Key West, Florida Listings

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Monthly Rent $10000.00 - $11800.00

Welcoming home w/ private pool & covered porch - walk to dining & attractions Key West, Florida, Listing ID: 26008

Head to the Keys for your next Florida getaway and set yourself up for comfort and convenience when you stay at this welcoming, well-equipped home with a private pool and charming covered porch. You'll be situated only a mile from South Beach, so the sand and water are...

  • Home
  • 1440
  •  3
  •  3
Monthly Rent $5100.00 - $13500.00

Dog-friendly home w/ private pool & space to lounge - walk to everything! Key West, Florida, Listing ID: 26013

Come to Key West and ensure your Floridian getaway is the best it can be when you make this desirable rental your home away from home. Your group of up to eight will experience tranquil comfort and tasteful style in this dog-friendly home with a private pool, luxurious patio...

  • Home
  • 1596
  •  3
  •  3 1/2
Monthly Rent $5100.00 - $13500.00

Dog-friendly home w/ private pool, jetted tub, & gardens - relax on a hammock! Key West, Florida, Listing ID: 26015

If you're headed to Key West, make the most of your vacation and stay in this comfortable dog-friendly home with a private pool, a jetted tub, and gardens for an unforgettable Florida experience. You'll be located in a quiet neighborhood in New Town and only a bike ride or...

  • Home
  • 1646
  •  3
  •  2
Monthly Rent $4100.00 - $11200.00

Dog-friendly home w/ private pool - walk to parks, shopping, & the beach! Key West, Florida, Listing ID: 26017

This Key West home is waiting for you and your group of up to six to come make yourselves at home and enjoy lazy days by your private pool. You'll be within easy reach of the beach, parks, and all the necessities. Walk to Higgs Beach and the pier, Indigenous Park, and dinner...

  • Home
  • 1672
  •  3
  •  3
Monthly Rent $6600.00 - $10950.00

Dog-friendly, comfortable home w/ shared pool - close to beaches & attractions Key West, Florida, Listing ID: 26019

Head to Key West and revel in access to a shared pool, dog-friendly accommodations, and close proximity to beautiful beaches and major attractions when you stay at this three-bedroom, three-bath home for six. This rental is located in the heart of Old Town, putting you one...

  • Home
  • 1455
  •  3
  •  3

Stylish, inviting home w/private pool in heart of downtown - walk to everything! Key West, Florida, Listing ID: 26043

Make this stylish, three-bedroom, two-and-a-half bath home for six yours when you come to Key West, and revel in amenities like a private heated pool and an ideal location. Located in downtown Key West, this home is a mere one block from Duval Street. Southernmost Point and...

  • Home
  • 1178
  •  3
  •  2 1/2
Monthly Rent $11200.00 - $16700.00

Home w/private pool & hot tub - walk to everything Key West, Florida, Listing ID: 26060

Sink into the comfort of this lovely Key West home for 10, and enjoy a luxurious Florida getaway, complete with private pool and hot tub and excellent location, allowing you to walk to dining and all the sights. This home is located on a quiet street in Old Town Key West, a...

  • Home
  • 2352
  •  4
  •  3 1/2
Monthly Rent $5500.00 - $12500.00

Spectacular, oceanfront, dog-friendly home w/ private pool & boat docks Key West, Florida, Listing ID: 26063

Bring your large group of up to 18 to Key West and stay in this spectacular five-bedroom, three-bath oceanfront home for an unforgettable Florida vacation. Amenities include a private pool, massive deck with seating, lush surrounding gardens, and two private docks, as well as...

  • Home
  • 3332
  •  5
  •  
Monthly Rent $5100.00 - $9200.00

Cozy, dog-friendly home w/ patio & private pool - walk to dining & shopping! Key West, Florida, Listing ID: 26071

Head to Key West for a rejuvenating reprieve and enjoy the patio and private pool at this cozy, two-bedroom home conveniently situated near dining, shopping, and all the must-see sights. Your beloved family dog is also welcome for a small nightly fee. You'll be about two...

  • Home
  • 792
  •  2
  •  2
Monthly Rent $2600.00 - $5500.00

Welcoming, conveniently-located, dog-friendly home - walk to everything! Key West, Florida, Listing ID: 26074

If Key West is on your itinerary, make this welcoming, conveniently located one-bedroom home yours and enjoy comfort and the benefit of being right in the heart of the island. You'll be in the center of Key West within walking distance to restaurants, bars, and shops, as well...

  • Home
  • 705
  •  1
  •  1
Monthly Rent $4300.00 - $11500.00

Fully-renovated home w/ yard, porch, shared pool - one block from Duval Street Key West, Florida, Listing ID: 26075

Originally built in 1933, this fully renovated, three-bedroom home has a yard, a cozy front porch where you can sit back and watch the day go by, and room for up to eight guests (six comfortably). Stroll to shopping, entertainment, and beaches, all within a few blocks of this...

  • Home
  • 1051
  •  3
  •  2
Monthly Rent $3300.00 - $7300.00

Dog-friendly home w/ private pool offers fantastic location in central Key West Key West, Florida, Listing ID: 26077

Leave your worries behind with a relaxing trip to the Florida Keys courtesy of this lovely vacation home! This traditional home in Key West features modern amenities and a location perfect for sightseeing. Nestled in Key West's old town, this home for four puts you only a few...

  • Home
  • 1062
  •  2
  •  1
Monthly Rent $5300.00 - $5500.00

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 $3000.00 - $8100.00

Charming cottage w/a private parking spot and private hot tub Key West, Florida, Listing ID: 26087

Trade in the daily grind for sugar-sand beaches and gentle ocean breezes when you book your getaway to this lovely Key West cottage. Featuring a private parking spot and a bubbling hot tub, stress won't stand a chance. Located just a mile from Fort Zachary Taylor Historic...

  • Home
  • 750
  •  2
  •  2
Monthly Rent $4500.00 - $7800.00

Breezy Florida home with shared swimming pool, dog-friendly - walk to beach! Key West, Florida, Listing ID: 26094

Small families and close groups of friends will love this dog-friendly home for four in Key West! A shared swimming pool and nearby beach access provide everything you need for a great vacation. Your new home away from home rests comfortably by the city's Old Town, where lots...

  • Home
  • 694
  •  2
  •  2
Monthly Rent $4050.00 - $7550.00

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

Sprawling condo w/ ocean views, dock, & shared pool - dog-friendly! Key West, Florida, Listing ID: 26557

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
  • 1300
  •  2
  •  2 1/2

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Monthly Rent $1000.00 - $1400.00

Ground Floor 1 BR, 1.5BA West of Ft. Lauderdale near golf, Sawgrass Mall Tamarac, Florida, Listing ID: 24275

Nice ground floor unit with updated kitchen, all new IKEA furniture. 1 large bedroom with Queen bed & full bath, one half bath in hallway. Couch in living room is a sleeper and porch is enclosed with a couch bed. Ceiling fans in living room & porch. For 2 persons, but can easily...

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Details No Image Available

$Multi-Month Discount!

Monthly Rent $2600.00 - $4950.00

+++ 2-BED 2-BATH LUXURY CONDO IN NAPLES, FLORIDA ++ LAKE VIEW ++ VERY PRESTIGIOUS AREA ++ NEAR DOWNTOWN AND BEACHES! +++ Naples, Florida, Listing ID: 26574

DESCRIPTION: Bright corner unit. Fully furnished. 2 bedroom, 2 full bathrooms. First floor (second floor is also available). Heated pool. Tennis courts. Close to beaches, restaurants, shopping, golf, tennis and attractions. Incredible lake view from everywhere in your...

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BEAUTIFUL WATER FRONT HOME W/ PRIVATE BEACH, JACUZZI, DOCK, RAMP, LIFT, KAYAKS, ETC. Key Largo, Florida, Listing ID: 27311

Beautiful home directly on the water, being able to watch stunning sunsets all year around! 180 degrees of open water views. Imagine yourself being able to enjoy your glass of wine every afternoon watching the sunset. Tranquil waterway perfect for swimming, paddle-boarding,...

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beautiful beach front property,steps to the water Key Largo, Florida, Listing ID: 27322

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  • 2000
  •  5
  •  3
Details No Image Available

$Multi-Month Discount!

Monthly Rent $3000.00 - $6000.00

Luxury Fiddler's Creek 3Br condo in gated golf resort community with tennis and multiple pools, paths, spa, fitness Naples, Florida, Listing ID: 27548

This luxury resort offers security at gate. The community is over 54,000 acres with walking paths, nature areas, water features, and gorgeous landscaping. Golf course on site. Tennis and pickleball. Each small community has a private pool and the clubhouse has a large waterfall...

  • Condo
  • 2100
  •  3
  •  2
Monthly Rent $5500.00

Ocean breezes and spectacular sunrises every morning from the Pier and the Marina. Great way for a gateway. 3 Floors. Key Largo, Florida, Listing ID: 28211

4 bedroom and 3.5 baths (Sleeps up to 10 People) 2 balconies, 3 floors, 1st floor storage & carport area. Neighborhood Feature: Clubhouse, Community Pool, Community Boat Ramp, Other Area Features, Community Dockage, Fire Hydrant, Manager on Premises, Security: Manned...

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  • 2665
  •  4
  •  3 1/2
Monthly Rent $5500.00

Walking distance from the ocean! KEY LARGO, Florida, Listing ID: 28212

Ocean breezes and spectacular sunrises every morning from the Pier and the Marina. ClubHouse and steps from the ocean.

  • Home
  • 2665
  •  4
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Details No Image Available

$Multi-Month Discount!

Monthly Rent $4400.00 - $4600.00

Beautiful Peaceful Home with a 60 foot cement dock on a deep water canal connected to a beautiful open bay. Tavernier, Florida, Listing ID: 28249

Lovely home on deep water canal with dockage. Located in a quiet neighborhood. It has a 60 foot cement dock with a fish cleaning table and outdoor shower head. Upon exiting the canal there is a great bay area for wake boarding, skiing, tubing etc. Snake creek and Tavernier creek...

  • Home
  • 1242
  •  2
  •  2
Monthly Rent $3500.00 - $5000.00

Modern second floor coach home with award-winning Player's Club and Spa. 3 bedrooms and 2 bath. 15 min drive to beach. Naples, Florida, Listing ID: 28409

Enjoy membership at the award-winning Player's Club and Spa which provides 13 tennis courts for the competitive or casual player, two resort saltwater pools with waterfalls, jacuzzi, lap pool, bocce courts, full-service spa, sauna, steam room, fitness center, full-service dining...

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  • 2400
  •  3
  •  2
Details No Image Available

$Multi-Month Discount!

Monthly Rent $3350.00 - $4350.00

Charming Naples seasonal & monthly rental in beautifully remodeled villa minutes from beaches, downtown & Marco Island Naples, Florida, Listing ID: 28418

This immaculate beautifully remodeled 1350 sf, 3-bedroom, 2-bathroom villa in Naples’ Shadowood Villas lives like a single-family home with one shared wall. Features open concept main level living, vaulted ceilings, attached 2-car garage, south facing screened lanai (both...

  • Villa
  • 1350
  •  3
  •  2
Monthly Rent $2500.00

COZY TOWNHOUSE 2/2 CANAL/OCEAN VIEW. BEST AREA OF THE KEYES My home is your home. TAVERNIER, Florida, Listing ID: 28438

Very clean Townhouse located in the best and secure area of Middle Florida Keyes. 2 bedroom and 2 private bathroom. Condo is in a canal with a DIRECT access to the ocean. Come and relax in this quite facility. Fall in love with the breathtaking sunset views over the water from...

  • Condo
  • 1200
  •  2
  •  1 1/2

This beautiful Sea Escape is equipped with your very own dock, 3 flrs of charismatic beachy-feel to set the stage! Islamorada, Florida, Listing ID: 28531

Contact me for Special Pricing!! This is a beautiful property rents between October and March rent it all 6 months or a few months at a time. Enjoy this beautiful oasis and recharge the batteries with amazing scenery from the moment you wake up till the moment you rest your head...

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  • 3,000
  •  2
  •  3