Key West Listings

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Monthly Rent $4800 - $10000

Cozy, chic cottage w/ private pool - close to beach and dog friendly, too! Key West, Florida, Listing ID: 26007

Make this cozy and chic Key West cottage your home away from home for your next Florida vacation, and revel in a private pool, deck, and covered back porch, as well as close proximity to the beach. And the real bonus: you can bring your favorite canine friend along,...

  • Home
  • 1400
  •  3
  •  2
Monthly Rent $2500 - $6300

Cute dog-friendly tropical condo close to attractions w/a pristine shared pool Key West, Florida, Listing ID: 26085

This dog-friendly cottage includes street parking, a shared pool, and a location near Duval Street. Nestled in a quiet neighborhood about a mile from Higgs Beach Dog Park and a little under a mile to Mallory Square, you'll be able to get out and about with ease. With fresh...

  • Condo
  • 731
  •  1
  •  1 1/2
Monthly Rent $3700 - $10000

Vibrant home w/hot tub & private pool blocks from the beach - dog-friendly! Key West, Florida, Listing ID: 26096

This colorful dog-friendly Florida home has everything you need for an unforgettable vacation, with a private swimming pool and hot tub and walking distance from the beach. Your home sits only a few blocks away from the soft sands and warm waters of Higgs Beach. If you'd...

  • Home
  • 2328
  •  2
  •  2 1/2
Monthly Rent $3400 - $6700

Sprawling condo w/ ocean views, dock, & shared pool - dog-friendly! Key West, Florida, Listing ID: 26100

Explore the tropical surroundings of Key West in style from the comfort of this dog-friendly condo! A shared pool, ocean views, and more await you. Nestled on the northern side of Key West, you have easy access to the shops and restaurants of Old Town, as well as a dock and...

  • Condo
  • 1237
  •  2
  •  2 1/2
Monthly Rent $2000 - $3900

Lovely home tucked away in northern Key West w/shared pool, near golf - dogs OK! Key West, Florida, Listing ID: 26103

Bring your family, friends, dog (for a small nightly fee) and golf clubs along for a stay in this lovely two-bedroom, one-and-a-half-bathroom home! A great location near the golf course, along with plenty of amenities (including a shared pool), ensure this will be a vacation to...

  • Home
  • 820
  •  2
  •  1 1/2
Monthly Rent $3700 - $10300

Welcoming home w/ shared pool boasts great Old Town location - dogs welcome! Key West, Florida, Listing ID: 26114

Amenities like a shared pool, dog-friendly accommodations, and a fantastic location all make this home perfect for your next trip to the Florida Keys! Your new getaway of choice is only a block away from Duval Street, right near Key West's Old Town. Shops and restaurants are...

  • Home
  • 1275
  •  2
  •  3

Similar Properties


Monthly Rent $5500 - $7500

Great Private Home with Spectacular Views of the Ocean from anywhere in Home!!!! Islamorada, Florida, Listing ID: 24289

Minimum Rental: 1 Month Location, location, location! This home has it all - ocean side Lower Matecumbe location, totally remodeled in 2009. Relax by the cocktail pool or sunbathe in the private roof top sunning area. There are blue water ocean views from almost every room...

  • Home
  • 1200-1400
  •  3
  •  3
Monthly Rent $3675 - $4750

"Meticulously" cared for Home the owners are now offering to share for your Vac! Islamorada, Florida, Listing ID: 24293

MINIMUM STAY: 28 DAYS Villa Riolo is an updated single family stilt home and perfect for your next holiday in Islamorada! It comfortably sleeps 4-6 in two bedrooms. This home has been meticulously cared for over the years and for the first time the owners are offering...

  • Home
  • 1000-1200
  •  2
  •  2
Monthly Rent $2875 - $3725

Bayfront townhouse located in the lush tropical setting of Rock Harbor Club. Key Largo, Florida, Listing ID: 24303

MINIMUM STAY: 28 Nights. Bayfront townhouse located in the lush tropical setting of Rock Harbor Club in Key Largo. You'll love the open water views from the two oversized screened balconies - one off the main living area and the other off the master suite. There's something...

  • Home
  • 1000-1200
  •  2
  •  2 1/2
Monthly Rent $3800 - $4850

3 BR Townhouse Oceanside with 30' Dock and Boat Lift Key Largo, Florida, Listing ID: 24304

Minimum Rental: 1 MONTH This is a gorgeous 3 bedroom townhouse in a private upscale ocean front condominium community! Everything you could want is located within the community - heated pool; hot tub; covered seating area; tennis court; children's playground;...

  • Condo
  • 2261
  •  3
  •  2
Monthly Rent $9500 - $11000

Magnificent Home mouth of a wide canal in Tavernier Phenomenal Open Water View Plantation Key, Florida, Listing ID: 24309

MINIMUM STAY: 29 DAYS This magnificent home is located at the mouth of a wide canal in Tavernier and offers phenomenal open water views. The furnishings are new and provide a comfortable and extremely inviting living environment. This 4 bedroom 3 bath single family home...

  • Home
  • 2500-3000
  •  4
  •  3
Monthly Rent $3750 - $4950

Stay in the Florida Keys! You will love this wonderful 2013 built stilt home!!!! Plantation Key, Florida, Listing ID: 24310

BEST PRICED WATERFRONT HOME IN AREA *******ALL NEW MONTHLY RATES******* MINIMUM STAY: 28 DAYS "Bayside Breeze" is a wonderful 2013 built stilt home centrally located in the Islamorada/Tavernier area. The open concept living area - kitchen, dining, and living - invites...

  • Home
  • 1400-1600
  •  3
  •  2
Monthly Rent $5950 - $7950

The Florida Keys at its best.3 Bedrooms and 2 Plantation Key, Florida, Listing ID: 24311

MINIMUM STAY: 28 DAYS NEW OPPORTUNITY to LIVE THE LIFE! This 3 Bedrooms and 2 ½ Baths home with POOL, Dock, and all new furnishings make this your opportunity to experience The Florida Keys at its best.  Conveniently located on a deep and wide canal with easy access to...

  • Home
  • 2000-2500
  •  3
  •  2 1/2
Monthly Rent $9975

!Tropical Retreat Wonderful Home Billiard/Game Room Pool Boat Dock A True Gem!!! Plantation Key, Florida, Listing ID: 24314

Minimum Rental: 1 Month Spacious elegant home with pool and dock. Gently swaying palm trees greet you at the gated entrance to this wonderful home. The ground level entry features a billiard/game room, bedroom and full bath. An open curved staircase leads to the 2nd floor...

  • Home
  • 2500-3000
  •  4
  •  3
Monthly Rent $4150

"Sunshine Place" Perfect for one or two people who treasure the tropical Live!!! Islamorada, Florida, Listing ID: 25398

"Sunshine Place" is setup perfectly for privacy and convenience. The owners of this wonderful property called Sunshine Place are willing to share a portion of their piece of Paradise with you. The ground level living area of this home is perfect for one or two people who...

  • Home
  • 800-1000
  •  1
  •  1
Monthly Rent $5200

harming vacation home located in the beautiful neighborhood of Port Antigua. You will love this home! Islamorada, Florida, Listing ID: 25667

MINIMUM RENTAL 1 MONTH Charming vacation home located in the beautiful neighborhood of Port Antigua. You will love this home! There is a wonderful open concept floor plan with 3 nicely proportioned bedrooms. Sliding doors open from the dining area into the sunroom ...

  • Home
  • 1494
  •  3
  •  2
Monthly Rent $3500

A 2 beds/1 bath vacation home located in a safe and quiet neighborhood surrounded by farmland perfect for snowbirds. Homestead, Florida, Listing ID: 26445

Located in a quiet neighborhood surrounded by farmland, gateway to the Keys, with just over 1,000 square feet of living space, this 2 beds/1 bath cozy single home built on 1.2 acre land, fully fenced-in with private driveway and parking lot. Amenities include a fully...

  • Home
  • 1100
  •  2
  •  1
Monthly Rent $1800 - $3300

Chill in the Florida Keys Key largo, Florida, Listing ID: 26642

3 Story Town house

  • Home
  • 1500
  •  3
  •  3
Monthly Rent $2700 - $3150

Beautiful completely updated 2/2 House in Tamarac with community pool Tamarac, Florida, Listing ID: 26663

In a quiet neighborhood .This house has everything you need to make you feel at home, secure and relaxed. Also included, is basic cable TV, internet, central A/C and much more. This beautiful spacious, self-contained fully equipped house has everything you need to make you feel...

  • Home
  • 1,275 sq. ft.
  •  2
  •  2
Monthly Rent $2500

Cypress Bend condo, 5 miles from beach! Lakeview, 2nd floor, corner unit, small pet OK ! Pompano Beach, Florida, Listing ID: 26745

Plenty of parking, master parking space right in front of unit, stairs or elevator access, access to 1 Olympic size pool. and 2 other pools, 2 hot tubs, 1.5 mile walking path, on lake, short drive to beach, restaurants, groceries. 1 small pet allowed. 2 Gyms. 1 clubhouse, 1...

  • Condo
  • 1000
  •  2
  •  2