50 Best Islamorada Vacation rentals on Holiday Lettings - House rentals

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407 Vacation rentals

(3) Very Good 

41

Vacation apartment in Islamorada

Florida Keys / Islamorada

3 6 14 nights min

  • 3 bedrooms
  • Sleeps 6
  • 14 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
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 …see more

from $198 / night

$1,385 - $2,085 / week

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from $198 / night

(2) Excellent 

14

Vacation condo in Islamorada

Florida Keys / Islamorada

2 5 5 nights min

  • 2 bedrooms
  • Sleeps 5
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
This condo has been completely restored after Hurricane Irma’s d is now ready for guests to return. There is new drywall, paint, carpets and new furniture and is safe to stay in. Paradise by the Atlantic Ocean and only 50' front the waters edge. Beautiful condominium …see more

from $150 / night

$1,000 / week

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from $150 / night

40

Vacation condo in Islamorada

Florida Keys / Islamorada

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
THE KING MASTER BEDROOM IS DRESSED IN ISLAND FINERY WITH PRIVATE BATHROOM, COMBINATION SHOWER/TUB, AND FLAT SCREEN TV MAKES FOR THE PERFECT RETREAT. THE SECOND BEDROOM OFFERS A QUEEN SIZE BED, A FLAT SCREEN TV, AND AN ATTACHED BATHROOM. YOU CAN “COOK YOUR CATCH” IN THE …see more

from $172 / night

$1,200 - $1,400 / week

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from $172 / night

(1) Excellent 

13

Vacation home in Islamorada

Florida Keys / Islamorada

2 6 28 nights min

  • 2 bedrooms
  • Sleeps 6
  • 28 nights min
  • Child friendly
  • Air conditioning
  • Pet friendly
The moment you step in the back yard, you'll know vacation has begun. . . time stands still as the laid-back island lifestyle takes over...Totally remodeled, canal-front home, quiet and in the nicest of neighborhoods (Plantation Key Colony). The 2 bed/2 bath stilted (up …see more

from $250 / night

$1,750 / week

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from $250 / night

24

Vacation home in Islamorada

Florida Keys / Islamorada

3 6 28 nights min

  • 3 bedrooms
  • Sleeps 6
  • 28 nights min
  • Child friendly
"The Beach Fixes Everything". That's the sign that greets visitors as they enter the living room of this newest Freewheeler Vacations home. But while the beach certainly is nice, an awesome vista doesn't hurt either. Located on a narrow residential peninsula in L …see more

from $183 / night

$1,281 / week

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from $183 / night

(2) Excellent 

33

Islamorada Vacation condo rental

Florida Keys / Islamorada

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Nearest beach 2 mi
  • Swimming pool
  • Child friendly
A Vacation Rental for View Lovers! FREE WIFI Best location in the complex. And new this year, a sandy beach. For two couples or a family with 2 kids. The two new extra long twin Pillow Top beds in 2nd bedroom convert to a comfy King Bed! Master bedroom has new Si …see more

from $129 / night

$900 - $1,900 / week

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from $129 / night

(4) Excellent 

19

Condo rental in Islamorada

Florida Keys / Islamorada

2 5 7 nights min

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Huge screened in terrace. Spacious and extremely clean.. Peaceful and away from the highway. Sleeps 2-5 people. , large pool on the ocean, . many water-front restaurants and bars nearby. Oceanfront mm 90, Plantation Key. Books up very quickly. Reserve early! Note: We a …see more

from $142 / night

$994 - $1,500 / week

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Responds fast!
avg. 2 hours 22 minutes

from $142 / night

23

Vacation townhouse rental

Florida Keys / Islamorada

2 6 30 nights min

  • 2 bedrooms
  • Sleeps 6
  • 30 nights min
  • Nearest beach 0.5 mi
  • Swimming pool
  • Child friendly
Wonderful two story townhome in a private, gated community with all of the amenities you'd expect while on vacation. Inside: Newly renovated and remodeled unit. Fully equipped kitchen and stainless appliances, large storage cabinets with pull outs. Granite counters e …see more

from $117 / night

$819 / week

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from $117 / night

(1) Excellent 

25

Vacation home rental

Florida Keys / Islamorada

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Swimming pool
  • Ask about children
Minimum Rental: 28 Days "The Palms #309" is an exceptional condo with panoramic views of the Atlantic Ocean. This condo is in one of the most popular condo complexes in Islamorada - The Palms of Islamorada. Comfortably furnished and ready for your arrival this unit …see more

from $81 / night

$567 / week

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from $81 / night

(1) Excellent 

21

Vacation apartment in Islamorada

Florida Keys / Islamorada

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Ask about children
Minimum Rental: 28 Days "Beacon Reef 310" 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 …see more

from $106 / night

$742 / week

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from $106 / night

(1) Excellent 

36

Vacation home in Islamorada

Florida Keys / Islamorada

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Child friendly
  • Air conditioning
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 upstai …see more

from $235 / night

$1,650 - $2,310 / week

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from $235 / night

(1) Excellent 

25

Villa rental in Islamorada

Florida Keys / Islamorada

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
This beautiful villa has all new furnishings and is located in the exclusive oceanfront gated community of Angler's Reef in Islamorada at Mile Marker 84. Angler's reef is a luxury retreat resort framed by mangroves and the clear waters of the Atlantic ocean with 52 col …see more

from $279 / night

$1,995 / week

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Responds fast!
avg. 20 minutes

from $279 / night

25

Vacation home accommodation

Florida Keys / Islamorada

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool
2 bedrooms, 2 full bathrooms, 1 half bathroom, sleeps 6 This magnificent oceanfront home is at Mile Marker 85 in exclusive Angler's Reef - 52 homes . Quaint streets & walking paths wind through this village-styled retreat. Enjoy a drink in the lushly landscaped pool are …see more

from $300 / night

$2,100 - $2,500 / week

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Responds fast!
avg. 3 hours 12 minutes

from $300 / night

26

Vacation home in Islamorada

Florida Keys / Islamorada

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Child friendly
This magnificent home with direct ocean views from the master bedroom, living room and balconies is located in Islamorada at Mile Marker 85 in the exclusive gated community of Angler's Reef. Lie in bed and view the Ocean! Home also overlooks the community pool. Anglers …see more

from $458 / night

$3,200 / week

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from $458 / night

(4) Excellent 

19

Condo rental in Islamorada

Florida Keys / Islamorada

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Nearest beach 0 mi
  • Swimming pool
  • Child friendly
Beautiful / tropical decorated one bedroom, one bath water front condo in Summer Sea Condominiums located at Mile Marker 88.5 Bayside Islamorada, FL. Bayside means amazing open water views & world famous Florida Keys sunsets from your own private balcony overlooking the …see more

from $129 / night

$900 - $1,025 / week

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from $129 / night

(5) Very Good 

29

Vacation home in Islamorada

Florida Keys / Islamorada

2 6 30 nights min

  • 2 bedrooms
  • Sleeps 6
  • 30 nights min
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
  • Child friendly
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 entere …see more

from $450 / night

$3,150 / week

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from $450 / night

(7) Excellent 

18

Villa rental in Islamorada

Florida Keys / Islamorada

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Our unit is a short walk to the beach and dock... No view of the ocean from our unit. 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 clubh …see more

from $260 / night

$1,800 / week

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Responds fast!
avg. 57 minutes

from $260 / night

20

Apartment rental in Islamorada

Florida Keys / Islamorada

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Child friendly
  • Car not necessary
Welcome to beautiful Islamorada located in the Florida Keys. Islamorada is known as the "Sport Fishing Capital of the World". Our ocean contains the world's most sought-after gamefish including tuna, dolphin, Marlin, permit, tarpon and bonefish. In addition to fishing, …see more

from $250 / night

$1,550 / week

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from $250 / night

(13) Very Good 

22

Vacation villa in Islamorada

Florida Keys / Islamorada

1 3 30 nights min

  • 1 bedroom
  • Sleeps 3
  • 30 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
Located in beautiful Plantation Key, the first Island of Islamorada. An area of all waterfront homes Wifi, boat dock, trailer parking, and all amenities are included also, Lovely Tiki Hut overlooking the water. Plus a huge covered entertainment area compl …see more

from $125 / night

$875 / week

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from $125 / night

35

Vacation home accommodation

Florida Keys / Islamorada

4 8 28 nights min

  • 4 bedrooms
  • Sleeps 8
  • 28 nights min
  • Child friendly
  • Pet friendly
This is a very spacious and very well-maintained 4 bedroom, 3 bathroom home toward the mouth of the canal on a quiet street in Plantation Key (Tavernier). You and your group will enjoy stunning views from the main level, master suite, & rooftop sundeck. There is approxi …see more

from $175 / night

$1,225 / week

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from $175 / night

25

Vacation home with swimming pool in Islamorada

Florida Keys / Islamorada

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Pet friendly
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 …see more

from $100 / night

$700 / week

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from $100 / night

(5) Excellent 

20

Islamorada Vacation condo rental

Florida Keys / Islamorada

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Nearest beach 2 mi
  • Swimming pool
  • Child friendly
This premier luxury home is situated in a very quiet and peaceful gated community. All the rooms are very spacious with quality furnishings. A large double wide lanai with breathtaking views will make your getaway in the Keys. For your enjoyment it comes with private bo …see more

from $265 / night

$1,850 - $2,600 / week

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Responds fast!
avg. 1 hour 44 minutes

from $265 / night

(5) Excellent 

20

Islamorada Vacation condo rental

Florida Keys / Islamorada

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Luxurious end unit in Bay Harbour with a boat slip. Upon entering the unit you are greeted with the tranquil views of the harbor and ocean. Enjoy the ocean breeze from the large screen porch. Beautiful Bay Harbour gated condo community on lower Matecumbe, mm 74 1/2. …see more

from $249 / night

$1,800 - $3,500 / week

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Responds fast!
avg. 2 hours 40 minutes

from $249 / night

(2) Excellent 

25

Vacation apartment rental

Florida Keys / Islamorada

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Swimming pool
  • Ask about children
Minimum Rental: 28 Days "The Palms #314" is a 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 more

from $80 / night

$560 / week

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from $80 / night

(3) Very Good 

14

Vacation home in Islamorada

Florida Keys / Islamorada

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Fabulous vacation home in the exclusive gated oceanfront community of Anglers Reef at mile marker 85 in Islamorada of the Florida Keys. Luxurious beach decor, plush furnishings, spacious accommodations that comfortably sleep 6 adults and children of all ages will feel r …see more

from $202 / night

$1,414 / week

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from $202 / night

19

Home accommodation in Islamorada

Florida Keys / Islamorada

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Child friendly
Relax in this great townhouse style condo, which overlooks the sparkling Atlantic Ocean. This condo features 3 bedrooms and 2 bathrooms, a balcony off the living room, a private balcony off the master bedroom, and the quaintness of only 4 other units in the complex. Enj …see more

from $171 / night

$1,200 - $1,650 / week

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from $171 / night

(4) Excellent 

29

Home rental in Islamorada

Florida Keys / Islamorada

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Child friendly
OSPREY BAY VILLA! Wonderful bayfront home in the heart of Islamorada in the fabulous Florida Keys for rent by the week or monthly. Offering 5 bedrooms and 3 full baths on 2 living levels overlooking the Florida Bay with its incredible sunset views. Sleeps 10 people comf …see more

from $786 / night

$5,200 - $6,200 / week

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from $786 / night

(10) Excellent 

23

Islamorada Vacation villa rental

Florida Keys / Islamorada

1 3 7 nights min

  • 1 bedroom
  • Sleeps 3
  • 7 nights min
  • Ask about children
  • Pet friendly
Minimum Rental: 7 Days "Sunshine Place" is setup perfectly for 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 perf …see more

from $158 / night

$1,100 - $1,300 / week

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from $158 / night

15

Vacation condo in Islamorada

Florida Keys / Islamorada

1 5 30 nights min

  • 1 bedroom
  • Sleeps 5
  • 30 nights min
  • Beach/lakeside relaxation
  • Child friendly
****Recently updated paint, furniture and a Beauty Rest Mattress!!**** Looking to escape reality? Look no further! Spacious 1 bedroom/1 bathroom condo located in the newly renovated Summer Seas Condominiums. Sit back and relax at the pool, go swimming at the private bea …see more

from $129 / night

$903 / week

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from $129 / night

(1) Excellent 

13

Vacation townhouse in Islamorada

Florida Keys / Islamorada

2 5 30 nights min

  • 2 bedrooms
  • Sleeps 5
  • 30 nights min
  • Child friendly
Stunning townhouse that sits on the undisputed best beach in the keys. Boat slippage up to 26 feet. Pictures speak for themselves. The beauty of the Keys surrounds you. Easy access to the ocean side for offshore fishing, or simply fish the canal or the beach. 75 miles t …see more

from $105 / night

$735 / week

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from $105 / night

35

Vacation home rental

Florida Keys / Islamorada

2 6 28 nights min

  • 2 bedrooms
  • Sleeps 6
  • 28 nights min
  • Child friendly
This townhome at Executive Bay will sure make your home away from home!  This unit has been completely renovated and decorated beautifully.  This  2 bedrooms and 3 bathrooms has a (1) King Bed, (1) Queen Bed and  there is a bonus room off the Master that has 2 twin beds …see more

from $100 / night

$700 / week

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from $100 / night

(2) Excellent 

25

Vacation apartment in Islamorada

Florida Keys / Islamorada

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Ask about children
Minimum Rental: 28 Days "Beacon Reef 222" is an 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 co …see more

from $146 / night

$1,022 / week

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from $146 / night

24

Islamorada Vacation home rental

Florida Keys / Islamorada

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.25 mi
  • Child friendly
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 …see more

from $365 / night

$2,550 - $2,900 / week

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from $365 / night

17

Vacation home in Islamorada

Florida Keys / Islamorada

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Child friendly
Enjoy the spectacular view of the Florida Bay from this beautiful townhome. This townhome is a 2 bedroom and 2-1/2 bath unit.  There are tons of things to keep you and your family busy without having to leave the Futura Condo complex. There are tennis courts and a swimm …see more

from $175 / night

$1,225 - $2,025 / week

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from $175 / night

(1) Excellent 

25

Vacation apartment rental

Florida Keys / Islamorada

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Ask about children
Minimum Rental: 28 Days "Beacon Reef 501" is an 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 - gran …see more

from $110 / night

$770 / week

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from $110 / night

(31) Excellent 

28

Vacation home in Islamorada

Florida Keys / Islamorada

1 2 30 nights min

  • 1 bedroom
  • Sleeps 2
  • 30 nights min
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
  • Air conditioning
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 loc …see more

from $225 / night

$1,575 / week

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Responds fast!
avg. 3 hours 46 minutes

from $225 / night

30

Vacation home in Islamorada

Florida Keys / Islamorada

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Child friendly
Beautiful 3 bedroom 2.5 bath luxury condo at MM 74.5 Complex comes complete with two tennis courts, weight room, pool, dockage, fish cleaning station, and free Wi-Fi at community clubhouse (this unit does not have Wi-Fi inside the condo) . The condo boasts some amazing …see more

from $286 / night

$2,000 - $2,750 / week

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from $286 / night

(1) Excellent 

27

Islamorada Vacation home rental

Florida Keys / Islamorada

3 6 28 nights min

  • 3 bedrooms
  • Sleeps 6
  • 28 nights min
  • Nearest beach 1 mi
  • Swimming pool
  • Child friendly
Beautifully Decorated, Fully Furnish and Equipped Vacation Pool Home, Located in a Quiet and Safe Residential Area in Islamorada, Florida Keys. Video of house and area available upon request. It consists of Two Levels, Each Separate Level Has 3 Bedrooms/2 Bathrooms. …see more

from $225 / night

$1,700 - $2,035 / week

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Responds fast!
avg. 2 hours 38 minutes

from $225 / night

27

Vacation villa in Islamorada

Florida Keys / Islamorada

4 10 7 nights min

  • 4 bedrooms
  • Sleeps 10
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Live your tropical dream at this palatial oceanfront estate. Located near mile marker 89, on Islamorada's Millionaires' Row, this 4 bedroom / 6 bath home comes with just about every convenience you can imagine, as well as some you probably haven't even considered. Enjoy …see more

from $2,143 / night

$15,000 / week

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from $2,143 / night

(2) Excellent 

24

Islamorada Vacation villa rental

Florida Keys / Islamorada

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Ask about children
Minimum Rental: 7 Days "Little Bay's Cottage" is one of three rental units on this property. The cottage is a ground level dwelling separate from two duplex units. It offers a unique floor plan with the main living area in the center of the house with kitchen, din …see more

from $358 / night

$2,500 / week

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from $358 / night