Key West, Florida Vacation Rentals

Key West, FL vacation rentals, browse Key West, Florida vacation home rentals and plan your next Florida Keys vacation in Key West. Imagine relaxing in the Florida Keys Vacationing by yourself, vacationing with your family or vacationing with friends, make your next vacation a Florida Keys vacation.

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Key West, FL

Key West, FL Area
Florida Keys Vacation Rentals

Conch Cottage, Old Town Location – Weekly Vacation Rental, Hot Tub, 1BD/1BA, Fully Equipped Kitchen, Private Rear Deck.

Sleeps: 2
Bedrooms: 1
Bathrooms: 1
Pets Considered

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Key West, FL

Key West, FL Area
Florida Keys Vacation Rentals

Downtown Cottage Just Off Famous Duval Street, Open Style Full Kitchen, Pool On Property, Free Off Street Parking Spot.

Sleeps: 6
Bedrooms: 2
Bathrooms: 2
Pets Considered

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Key West, FL

Key West, FL Area
Florida Keys Vacation Rentals

~ Martha Truman Suite ~ Luxury Suite w/Spacious Sundeck & Shared Plunge Pool! Beach Towels Provided.

Sleeps: 3
Bedrooms: 1
Bathrooms: 1
No Pets

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Key West, FL

Key West, FL Area
Florida Keys Vacation Rentals

Casa Loca- One Of A Kind Estate 1/2 Block From Duval In Old Town Key West, Heated Private Pool, Galley Kitchen.

Sleeps: 8
Bedrooms: 3
Bathrooms: 2.5
Pets Considered

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Key West, FL

Key West, FL Area
Florida Keys Vacation Rentals

~ Poinciana Garden, Updated Condo w/Private Hot Tub & Parking In Perfect Location, 1BR First Floor Unit, Shared Gas Grill.

Sleeps: 3
Bedrooms: 1
Bathrooms: 1
No Pets

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Key West, FL

Key West, FL Area
Florida Keys Vacation Rentals

Beach Club #103 – Unique Oceanfront Living With Breathtaking Views, Large Oceanfront Balcony, 2 Ocean Side Pools, Tennis Court.

Sleeps: 6
Bedrooms: 2
Bathrooms: 2
No Pets

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Key West, FL

Key West, FL Area
Florida Keys Vacation Rentals

“In Good Spirits” ~ Waterfront Condo With Wrap-Around Balcony & Community Pool! Perfect Setting For Families.

Sleeps: 6
Bedrooms: 2
Bathrooms: 2
No Pets

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Key West, FL

Key West, FL Area
Florida Keys Vacation Rentals

Casa De Cuba A Beach House – Cuban Flair Steps From Duval, Location! Style! Elegance! Private Pool, Furnished Very Nice & Updated.

Sleeps: 6
Bedrooms: 3
Bathrooms: 2
No Pets

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Key West, FL

Key West, FL Area
Florida Keys Vacation Rentals

~ Poinciana Treetop ~ Updated Suite w/Private Parking In Great Location! Less Than 2 Blocks From Duval Street.

Sleeps: 3
Bedrooms: 1
Bathrooms: 1
No Pets

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Key West, FL

Key West, FL Area
Florida Keys Vacation Rentals

Casa Margarita: Amazing Location w/Private Heated Pool, Huge Deck, Private Parking, Large Backyard w/Lush Tropical Landscaping.

Sleeps: 8
Bedrooms: 3
Bathrooms: 3
Pets Considered

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Key West, FL

Key West, FL Area
Florida Keys Vacation Rentals

~ Petite Maison ~ Luxury Home Steps To Duval St w/Private Parking, Dogs OK, Two-Story Cottage, Covered Second Floor Terrace.

Sleeps: 4
Bedrooms: 2
Bathrooms: 2
Pets Considered

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Key West, FL

Key West, FL Area
Florida Keys Vacation Rentals

Secret Villa I @ Old Town w/Private Heated Pool, Close To Duval! Private Sanctuary, Lush Gardens, Natural Vegetation, Tropical Canopies.

Sleeps: 6
Bedrooms: 3
Bathrooms: 3
No Pets

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Key West, FL

Key West, FL Area
Florida Keys Vacation Rentals

3 Story Spacious Conch Style Home w/Private Pool, Private Back Yard, Chaise Lounges, Fully Equipped Chef’s Kitchen.

Sleeps: 10
Bedrooms: 4
Bathrooms: 3.5
No Pets

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Key West, FL

Key West, FL Area
Florida Keys Vacation Rentals

Galleon Resort Waterfront Luxury In Old Town, Huge Deck, Private Hot Tub, Private Rooftop Deck, Fully Equipped Kitchen.

Sleeps: 5
Bedrooms: 1
Bathrooms: 1
No Pets

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Key West, FL

Key West, FL Area
Florida Keys Vacation Rentals

“Tides On Simonton” ~ Perfectly Located Just Off Duval & All The Fun! Sit Back, Relax & Enjoy! Perfect For A Couple’s Getaway.

Sleeps: 4
Bedrooms: 1
Bathrooms: 1
Pets Considered

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Key West, FL

Key West, FL Area
Florida Keys Vacation Rentals

Sea Biscuit 1/2 Block To Duval, Private Pool, Relax & Enjoy Your Coffee Or Margarita, This Home Is Ready For You To Enjoy. Perfect Location!!!

Sleeps: 8
Bedrooms: 4
Bathrooms: 4
Pets Considered

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Key West, FL

Key West, FL Area
Florida Keys Vacation Rentals

The Smiling Ibis @ Old Town** Home & Private Pool Near Duval + Last Key
Services…Wet Bar, Fully Fenced For Privacy.

Sleeps: 8
Bedrooms: 3
Bathrooms: 3
Pets Considered

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Key West, FL

Key West, FL Area
Florida Keys Vacation Rentals

Mango Cottage- 2BR/2BA Family-Friendly Old Town Private Home w/Private Pool, Outdoor Patio, Lush Tropical Landscaping.

Sleeps: 6
Bedrooms: 2
Bathrooms: 2
No Pets

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Key West, FL

Key West, FL Area
Florida Keys Vacation Rentals

Pete’s Cottages: Twin Cypress Cottages, Large Kidney Shaped Pool w/Waterfall, Semi-Private Deck & Lounge Area, Steps From Duval.

Sleeps: 8
Bedrooms: 4
Bathrooms: 2
No Pets

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Key West, FL

Key West, FL Area
Florida Keys Vacation Rentals

Alegre In Fabulous Key West Awaits – Free Bikes, Wifi & Parking, Gated Community, Private Balcony For Cocktails.

Sleeps: 6
Bedrooms: 2
Bathrooms: 2.5
No Pets

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Key West, FL

Key West, FL Area
Florida Keys Vacation Rentals

Henry’s Piece Of Paradise On The Ocean In Key West,
Weekly/Nightly, Second Floor, 38-Foot Private Balcony.

Sleeps: 5
Bedrooms: 2
Bathrooms: 2
No Pets

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Key West, FL

Key West, FL Area
Florida Keys Vacation Rentals

Located In Old Town, Pet
Friendly Property! Amelia Home Offers Private Pool, Covered Porch, 4 Blocks From The Atlantic Ocean.

Sleeps: 6
Bedrooms: 2
Bathrooms: 2
Pets Considered

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Key West, FL

Key West, FL Area
Florida Keys Vacation Rentals

Downtown Location In Historic District, Private Deck, Shared Common Pool Area, Enjoy Your Stay In A True Conch Home!

Sleeps: 4
Bedrooms: 1
Bathrooms: 1
No Pets

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Key West, FL

Key West, FL Area
Florida Keys Vacation Rentals

Seaside Place Key West – Huge Pool & House, Beach Across The Street & Parking! Private Master Suite, Covered Dining Space.

Sleeps: 12
Bedrooms: 5
Bathrooms: 4.5
No Pets

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Key West, FL

Key West, FL Area
Florida Keys Vacation Rentals

Duval Breeze Offers Walking Distance To Restaurants, Nightlife And The Beach, Historic Sites, Well Stocked Kitchen.

Sleeps: 6
Bedrooms: 2
Bathrooms: 2.5
No Pets

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Key West, FL

Key West, FL Area
Florida Keys Vacation Rentals

~ Cloud 9 ~ Perfect Home In Heart Downtown Key West w/Heated Black Bottom Pool & Parking, Front Courtyard, Plenty Of Loungers.

Sleeps: 7
Bedrooms: 3
Bathrooms: 3
No Pets

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Key West, FL

Key West, FL Area
Florida Keys Vacation Rentals

Steps From Duval, 1BR Townhouse In Great Complex, Bi-Level Suite, Hidden Secret, State-Of-The-Art Kitchen, 2 Gas BBQ Grills.

Sleeps: 4
Bedrooms: 1
Bathrooms: 1
No Pets

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Key West, FL

Key West, FL Area
Florida Keys Vacation Rentals

Downtown Cottage In Historic District, Common Area Swimming Pool w/Lush Landscaping, Large Front Porch.

Sleeps: 6
Bedrooms: 2
Bathrooms: 1
No Pets

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Key West, FL

Key West, FL Area
Florida Keys Vacation Rentals

“Lost Shaker Of Salt” ~ 3BR/2BA Pet Friendly Home w/40′ Private Pool, Front Porch, 4 Lounge Chairs, Tropical Landscaping.

Sleeps: 8
Bedrooms: 3
Bathrooms: 2
Pets Considered

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Key West, FL

Key West, FL Area
Florida Keys Vacation Rentals

Very Rare-The Galleon 3 King Bd, 3BA w/4th King Bed In Loft + Sleeper Sofa, Private Sun-Deck, The Galleon Resort Has It All!

Sleeps: 10
Bedrooms: 3
Bathrooms: 3
No Pets

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Key West, FL

Key West, FL Area
Florida Keys Vacation Rentals

Affordable Key West Beach Front Condo, Short Ride To Downtown Entertainment, Tropical Garden w/Sweeping Balconies, Very Quiet.

Sleeps: 6
Bedrooms: 2
Bathrooms: 2
No Pets

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Key West, FL

Key West, FL Area
Florida Keys Vacation Rentals

Jasmine Place, 1 Block To Duval, Private Pool, Large Front Porch & Grand Balcony, Plenty Of Outdoor Seating.

Sleeps: 4
Bedrooms: 2
Bathrooms: 2
Pets Considered

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Key West, FL

Key West, FL Area
Florida Keys Vacation Rentals

Pineapple Cottage: 2BR/2BA-Private Pool -1/2 Block To Duval, Multiple Seating, Lounging Locations, Lush Tropical Landscaping.

Sleeps: 4
Bedrooms: 2
Bathrooms: 2
No Pets

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Key West, FL

Key West, FL Area
Florida Keys Vacation Rentals

Absolutely Paradise- A Tropical Getaway In Old Town, Bar w/4 Stools, Small Private Pool & Deck, Paradise Is The Perfect Luxury Retreat.

Sleeps: 8
Bedrooms: 3
Bathrooms: 2.5
No Pets

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Key West, FL

Key West, FL Area
Florida Keys Vacation Rentals

Catherine House: A Charming Old Town Key West Cottage, 3 Blocks To A Beach, Small Pool, Covered Front Porch, Patio/Pool Area.

Sleeps: 4
Bedrooms: 2
Bathrooms: 2
No Pets

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Key West, FL

Key West, FL Area
Florida Keys Vacation Rentals

Rose Lane Villas, Villa Vista, 
Deck, Patio, Heated Pool, Excellent Location, 2BR Downtown Key West.

Sleeps: 4
Bedrooms: 2
Bathrooms: 2
Pets Considered

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Key West, FL

Key West, FL Area
Florida Keys Vacation Rentals

“Tranquility ” At Ann Street Gardens, Private Courtyard w/Deck, Shared Tropical Outdoor Spaces, Steps From Duval.

Sleeps: 2
Bedrooms: 1
Bathrooms: 1
No Pets

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Key West, FL

Key West, FL Area
Florida Keys Vacation Rentals

Pelican Landing St. Thomas Penthouse, Open-Air Poolside Grill, Heated Pool, 1 Mile From Duval Street Area.

Sleeps: 12
Bedrooms: 4
Bathrooms: 4
Pets Considered

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Key West, FL

Key West, FL Area
Florida Keys Vacation Rentals

“Dancing Palms” ~ Truman Annex, Covered Parking Spot, Gas Grill, Hot Tub! Covered Porch, Hot Tub, Bikes, Community Pool.

Sleeps: 4
Bedrooms: 2
Bathrooms: 2
Pets Considered

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Key West, FL

Key West, FL Area
Florida Keys Vacation Rentals

“Stripes” ~ Delightful Condo Located In The Heart Of Old Town Key West! Tree Top Views & Beautiful Balconies.

Sleeps: 10
Bedrooms: 4
Bathrooms: 2
No Pets

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Key West, FL

Key West, FL Area
Florida Keys Vacation Rentals

Blue Coral: A Private Oasis In The Heart Of Old Town Key West, Heated Pool w/Large Sun Deck, Public Beach Is 4 Blocks Away.

Sleeps: 6
Bedrooms: 3
Bathrooms: 3.5
Pets Considered

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Key West, FL

Key West, FL Area
Florida Keys Vacation Rentals

William Skelton Home, Heart Of Key West, Perfect Location, Private Pool, Save 10% On
Your 5+ Night Stay!

Sleeps: 14
Bedrooms: 6
Bathrooms: 4
No Pets

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Key West, FL

Key West, FL Area
Florida Keys Vacation Rentals

The Palm Villa, Unparalleled Luxury, Large Private Japanese Garden, Crystal Clear Pool & Heated Spa, Island Oasis Blocks From Duval.

Sleeps: 4
Bedrooms: 2
Bathrooms: 2
No Pets

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Key West, FL

Key West, FL Area
Florida Keys Vacation Rentals

Cuban Club Suites – 2BR/2BA – Shared Pool – Sleeps Up To 8- Summer Rates, 30Ft. Balcony, Enjoy Key West In Style & Comfort!

Sleeps: 8
Bedrooms: 2
Bathrooms: 2
Pets Considered

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Key West, FL

Key West, FL Area
Florida Keys Vacation Rentals

Truman Annex, 2 Blocks From Duval, Private Balcony, Tropical Garden, Shared Heated Swimming Pool, Come Enjoy.

Sleeps: 4
Bedrooms: 2
Bathrooms: 2.5
No Pets

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Key West, FL

Key West, FL Area
Florida Keys Vacation Rentals

Steps From Duval, Heated Pool, $99-$219 Night, Free Bikes Incl.! Guest Room, Eat Under The Palm Trees, Back Deck, Lounge Chairs.

Sleeps: 2
Bedrooms: Studio
Bathrooms: 1
No Pets

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Key West, FL

Key West, FL Area
Florida Keys Vacation Rentals

Architect’s Personal Residence, Private Pool, 1 Blk. To Duval, Private Courtyard w/A Solar-Heated Pool & Spa.

Sleeps: 6
Bedrooms: 2
Bathrooms: 2.5
Pets Considered

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Key West, FL

Key West, FL Area
Florida Keys Vacation Rentals

Tom’s Chicken Coop: Nice Ocean View, Spa, Parasailing is Available, Balcony, Pool, Renovated, Close To Beach.

Sleeps: 6
Bedrooms: 2
Bathrooms: 2
No Pets

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Key West, FL

Key West, FL Area
Florida Keys Vacation Rentals

“Southernmost Belle”, Heated Pool, Gourmet Kitchen & Elegant Large Bedrooms! Gated, Peaceful And Quiet.

Sleeps: 10
Bedrooms: 5
Bathrooms: 4
No Pets

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Key West, FL

Key West, FL Area
Florida Keys Vacation Rentals

Top Floor Ocean Views From Every Window Newly Renovated For 2020,
Breathtaking View Of The Deep Blue Ocean.

Sleeps: 6
Bedrooms: 2
Bathrooms: 2
No Pets

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Key West, FL

Key West, FL Area
Florida Keys Vacation Rentals

Sunshine Daydream, Private Home 1/2 Block Off Duval, Tropical Foliage, In Gallery District, Saltwater Heated Pool.

Sleeps: 4
Bedrooms: 2
Bathrooms: 2
No Pets

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Key West, FL

Key West, FL Area
Florida Keys Vacation Rentals

Your Condo By The Beach w/Ocean View Of Swaying Palms & Turquoise Waters, Communal Pool, Hot Tub, Spa Whirlpool.

Sleeps: 4
Bedrooms: 1
Bathrooms: 1
No Pets

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Key West, FL

Key West, FL Area
Florida Keys Vacation Rentals

The Caribbean Suite – 2-K-BR/1BA, Kitchenette, Sleeps Up To 6, Restored Victorian Home, Tropical Gardens Surrounding.

Sleeps: 4
Bedrooms: 2
Bathrooms: 1
No Pets

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Key West, FL

Key West, FL Area
Florida Keys Vacation Rentals

Book Today Anchor Drop Key West, Short Bike Ride From Old Town, 40Ft Private Balcony, Kayak/Canoe, Communal Pool.

Sleeps: 6
Bedrooms: 2
Bathrooms: 2
No Pets

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Key West, FL

Key West, FL Area
Florida Keys Vacation Rentals

“Lady Admiral” ~ Sweet Cottage & Guest House w/Private Pool Off Duval, Tropical Vegetation & Spacious Decks For Sunbathing.

Sleeps: 8
Bedrooms: 3
Bathrooms: 2.5
No Pets

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Key West, FL

Key West, FL Area
Florida Keys Vacation Rentals

Luxury High End New Reno, Free Bikes, Free Wi-Fi, Pool, Hot Tub, Gym, Tennis, Penthouse Unit, Balcony, King + Queen Murphy In Living Room.

Sleeps: 4
Bedrooms: 1
Bathrooms: 1
Pets Considered

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Key West, FL

Key West, FL Area
Florida Keys Vacation Rentals

Poolside Breeze Retreat A103: 2BR/2BA Condominium In Key West, Sleeps 6, Extensive Private Balcony, Lush Tropical Courtyard.

Sleeps: 6
Bedrooms: 2
Bathrooms: 2
No Pets

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Key West, FL

Key West, FL Area
Florida Keys Vacation Rentals

Spacious Ocean Front Resort – 3BR Condo, Olympic-Size Pool Overlooking The Atlantic Ocean, Private Beach, Hot Tub, Sauna’s.

Sleeps: 8
Bedrooms: 3
Bathrooms: 3
No Pets

Key West, FL

Key West, FL Area
Florida Keys Vacation Rentals

Beachfront, Deluxe 3BR Oceanfront Condo, Great Rates, Your Own Private Oasis Overlooking Beautiful Smathers Beach.

Sleeps: 7
Bedrooms: 3
Bathrooms: 2
No Pets

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Key West, FL

Key West, FL Area
Florida Keys Vacation Rentals

Summer Is Here…Enjoy The Best Deal In The Keys, Video Library, Balcony, Community Pool, Full Kitchen & Laundry.

Sleeps: 6
Bedrooms: 2
Bathrooms: 1
No Pets