50 Best Islamorada Vacation rentals on Holiday Lettings - House rentals

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137 Vacation rentals

(2) Excellent 

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

$1386 - $2085 / week

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Responds fast!
avg. 2 hours 48 minutes

from $198 / 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 $229 / night

$1600 - $2500 / week

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Responds fast!
avg. 3 hours 22 minutes

from $229 / 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 $250 / night

$1800 - $3800 / week

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Responds fast!
avg. 47 minutes

from $250 / night

(3) Excellent 

22

Condo rental in Islamorada

Florida Keys / Islamorada

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Huge screened in terrace. Spacious and extremely clean.. Peaceful and away from the highway. Sleeps 4-6 people. Enjoy the tennis courts, large pool on the ocean, beach-side BBQ grills. Relax, dine and drink under one of the tiki huts or visit one of the many water-front …see more

from $142 / night

$994 - $1500 / week

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Responds fast!
avg. 3 hours 32 minutes

from $142 / night

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 $213 / night

$1491 / week

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from $213 / 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 $114 / night

$795 - $1025 / week

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Responds fast!
avg. 3 hours 29 minutes

from $114 / night

(16) Very Good 

24

Home rental in Islamorada

Florida Keys / Islamorada

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Child friendly
This is a neat house! It sits right on the ocean with a large yard (by keys standards!). Very nicely landscaped (hibiscus, palm trees, tall pine trees, green grass)with statues from all over the world. Very private with a big gate. The house is decorated with pictures t …see more

from $214 / night

$1500 - $1650 / week

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from $214 / 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 $97 / night

$833 / week

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from $97 / 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 $100 / night

$903 / week

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from $100 / night

(1) Excellent 

21

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. For two couples or a family with 2 kids. The two new extra long twin beds in 2nd bedroom convert to a comfy King Bed! Master bedroom has new king bed, ocean view and private bath. 2nd ba …see more

from $239 / night

$950 - $1150 / week

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Responds fast!
avg. 3 hours 9 minutes

from $239 / night

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
Paradise by the Atlantic Ocean and only 50' front the waters edge. Beautiful condominium complex with heated out door pool, gym, plenty of parking, secured entrances, elevator, and quiet. My condo is kept meticulously with attention to detail. Linens, towels and pool …see more

from $125 / night

$850 - $1375 / week

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Responds fast!
avg. 3 hours 57 minutes

from $125 / 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
*** 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 $97 / night

$833 / week

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from $97 / 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

(3) Excellent 

25

Vacation home with shared pool in Islamorada

Florida Keys / Islamorada

2 8 28 nights min

  • 2 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 $100 / night

$903 / week

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from $100 / night

13

Islamorada Vacation apartment rental

Florida Keys / Islamorada

2 4 30 nights min

  • 2 bedrooms
  • Sleeps 4
  • 30 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Premier condo in Islamorada in Upper Florida Keys. Located on 12-acre property with 1,100 feet of oceanfront. Gated complex, large swimming pool, sand beach, and two tennis courts as well as boat ramp and dedicated slip. Spectacular Atlantic Ocean views. This top-floor, …see more

from $214 / night

$1498 / week

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from $214 / night

16

Vacation home in Islamorada

Florida Keys / Islamorada

3 10 30 nights min

  • 3 bedrooms
  • Sleeps 10
  • 30 nights min
  • Child friendly
  • Air conditioning
Corner lot, Clear and deep waterways, 3 bedrms, 3 bath, sleeps 8+ Granit Tops This home is located in a prime neighborhood with 150lf of seawall for all your water toys. 3 bedrooms, 3 full bath ,1 king, 2 queens and bunkbeds, Laundry room, Wet bar, Library/Sitting roo …see more

from $218 / night

$1520 / week

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from $218 / night

(7) Excellent 

18

Villa rental in Islamorada

Florida Keys / Islamorada

2 6 30 nights min

  • 2 bedrooms
  • Sleeps 6
  • 30 nights min
  • 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 $127 / night

$887 / week

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from $127 / night

(11) Excellent 

25

Vacation apartment rental

Florida Keys / Islamorada

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Ask about children
Minimum Rental: 7 Days (Saturday to Saturday) "Brock Haus on the Gulf" is an end unit townhouse on the water's edge with water views on 3 sides! The main living area faces the Florida Bay, one side faces the inlet leading to the marina basin and the back faces the ma …see more

from $225 / night

$1575 - $1995 / week

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from $225 / 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

$1200 - $1650 / week

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from $171 / night

14

Islamorada Vacation home rental

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

$1200 - $1650 / week

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from $171 / 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

$1995 / week

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Responds fast!
avg. 1 hour 39 minutes

from $279 / night

(3) Very Good 

26

Vacation home with shared pool 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 "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 w …see more

from $175 / night

$1225 / week

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from $175 / night

(3) 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 $785 / night

$5200 - $6200 / week

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from $785 / night

23

Home rental in Islamorada

Florida Keys / Islamorada

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.1 mi
  • Swimming pool
This relaxing private home, known as "Windley Cottage" is located in Angler's Reef, Islamorada's premier gated oceanfront community with private beaches, boat docks (available for rent), and a resort-style swimming pool overlooking the boat dock lagoon, beaches, and th …see more

from $229 / night

$1599 - $2499 / week

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Responds fast!
avg. 1 hour 49 minutes

from $229 / night

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

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 $265 / night

$1850 - $2450 / week

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Responds fast!
avg. 2 hours 52 minutes

from $265 / night

(6) 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

$1100 - $1300 / week

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from $158 / 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 Lower Ma …see more

from $183 / night

$1281 / week

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from $183 / night

20

Vacation condo rental

Florida Keys / Islamorada

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Child friendly
Welcome to Modern Keys Living with Bay Views! New from top to bottom!!! Newly remodeled and beautifully decorated 1st floor corner unit with a private entrance. Enjoy the mix of vintage and new furniture and the most comfortable sofas, beds, linens and more! This home …see more

from $150 / night

$1050 - $1599 / week

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from $150 / night

(1) 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

$1050 / week

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from $150 / 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 $134 / night

$938 / week

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from $134 / 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

(1) 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

(23) Excellent 

31

Islamorada Vacation apartment rental

Florida Keys / Islamorada

1 4 30 nights min

  • 1 bedroom
  • Sleeps 4
  • 30 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
Get away from it all in our tranquil waterfront condo at Summer Sea in beautiful Islamorada. Fully equipped, with newly updated kitchen and bathroom, flat screen televisions, and stunning views of Florida Bay from our patio. Located right in the heart of all the Keys …see more

from $94 / night

$654 / week

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from $94 / night

26

Islamorada Vacation home rental

Florida Keys / Islamorada

2 6 28 nights min

  • 2 bedrooms
  • Sleeps 6
  • 28 nights min
  • Swimming pool
  • Suitable for children age 5+
  • Air conditioning
Tropical weather, sunshine, and a little magic await you in the Florida Keys! Look no further than this exquisite Islamorada vacation rental home as your personal oasis during your upcoming tropical getaway. This 2-bedroom, 2 and a half bathroom island home sleeps 6 in …see more

from $289 / night

$2023 - $2443 / week

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Responds fast!
avg. 9 minutes

from $289 / night

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 "The Palms #402" is a beautifully remodeled and immaculate condo. You'll love the uncluttered and modern décor along with the recent renovations. Enjoy the picturesque views of Alligator Reef and the Atlantic Ocean from this 4th floor balc …see more

from $80 / night

$560 / week

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from $80 / night

(1) Excellent 

24

Vacation home with shared 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 $218 / night

$1520 / week

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from $218 / night

17

Vacation caravan/mobile home rental

Florida Keys / Islamorada

1 3 30 nights min

  • 1 bedroom
  • Sleeps 3
  • 30 nights min
  • Child friendly
Please call or email to inquire about specific dates. We can be accommodating depending on your dates and needs. Come experience the Keys vibe the way locals do it. This cute, cozy and totally remodeled mobile home is located in the heart of the Keys. It is close to e …see more

from $100 / night

$700 / week

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from $100 / night

34

Islamorada Vacation home rental

Florida Keys / Islamorada

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Child friendly
  • Pet friendly
Alligator Reef is a truly special slice of Paradise with 4 individual homes nestled on a privately gated oceanfront estate. This home, the Conch House (pronounced konk), is a 3 bedroom, 2 bathroom ocean front home featuring beautiful views, ocean breezes, and your own p …see more

from $560 / night

$3920 - $5390 / week

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from $560 / 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
Welcome to your beach-front oasis on the bay side at mile marker 74 in Islamorada, the Sport Fishing Capital of the World. Dig your toes in the sand, bask in the warm, clean waters and soak up the sun at this beautiful retreat. For the fishermen and divers there is a sh …see more

from $141 / night

$1253 / week

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from $141 / night