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49 house rentals

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Beautiful Captain's Cove

Islamorada villa

3 bedrooms
2 bathrooms

sleeps 6

Match: Bicycles available Swimming pool

All filters match

Price per night from

$574

Luxury condo overlooking harbor with ocean view

Islamorada condo

3 bedrooms
3 bathrooms

sleeps 6

Match: Bicycles available Swimming pool

All filters match

Price per night from

$392

Oceanfront Anglers Reef Islamorada Florida Keys

Islamorada house

2 bedrooms
3 bathrooms

sleeps 6

Match: Bicycles available Swimming pool

All filters match

Price per night from

$458

Paradise at Islamorada

Islamorada townhouse

2 bedrooms
2 bathrooms

sleeps 8

Match: Bicycles available Swimming pool

All filters match

Price per night from

$161

Majestic estate, 200' of private oceanfront beach & pool, 3,600sqft tiki

Islamorada house

3 bedrooms
3 bathrooms

sleeps 8

Match: Bicycles available Swimming pool

All filters match

Price per night from

$1,474

EXECUTIVE BAY ISLAMORADA BY SoFLA VACATIONS

Islamorada townhouse

2 bedrooms
2 bathrooms

sleeps 6

Match: Bicycles available Swimming pool

All filters match

Price per night from

$285

Gorgeous waterfront home

Islamorada house

3 bedrooms
2 bathrooms

sleeps 8

1 of 2 match: Swimming pool, Bicycles available

1 of 2 filters match

Price per night from

$459

Executive Bay Club- great unit, great location!,

Islamorada villa

2 bedrooms
2 bathrooms

sleeps 4

Responds fast! avg. 20 minutes

1 of 2 match: Bicycles available, Swimming pool

1 of 2 filters match

Price per night from

$206

Islamorada Waterfront Paradise Getaway!

Islamorada house

1 bedroom
1 bathroom

sleeps 2

“Wonderful Romantic Get-Away” We absolutely enjoyed our stay here and would recommend it to others. The owners were very friendly and pleasant, and the apartment was incredibly clean. The tiki hut over the private lagoon was amazing. We kept finding little things all over the apartment while we were there - drinks, books, games, etc. It was a totally wonderful time, and we want to go back!

1 of 2 match: Swimming pool, Bicycles available

1 of 2 filters match

Price per night from

$574

Islamorada Waterfront Paradise 2

Islamorada house

2 bedrooms
2 bathrooms

sleeps 6

1 of 2 match: Swimming pool, Bicycles available

1 of 2 filters match

Price per night from

$517

Cozy Keys Cottage Islamorada FL.

Islamorada house

3 bedrooms
3 bathrooms

sleeps 6

Responds fast! avg. 2 hours 10 minutes

1 of 2 match: Swimming pool, Bicycles available

1 of 2 filters match

Price per night from

$409

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

Islamorada house

2 bedrooms
1 bathroom

sleeps 6

1 of 2 match: Bicycles available, Swimming pool

1 of 2 filters match

Price per night from

$821

Reel Paradise Islamorada

Lower Matecumbe Key condo

1 bedroom
1 bathroom

sleeps 4

1 of 2 match: Bicycles available, Swimming pool

1 of 2 filters match

Price per night from

$213

Anglers Reef Islamorada Florida Sleeps 6

Islamorada house

2 bedrooms
3 bathrooms

sleeps 6

1 of 2 match: Bicycles available, Swimming pool

1 of 2 filters match

Price per night from

$378

2 BDR ISLAMORADA HOME in WATERFRONT - FREE DOCK!!

Islamorada studio

Studio
2 bathrooms

sleeps 2

1 of 2 match: Bicycles available, Swimming pool

1 of 2 filters match

Price per night from

$285

ISLAMORADA 3bd in WATERFRONT COMMUNITY w BEACH!!

Islamorada apartment

3 bedrooms
2 bathrooms

sleeps 6

1 of 2 match: Bicycles available, Swimming pool

1 of 2 filters match

Price per night from

$363

ISLAND DREAM

Lower Matecumbe Key house

4 bedrooms
3 bathrooms

sleeps 8

1 of 2 match: Bicycles available, Swimming pool

1 of 2 filters match

Price per night from

$775

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

Islamorada apartment

1 bedroom
1 bathroom

sleeps 4

1 of 2 match: Bicycles available, Swimming pool

1 of 2 filters match

Price per night from

$201

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

Islamorada house

4 bedrooms
2 bathrooms

sleeps 8

1 of 2 match: Bicycles available, Swimming pool

1 of 2 filters match

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: Bicycles available, Swimming pool

1 of 2 filters match

Price per night from

$912

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

Islamorada house

3 bedrooms
2 bathrooms

sleeps 8

1 of 2 match: Bicycles available, Swimming pool

1 of 2 filters match

Price per night from

$207

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

Islamorada house

2 bedrooms
3 bathrooms

sleeps 6

1 of 2 match: Bicycles available, Swimming pool

1 of 2 filters match

Price per night from

$459

WATERFRONT TOWNHOME IN ISLAMORADA K1

Islamorada apartment

3 bedrooms
3 bathrooms

sleeps 6

1 of 2 match: Bicycles available, Swimming pool

1 of 2 filters match

Price per night from

$184

Newly refinished condo open water views very nice

Islamorada condo

2 bedrooms
2 bathrooms

sleeps 6

1 of 2 match: Bicycles available, Swimming pool

1 of 2 filters match

Price per night from

$230

"Irish Ayes" Elegant Waterfront Home with Pool

Islamorada house

4 bedrooms
4 bathrooms

sleeps 10

1 of 2 match: Bicycles available, Swimming pool

1 of 2 filters match

Price per night from

$803

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!

1 of 2 match: Bicycles available, Swimming pool

1 of 2 filters match

Price per night from

$254

Experience the Florida Keys like never before!!!

Islamorada condo

2 bedrooms
2 bathrooms

sleeps 6

1 of 2 match: Bicycles available, Swimming pool

1 of 2 filters match

Price per night from

$246

Gorgeous Vacation Home with Beach Access!

Islamorada townhouse

3 bedrooms
2 bathrooms

sleeps 7

1 of 2 match: Bicycles available, Swimming pool

1 of 2 filters match

Price per night from

$601

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

Islamorada townhouse

2 bedrooms
3 bathrooms

sleeps 5

1 of 2 match: Bicycles available, Swimming pool

1 of 2 filters match

Price per night from

$601

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

Islamorada house

2 bedrooms
2 bathrooms

sleeps 6

1 of 2 match: Bicycles available, Swimming pool

1 of 2 filters match

Price per night from

$601

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

Islamorada townhouse

2 bedrooms
2 bathrooms

sleeps 6

1 of 2 match: Bicycles available, Swimming pool

1 of 2 filters match

Price per night from

$601

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: Bicycles available, Swimming pool

1 of 2 filters match

Price per night from

$671