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Found 129 Islamorada FL vacation rentals
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4/5
6
Sleeps
2
Bedrooms
2
Baths
Villa-House
4/5 Reviews (5)
verified_user Book Online  
(€ 2,878  £ 2,443)
From
$ 3,150 /Week 
or $450 /night (Min Stay 30 nights)
4/5 Reviews (5)
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Islamorada FL, Florida USA

(minimum stay 30 nights)
ac_unit Air Conditioning
Islamorada Waterfront Paradise 2
iF YOUR PLANS CALL FOR LESS THAN A MONTH, PLEASE CONTACT ME. i MAY BE ABLE TO HELP. **PLEASE INQUIRE ABOUT SPECIAL DISCOUNTED RATES AND SEASONAL AVAILABILITY** Please contact us for all of our rates! For shorter stays...make sure you have a minimum of 28 days entered in your contact form! *We do not use the optional calendar feature on this listing. * This is a very popular rental, so book your preferred time well in advance of peak season! I reply to EVERY inquiry. If you do not receive a reply. EVERY RENTER IS PROVIDED WITH A COMPLIMENTARY BOTTLE OF WINE. Dive right into paradise while staying at Casa Rio. With a beautiful view of a sleepy natural waterway in the Florida Keys you can quickly relax and transform into 'island time.' This exclusive bayside home is situated in a secluded location on Islamorada with quick access to the Florida Bay and Atlantic Ocean. Your islan...

Booked      Available           highlight_off   
0/5
6
Sleeps
2
Bedrooms
2
Baths
pets
pool
Villa-House
0/5 Reviews (1)
verified_user Book Online  
(€ 640  £ 543)
From
$ 700 /Week 
or $100 /night (Min Stay 30 nights)
0/5 Reviews (1)
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Islamorada FL, Florida USA

(minimum stay 30 nights)
pool Swimming Pool
pets Pets Allowed
FLAMINGO COTTAGE
MINIMUM STAY: 28 DAYS "Flamingo Cottage" is an adorable 3 bedroom stilt home nestled among tropical foliage. There are two bedrooms and one bath on the main living level of this home plus a private studio type apartment with a private bath on the ground level. This home has a cozy cottage like feeling with an open living floor plan, small dining area with sliding doors to a balcony on the side of the house and a fully equipped kitchen. A brand new heated swimming pool has just been completed. New tropical foliage surrounds the property and there are numerous places to relax and enjoy the surroundings. You'll love the balcony off the kitchen with outdoor table and chairs for dining. There's also a balcony across the front of the house that offers views of the sunrise and partial ocean views. Outdoor seating areas are located throughout the property. There's a covered...

Booked      Available           highlight_off   
4
Sleeps
2
Bedrooms
2
Baths
pool
Villa-House
 
verified_user Book Online  
(€ 671  £ 570)
From
$ 735 /Week 
or $105 /night (Min Stay 7 nights)
 
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Islamorada FL, Florida USA

(minimum stay 7 nights)
pool Swimming Pool
ac_unit Air Conditioning
Sixth-floor oceanfront condo w/sweeping ocean views & shared pool
Tavernier Waterfront Retreat Treat yourself to a sun-filled vacation in this cute oceanfront condo with breathtaking ocean views and shared amenities that include a pool and barbecues. Here in the Sea Gull Condos complex, you'll be less than one mile off Old Highway 1 in the upper Florida Keys, and you'll enjoy all the comforts of home. Decorated with light blues, sea foam green pastels, and casual wicker furniture, this cute condo will make you feel right at home while you enjoy the calming perks of living in oceanside luxury. Enjoy the flatscreen cable TV in the living room, or curl up for a reading session with a book from the bookcase. Take a break from it all and lounge on the balcony, which is accessible through sliding glass doors. And if you want to stay plugged in, no problem, as you'll have WiFi access. The kitchen bar seats four and is open, bright, and roomy, with...

Booked      Available           highlight_off   
5/5
6
Sleeps
3
Bedrooms
2
Baths
Villa-House
5/5 Reviews (2)
verified_user Book Online  
(€ 1,919  £ 1,629)
From
$ 2,100 /Week 
or $300 /night (Min Stay 7 nights)
5/5 Reviews (2)
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Islamorada FL, Florida USA

(minimum stay 7 nights)
ac_unit Air Conditioning
107 San Remo Drive
Comfortable Venetian Shores canal home that has two bedroom/one bath upstairs and a one bedroom/one bath apartment downstairs. The downstairs apartment has a complete kitchen and living room and separate bedroom. There is a screened in porch of the living room upstairs. The home has awesome dockage that is 70'. Easy ocean or bay access via Snake Creek. Walking distance to Founder's Park which you get free access into the park and there is a small beach area. If booking more than a year in advance current prices may not reflect annual cost of living increase. Many of our guests re-book the same property on an annual basis. No reservation is confirmed until you speak with us. Amenities: AIR CONDITIONING DISHWASHER INTERNET ACCESS MICROWAVE TOASTER WIFI Suitabilities: ALL...

Booked      Available           highlight_off   
8
Sleeps
4
Bedrooms
3
Baths
pool
Villa-House
 
verified_user Book Online  
(€ 4,566  £ 3,877)
From
$ 4,998 /Week 
or $714 /night (Min Stay 7 nights)
 
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Islamorada FL, Florida USA

(minimum stay 7 nights)
pool Swimming Pool
50 Schooner Bay
Dubbed Aguazul, the home has four bedrooms and three bathrooms.  Two separate kitchens, one on each of the home's two levels, are another unique feature. Cool off in the home's oceanfront swimming pool, fish or swim from its dock, play in the sand of its private beach or merely sip a beverage on one of the home's four balconies and patios. Whatever your choice, at Aguazul you'll feel the cooling breezes of the Atlantic day and night. When the time comes to adjourn inside, the home still provides stunning ocean views, plus plenty of lounging options. Downstairs, a cozy living area is separated from the elegant dining room by a central staircase. Upstairs, another living room features the largest of the home's four flat screen televisions. The upstairs also has two bedroom suites. The smaller suite has direct access to a wraparound second-level balcony. The master suit...

Booked      Available           highlight_off   
4/5
4
Sleeps
2
Bedrooms
2
Baths
Villa-House
4/5 Reviews (17)
verified_user Book Online  
(€ 1,464  £ 1,243)
From
$ 1,603 /Week 
or $229 /night (Min Stay 7 nights)
4/5 Reviews (17)
verified_user Book Online  

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Islamorada FL, Florida USA

(minimum stay 7 nights)
132 Columbus Drive
Beautifully renovated home sits right on the ocean. With panoramic ocean views from every room in the house, you'll never want to leave. This 2 bedroom, 2 bath home has a great back porch, large yard, and shaded carport/ sitting area. Located in Lower Matecumbe, this house is close to downtown Islamorada, with shopping, grocery stores, marinas and more! VACATION RENTAL LICENSE: VR-068 Additional amenities: Beach Chairs Amenities: DISHWASHER INTERNET ACCESS MICROWAVE TOASTER WIFI Suitabilities: ALL...

Booked      Available           highlight_off   
5/5
18
Sleeps
5
Bedrooms
6
Baths
pets
Villa-House
5/5 Reviews (2)
verified_user Book Online  
(€ 6,171  £ 5,239)
From
$ 6,755 /Week 
or $965 /night (Min Stay 7 nights)
5/5 Reviews (2)
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Islamorada FL, Florida USA

(minimum stay 7 nights)
pets Pets Allowed
Little Bay Compound
Located just off US-1 behind a gated fence awaits a Fantastic Keys Getaway. Little Bay is a private compound situated on a beautiful 1-acre piece of paradise on the Florida Bay. The property has a total of three separate rental units, accommodating a total of 18 people. The Upper Duplex & The Lower Duplex are each 1,500 sq ft units, each with 2 bedrooms, 2 full baths, full modern kitchen, laundry, family room, and 10' x 40' porch overlooking the Bay. Each unit accommodates 6 people (Upper master bedroom: King and twin Murphy, Guest bedroom: 2 twins, sofa sleeper) (Lower master bedroom: Queen and twin Murphy, guest bedroom: 2 twins, sofa sleeper) The Cottage is a bright and airy 1,250 sq ft unit with a huge Master bedroom (king & sofabed), 2nd Sun Room with sofabed and twin Murphy bed, 2 full baths, laundry room, and combined family room, kitchen, & great room. The Cottage a...

Booked      Available           highlight_off   
4
Sleeps
2
Bedrooms
2
Baths
Condo
 
verified_user Book Online  
(€ 4,796  £ 4,072)
From
$ 5,250 /Week 
or $750 /night (Min Stay 7 nights)
 
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Islamorada FL, Florida USA

(minimum stay 7 nights)
ac_unit Air Conditioning
Discover the Charm of Island Living
Privately owned condominium unit at the Futura Yacht Club in the Village of Islamorada. Futura is located on the Gulf of Mexico and is a gated complex consisting of 70 units. Enjoy wonderful Bay views and sunsets from our two bedroom / two bath condominium unit that sleeps up to 6 people. Stay in touch with family & friends with free wireless internet. The master bedroom has a king size bed with two twin beds in the 2nd bedroom. If your children are small, we have a crib, hi chair and various toys, videos and games. Our condo has a full kitchen with stove, dishwasher, microwave, coffee maker, blender & breakfast bar. All linens & utensils are provided. There is a separate dining room that seats 5 people. Vacation Rental License #VR-006 Amenities: Heated Pool, Beach, Tennis Courts - Lighted, Basketball & Volleyball Courts, Boat Dockage (Advance Request), Boat Ramp, Private Balcony, Centr...

Booked      Available           highlight_off   
8
Sleeps
4
Bedrooms
4
Baths
pool
Villa-House
 
verified_user Book Online  
(€ 2,398  £ 2,036)
From
$ 2,625 /Week 
or $375 /night (Min Stay 28 nights)
 
verified_user Book Online  

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Islamorada FL, Florida USA

(minimum stay 28 nights)
pool Swimming Pool
100 Palo De Oro Drive
Looking for an amazing home in Venetian Shores? This beautifully updated 4 bedroom, 4 bath home has everything you need for a perfect vacation. This home is suited for entertaining, with a spacious kitchen, open living and dining room and large screened in porch overlooking the canal. The 3rd floor floor is a lofted master bedroom suite with a walk-in closet. The 1st floor has a beautiful kitchen along with it's own living room, bedroom and full bath. Splash in your own private pool or enjoy a relaxing glass of wine in the jacuzzi. You have about 35'' of dockage available for your boat. This great Venetian Shores home is waiting for you. Minimum 28 nights If booking more than a year in advance current prices may not reflect annual cost of living increase. Many of our guests re-book the same property on an annual basis. No reservation is confirmed until you speak with us. Am...

Booked      Available           highlight_off   
5/5
4
Sleeps
1
Bedrooms
1
Baths
pool
Apartment
5/5 Reviews (3)
verified_user Book Online  
(€ 1,119  £ 950)
From
$ 1,225 /Week 
or $175 /night (Min Stay 7 nights)
5/5 Reviews (3)
verified_user Book Online  

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Islamorada FL, Florida USA

(minimum stay 7 nights)
pool Swimming Pool
ac_unit Air Conditioning
Come relax in Islamorada, the tropical jewel of the Florida Keys!!
Beautiful 1 BDRM apartment located in Islamorada. Full kitchen and 1 full bath. Home is located on canal within 100 yards of the ocean. You will enjoy access to fully screened and heated pool. WiFi and cable TV included. Close proximity to shopping, restaurants and all the best the Keys have to offer. House is located on private, residential street. One of the best locations in all of Islamorada for family fun. *PLEASE NOTE: CURRENTLY THE VILLAGE OF ISLAMORADA ALLOWS FOR RENTALS ONLY ONCE EVERY 28 DAYS. IF YOU WISH TO BOOK FOR A WEEK OR MORE (LESS THAN 28 DAYS), PLEASE REQUEST BOOKING AND I WILL LET YOU KNOW ABOUT AVAILABILITY. CALANDER MAY NOT BE ACCURATE DUE TO THESE REQUIREMENTS. SORRY FOR ANY INCONVENIENCE. THANK YOU.* Amenities: PRIVATE OUTDOOR POOL HEATED PRIVATE YARD AIR CONDITIONING INTERNET ACCESS PARKING SATELLITE TV WIFI ELDERLY A...

Booked      Available           highlight_off   
5/5
8
Sleeps
3
Bedrooms
2
Baths
pets
pool
Villa-House
5/5 Reviews (2)
verified_user Book Online  
(€ 1,273  £ 1,080)
From
$ 1,393 /Week 
or $199 /night (Min Stay 30 nights)
5/5 Reviews (2)
verified_user Book Online  

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Islamorada FL, Florida USA

(minimum stay 30 nights)
pool Swimming Pool
pets Pets Allowed
MANATEE MANOR
Minimum Rental: 28 Days "Manatee Manor" is a 3 Bedrooms and 2 ˝ Baths home with POOL, Dock, and all new furnishings make this your opportunity to experience The Florida Keys at its best. Conveniently located on a deep and wide canal with easy access to the Bay or a short ride to Tavernier Creek to cut over to the Ocean provides easy access to all water sports. Relax by the sparkling pool on one of the lounge chairs or curl up on the outdoor sofa or one of the chairs in the covered area and read a book or plan your next adventure. This home is all about convenience and comfort. Indoors you'll enjoy the open concept living with spacious gourmet kitchen, living and dining areas and the split bedroom plan. There's a large flat screen TV and entertainment center in the open area and access to the screened balcony. The kitchen bar has chairs (not stools) surrounding the o...

Booked      Available           highlight_off   
5/5
10
Sleeps
4
Bedrooms
3
Baths
pets
pool
Villa-House
5/5 Reviews (2)
verified_user Book Online  
(€ 1,675  £ 1,422)
From
$ 1,834 /Week 
or $262 /night (Min Stay 30 nights)
5/5 Reviews (2)
verified_user Book Online  

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Islamorada FL, Florida USA

(minimum stay 30 nights)
pool Swimming Pool
pets Pets Allowed
LYONS LANDING
Minimum Rental: 28 Days "Lyons Landing" is an exceptional VENETIAN SHORES single family home with pool, dock, boat lift and outdoor living area! Everything you need for a spectacular vacation awaits you in this extraordinary home. 3 bedrooms and two baths on the upper level plus a bedroom and bath on the ground level offer comfortable sleeping accommodations for up to 10. This home features open concept living on the main living level with high end furnishings plus a magnificent screened balcony with dining facilities and comfortable sitting areas overlooking the pool and dock. On the ground level, you'll love the covered outdoor living area with flat screen TV and outdoor furnishings. The bar with bar stools, ice machine, large gas BBQ grill, padded lounge chairs and an umbrella complete the outdoor furnishings. The concrete dock offers a fish cleaning station, water...

Booked      Available           highlight_off   
4/5
6
Sleeps
3
Bedrooms
2
Baths
pets
pool
Apartment
4/5 Reviews (4)
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(€ 1,509  £ 1,281)
From
$ 1,652 /Week 
or $236 /night (Min Stay 28 nights)
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Islamorada FL, Florida USA

(minimum stay 28 nights)
pool Swimming Pool
pets Pets Allowed
ac_unit Air Conditioning
3 bedrooms at Ocean Harbour Apartment, Islamorada, Florida Keys.
Located in Islamorada, Florida Keys, Ocean Harbour is our beautiful and luxurious home away from home surrounded by the tropical beauty of the Florida Keys. The location is in the perfect proximity for visiting Key West & Miami. With its exceptional location and gated security, this premium condominium is a haven of paradise. Enjoy this beautifully furnished, second floor, 3 bedroom, 2 bathroom, 1810 square foot condominium. The master bedroom has a king size bed and the 2nd bedroom has a queen size bed and there are 2 twins (singles) in the third. There is an allocated ground level parking space and room for guest vehicles. There is a lift to the well appointed and extremely comfortable apartment with Wi-Fi internet and tvs. There is a heated pool in the grounds and 2 tennis courts. We have a 30 -35 foot boat slip available for use which is visible from the balcony of the apartment. ...

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8
Sleeps
3
Bedrooms
3
Baths
Villa-House
 
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(€ 857  £ 728)
From
$ 938 /Week 
or $134 /night (Min Stay 30 nights)
 
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Islamorada FL, Florida USA

(minimum stay 30 nights)
Lower Mat Canal Front Home w/ 60' dock and access to private beach on the bay!
THIS HOME ONLY OFFERS MONTHLY RENTALS. Islamorada is known as the 'Sport Fishing Capital of the World.' This property is located just minutes from the Atlantic Ocean, where you can head off shore to the Gulf Stream and reel in the big game, or travel into the Florida Bay, where you will find vast amounts of flats for fishing. Charter Boats and rental boats are within a 1/2 a mile or bring your own and enjoy our 60' concrete dock with fish cleaning station. Boat ramps are close by. For the dive and snorkel enthusiasts there are many reefs to explore; Alligator Reef, Tennessee Reef, Hens and Chickens are just to name a few. Islamorada is the best place to boat - there are many bridges to access the ocean / bay; number of restaurants on the water to enjoy cocktails, fabulous foods and live entertainment. There is also a Homeowner's Beach directly on the Bay. Sandy beach, grills and picn...

Booked      Available           highlight_off   
4/5
8
Sleeps
3
Bedrooms
2
Baths
pool
Apartment
4/5 Reviews (3)
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(€ 576  £ 489)
From
$ 630 /Week 
or $90 /night (Min Stay 28 nights)
4/5 Reviews (3)
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Islamorada FL, Florida USA

(minimum stay 28 nights)
pool Swimming Pool
ac_unit Air Conditioning
Executive Bay Townhouse w/Heated Pool, Private Beach, Tennis, Fishing Dock & nea
Come and relax at our beautiful townhome in The Executive Bay Club on mile marker 87 in the Florida Keys. The Executive Bay Club is located in Islamorada, the Sport Fishing Capital of the World. It is a private, gated community and the grounds have 2 tennis courts, a swimming pool, a clubhouse, a private beach area and a fishing dock. The waters are filled with plant and marine life, ideal for snorkeling. Boats may not be docked unfortunately. Accommodation - Sleeps 8 - All bedrooms are upstairs Master Bedroom: (Upstairs) - Two Queen Size Beds - Flat Screen TV Second Bedroom: (Upstairs) - Queen Size Bed - Flat Screen TV Loft Bedroom: (Upstairs) - Two Twin Size Beds Guest Bathroom (Upstairs): - Standup Shower Guest Bathroom (Downstairs): - Standup Shower Living Room: - Sectional Sofa - Flat Screen TV Dining Room: - Dining Table with Seating for 8 Kitchen: - Fully equipped (all...

Booked      Available           highlight_off   
5/5
6
Sleeps
3
Bedrooms
2
Baths
pets
Villa-House
5/5 Reviews (6)
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(€ 1,675  £ 1,422)
From
$ 1,834 /Week 
or $262 /night (Min Stay 30 nights)
5/5 Reviews (6)
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Islamorada FL, Florida USA

(minimum stay 30 nights)
pets Pets Allowed
MY PARADISE
Minimum Rental: 28 Days "My Paradise" is an oceanfront beach house with protected dockage 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 moment you arrive, you'll know you made the right decision. Spend a month or longer, escape from the city or the snow and ice, relax and enjoy life. The home is built on a direct oceanfront lot with the most magnificent views you can imagine. MY PARADISE is a comfortably furnished stilt home designed to take full advantage of the unobstructed ocean views. This home "lives" outside. The master suite and living area open to an oversized deck. A wall of glass doors by the dining area folds open to completely expose the interior living space to the outside. You ca...

Booked      Available           highlight_off   
4/5
8
Sleeps
3
Bedrooms
3
Baths
pets
pool
Villa-House
4/5 Reviews (3)
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(€ 1,177  £ 999)
From
$ 1,288 /Week 
or $184 /night (Min Stay 30 nights)
4/5 Reviews (3)
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Islamorada FL, Florida USA

(minimum stay 30 nights)
pool Swimming Pool
pets Pets Allowed
BLUE WATER RETREAT
Minimum Rental: 28 Days "Blue Water Retreat" is all about the location, location, location! This home has it all - ocean side Lower Matecumbe location, 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 this home. It is located on a canal front lot, offers dockage for a boat up to 30' and easy access to the ocean - a straight shot of about 200 yards to open water from the dock. The wrap-around screened balcony provides a respite after a day on the water. Take a dip in the pool and enjoy some afternoon refreshment. Grill your day's catch on the gas grill and dine at home or take it to one of our many fine local restaurants and let the chef cook it to your specifications. This is a stilt house with the main living area on the 2nd level. You'll enjoy the open great ro...

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4
Sleeps
2
Bedrooms
2
Baths
pool
Apartment
 
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(€ 640  £ 543)
From
$ 700 /Week 
or $100 /night (Min Stay 30 nights)
 
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Islamorada FL, Florida USA

(minimum stay 30 nights)
pool Swimming Pool
BEACON REEF 306
Minimum Rental: 1 Month Enjoy a relaxing summer and fall here in the Keys at this immaculate and charming two bedroom and two bath condo. While the owners attend to their other property "up north" you can relish all the delightful amenities of their condo. This unit is beautifully appointed and offers comfortable accommodations - fully equipped kitchen, full size washer and dryer, king size bed in the master and queen bed for your guests. Located in the heart of Islamorada, you'll love the charm of an ocean front complex with the large freeform pool, hot tub, sandy beach and dock privileges. There's even a well-equipped gym for exercise enthusiasts. You'll find this location exceptionally convenient to fabulous dining and recreational opportunities. Sit by the pool, on the sandy beach or on the screened balcony of your unit and enjoy the magnificent tropical view...

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8
Sleeps
3
Bedrooms
2
Baths
Villa-House
 
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(€ 2,558  £ 2,172)
From
$ 2,800 /Week 
or $400 /night (Min Stay 30 nights)
 
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Islamorada FL, Florida USA

(minimum stay 30 nights)
ac_unit Air Conditioning
Gorgeous waterfront home
Beautiful and spacious home with three bedrooms, two and half baths, huge new kitchen, new bathrooms, and screened in porches facing East and West. There are great views from every room!!! Tastefully furnished with all linens, comfortable memory foam mattresses, all new appliances, and completely remodeled in 2015. For entertainment there is a brand new big-screen TV, premium cable channels HBO and Showtime, and high speed Wi-Fi. The house is on a dead end street with the ocean on one side and a big lagoon on the other. No highway noise! Situated in a quiet neighbourhood, yet just minutes to Islamorada restaurants, night life and shopping. Beautiful water views from both sides of the home. Sixty five feet of protected concrete dock (no wave action), with lighted cleaning station, and direct ocean access just two hundred yards away on the Atlantic side . It is literally minutes to grea...

Booked      Available           highlight_off   
3/5
8
Sleeps
4
Bedrooms
3
Baths
pets
Villa-House
3/5 Reviews (2)
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(€ 64  £ 54)
From
$ 70 /Week 
or $10 /night (Min Stay 7 nights)
3/5 Reviews (2)
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Islamorada FL, Florida USA

(minimum stay 7 nights)
pets Pets Allowed
ac_unit Air Conditioning
Oceanfront Islamorada Home with Private Beach - Great for Kite Surfing!
We help make the most of your vacation by providing Free Admission to some of the area's top attractions each and every day! Create exciting memories, have more fun, and truly experience your destination! **Free Fun Rules and Restrictions Apply ** Beautiful four bedroom, Ocean Front home with private beach in sunny Islamorada (near Key Largo, on mile marker 74). Come and relax at our beautiful ocean front home with breathtaking, panoramic views of the Atlantic ocean. This spit level home is located in Islamorada; the Sport Fishing Capital of the World. It is a private home with private beach access, ideal for kite boarding enthusiasts, tucked away in a lovely neighborhood just off of the main road.If you are accustomed to quality, and want to stay in a beautiful place that is centrally located, this is the place for you. Everything you need is right here waiting. *No weddings or e...

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12
Sleeps
5
Bedrooms
4
Baths
pool
Villa-House
 
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(€ 2,430  £ 2,063)
From
$ 2,660 /Week 
or $380 /night (Min Stay 3 nights)
 
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Islamorada FL, Florida USA

(minimum stay 3 nights)
pool Swimming Pool
ac_unit Air Conditioning
Islamorada Beach House
VACATION HOME RENTAL . The home is located in one of the finest Private Community of the Florida Keys- Port Antigua in Islamorada with Private Beach, BBQ area, Boat Ramp and much more. Watch the sunrise from the 2 spacious Balconies. This comfortable 4,200 sq ft sleeps 12 people comfortably with 5 bedrooms and 4 baths. Home does not have a No Pool or Dock but you have a beautiful private beach area just 1 min driving distance and 5min walking. Residents have access to boat ramp located in the private community for boat docking. Amenities: PRIVATE YARD SECURE PARKING AIR CONDITIONING INTERNET ACCESS PARKING SATELLITE TV WIFI ELDERLY ACCESSIBLE Suitabilities: ALL...

Booked      Available           highlight_off   
6
Sleeps
3
Bedrooms
3
Baths
pool
Villa-House
 
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(€ 2,238  £ 1,900)
From
$ 2,450 /Week 
or $350 /night (Min Stay 30 nights)
 
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Islamorada FL, Florida USA

(minimum stay 30 nights)
pool Swimming Pool
ac_unit Air Conditioning
Paradise Found - Sandy Beach, Beachside Bar, Great Views, And Dock
3 Bedrooms, 3 Bathrooms, Sleeps 6 MINIMUM STAY REQUIRED - NOT A SHORT TERM RENTAL - PLEASE CONTACT US FOR SPECIFIC DATES, AVAILABILITY AND RATES. Every time we stay, we never want to leave. 3 story bayside villa with its own beach. Great location. Views of both the Bay and the Ocean. Three good sized bedrooms and 3 baths. Each bedroom has its own distinctive views. Downstairs - Beach, Covered Beachside bar and dining area, with TV, jacuzzi, BBQ, private outdoor shower, and pool table. 120 foot dock shared with neighbor that extends out towards the Bay. Great for fishing and with dockage for a 28 ft to 30 ft boat. Second Floor - Living Room, Dining Room, and 2 bedrooms - each with large covered balconies - one facing the Bay and the other the Ocean. Third Floor - Large bedroom with bath with balcony facing Ocean and huge terrace facing the Bay. This is a special place in a great locatio...

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8
Sleeps
3
Bedrooms
2
Baths
pool
Apartment
 
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(€ 844  £ 717)
From
$ 924 /Week 
or $132 /night (Min Stay 30 nights)
 
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Islamorada FL, Florida USA

(minimum stay 30 nights)
pool Swimming Pool
ac_unit Air Conditioning
DEC & APRIL DEAL MONTH MINIMUM ENJOY! 9545791140
ENJOYABLE, CENTRAL LOCATION, PLANTATION KEY, 3 bedroom + loft, 2 bath; 1400 sf 2 story, all bedrooms and 1 full bath are upstairs & downstairs is the living area and 1 additional full bath. The unit is clean, comfortable, quiet and restful. The community is gated with security, no pets are allowed; great pool , tennis, clubhouse, dock and beach area. Amenities: BBQ HAIRDRYER IRON PRIVATE FISHING PRIVATE OUTDOOR POOL HEATED PRIVATE OUTDOOR POOL UNHEATED PRIVATE TENNIS SECURE PARKING SHARED OUTDOOR POOL HEATED SHARED OUTDOOR POOL UNHEATED SHARED TENNIS DSC RURAL DSC WINTER SUN FRIDGE AIR CONDITIONING BALCONY TERRACE CENTRAL HEATING DRYER DISHWASHER DVD INTERNET ACCESS LINENS PROVIDED TOWELS PROVIDED MICROWAVE PARKING SATELLITE TV TOASTER TV WASHING MACHINE STO...

Booked      Available           highlight_off   
6
Sleeps
2
Bedrooms
3
Baths
pool
Villa-House
 
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(€ 2,334  £ 1,982)
From
$ 2,555 /Week 
or $365 /night (Min Stay 7 nights)
 
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Islamorada FL, Florida USA

(minimum stay 7 nights)
pool Swimming Pool
ac_unit Air Conditioning
Keys home in Anglers Reef with ocean view, dock, community pool & private beach
Keys home in Anglers Reef with ocean view, dock, community pool & private beach This magnificent home with ocean views from all 4 balconies is located in Islamorada at Mile Marker 85 in the exclusive gated community of Angler's Reef, a quiet oceanfront community in the Florida Keys. Anglers Reef is a boutique complex of 52 homes inspired by Native Conch & British West Indies architecture. Quaint streets & walking paths wind through this village-styled retreat. Amenities include a community pool overlooking the Atlantic Ocean and 500ft of private beach. The home's boat slip is available for rent with a deep channel out to the Atlantic ($250/week). Or launch your kayak from the private beach (kayak rentals available for drop-off). Built in 2007, this home has 2 bedrooms located on the 2nd floor (Master has Tempur-Pedic Mattress), each having a private porch with an ocean view, and has 2 m...

Booked      Available           highlight_off   
5/5
10
Sleeps
4
Bedrooms
4
Baths
pets
pool
Villa-House
5/5 Reviews (3)
verified_user Book Online  
(€ 4,937  £ 4,191)
From
$ 5,404 /Week 
or $772 /night (Min Stay 7 nights)
5/5 Reviews (3)
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Islamorada FL, Florida USA

(minimum stay 7 nights)
pool Swimming Pool
pets Pets Allowed
Paradise Beach Sandy Oceanfront
Endless open water views with spectacular sunrises and sunset colored skies await in this private gated estate. Sink your toes into the natural sand beach. Enjoy your privacy at the heated pool and spa among lush tropical vegetation and palm trees. This Key West styled house offers stunning architectural details, complete with shutters, woodwork and Chicago brick pavers. You can swim. snorkel, paddle board, kayak, walk the beach, and enjoy the spectacular sun rise. You can grille out by the pool or eat at the wonderful Islamorada restaurants. The pool and spa are saltwater that is gentle for swimming. Biking, jogging or walking path located just across the street. Amenities: BBQ IRON JACUZZI AREA FISHING NEAR AREA WATERSPORTS NEAR DSC CITY DSC BEACHFRONT FRIDGE BALCONY TERRACE DRYER DISHWASHER LINENS PROVIDED TOWELS PRO...

Booked      Available           highlight_off   
5/5
8
Sleeps
3
Bedrooms
3
Baths
pool
Villa-House
5/5 Reviews (9)
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(€ 2,974  £ 2,525)
From
$ 3,255 /Week 
or $465 /night (Min Stay 7 nights)
5/5 Reviews (9)
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Islamorada FL, Florida USA

(minimum stay 7 nights)
pool Swimming Pool
ac_unit Air Conditioning
Islamorada Luxury Home Ocean & Bay Access
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' of dock, less than two minutes to the ocean or the bay. Three stories with tremendous water views. Canal is 25 feet deep and can accommodate any size boat or yacht up to 90 feet. Owner in the Keys over 20 years and is a south Florida businessman. We are the owners, not a broker. You can get us at 888 then 226 and last 9010 Beds: 2 King Beds, 2 Twin Beds, 1 Sofa Bed Amenities: BBQ BOAT HAIRDRYER IRON PRIVATE OUTDOOR POOL HEATED AREA FISHING NEAR AREA GOLF FAR AREA HORSE RIDING NEARBY AREA TENNIS NEAR AREA WATERSPORTS NEAR DSC CYCLING DSC HIKING FRIDGE<b...

Booked      Available           highlight_off   
4
Sleeps
2
Bedrooms
3
Baths
pets
pool
Condo
 
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(€ 620  £ 527)
From
$ 679 /Week 
or $97 /night (Min Stay 120 nights)
 
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Islamorada FL, Florida USA

(minimum stay 120 nights)
pool Swimming Pool
pets Pets Allowed
Wake up in Paradise! Florida Keys - Islamorada (6 month minimum rental)
(6 month minimum rental) - $2,900 per month (without boat slip). Slip an additional $200 a month. Situated on a quiet street in Port Antigua, unwind in this fully renovated 3-story townhouse. The unique three story layout has a large entertainment living area with a half-bath, pool table, bar and living area and two terraces on the first floor, a spacious bedroom, full-bath, updated kitchen, living area, and large terrace overlooking the cove and ocean on the second floor, and a spiral staircase which leads you to the large master bedroom with walk-in closet, full-bath, and large terrace on the third floor. Wake up each morning enjoying your coffee with a unique and spectacular ocean view. Looking to get away from the harsh winter? It's a little sanctuary where you can relax, decompress, and immerse yourself in the true Florida Keys' life. Seasonal - 6 months rental. Amenities:...

Booked      Available           highlight_off   
5/5
2
Sleeps
1
Bedrooms
1
Baths
Villa-House
5/5 Reviews (33)
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(€ 1,439  £ 1,222)
From
$ 1,575 /Week 
or $225 /night (Min Stay 30 nights)
5/5 Reviews (33)
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Islamorada FL, Florida USA

(minimum stay 30 nights)
ac_unit Air Conditioning
Islamorada Waterfront Paradise Getaway!
Please contact us for all of our rates for different length of stays! For shorter stays...make sure you have a minimum of 28 days entered in your contact form! This is a very popular rental, so ask about your preferred dates early! This best Islamorada waterfront location, has quick easy access to the Bay, Ocean, backcountry, Marine Sanctuary, Everglades National Park, close to amenities & fine dining. Fishing & diving capital of the world...something for everyone! If you do not receive a prompt reply, please contact again, and if you have problems with the form, make sure to put 28 days+ in the date range. Email for additional pictures of this wonderful retreat & links to videos of a manatee family of 3 adults & baby visiting our dock! This wonderful island studio bedroom, at the side of a beautiful, bayfront lagoon home, features a private patio entrance & French doors with scree...

Booked      Available           highlight_off   
5/5
5
Sleeps
2
Bedrooms
3
Baths
pool
Villa-House
5/5 Reviews (26)
verified_user Book Online  
(€ 2,193  £ 1,862)
From
$ 2,401 /Week 
or $343 /night (Min Stay 7 nights)
5/5 Reviews (26)
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Islamorada FL, Florida USA

(minimum stay 7 nights)
pool Swimming Pool
ac_unit Air Conditioning
Luxurious Anglers Reef with Boat Slip, Pool, Ocean
House, 2 Bedrooms + Convertible Bed(s), 2.5 Baths (Sleeps 5) Islamorada home set in OceanFront gated community with swimming pool and private boat dock This charming home has 2 Bedrooms, 2.5 Bathrooms, A/C, Granite work tops, modern stainless steel appliances. Open porches and balconies, rich hard wood floors, dining room seating for 5, tasteful décor, delightful ‘gingerbread style ‘ house. A truly unique place to stay in the keys, with a boutique – style feel. Anglers Way is a private gated community, which comprises of 52 luxurious homes. Set in meticulously landscaped gardens, overlooking a private heated swimming pool, 2 private beaches and the magnificent Atlantic Ocean. Aptly named, Anglers Way is the perfect base for all fishing enthusiasts and anyone who enjoys beautiful sunrises, the wonderful Florida sun, kayaking, paddle boarding, jet skiing – the list is endless. You may...

Booked      Available           highlight_off   
4
Sleeps
2
Bedrooms
2
Baths
pets
Villa-House
 
verified_user Book Online  
(€ 1,119  £ 950)
From
$ 1,225 /Week 
or $175 /night (Min Stay 21 nights)
 
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Islamorada FL, Florida USA

(minimum stay 21 nights)
pets Pets Allowed
ac_unit Air Conditioning
Relaxation in the Keys! MM 74 1/2
2 bedroom / 2 bath / light and airy - large balcony backing up to a quiet nature preserve. Perfect home for a getaway! Centrally located in gorgeous Islamorada. Two bedroom / two bath. Gorgeous private homeowners beach and private dock, close to the best restaurants, and sightseeing. Our home backs up to a nature preserve and is 30 feet from our dock. Peaceful, quiet and relaxing! Just what is needed to take your mind off of the business of the world - turquoise, warm waters. Read a book, swim, kayak, explore the Keys... you can stay as busy or as relaxed as you like. Amenities: IRON PRIVATE YARD AREA FISHING NEAR FRIDGE AIR CONDITIONING BALCONY TERRACE CENTRAL HEATING DRYER DISHWASHER INTERNET ACCESS LINENS PROVIDED TOWELS PROVIDED MICROWAVE PARKING SATELLITE TV TOASTER TV WASHING MACHINE WIFI S...

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Welcome to our Islamorada FL vacation rentals and American vacation home rentals page.

Find Islamorada FL villa rentals using the search facility or use the region links to browse through specific Islamorada FL vacation region. We advertise holiday home ads listed direct by owners or agents. Vacation rentals in Islamorada FL are all furnished self catering lets in Islamorada FL that rent on short term bases and all of our listings come with weekly prices and pictures. To search for a specific type of vacation accommodation, select your letting type, Villa, House, Apartment, Condo, Townhouse, Barn, Farm, Chateau, Island, Castle, Flat, Penthouse, Hotel or even beach front mansions, lakeside cabins or winter skiing chalets. You can also search for condo rentals with pools or other suitability using our advanced search facility, Golfing getaways, Fishing Cabins, surfing and beachfront condos. All of our Islamorada FL holiday rental adverts are updated daily and you are free to contact the owner or agent directly. With a large selection of property adverts, from cheap Islamorada FL properties to luxury resort homes for rent in Islamorada FL . Property owners easily advertise your vacation home in Islamorada FL , see our advertising packages for full details.
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