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Vacation Rentals & House Rentals in Islamorada

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45 house rentals

Islamorada Waterfront Paradise Getaway!

Islamorada house

1 bedroom / 1 bathroom / sleeps 2

“AMAZING!!!!!!!” Ewa and Peter were incredible hosts at this beautiful property. We felt right at home immediately and had so many activities to do plus Ewa and Peter had loads of great tips when we asked. The studio was so well stocked with all the essentials and then even the ones you forgot! It was wonderful to see a manatee swim up past the dock our first morning there. A very magical spot with generous hosts. It had everything we wanted and then some. After a week there and driving around the whole Keys it was 100% the most perfect choice for us. I miss those hammocks!

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$259

Luxury condo overlooking harbor with ocean view

Islamorada condo

3 bedrooms / 3 bathrooms / sleeps 6

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$310

Bay Front Beauty/ Summer Sea Must See!!!!

Islamorada condo

1 bedroom / 1 bathroom / sleeps 4

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$158

Peacock Shores Oceanfront Islamorada

Islamorada townhouse

2 bedrooms / 3 bathrooms / sleeps 4

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Price per night from

$366

EXECUTIVE BAY ISLAMORADA BY SoFLA VACATIONS

Islamorada townhouse

2 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$286

Great rentals within 20 miles that match your search

Sailing Catamaran in the Florida Keys, Sailing, diving, adventure experience.

Key Largo yacht

3 bedrooms / 3 bathrooms / sleeps 6

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$1,614

Buttonwood Bay Key Largo Waterfront Townhouse

Key Largo apartment

2 bedrooms / 3 bathrooms / sleeps 8

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$178

Motel Room #2, Private Entrance, Beach and Marina

Key Largo apartment

1 bedroom / 1 bathroom / sleeps 2

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$114

Spacious 1 Bedroom Duplex, Full Kitchen, Beach and Marina

Key Largo apartment

1 bedroom / 1 bathroom / sleeps 4

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Price per night from

$209

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Price per night from

$209

Motel Room #1, Private Entrance, Beach and Marina

Key Largo apartment

1 bedroom / 1 bathroom / sleeps 2

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$107

Spacious Studio, Full Kitchen, Beach and Marina, Capt Jax #12 R

Key Largo apartment

1 bedroom / 1 bathroom / sleeps 2

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Price per night from

$195

1 Bedroom, Full Kitchen, Mini Split Air, Beach and Marina Apt #1

Key Largo apartment

1 bedroom / 1 bathroom / sleeps 3

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$209

OCEAN VIEW 1BR APARTMENT! PRIVATE BEACH, TENNIS, POOL, PARKING, HOT TUB!

Tavernier apartment

1 bedroom / 1 bathroom / sleeps 4

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$160

FLORIDA KEYS GETAWAY! COMFY OCEAN VIEW 1BR! PRIVATE BEACH, MARINA, POOL, BBQ

Tavernier apartment

1 bedroom / 1 bathroom / sleeps 4

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Price per night from

$160

BEACH VACAY STARTS HERE! OCEAN VIEW, 1BR APT! PRIVATE BEACH, TENNIS, POOL

Tavernier apartment

1 bedroom / 1 bathroom / sleeps 4

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$160

PRIVATE BEACH OPEN!! Comfy Ocean View 2BR/2BA with Balcony, Pool, Tennis!

Tavernier apartment

2 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$171

OCEAN ESCAPE! GREAT 2BR/2BA APARTMENT, PRIVATE BEACH, POOL, BBQ, TENNIS PARKING

Tavernier apartment

2 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$171

PRIVATE BEACH OPEN!! Two Spacious 2BR/2BAs for 12, Pool, Parking

Tavernier apartment

4 bedrooms / 4 bathrooms / sleeps 12

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Price per night from

$378

FAMILY BEACH ESCAPE, 2 x OCEAN VIEW 2BR/2BA APTS! BEACH/POOL/BBQ/PARKING

Tavernier apartment

4 bedrooms / 4 bathrooms / sleeps 12

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Price per night from

$378

RARE FIND! THREE OCEAN VIEW 2BR/2BA APTS! BEACH ACCESS, POOL, TENNIS, PARKING

Tavernier apartment

6 bedrooms / 6 bathrooms / sleeps 18

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Price per night from

$515

BEACH FAMILY VACATION! 3 OCEAN VIEW 2BR APTS! POOL, PARKING, TENNIS, MARINA

Tavernier apartment

6 bedrooms / 6 bathrooms / sleeps 18

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Price per night from

$515

New Listing! Three Cozy Ocean View 2BR Apartments, Private Beach, Balcony, BBQ

Tavernier apartment

6 bedrooms / 6 bathrooms / sleeps 18

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Price per night from

$538

BEACH VACAY STARTS HERE! THREE x 2BRs WITH OCEAN VIEW FOR 18, BALCONY, POOL, BBQ

Tavernier apartment

6 bedrooms / 6 bathrooms / sleeps 18

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Price per night from

$538

BEACH VACATION! THREE x OCEAN VIEW 2BRs! POOL, HOT-TUB, TENNIS, BBQ, PARKING

Tavernier apartment

6 bedrooms / 6 bathrooms / sleeps 18

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$538

FLORIDA KEYS ESCAPE! 4 x 2BR/2BAs FOR 24! OCEAN VIEWS, BEACH, POOL, BBQ

Tavernier apartment

8 bedrooms / 8 bathrooms / sleeps 24

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Price per night from

$744

BEACH VACAY STARTS HERE! FOUR x 2BRs WITH OCEAN VIEWS, BALCONY, POOL, BBQ!

Tavernier apartment

8 bedrooms / 8 bathrooms / sleeps 24

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Price per night from

$744

Rare Find! Four Ocean View 2BR Apartments for 24 Guests, Private Beach, Pool!

Tavernier apartment

8 bedrooms / 8 bathrooms / sleeps 24

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Price per night from

$744

Sleeping Room, Private Entrance and use of RV Park Bathrooms, Beach and Marina

Key Largo private room

1 bedroom / 1 bathroom / sleeps 2

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Price per night from

$81

3 x OCEAN VIEW 2BRs! FL KEYS FANILY GETAWAY!

Tavernier apartment

6 bedrooms / 6 bathrooms / sleeps 18

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Price per night from

$538

Spacious Studio, Full Kitchen, Mini Split Air, Waterview, Beach, Marina, Apt #2

Key Largo apartment

1 bedroom / 1 bathroom / sleeps 3

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Price per night from

$209

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Price per night from

$212

Spacious 1 Bedroom, Full Kitchen, Central Air, Beach, Marina and Docks

Key Largo apartment

1 bedroom / 1 bathroom / sleeps 3

“Tranquil and friendly” This was a place we found after months of searching and having another owner cancel out on us. We came in with a pre judgement of the place and BOY were we wrong. Everyone is super nice, everyone there(employees and guests) are very caring and friendly. The apartment was very comfy and well equipped, although anextra blanky or throw would have been nice to have for the sofa lounging. We are only 4 days into it but all is great!

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$195

FAMILY GETAWAY! OCEAN VIEW 2BR/2BA! PRIVATE BEACH, POOL, PARKING, BBQ, TENNIS

Tavernier apartment

2 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$171

FLORIDA KEYS VACATION! LOVELY OCEAN VIEW 2BR/2BA! PRIVATE BEACH, POOL, PARKING

Tavernier apartment

2 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$171

PRIVATE BEACH OPEN!! Superb Ocean View 2BR/2BA, Balcony, Pool, Tennis

Tavernier apartment

2 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$171

TWO AMAZING OCEAN VIEW 2BR/2BA APARTMENTS! TENNIS, POOL, BBQ, PARKING!

Tavernier apartment

4 bedrooms / 4 bathrooms / sleeps 12

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Price per night from

$343

FAMILY BEACH ESCAPE! 2 FANTASTIC 2BR/2BAs! TENNIS, POOL, BBQ, MARINA

Tavernier apartment

4 bedrooms / 4 bathrooms / sleeps 12

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Price per night from

$343

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