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70 house rentals

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Newly refinished condo open water views very nice

Islamorada condo

2 bedrooms
2 bathrooms

sleeps 6

Match: Shared outdoor pool (heated) Swimming pool

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Price per night from

$229

Bayside Condo, marina, pool and beach

Islamorada condo

3 bedrooms
2 bathrooms

sleeps 6

“Phenomenal keys experience!” This bay front condo is the perfect destination for the entire family! The fishing ranks up with the best in the world, there are plenty of other activities, and Key West is just a short trip down the beautiful HWY 1. I've had the pleasure of staying at this condo several times and have honestly never had a bad time (even during a cat 5 Trop Storm). There is too much to do, the condo is comfy, and the weather is always beautiful. Definitely recommend this condo!

Match: Shared outdoor pool (heated) Swimming pool

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Price per night from

$253

LUXURY KEYS HOME IN PARADISE-106 ANGLERS REEF

Islamorada villa

2 bedrooms
3 bathrooms

sleeps 6

Match: Shared outdoor pool (heated) Swimming pool

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Price per night from

$355

Luxury condo overlooking harbor with ocean view

Islamorada condo

3 bedrooms
3 bathrooms

sleeps 6

Match: Shared outdoor pool (heated) Swimming pool

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Price per night from

$391

Experience the Florida Keys like never before!!!

Islamorada condo

2 bedrooms
2 bathrooms

sleeps 6

Match: Shared outdoor pool (heated) Swimming pool

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Price per night from

$245

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

Islamorada condo

1 bedroom
1 bathroom

sleeps 4

Match: Shared outdoor pool (heated) Swimming pool

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Price per night from

$158

Oceanfront Anglers Reef Islamorada Florida Keys

Islamorada house

2 bedrooms
3 bathrooms

sleeps 6

Match: Shared outdoor pool (heated) Swimming pool

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Price per night from

$457

Lazy Daze Beach House 5 Star Modern Oceanfront Islamorada Townhome on the Beach!

Islamorada townhouse

2 bedrooms
3 bathrooms

sleeps 6

Match: Shared outdoor pool (heated) Swimming pool

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Price per night from

$446

Anglers Reef Islamorada Florida Sleeps 6

Islamorada house

2 bedrooms
3 bathrooms

sleeps 6

Match: Shared outdoor pool (heated) Swimming pool

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Price per night from

$377

Paradise at Islamorada

Islamorada townhouse

2 bedrooms
2 bathrooms

sleeps 8

Match: Shared outdoor pool (heated) Swimming pool

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Price per night from

$161

Executive Bay Club- great unit, great location!,

Islamorada villa

2 bedrooms
2 bathrooms

sleeps 4

Responds fast! avg. 20 minutes

Match: Shared outdoor pool (heated) Swimming pool

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Price per night from

$205

Islamorada Escape - Executive Bay w/Pool, Fishing Dock, Beach, Tennis/Pickleball

Islamorada house

3 bedrooms
2 bathrooms

sleeps 8

Match: Shared outdoor pool (heated) Swimming pool

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Price per night from

$207

Bayview house with bayviews. Pool with Spa, dock center of town great fishing !!

Islamorada house

2 bedrooms
1 bathroom

sleeps 6

Match: Shared outdoor pool (heated) Swimming pool

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Price per night from

$821

New Listing! Charming Angler's Reef Home with Pool, Dockage

Islamorada house

2 bedrooms
3 bathrooms

sleeps 6

Match: Shared outdoor pool (heated) Swimming pool

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Price per night from

$459

Reel Paradise Islamorada

Lower Matecumbe Key condo

1 bedroom
1 bathroom

sleeps 4

1 of 2 match: Shared outdoor pool (heated), Swimming pool

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Price per night from

$213

2 BDR ISLAMORADA HOME in WATERFRONT - FREE DOCK!!

Islamorada studio

Studio
2 bathrooms

sleeps 2

1 of 2 match: Shared outdoor pool (heated), Swimming pool

1 of 2 filters match

Price per night from

$286

ISLAMORADA 3bd in WATERFRONT COMMUNITY w BEACH!!

Islamorada apartment

3 bedrooms
2 bathrooms

sleeps 6

1 of 2 match: Shared outdoor pool (heated), Swimming pool

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Price per night from

$365

Islamorada trop paradise pool, fishing, 2fls luxury with a filet stationn

Islamorada house

4 bedrooms
2 bathrooms

sleeps 8

1 of 2 match: Shared outdoor pool (heated), Swimming pool

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Price per night from

$785

New Upscale, private pool, Dockage, kayaks, bikes, downtown Islamorada locale

Islamorada house

3 bedrooms
4 bathrooms

sleeps 6

1 of 2 match: Shared outdoor pool (heated), Swimming pool

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Price per night from

$913

WATERFRONT TOWNHOME IN ISLAMORADA K1

Islamorada apartment

3 bedrooms
3 bathrooms

sleeps 6

1 of 2 match: Shared outdoor pool (heated), Swimming pool

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Price per night from

$184

ISLAND DREAM

Lower Matecumbe Key house

4 bedrooms
3 bathrooms

sleeps 8

1 of 2 match: Shared outdoor pool (heated), Swimming pool

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Price per night from

$773

Come relax in Islamorada, the tropical jewel of the Florida Keys!!

Islamorada apartment

1 bedroom
1 bathroom

sleeps 4

1 of 2 match: Shared outdoor pool (heated), Swimming pool

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Price per night from

$201

Islamorada Waterfront Townhome w Priv. Beach! Comfortable Family Vacation Rental

Islamorada townhouse

2 bedrooms
2 bathrooms

sleeps 6

1 of 2 match: Shared outdoor pool (heated), Swimming pool

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Price per night from

$604

Beautiful Waterfront Townhome in Islamorada! Perfect for Florida Keys Vacation!

Islamorada house

2 bedrooms
2 bathrooms

sleeps 6

1 of 2 match: Shared outdoor pool (heated), Swimming pool

1 of 2 filters match

Price per night from

$604

Gorgeous Vacation Home with Beach Access!

Islamorada townhouse

3 bedrooms
2 bathrooms

sleeps 7

1 of 2 match: Shared outdoor pool (heated), Swimming pool

1 of 2 filters match

Price per night from

$604

Vacation in Tropical Paradise with the Family! Waterfront Townhome in Islamorada

Islamorada townhouse

2 bedrooms
3 bathrooms

sleeps 5

1 of 2 match: Shared outdoor pool (heated), Swimming pool

1 of 2 filters match

Price per night from

$604

"Irish Ayes" Elegant Waterfront Home with Pool

Islamorada house

4 bedrooms
4 bathrooms

sleeps 10

1 of 2 match: Shared outdoor pool (heated), Swimming pool

1 of 2 filters match

Price per night from

$802

Remodeled Townhome in Waterfront Community - 20% for Spring/Summer!

Islamorada house

2 bedrooms
2 bathrooms

sleeps 4

1 of 2 match: Shared outdoor pool (heated), Swimming pool

1 of 2 filters match

Price per night from

$604

Perfect Family Getaway! Waterfront Vacation Home in Islamorada, Florida Keys!

Islamorada townhouse

3 bedrooms
2 bathrooms

sleeps 6

1 of 2 match: Shared outdoor pool (heated), Swimming pool

1 of 2 filters match

Price per night from

$661

Townhome in Beachfront Community: Perfect for Florida Keys Vacation!

Islamorada townhouse

3 bedrooms
3 bathrooms

sleeps 7

1 of 2 match: Shared outdoor pool (heated), Swimming pool

1 of 2 filters match

Price per night from

$661

Islamorada Townhome w/Beach View, Pool, Marina,Tennis! Perfect Family Getaway!!

Islamorada townhouse

2 bedrooms
3 bathrooms

sleeps 6

1 of 2 match: Shared outdoor pool (heated), Swimming pool

1 of 2 filters match

Price per night from

$204

Gorgeous Florida Keys Vacation Home with Beach Access in Islamorada!

Islamorada townhouse

2 bedrooms
3 bathrooms

sleeps 6

1 of 2 match: Shared outdoor pool (heated), Swimming pool

1 of 2 filters match

Price per night from

$604

Venetian Tropics 3 bedroom pool home on sailboat canal weekly vacation rental

Islamorada house

3 bedrooms
3 bathrooms

sleeps 8

“Comfortable home for family get-together” Positive experience overall: Our family of six adults had a tropical-feeling destination Christmas here. The house easily accommodated all of us, and we enjoyed the wrap-around porch and pool. We appreciated the commodious kitchen with a two-tier dishwasher and side-by-side refrigerator with ice/water dispenser. Having a washer and dryer on the premises was very helpful, since guests are requested to wash linens and towels before departing. Some drawbacks: the house did not come equipped with adequate staples, such as paper products, laundry detergent, and garbage bags, so be prepared to purchase these. There are no beaches or stores within walking distance. On a couple of nights, noisy neighbors talking on the street woke us up. (In general, though, the area is quiet.)

Responds fast! avg. 1 hour 0 minutes

1 of 2 match: Shared outdoor pool (heated), Swimming pool

1 of 2 filters match

Price per night from

$670