50 Best Islamorada Vacation rentals on Holiday Lettings - House rentals

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413 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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Responds fast!
avg. 3 hours 32 minutes

from $198 / night

(4) Excellent 

29

Home rental in Islamorada

Florida Keys / Islamorada

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • 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 $785 / night

$5,200 - $6,200 / week

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from $785 / night

(2) Excellent 

14

Vacation condo in Islamorada

Florida Keys / Islamorada

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • 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 $125 / night

$850 - $1,200 / week

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from $125 / 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 $107 / night

$749 / week

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from $107 / night

16

Vacation apartment with shared pool in Islamorada

Florida Keys / Islamorada

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Ask about children
Minimum Rental: 1 Month Enjoy the magnificent ocean views of this wonderful condominium complex. You'll love the newly completed renovations. The kitchen has been totally remodeled with all new cabinets and appliances. The living room furniture is brand new and t …see more

from $127 / night

$889 / week

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from $127 / night

(2) Excellent 

25

Vacation home in Islamorada

Florida Keys / Islamorada

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Pet friendly
Minimum Rental: 28 Days "Manatee Manor" is a 3 Bedrooms and 2 ½ 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 …see more

from $199 / night

$1,393 / week

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from $199 / 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 50 minutes

from $300 / 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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avg. 2 hours 4 minutes

from $279 / night

(4) 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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avg. 1 hour 30 minutes

from $265 / night

(4) Excellent 

23

Islamorada Vacation villa rental

Florida Keys / Islamorada

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Ask about children
  • Pet friendly
Minimum Rental: 7 Days Little Bay's Lower Duplex 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, …see more

from $358 / night

$2,500 / week

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from $358 / 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

10

Vacation home in Islamorada

Florida Keys / Islamorada

4 8 3 nights min

  • 4 bedrooms
  • Sleeps 8
  • 3 nights min
  • Child friendly
  • Pet friendly
SuCasa is located next to Robbie’s Marina where you can hand feed the Tarpon on Lower Matacumbe. The Main House sleeps eight comfortably in four bedrooms with 3 queen-sized beds and two twin beds and comfortably sleeps 8. It has a fully equipped kitchen with a stove, d …see more

from $540 / night

$3,780 / week

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from $540 / 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

24

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 $422 / night

$2,950 / week

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from $422 / night

(3) Excellent 

18

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. 1 hour 23 minutes

from $142 / night

(1) Excellent 

24

Vacation apartment with shared pool 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 "The Palms #214" is a 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 cur …see more

from $77 / night

$539 / week

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from $77 / night

(1) 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 $147 / night

$1,029 / week

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from $147 / night

9

Vacation condo with golf nearby in Islamorada

Florida Keys / Islamorada

2 6 21 nights min

  • 2 bedrooms
  • Sleeps 6
  • 21 nights min
  • Beach/lakeside relaxation
  • Child friendly
Highend remodeled and luxuriously furnished bay view condo in the gated community of Futura Yacht Club. 2 bedroom 2 full bath Condo with a open den that can be closed off as a third room (queen size murphy bed). Flat screen tv in every room with cable and wifi. Gorgeous …see more

from $143 / night

$1,000 / week

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from $143 / night

(1) Excellent 

28

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 $82 / night

$574 / week

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from $82 / night

26

Vacation home rental

Florida Keys / Islamorada

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Child friendly
  • Air conditioning
Property description Framed by mangroves and the Atlantic Ocean this exquisite Key West style 2 bedroom, 2.5 bathroom home, is located in the quiet oceanfront private community of Anglers Reef -one of the best kept secrets in the Keys. Florida State Licensed Single Fa …see more

from $372 / night

$2,600 / week

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Responds fast!
avg. 34 minutes

from $372 / night

(1) Excellent 

25

Apartment rental in Islamorada with shared pool

Florida Keys / Islamorada

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Ask about children
Minimum Rental: 28 Days "The Palms #417" has 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 restaurants. Watch the sun rise over the ocean as fishing boats …see more

from $67 / night

$469 / week

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from $67 / night

24

Vacation home in Islamorada

Florida Keys / Islamorada

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • 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

(4) Excellent 

19

Condo rental in Islamorada

Florida Keys / Islamorada

1 4 30 nights min

  • 1 bedroom
  • Sleeps 4
  • 30 nights min
  • 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 $147 / night

$1,025 / week

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Responds fast!
avg. 3 hours 24 minutes

from $147 / night

(2)  

44

Vacation home in Islamorada

Florida Keys / Islamorada

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
This unit's kitchen, bathrooms, windows, and doors received a facelift in January 2014! Enjoy the spectacular view of the Florida Bay from either one of the TWO balconies in this 2 story townhome, located off the master bedroom or the living room. Amenities inclu …see more

from $175 / night

$1,225 - $2,025 / week

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from $175 / night

35

Vacation home rental

Florida Keys / Islamorada

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • 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

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 $300 / night

$2,100 / week

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from $300 / night

(1) Excellent 

25

Vacation home in Islamorada

Florida Keys / Islamorada

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Ask about children
  • Pet friendly
Minimum Rental: 28 Days "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 off …see more

from $117 / night

$819 / week

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from $117 / night

(3) Excellent 

25

Islamorada Vacation villa rental

Florida Keys / Islamorada

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Ask about children
  • Pet friendly
Minimum Rental: 7 Days Little Bay's Upper Duplex 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 th …see more

from $358 / night

$2,500 / week

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from $358 / night

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 "The Palms #407" is a charming 2 bedroom, 2 bath condo with updated kitchen and baths. Walk out onto your balcony and enjoy the sea breezes and ever changing ocean views. The comfortable furnishings and convenient floor plan provide an invit …see more

from $100 / night

$700 / week

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from $100 / night

16

Vacation home in Islamorada

Florida Keys / Islamorada

4 8 28 nights min

  • 4 bedrooms
  • Sleeps 8
  • 28 nights min
  • Pet friendly
'Irish Ayes' - Elegant tropical waterfront home with pool, Jacuzzi, dock and custom elevator. Plan your Keys getaway to this absolutely beautiful, spacious, tropical waterfront home located in the prestigious Venetian Shores subdivision of Islamorada. Enjoy unforgettab …see more

from $10 / night

$20 / week

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Responds fast!
avg. 52 minutes

from $10 / night

30

Vacation apartment with swimming pool, tennis court in Islamorada

Florida Keys / Islamorada

3 8 30 nights min

  • 3 bedrooms
  • Sleeps 8
  • 30 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.32 mi
  • Swimming pool
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 s …see more

from $132 / night

$924 / week

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Responds fast!
avg. 3 hours 13 minutes

from $132 / night

(2) Excellent 

25

Vacation home in Islamorada

Florida Keys / Islamorada

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Ask about children
  • Pet friendly
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 ind …see more

from $244 / night

$1,708 / week

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from $244 / night

43

Vacation home rental

Florida Keys / Islamorada

4 12 7 nights min

  • 4 bedrooms
  • Sleeps 12
  • 7 nights min
  • Nearest beach 0 mi
  • Swimming pool
  • Child friendly
Welcome to Murphy’s Paradise, a one acre private gated beachfront estate in the heart of Islamorada, Florida. This home features a private beach, 5 bedrooms, 3 ½ baths, family room, living room, game rooms, pool and bar. This home can comfortably accommodate 10-12 peo …see more

from $1,000 / night

$7,000 / week

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Responds fast!
avg. 1 hour 5 minutes

from $1,000 / 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 $300 / night

$2,200 - $2,500 / week

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Responds fast!
avg. 2 hours 24 minutes

from $300 / 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

25

Vacation apartment with shared pool in Islamorada

Florida Keys / Islamorada

2 6 28 nights min

  • 2 bedrooms
  • Sleeps 6
  • 28 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
*** Owner is highly motivated to rent! Contact us for discounts *** Come and relax at our beautiful town home 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 …see more

from $110 / night

$833 / week

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Responds fast!
avg. 2 hours 8 minutes

from $110 / night

(2) Excellent 

25

Vacation home in Islamorada

Florida Keys / Islamorada

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Ask about children
  • Pet friendly
Minimum Rental: 28 Days "Matecumbe Jewel" is a 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 a …see more

from $150 / night

$1,050 / week

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from $150 / night

(7) 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

14

Islamorada Vacation condo rental

Florida Keys / Islamorada

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool
Watch the sunrise from the spacious balcony overlooking the Atlantic Ocean. This brand new three bedroom, two and-a-half bath condominium sleeps eight people. Master bedroom has a king bed with access to the balcony. Second bedroom has a queen bed and third one has two …see more

from $358 / night

$2,500 / week

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Responds fast!
avg. 3 hours 25 minutes

from $358 / night

(3) Very Good 

25

Apartment rental in Islamorada with shared pool

Florida Keys / Islamorada

3 8 28 nights min

  • 3 bedrooms
  • Sleeps 8
  • 28 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
*** Owner is highly motivated to rent! Contact us for discounts *** Come and relax at our beautiful town home 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 …see more

from $129 / night

$903 / week

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Responds fast!
avg. 2 hours 8 minutes

from $129 / night