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Islamorada Rentals with Hot Tubs

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Islamorada Rentals with Hot Tubs

132 vacation rentals

Islamorada Luxury Waterfront Condo with Boat Slip

Islamorada apartment

2 bedrooms / 3 bathrooms / sleeps 6

“Beautifully appointed, waterside condo!” This property is a beautiful, two bedroom condo, very well appointed, with everything we needed for a great stay! Islamorada is a great middle point to see the other parts of the Keys, and close to great restau

Price per night from

$214

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Incredible Luxury Home with Waterfront!! Paradise

Islamorada house

5 bedrooms / 6 bathrooms / sleeps 12

Price per night from

$1,128

1 / 17

BEACON REEF 310

Islamorada apartment

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$110

1 / 21

SPACIOUS 2 BEDROOM TROPICAL OASIS WITH FLORIDA BAY SUNSET VIEWS!

Islamorada condo

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$171

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100 Palo De Oro Drive

Islamorada house

4 bedrooms / 4 bathrooms / sleeps 8

Price per night from

$422

1 / 65

THE PERFECT GETAWAY

Islamorada house

4 bedrooms / 3 bathrooms / sleeps 10

“The owner was understanding and worked with us” I was scheduled to rent from Dec 29th to Jan 4th and expected 7 friends to join me. For multiple personal reasons four of the seven had to back out and it is not the place you want to be without the full

Price per night from

$357

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PALMS 309

Islamorada house

2 bedrooms / 2 bathrooms / sleeps 5

Price per night from

$85

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Dog-friendly, waterfront home w/ a private pool, hot tub, & private beach

Islamorada house

4 bedrooms / 4 bathrooms / sleeps 14

Price per night from

$858

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82754 Overseas Highway

Islamorada house

5 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$884

1 / 29

Paradise Beach Sandy Oceanfront

Islamorada house

4 bedrooms / 4 bathrooms / sleeps 10

Responds fast! avg. 1 hour 27 minutes

Price per night from

$601

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PALMS 314

Islamorada apartment

2 bedrooms / 2 bathrooms / sleeps 5

“Wow, what a beautiful view” This condo was clean, nicely furnished and had a view to die for. We really appreciated the washer and dryer in the unit, which most did not have. Also, being on the end we had "the window" in the master bedroom and in the

Price per night from

$80

1 / 25

SANCTUARY IN PARADISE

Islamorada house

4 bedrooms / 4 bathrooms / sleeps 10

“What Florida dreams are made of” Growing up in South Florida and the Keys but now moved farm away, I wanted to show my husband and young children the Florida I remembered as a child. This my friends was more than my dreams could have asked for! We wer

Price per night from

$500

1 / 21

BEACON REEF 222

Islamorada apartment

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$146

1 / 25

PALMS 214

Islamorada apartment

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$76

1 / 24

THE PALMS 405 - 93

Islamorada apartment

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$103

1 / 25

Luxury condo overlooking harbor with ocean view

Islamorada condo

3 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 1 hour 7 minutes

Price per night from

$269

1 / 20

PALMS 402

Islamorada apartment

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$80

1 / 25

BEACON REEF 501

Islamorada apartment

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$110

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Luxury 3 BR condo, boatslip, easy accces to ocean

Islamorada condo

3 bedrooms / 6 bathrooms / sleeps 8

Responds fast! avg. 3 hours 49 minutes

Price per night from

$249

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PALMS 417

Islamorada apartment

1 bedroom / 2 bathrooms / sleeps 4

“Paradise on the ocean” We rented Palm 417 for the month of March 2014. The condo has been very nicely updated and although not direct ocean front view; it does have partial view of the ocean side and a good view of the bay side with amazing sunsets. P

Price per night from

$70

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BEAUTIFUL BAY HARBOUR CONDO W/ BOAT DOCK! OFFSEASON RATES FOR OCT AND NOV!

Islamorada condo

3 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 1 hour 41 minutes

Price per night from

$357

1 / 14

Fabulous 6 Bedrooms /4 Bathrooms Tropical Waterfront Pool Home!

Islamorada house

3 bedrooms / 4 bathrooms / sleeps 12

Responds fast! avg. 2 hours 17 minutes

Price per night from

$234

1 / 15

San Roc - Private 150 Ft Oceanfront 2.5 Acre Millionaire Row Estate, Pool, Spa,

Islamorada house

4 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 1 hour 27 minutes

Price per night from

$601

1 / 20

PALMS 407

Islamorada apartment

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$100

1 / 29

Elegant Bay Harbour Condo with 50 Foot Boat Slip

Islamorada apartment

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$429

1 / 21

Paradise Found - Sandy Beach, Beachside Bar, Great Views, And Dock

Islamorada villa

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$350

1 / 19

PALMS 301

Islamorada apartment

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$76

1 / 24

AZALEA WARTERFRONT

Islamorada house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$150

1 / 29

Oceanfront Islamorada Condo with Huge T-Dock

Islamorada condo

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$133

1 / 24

Islamorada cottage on deep water canal

Islamorada house

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$150

1 / 15

Oceanfront 2/2 Condo in Beacon Reef - Free boat dock

Islamorada condo

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$501

1 / 4

**Winter Promo** Luxurious Ocean View Condo w/Heated Pool & Jacuzzi

Islamorada apartment

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 1 hour 45 minutes

Price per night from

$202

1 / 25

The PERFECT Escape with pool & jacuzzi

Islamorada house

4 bedrooms / 4 bathrooms / sleeps 8

Price per night from

$322

1 / 22

3 bedrooms at Ocean Harbour Apartment, Islamorada, Florida Keys.

Islamorada apartment

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$236

1 / 41

Great rentals within 20 miles that match your search

Ocean Front Executive Retreat

Key Largo house

6 bedrooms / 7 bathrooms / sleeps 13

“A Great Time Was Had By all” We had the pleasure of staying in this house for two weeks in mid June. Our family of twelve had a great time and we never felt crowded. The house has a spectacular setting and view with a terific pool and large pool dec

Price per night from

$1,087

1 / 55

Margarita Beach House

Tavernier house

3 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$107

1 / 18

Buttonwood Bay Key Largo Waterfront Townhouse

Key Largo apartment

2 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$142

1 / 36

OCEAN VIEW 2BR/2BA SUITE, PRIVATE BEACH, POOL, TENNIS COURTS, RESTAURANT, GRILL

Tavernier apartment

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$178

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