Vacation Rentals & House Rentals in Florida Keys

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146 house rentals

NEW LISTING! 40’ Luxury Catamaran Yacht!

Key West yacht

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

Match: Boat available Shared outdoor pool (unheated)

All filters match

Price per night from

$1,946

Home w/Gourmet Kitchen- Marlin Bay Resort & Marina

Marathon house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Boat available Shared outdoor pool (unheated)

All filters match

Price per night from

$639

Botanical Island Delight Key West fantastic discounts for Summer & Fall

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Boat available Shared outdoor pool (unheated)

All filters match

Price per night from

$745

Expertly Decorated-Marlin Bay Resort & Marina

Marathon house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Boat available Shared outdoor pool (unheated)

All filters match

Price per night from

$580

Anchor Drop modern elegance upgrades throughout views of Atlantic Ocean

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Boat available Shared outdoor pool (unheated)

All filters match

Price per night from

$1,374

Clean & Pristine Home - Marina Bay Resort & Marina

Marathon house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Boat available Shared outdoor pool (unheated)

All filters match

Price per night from

$640

Ocean Hideaway a Key West Nature retreat close to Smathers & 15 to Duval

Stock Island condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Boat available Shared outdoor pool (unheated)

All filters match

Price per night from

$859

Caribbean Conch 5 Minutes to Smathers Beach & 10 minute Bike Downtown - Value

Stock Island condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Boat available Shared outdoor pool (unheated)

All filters match

Price per night from

$859

Hidden Gem Sunset Views-Marlin Bay Resort & Marina

Marathon house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Boat available Shared outdoor pool (unheated)

All filters match

Price per night from

$1,369

Boaters’ Paradise - Marlin Bay Resort & Marina

Marathon house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

Match: Boat available Shared outdoor pool (unheated)

All filters match

Price per night from

$1,848

SEAPORT SERENITY in Old Town—Beach-Pool-BBQ-Hot Tub

Key West condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Boat available Shared outdoor pool (unheated)

All filters match

Price per night from

$911

Boutique Resort w/Pool- Marlin Bay Resort & Marina

Marathon house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Boat available Shared outdoor pool (unheated)

All filters match

Price per night from

$640

Leaward Isle close to the Ocean' & a short bike downtown. Best value at 1800

Stock Island condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Boat available Shared outdoor pool (unheated)

All filters match

Price per night from

$859

4 Bd w/Pool, Bayside - Marlin Bay Resort & Marina

Marathon house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

Match: Boat available Shared outdoor pool (unheated)

All filters match

Price per night from

$1,848

Casa Coastal East, Morning sunrises, Evening night time vibes An Island home.

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Boat available Shared outdoor pool (unheated)

All filters match

Price per night from

$478

High Tide awaits your next visit upgraded condo close to Smathers Beach

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Boat available Shared outdoor pool (unheated)

All filters match

Price per night from

$859

Family Friendly w/Pool- Marlin Bay Resort & Marina

Marathon house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Boat available Shared outdoor pool (unheated)

All filters match

Price per night from

$579

Attn:Couples, 3 Kings - Marlin Bay Resort & Marina

Marathon house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Boat available Shared outdoor pool (unheated)

All filters match

Price per night from

$580

Our Nautical Home in Key West is available for amazing prices Summer of 2023

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Boat available Shared outdoor pool (unheated)

All filters match

Price per night from

$859

Terrace & Roof Top Deck-Marlin Bay Resort & Marina

Marathon house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Boat available Shared outdoor pool (unheated)

All filters match

Price per night from

$580

Roof Top Water Views - Marlin Bay Resort & Marina

Marathon house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Boat available Shared outdoor pool (unheated)

All filters match

Price per night from

$640

Mar Y Sol a spectacular Ocean Front Oasis 10 minutes to Historic District

Key West apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Boat available Shared outdoor pool (unheated)

All filters match

Price per night from

$1,718

Top floor Ocean Views, Spacious 2 Bedroom Condo, Views from every room

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Boat available Shared outdoor pool (unheated)

All filters match

Price per night from

$974

Poolside Breeze a Tropical Retreat has a wrap around Balcony best location

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Boat available Shared outdoor pool (unheated)

All filters match

Price per night from

$859

Gated w/Bayside Marina- Marlin Bay Resort & Marina

Marathon house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Boat available Shared outdoor pool (unheated)

All filters match

Price per night from

$640

Couples Getaway, Suites-Marlin Bay Resort & Marina

Marathon house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Boat available Shared outdoor pool (unheated)

All filters match

Price per night from

$580

Walk to Duval and Mallory Square!

Stock Island condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Boat available Shared outdoor pool (unheated)

All filters match

Price per night from

$622

Hyatt Sunset Harbor

Stock Island condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Boat available Shared outdoor pool (unheated)

All filters match

Price per night from

$525

Hyatt Windward Pointe

Stock Island apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Boat available Shared outdoor pool (unheated)

All filters match

Price per night from

$525

Hyatt Sunset Harbor

Stock Island condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Boat available Shared outdoor pool (unheated)

All filters match

Price per night from

$523

Hyatt Windward Pointe

Stock Island apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Boat available Shared outdoor pool (unheated)

All filters match

Price per night from

$445

Hyatt Windward Pointe

Stock Island apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Boat available Shared outdoor pool (unheated)

All filters match

Price per night from

$484

Coconut Mallory Resort and Marina

Stock Island condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Boat available Shared outdoor pool (unheated)

All filters match

Price per night from

$346

Hyatt Beach House! Quiet Key West Location!

Stock Island condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Boat available Shared outdoor pool (unheated)

All filters match

Price per night from

$471

Walk to Duval and Mallory Square!

Stock Island condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Boat available Shared outdoor pool (unheated)

All filters match

Price per night from

$654

Walk to Duval and Mallory Square!

Stock Island condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Boat available Shared outdoor pool (unheated)

All filters match

Price per night from

$667

These homes match some but not all of your filters. Clear all filters

Lovely 2 bedroom, 2 bath condo at La Brisa.

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Boat available, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$161

ISLAMORADA 3bd in WATERFRONT COMMUNITY w BEACH!!

Islamorada apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Boat available, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$363

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rentals in Florida Keys

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