Key West Listings

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Monthly Rent $11928.00 - $23051.00

3BR Dog Friendly | Pool | Balcony | W/D Key West, Florida, Listing ID: 32690

This home only allows minimum night stays of 28 nights or longer. This is enforced by the HOA and we cannot make any exceptions. This Key West home is waiting for you and your group to make yourselves at home and enjoy lazy days by your private pool. You'll be within easy reach...

  • House
  • 1672
  •  3
  •  3
Monthly Rent $10622.00 - $19544.00

Prime 2BR | Balcony | Dog Friendly Key West, Florida, Listing ID: 32691

*Please note that this home only allows minimum night stays of 28 nights or longer. This is enforced by the HOA and we cannot make any exceptions. Get away from it all and head to Key West for a sun-filled vacation with this two-bedroom, two-bath condo for six and enjoy easy...

  • Condo
  • 1800
  •  2
  •  2
Monthly Rent $5847.00 - $11482.00

Welcoming 1BR Dog Friendly | W/D Key West, Florida, Listing ID: 32692

*Please note that this home only allows minimum night stays of 28 nights or longer. This is enforced by the HOA and we cannot make any exceptions. If Key West is on your itinerary, make this welcoming, conveniently located one-bedroom home yours and enjoy comfort and the benefit...

  • House
  • 700
  •  1
  •  1
Monthly Rent $5971.00 - $9574.00

Sunny 2BR Dog Friendly | Chef's Kitchen| Hot Tub Key West, Florida, Listing ID: 32693

Sunshine comes easy in Key West, and you can enjoy it all here. Built in 1945, this beautiful home has been restored to perfection with amenities galore for modern guests to enjoy. Central air conditioning pairs perfectly with the home's high ceilings, creating a sunny...

  • House
  • 1053
  •  2
  •  3
Monthly Rent $4247.00 - $8202.00

Charming 1BR Dog Friendly | Deck | W/D Key West, Florida, Listing ID: 32695

*Please note that this home only allows minimum night stays of 28 nights or longer. This is enforced by the HOA and we cannot make any exceptions. Take advantage of all that Key West has to offer from the incredible location of this adorable Key West home. This home features a...

  • House
  • 524
  •  1
  •  1
Monthly Rent $8950.00 - $16692.00

Large 3BR Dog Friendly | Pool | Balcony | W/D Key West, Florida, Listing ID: 32696

This beautiful Key West home has just the right mix of beach vibes and modern amenities to make you feel right at home during your Florida vacation. Multiple Smart TVs, an Alexa home speaker, and Netflix account let you play music and relax on lazy days. A spacious kitchen opens...

  • House
  • 1584
  •  3
  •  3
Monthly Rent $5377.00 - $8425.00

Charming 2BR Dog Friendly | Deck | W/D Key West, Florida, Listing ID: 32697

This gorgeous home is a perfect escape for a private and quiet getaway. The home is surrounded by palm trees which creates a shaded and private patio. The home has a large 750 square foot master suite that is super luxurious - you may not want to leave the bedroom! A fully...

  • House
  • 1873
  •  2
  •  2
Monthly Rent $4131.00 - $7152.00

3BR Oceanview Dog Friendly | Dock | Patio Key West, Florida, Listing ID: 32698

Beautifully situated among the palms and right on a canal that leads out to open water, this three-bedroom home on Big Coppitt Key is the perfect Florida Keys escape for boating enthusiasts, anglers, and families and friends in search of waterfront relaxation. This single-story...

  • House
  • 1408
  •  3
  •  2
Monthly Rent $5424.00 - $9549.00

Upscale 3BR Lakeview Dog Friendly | Pool | Deck Key West, Florida, Listing ID: 32700

Nestled in a peaceful gated community, this two-level townhome is located right on a golf course in the gated grounds of the Key West Golf Club, only a few miles from those pristine Key West beaches. Your group will have multiple private outdoor areas to choose from, depending...

  • Townhouse
  • 1060
  •  3
  •  3
Monthly Rent $9417.00 - $12388.00

Colorful 2BR Oceanview 2nd-Floor | Balcony Key West, Florida, Listing ID: 32701

All the best of Key West is right at your doorstep at this colorful, second-floor condo just across the street from the gorgeous aquamarine water the Keys are known for. Smathers Beach is just down the road, and all the restaurants, bars, and cafs of Duval St. and the historic...

  • Condo
  • 1186
  •  2
  •  2
Monthly Rent $10393.00 - $19250.00

3BR Waterview Dog Friendly | Pool | Deck | W/D Key West, Florida, Listing ID: 32702

Featuring its own backyard oasis, this two-story retreat invites you to experience the best of island living right at home. Surrounded by lush landscaping, the fenced backyard features a private heated pool with a waterfall as well as an outdoor seating area where you can dine...

  • House
  • 1750
  •  3
  •  3
Monthly Rent $4628.00 - $5923.00

2BR Oceanfront Dog Friendly | Dock | Balcony Key West, Florida, Listing ID: 32703

A serene, canal-front oasis is yours at this Big Coppitt Key retreat. Complete with a private dock and boat ramp offering direct access to the Gulf of Mexico, this dreamy two-story condo comes primed for island living. A breezy, canal-view deck makes a perfect perch for sipping...

  • Duplex
  • 1095
  •  2
  •  2
Monthly Rent $6750.00 - $9532.00

Upscale 3BR Golf Course View Dog Friendly | Pool Key West, Florida, Listing ID: 32704

This vacation home is perfect for your next adventure with family and furry companions. Enjoy a quiet afternoon in the hammock on the balcony that overlooks the golf course and the private pool, where you can venture down for a splash. The enclosed backyard is filled with...

  • House
  • 1600
  •  3
  •  3
Monthly Rent $4528.00 - $7975.00

Walk to Beach 2BR Dog Friendly | Pool | Patio Key West, Florida, Listing ID: 32705

*Please note that this home only allows minimum night stays of 28 nights or longer. This is enforced by the HOA and we cannot make any exceptions.* Small families and close groups of friends will love this dog-friendly home for four in Key West! A shared swimming pool and nearby...

  • House
  • 694
  •  2
  •  1
Monthly Rent $2000.00 - $6000.00

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

2bedroom/2bathroom Beach House Key West, Florida, Listing ID: 31954

his two-bedroom, two-bath classic contemporary is the perfect headquarters for your dream vacation. The entire inside is painted cloud white. This choice creates not only a crisp, clean elegance but also serves as the perfect backdrop for an amazing art collection. It's fitting...

  • House
  • 881
  •  2
  •  1/2

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Monthly Rent $3880.00 - $7293.00

BOAT-FRIENDLY, DOG-FRIENDLY, newly renovated 2BR Home (Sleeps 6) High-Speed WiFi, Canal-front Dock, Private Boat Ramp! Tavernier, Florida, Listing ID: 31490

Book this newly renovated home that sits on a major canal, where guests can tie off a boat, in the Indian Waterways neighborhood. The nautical-themed decoration throughout the house will truly help you leave all of your worries behind and focus on having a great time!...

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  • 0
  •  2
  •  1
Monthly Rent $5630.00 - $7856.00

3BR Oceanfront Dog Friendly | Dock | Balcony Big Pine Key, Florida, Listing ID: 32350

Situated along the canal with approximately 150 feet of seawall, this newly constructed home puts water activities right outside your doorstep. Untie your boat from the provided dock space and take a laidback boat ride into ocean or Gulf waters via the Bogie Channel. Enjoy...

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  • 1190
  •  3
  •  2
Monthly Rent $3690.00 - $6071.00

2BR Waterview Dog Friendly | Patio | W/D Cudjoe Key, Florida, Listing ID: 32402

With a waterfront location overlooking the canals of Cudjoe Key, this comfy and convenient home is going to be the ideal place to enjoy some time with family and friends. The living room is spacious and attractive, featuring burnished floors, a mounted flatscreen TV, and a large...

  • House
  • 1200
  •  2
  •  3
Monthly Rent $9800.00 - $12582.00

2BR Oceanfront Dog Friendly | Pool | Dock Cudjoe Key, Florida, Listing ID: 32403

Set on a quiet corner lot with a private, heated pool, 50-foot seawall, outdoor bar, and a yard peppered with key lime, dragon fruit, mango, and coconut trees, this unique waterfront retreat is sure to be the highlight of your next vacation in the Keys! When you want to get out...

  • House
  • 1120
  •  2
  •  2
Monthly Rent $2765.00 - $5505.00

Canal-front, dog-friendly 2BR with dock & pool Duck Key, Florida, Listing ID: 32477

Lobster Lodge is the perfect retreat for your family getaway to the Sunshine State! This canal-front half-duplex features a 35-foot seawall dock. Relax out on the patios overlooking the canal or sit by the shared pool after taking a refreshing dip. Cozy up in the living area for...

  • Duplex
  • 1554
  •  2
  •  2
Monthly Rent $2765.00 - $5748.00

Dog-friendly 2BR on the canal with pool & dock Duck Key, Florida, Listing ID: 32479

Make yourself at home at this lovely, dog-friendly getaway featuring a 35-foot seawall dock! Prepare delicious meals and beach snacks and enjoy them on the expansive deck overlooking the canal. This family-friendly home also grants you access to a shared, heated swimming pool -...

  • Duplex
  • 1554
  •  2
  •  2
Monthly Rent $1554.00 - $2581.00

Inviting 1BR Dog Friendly | Balcony | Firepit Key Largo, Florida, Listing ID: 32672

*Please note that this home only allows minimum night stays of 28 nights or longer. This is enforced by the HOA and we cannot make any exceptions. Escape the rat race and unwind in the beauty of the tropics when you book your soothing vacation to this Key Largo retreat. Built in...

  • House
  • 880
  •  1
  •  1
Monthly Rent $3625.00 - $4393.00

Sunny 2BR Dog Friendly | Private Pool | Deck Key Largo, Florida, Listing ID: 32673

Craving a beachy house with a yard? This home is perfect for those who want to get away from the hustle and bustle of the city and sink into a stool at the tiki bar. Relax on the shaded porch or in the private pool Throw some fish or hot dogs on the private gas grill, or just go...

  • House
  • 896
  •  2
  •  2
Monthly Rent $4256.00 - $8286.00

3BR Dog Friendly | Balcony | W/D Key Largo, Florida, Listing ID: 32674

Full of sunlight and modern coastal furniture, this home is ideal for a family or group looking to get away from it all. Recline on your personal screened-in balcony, or spread out within the comfortable living room. The open kitchen features everything guests need to cook up...

  • House
  • 1467
  •  3
  •  2
Monthly Rent $2760.00 - $14840.00

3BR Oceanview Dog Friendly | Pool | Dock | Patio Marco Island, Florida, Listing ID: 32741

This lovely canal-side home is sure to make your stay on Marco Island one to remember. Spacious, this single-family home is packed with enjoyable amenities. Enjoy water views from the lanai, or while going for a swim in the west-facing heated pool. Cook on the grill while taking...

  • House
  • 1900
  •  3
  •  2
Monthly Rent $3600.00 - $18650.00

3BR Lakefront Dog Friendly | Pool | Patio | W/D Naples, Florida, Listing ID: 32817

Cheerful, bright, and full of amenities, this lovely home is ready to welcome families and groups. Enjoy views of a local lake just outside your window, You may spend most of your stay out next to the private pool - the lanai makes it easy to get comfortable no matter what the...

  • House
  • 1998
  •  3
  •  2
Monthly Rent $8130.00 - $14748.00

3BR Dog Friendly | Private Pool | Deck | W/D Naples, Florida, Listing ID: 32818

Nestled within the Moorings, this home is ready to welcome guests with refined furnishings and helpful amenities. From the moment you walk through the front door, you'll feel at ease within the upscale nautical design. The star of the home is undoubtedly the bright private pool,...

  • House
  • 3088
  •  3
  •  3