50 Best Islamorada Vacation rentals on Holiday Lettings - House rentals

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403 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 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 $150 / night

$1,000 - $1,200 / week

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from $150 / 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 

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 

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

(1) Excellent 

26

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 $143 / night

$1,000 - $1,850 / week

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Responds fast!
avg. 3 hours 0 minutes

from $143 / 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 - gra …see more

from $110 / night

$770 / week

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from $110 / 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

25

Vacation home in Islamorada

Florida Keys / Islamorada

2 6 28 nights min

  • 2 bedrooms
  • Sleeps 6
  • 28 nights min
  • Child friendly
  • Air conditioning
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! Welcome to your beach-front oasis on the bay side at mile marke …see more

from $141 / night

$1,253 / week

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Responds fast!
avg. 1 hour 23 minutes

from $141 / 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

19

Islamorada Vacation home rental

Florida Keys / Islamorada

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
  • Ask about children
  • Pet friendly
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 sunr …see more

from $173 / night

$1,211 / week

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from $173 / 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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Responds fast!
avg. 3 hours 22 minutes

from $250 / 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

(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
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 *** Come and relax at …see more

from $111 / night

$1,120 / week

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Responds fast!
avg. 1 hour 23 minutes

from $111 / 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

(3) 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 $243 / night

$1,701 / week

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from $243 / night

(2) Excellent 

24

Vacation home with swimming pool in Islamorada

Florida Keys / Islamorada

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Pet friendly
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 holiday awaits you in this extraordinary home. 3 bedrooms and two baths on the u …see more

from $231 / night

$1,617 / week

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from $231 / 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

(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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Responds fast!
avg. 2 hours 59 minutes

from $129 / 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

(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

(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 $76 / night

$532 / week

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from $76 / 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

(2) Excellent 

9

Vacation apartment in Islamorada

Florida Keys / Islamorada

1 4 7 nights min

  • 1 bedroom
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
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 …see more

from $175 / night

$1,225 - $2,500 / week

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Responds fast!
avg. 2 hours 18 minutes

from $175 / night

(3) 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

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

(9) 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

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 14 minutes

from $300 / night

(2) Good 

25

Vacation home in Islamorada

Florida Keys / Islamorada

4 10 7 nights min

  • 4 bedrooms
  • Sleeps 10
  • 7 nights min
  • Child friendly
  • Air conditioning
  • Pet friendly
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 be …see more

from $575 / night

$2,755 - $5,380 / week

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Responds fast!
avg. 1 hour 23 minutes

from $575 / 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

23

Vacation home in Islamorada

Florida Keys / Islamorada

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Ask about children
Minimum Rental: 28 Days "West Plaza Del Lago" promises to be a favorite. Beautifully remodeled roomy single family stilt home with vaulted ceilings and located in prestigious Port Antigua on a deep and wide canal. You will love the interior of this home as much as …see more

from $133 / night

$931 / week

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from $133 / 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

(1) Excellent 

24

Vacation home in Islamorada

Florida Keys / Islamorada

3 10 Min stay varies

  • 3 bedrooms
  • Sleeps 10
  • Min stay varies
  • Ask about children
Minimum Rental: 28 Days "Gulfview Getaway" is a FABULOUS BEACH FRONT HOME! This is what you've been dreaming of - your very own single family home with a private sandy beach in the Keys. This home is new to the rental market. It is located in a highly desirable …see more

from $400 / night

$2,800 / week

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from $400 / 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 $198 / night

$1,386 / week

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from $198 / night

19

Islamorada Vacation home rental

Florida Keys / Islamorada

2 4 28 nights min

  • 2 bedrooms
  • Sleeps 4
  • 28 nights min
  • Child friendly
This 2 bedroom, 2 bathroom condo located directly on the Florida Bay is the perfect sunny getaway! Situation with perfect views of the community pool, community marina, and open bay, you'll enjoy coffee in the morning while watching the boaters head out for their perfec …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
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 *** *** Owner is high …see more

from $110 / night

$833 / week

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Responds fast!
avg. 1 hour 23 minutes

from $110 / night

(10) Excellent 

25

Home rental in Islamorada with shared pool

Florida Keys / Islamorada

3 6 28 nights min

  • 3 bedrooms
  • Sleeps 6
  • 28 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
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 *** *** Owner is high …see more

from $100 / night

$833 / week

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Responds fast!
avg. 1 hour 23 minutes

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 45 minutes

from $265 / 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

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