
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 - Townhouse
1 / 9

Islamorada Townhouse
2 Bedrooms / 2.5 Bathrooms / Sleeps 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:No
Internet:No

Sunset view, tennis courts, heated pool, recently remodeled, fish from the dock, boat slip right in front of unit. quiet gated community, monthly $3000. 00 in season, $1900. 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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Islamorada Florida Vacation Rentals - Home
1 / 16

Islamorada Home
3 Bedrooms / 2 Bathrooms / 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:Yes
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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1 / 23

Islamorada Cottage
2 Bedrooms / 1 Bathroom / Sleeps 4

from

$150

/ night

Email Owner
Bedrooms:2
Bathrooms:1
Sleeps:4
Type:Cottage
Per night:$150 - $250
Per week:$980 - $1,225
Pets allowed:No
Internet:Yes

Enjoy spectacular water views from the private petite beach, large TIKI hut and boat dock at the end of the community, You'll be just steps away from the ocean, Enjoy spectacular water views and amazing sunsets, just steps away from Founder's park with private beach, private ...

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Back View
1 / 15

Islamorada Home
3 Bedrooms / 3 Bathrooms / Sleeps 8

“ Excellent ”3 Reviews

from

$230

/ night

Email Owner
Bedrooms:3
Bathrooms:3
Sleeps:8
Type:Home
Per night:$230
Per week:$1,610
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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Perfect house/perfect location

“ Excellent ”
August 1, 2014
This is an awesome house in the perfect location. The house is spacious and comfortable. Pool is NICE. Great dock. Tony was EXTREMELY helpful and accomodating and gave plenty of information and answered all questions quickly. We are picky about accomodations when traveling and this house exceeded our expectations. Pictures don't do justice. It's perfect! Plenty of restaurants nearby accessible by boat or land. Easy to get out to ocean or bay in 2-3 minutes. We had a perfect week in Islamorada!
Kathy Riley, Ocala, Florida

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Front View
1 / 29

Islamorada Home
3 Bedrooms / 2 Bathrooms / Sleeps 6

“ Excellent ”4 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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getaway

“ Excellent ”
January 23, 2015
5 girlfriends snuck away for a long weekend retreat to celebrate a birthday. The house had all that we needed! We loved all of the "extras" including the Gheenoe, the kayak, the bikes, the hammocks. They made the trip extra special. The house was super clean, and we are tough critics! A wonderful time and easy access to fun activities, restaurants, beaches, etc. nearby
Terri woellner, Denver

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Islamorada Florida Vacation Rentals - Home
1 / 24

Islamorada Home
3 Bedrooms / 3 Bathrooms / Sleeps 8

“ Excellent ”1 Review

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:Yes

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 / 9

Islamorada Condo
2 Bedrooms / 2 Bathrooms / Sleeps 6

“ 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

“ Excellent ”13 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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Peaceful

“ Excellent ”
February 12, 2015
There were 6 of us that stayed at this property and we had a great time! Everything was as they described. Nice pool and right on the ocean, couldn't have asked for anything better for the price. If we go back we rent again. My husband really enjoyed the dock where he spent many hours fishing and caught many different kinds of fish!!
Lori Lems, Canton, SD USA

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Islamorada Florida Vacation Rentals - Home
1 / 15

Islamorada Home
2 Bedrooms / 2 Bathrooms / 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 - Home
1 / 24

Islamorada Home
3 Bedrooms / 3 Bathrooms / 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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Islamorada Florida Vacation Rentals - Home
1 / 17

Islamorada Home
2 Bedrooms / 2 Bathrooms / Sleeps 4

from

$134

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:4
Type:Home
Per night:$134 - $160
Per week:$934 - $1,120
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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Islamorada Florida Vacation Rentals - Home
1 / 25

Islamorada Home
3 Bedrooms / 2 Bathrooms / 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:No
Internet:Yes

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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Islamorada Florida Vacation Rentals - Home
1 / 17

Islamorada Home
4 Bedrooms / 3 Bathrooms / Sleeps 12

“ Excellent ”15 Reviews

from

$400

/ night

Email Owner
Bedrooms:4
Bathrooms:3
Sleeps:12
Type:Home
Per night:$400 - $458
Per week:$2,800 - $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

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 - Villa
1 / 22

Islamorada Villa
2 Bedrooms / 2 Bathrooms / 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 - Townhouse
1 / 6

Islamorada Townhouse
3 Bedrooms / 2 Bathrooms / Sleeps 6

“ Excellent ”3 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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Fabulous Vacation

“ Excellent ”
September 15, 2014
We had a fabulous time at David's place. Everything was wonderful. Beautiful view, manatees at our front door, just everything you would want in a Keys vacation.
Betty Cameron, Daytona Beach, Florida USA

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1 / 16

Islamorada Townhouse
2 Bedrooms / 1.5 Bathrooms / Sleeps 6

“ 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 / 6

Islamorada Home
3 Bedrooms / 2 Bathrooms / Sleeps 7

“ Excellent ”2 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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Fun at 107 San Remo

“ Excellent ”
March 15, 2013
Four of us retired persons contracted this unit for 10 days of fishing. The weather was marginally cooperative, however, the location was ideal. The owners had a nice touch to the decor and were available for any amenities desired. I especially appreciated the champagne as a welcome gift. We caught 33 species of fish and were able to eat fresh fish tacos on several occaisions. The local cuisine was outstanding. We were visited by several local birds waiting for handouts...an iguana, and a manatee that cruised into the canal.I would highly recommend this facility to any fishermen or women, or even those seeking a relaxing quiet location centrally located on the key.
Charles Clouse, Bridgewater, VA

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Islamorada Florida Vacation Rentals - Condo
1 / 8

Islamorada Condo
2 Bedrooms / 2 Bathrooms / Sleeps 5

“ Excellent ”15 Reviews

from

$129

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:5
Type:Condo
Per night:$129 - $200
Per week:$900 - $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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Belated Accolades!

“ Excellent ”
January 29, 2015
We had the most wonderful time here. The owner was very friendly and helpful. The condo was spotless and spacious. Airy and well equipped. We loved sitting out on the deck overlooking the ocean. There was a binder in which recent guests could write comments and suggestions for great places to eat and places to visit. We took many of their suggestions and were never disappointed! We would definitely rent this place again and highly recommend it. You will be glad you came!
Cathleen Newton, West Hartford, Vermont

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Islamorada Florida Vacation Rentals - Home
1 / 24

Islamorada Home
4 Bedrooms / 4 Bathrooms / Sleeps 8

from

$358

/ night

Email Owner
Bedrooms:4
Bathrooms:4
Sleeps:8
Type:Home
Per night:$358
Per week:$2,500
Pets allowed:No
Internet:Yes

This spacious pool home comes with all the amenities to turn your dream vacation into a reality, including a 100- foot long dock and a custom pool overlooking the deepwater canal with an integrated spa. The pool has a waterfall on one end and a trickling stream on the other it is...

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Islamorada Florida Vacation Rentals - Condo
1 / 25

Islamorada Condo
2 Bedrooms / 2.5 Bathrooms / Sleeps 6

from

$179

/ night

Email Owner
Bedrooms:2
Bathrooms:2.5
Sleeps:6
Type:Condo
Per night:$179 - $236
Per week:$1,250 - $1,650
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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Islamorada Florida Vacation Rentals - Home
1 / 24

Islamorada Home
2 Bedrooms / 2 Bathrooms / 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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Islamorada Florida Vacation Rentals - Condo
1 / 22

Islamorada Condo
2 Bedrooms / 2 Bathrooms / 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 / 23

Islamorada Home
2 Bedrooms / 2 Bathrooms / 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 / 23

Islamorada Home
5 Bedrooms / 6.5 Bathrooms / 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
4 Bedrooms / 3 Bathrooms / 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 / 19

Islamorada Home
1 Bedroom / 1.5 Bathrooms / 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 - Home
1 / 21

Islamorada Home
2 Bedrooms / 2 Bathrooms / Sleeps 6

“ 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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Islamorada Florida Vacation Rentals - Cottage
1 / 19

Islamorada Cottage
2 Bedrooms / 2 Bathrooms / 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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Islamorada Florida Vacation Rentals - Home
1 / 16

Islamorada Home
3 Bedrooms / 3 Bathrooms / 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 / 14

Islamorada Home
1 Bedroom / 2 Bathrooms / 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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Islamorada Florida Vacation Rentals - Condo
1 / 21

Islamorada Condo
2 Bedrooms / 2 Bathrooms / 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 - Home
1 / 25

Islamorada Home
3 Bedrooms / 2 Bathrooms / 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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Islamorada Florida Vacation Rentals - Townhouse
1 / 8

Islamorada Townhouse
2 Bedrooms / 2.5 Bathrooms / Sleeps 8

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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Islamorada Florida Vacation Rentals - Home
1 / 15

Islamorada Home
3 Bedrooms / 2 Bathrooms / 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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1 / 8

Islamorada Home
8 Bedrooms / 5.5 Bathrooms / Sleeps 16

from

$536

/ night

Email Owner
Bedrooms:8
Bathrooms:5.5
Sleeps:16
Type:Home
Per night:$536 - $858
Per week:$3,750 - $6,000
Pets allowed:No
Internet:Yes

The Florida Keys Largest, Most Prestigious Vacation Rental Home Available! ! Come stay in your own luxurious Oceanfront Mansion... for less than the price of a hotel room! (see rate breakdown below) Enter this vacation paradise through the private gated drive, lined with...

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Islamorada Florida Vacation Rentals - Home
1 / 23

Islamorada Home
3 Bedrooms / 2 Bathrooms / 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 - Condo
1 / 17

Islamorada Condo
2 Bedrooms / 2 Bathrooms / 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 - Home
1 / 20

Islamorada Home
2 Bedrooms / 2 Bathrooms / 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 - Condo
1 / 13

Islamorada Condo
2 Bedrooms / 2 Bathrooms / Sleeps 6

from

$70

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:6
Type:Condo
Per night:$70 - $120
Per week:$490 - $840
Pets allowed:No
Internet:No

MINIMUM RENTAL 1 MONTH: This exceptional condo has been impeccably maintained and is located in one of the finest condo complexes in Islamorada. It features an updated kitchen, remodeled baths and is comfortably furnished. This unit is ready for your arrival. The owners frequently...

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Islamorada Florida Vacation Rentals - Home
1 / 20

Islamorada Home
2 Bedrooms / 1.5 Bathrooms / 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 / 7

Islamorada Home
3 Bedrooms / 2 Bathrooms / Sleeps 6

“ 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 / 22

Islamorada Home
3 Bedrooms / 2 Bathrooms / 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 - Condo
1 / 12

Islamorada Condo
2 Bedrooms / 2 Bathrooms / 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 / 25

Islamorada Condo
2 Bedrooms / 2 Bathrooms / 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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EXTERIOR OF HOUSE
1 / 9

Islamorada Home
4 Bedrooms / 4 Bathrooms / Sleeps 8

“ Excellent ”4 Reviews

Bedrooms:4
Bathrooms:4
Sleeps:8
Type:Home
No rental rates available - please contact the owner
 
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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Wonderful Month in Key Largo

“ Excellent ”
January 9, 2015
It had been several years since we've been in the Keys, and my family and I decided it would be nice to spend Christmas there this year. We rented this property for the month of December. It was absolutely fantastic. The outside space is wonderful; the pictures just don't fully convey how great this space is. Each morning I'd spend time on the deck in "tequilaville" having coffee and watching the manatees in the canal. It was so relaxing. The flowers are spectacular; and the lights at night in the garden and the fountain are breathtaking. The house itself is comfortable and perfect; it's decorated in a caribbean/keys style which is perfect.Deborah is a job to deal with. She kept me very informed as we went through the rental process. And, she personally met me at the property for check in and to give me the grand tour. It was fantastic.There are so many things in the area to take advantage of. There is a flea market/farmers market within short walking distance; Pennekamp state park is close by; and there are so many restaurants in the area.I can't recommend this property highly enough. If you're looking for the perfect Keys experience, this property is great!! I've been home for over a week now, and I already miss Key Largo.
steve weigler, Woodbridge, VA

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Islamorada Florida Vacation Rentals - Home
1 / 17

Islamorada Home
3 Bedrooms / 2 Bathrooms / 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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1  2 

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 Florida marine life. The waters are shallow, and Anne’s Beach is a popular destination for kite-boarders. Beginning kite-boarders can test their skills on the tropical waters. As there is little wave activity, Anne’s Beach is a good choice for families with young children.
Families staying in the Florida Keys will find many advantages to choosing vacation rentals. Islamorada is a top destination in the Florida Keys and offers a wide array of activities and events. When visiting Islamorada, condo rentals are also a great choice. You can save on the total cost of your trip by choosing Islamorada vacation rentals as opposed to hotels.
Events
Islamorada has plenty of year-round events and activities to keep families entertained. Every December is the holiday festival hosted at Founders Park. In March, there is the annual art show, and the Fourth of July celebration occurs each summer. There are always family-friendly events taking place, making Islamorada a perfect destination.
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