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Swimming pool
Private pool

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Skiing – property near ski resort
Walking trips
Tennis in town
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Golf course on site or within 15 min walk
Golf within 30mins drive
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170 Houses

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Welcome to Paradise

Long Key townhouse

2 bedrooms
3 bathrooms

sleeps 5

Price per night from

$205

Luxury beachfront home with pool in Islamorada

Layton house

3 bedrooms
4 bathrooms

sleeps 6

Responds fast! avg. 1 hour 30 minutes

Price per night from

$589

Sea Renity: Experience Tranquility, 2-Story Oceanfront Condo, Breathtaking Views

Layton condo

2 bedrooms
2 bathrooms

sleeps 6

Responds fast! avg. 2 hours 34 minutes

Price per night from

$172

Great rentals within 20 miles that match your search

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

Islamorada house

3 bedrooms
4 bathrooms

sleeps 6

Price per night from

$918

3Bd/2Ba POOL on Canal, Dock, Kayaks, Bikes, Fishing Poles, Sombrero Beach 2.3mi

Marathon Shores apartment

3 bedrooms
2 bathrooms

sleeps 8

Price per night from

$577

Key Colony Beach Oasis

Key Colony Beach house

4 bedrooms
3 bathrooms

sleeps 10

Price per night from

$1,154

Oceanside waterfront 2/2 home with 55ft dock and paddle equipment

Marathon Shores house

2 bedrooms
2 bathrooms

sleeps 6

Price per night from

$289

Beachfront Islamorada Villa with Dockage and Bay Views

Lower Matecumbe Key house

3 bedrooms
3 bathrooms

sleeps 6

Price per night from

$351

Reel Paradise Islamorada

Lower Matecumbe Key condo

1 bedroom
1 bathroom

sleeps 4

Price per night from

$214

Harbor Hideaway 4 Bedrooms-3 Bathrooms Waterfront- Indoor Pool

Marathon Shores house

4 bedrooms
3 bathrooms

sleeps 8

Price per night from

$749

The Butterfly Cottage

Marathon house

3 bedrooms
2 bathrooms

sleeps 8

Price per night from

$253

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

Islamorada house

2 bedrooms
3 bathrooms

sleeps 6

Price per night from

$462

The Mini Coconut

Marathon Shores house

2 bedrooms
1 bathroom

sleeps 6

Responds fast! avg. 1 hour 48 minutes

Price per night from

$260

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

Islamorada house

3 bedrooms
2 bathrooms

sleeps 8

Price per night from

$208

Hammerhead Hideaway- 2 Bed 2Bath Canal Front Home w/Cabana Club!

Key Colony Beach house

2 bedrooms
2 bathrooms

sleeps 6

Price per night from

$345

Key Colony Beach-2 Bed 2 Bath Canal Front Home with Cabana Club!

Key Colony Beach house

2 bedrooms
2 bathrooms

sleeps 6

Price per night from

$310

Oasis Canal-Front Home: Pool, 30ft Dock, BBQ, and more!

Marathon house

3 bedrooms
3 bathrooms

sleeps 8

Price per night from

$518

Pet Friendly Half-Duplex, Cottage with 40' Slip Option at The Boat House Marina

Marathon Shores cottage

1 bedroom
1 bathroom

sleeps 3

Price per night from

$196

Thirty Three by The Sea - Vacation Rental Key Colony Beach, FL

Key Colony Beach condo

2 bedrooms
2 bathrooms

sleeps 4

Price per night from

$345

Immaculate Waterfront ~ 2 BR ~ Private Pool, Tiki on Canal! 2 Min Walk to Beach!

Key Colony Beach house

2 bedrooms
1 bathroom

sleeps 4

Price per night from

$344

Gorgeous Florida Keys Vacation Home with Beach Access in Islamorada!

Islamorada townhouse

2 bedrooms
3 bathrooms

sleeps 6

Price per night from

$604

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

Islamorada townhouse

2 bedrooms
3 bathrooms

sleeps 5

Price per night from

$604

Townhome in Beachfront Community: Perfect for Florida Keys Vacation!

Islamorada townhouse

3 bedrooms
3 bathrooms

sleeps 7

Price per night from

$661

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

Islamorada house

2 bedrooms
2 bathrooms

sleeps 4

Price per night from

$604

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

Islamorada townhouse

2 bedrooms
3 bathrooms

sleeps 6

Price per night from

$204

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

Islamorada house

2 bedrooms
2 bathrooms

sleeps 6

Price per night from

$604

Gorgeous Vacation Home with Beach Access!

Islamorada townhouse

3 bedrooms
2 bathrooms

sleeps 7

Price per night from

$604

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

Islamorada townhouse

2 bedrooms
2 bathrooms

sleeps 6

Price per night from

$604

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

Islamorada townhouse

3 bedrooms
2 bathrooms

sleeps 6

Price per night from

$661

Boater's Paradise

Lower Matecumbe Key house

4 bedrooms
3 bathrooms

sleeps 10

Price per night from

$378

Villa Bella 3/3 with Private Pool and Dock

Key Colony Beach house

3 bedrooms
3 bathrooms

sleeps 7

Price per night from

$414

Sunchasers Paradise - spacious lux canal front home, private pool/spa, 80' dock

Marathon house

4 bedrooms
4 bathrooms

sleeps 10

Price per night from

$822

Luxury condo overlooking harbor with ocean view

Islamorada condo

3 bedrooms
3 bathrooms

sleeps 6

Price per night from

$391

Executive Bay Club- great unit, great location!,

Islamorada villa

2 bedrooms
2 bathrooms

sleeps 4

Responds fast! avg. 20 minutes

Price per night from

$205

"Irish Ayes" Elegant Waterfront Home with Pool

Islamorada house

4 bedrooms
4 bathrooms

sleeps 10

Price per night from

$802

Keys Kottage

Islamorada villa

2 bedrooms
2 bathrooms

sleeps 6

Price per night from

$315

Islamorada cottage on deep water canal

Islamorada house

2 bedrooms
2 bathrooms

sleeps 6

Price per night from

$287

Beautiful Captain's Cove

Islamorada villa

3 bedrooms
2 bathrooms

sleeps 6

Price per night from

$573

Viewing 38 of 170
rentals in Long Key

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Long Key Rentals

Per night

170 Houses

Viewing 38 of 170rentals in Long Key

Also consider

Viewing 38 of 170
rentals in Long Key