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From $305 per night (USD)
VRBO
Sumptuous Home with Private Pool, Central AC, WiFi, and Private Washer/Dryer
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Flagler Station Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $305 per night (USD)
VRBO
From $446 per night (USD)
Expedia
Old Town 2 Bicycles, Grill, WiFi, 1st Floor, Pool! Rent 30 days get 20% discount
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
We are moving to a monthly rental model and passing on the savings to you. Here in Key West we believe in One Human Fam ...
From $446 per night (USD)
Expedia
From $295 per night (USD)
VRBO
MAJESTIC PARADISE @ Truman Annex - Heart of Old Town, Key West
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
This wonderful 2 bedroom downstairs unit is owner's second home and has just been beautifully and professionally decorat ...
From $295 per night (USD)
VRBO
From $2372 per night (USD)
Expedia
~DREAMING ON DUVAL~ Grand 5 bedroom, 4.5 bath home with private pool/parking
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
THE PROPERTY: Dreams do come true in Key West! As you enter the front gate of this luxury property, you arrive in a priv ...
From $2372 per night (USD)
Expedia
From $566 per night (USD)
VRBO
Henry's Penthouse on the Ocean in Key West - weekly / nightly rentals
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Spectacular ocean views from this condo located on the top floor with 1350 sq ft of fabulous living space and a 45 ft pr ...
From $566 per night (USD)
VRBO
From $556 per night (USD)
Expedia
**OLD TOWN OASIS @ THE ANNEX** Oceanside Condo & Pool + LAST KEY SERVICES…
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! OLD TOWN OASI ...
From $556 per night (USD)
Expedia
From $467 per night (USD)
VRBO
Craig & Cindy Key West Truman Annex Shipyard Condo with a deck at Mile Marker 0!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Partial list of rental amenities at Craig & Cindy's Truman Annex Shipyard Condos include: 2 bedrooms 1 bath {queen and ...
From $467 per night (USD)
VRBO
From $475 per night (USD)
Expedia
Craig & Cindy Truman Annex Foundry Townhouse 2 bedrooms 2.5 baths
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Craig & Cindy Truman Annex Foundry Townhouse is a 2 bedroom 2 1/2 bath townhouse in the best location in all of Key West ...
From $475 per night (USD)
Expedia
From $341 per night (USD)
VRBO
COCONUT Adorable cottage in Old Town
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
The 'Coconut' as it's so lovingly referred to is the perfect Pied A Terre for your vacation in the Florida Keys. Open l ...
From $341 per night (USD)
VRBO
From $369 per night (USD)
Expedia
**COASTLINE COMFORT @ COCONUT MALLORY** Condo + LAST KEY SERVICES…
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! When your vac ...
From $369 per night (USD)
Expedia
From $410 per night (USD)
VRBO
**SET SAIL @ COCONUT MALLORY** Condo + LAST KEY SERVICES…
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! SET SAIL cele ...
From $410 per night (USD)
VRBO
Click For Pricing
Expedia
Cozy studio cottage in Old Town Key West
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Cute Studio cottage with additional sleeping loft. Nicely landscaped shared pool and outside area. Walking distance to ...
Click For Pricing
Expedia
From $674 per night (USD)
VRBO
Heart of Key West - 2BR Waterfront at the Galleon Resort
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Located in the heart of Old Town Key West. This resort overlooks the Gulf of Mexico with a private marina, private beach ...
From $674 per night (USD)
VRBO
From $405 per night (USD)
Expedia
Welcome to the Shady Palms - Private Pool - RealKeyWest
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Step into this beautifully restored and redecorated 1933 Key West home. This first-floor home has Bahama shutters throug ...
From $405 per night (USD)
Expedia
From $895 per night (USD)
VRBO
**ENVY OF THE ISLAND @ OLD TOWN** Pristine Home & Pool + LAST KEY SERVICES...
Bedrooms:
6
Bathrooms:
5
Sleeps:
10
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! While Old Tow ...
From $895 per night (USD)
VRBO
From $123 per night (USD)
Expedia
Ground-level getaway with free WiFi, private deck, & shared outdoor pool
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Louisa's Garden Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $123 per night (USD)
Expedia
From $494 per night (USD)
VRBO
SOUTHERNMOST SWIM AND SOCIAL CLUB
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Look no further! You've found your home away from home. Where your family and friends can share their own piece of para ...
From $494 per night (USD)
VRBO
From $623 per night (USD)
Expedia
Treasure Cove- 2BDR/2.5BA | 2 Bed, 2.5 Bath
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
~~7 day minimum~~Experience the famous island city of Key West and stay at the Treasure Cove Townhouse in the private P ...
From $623 per night (USD)
Expedia
From $351 per night (USD)
VRBO
Quiet Lane in the Heart of Old Town, Sleeps 4 + 🐶🐾
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Unbeatable location just 1 block from the iconic Green Parrot Bar and 2 blocks from world famous Duval Street. Blue Heav ...
From $351 per night (USD)
VRBO
From $784 per night (USD)
Expedia
ISLAND TIME - 5 Bed/3 Bath OldTown Complex - MONTHLY - Private pool
Bedrooms:
3
Bathrooms:
5
Sleeps:
12
WELCOME TO ISLAND TIME! Key West Island Time is a rare find in old town Key West. It is a total of 5 bedrooms and three ...
From $784 per night (USD)
Expedia
From $737 per night (USD)
VRBO
TROPICAL PROPERTIES VACATION RENTAL - KEY WEST
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
****This property requires a minimum stay of 28 nights in the same calendar month**** ***Brand New Pool with waterfall, ...
From $737 per night (USD)
VRBO
From $278 per night (USD)
Expedia
Tropical Jewel: Historic Seaport Oldtown - 2BR/2BA - Pool - RealKeyWest
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
WELCOME TO TROPICAL JEWEL! Near all the action of the historic seaport and Duval Street, you can get out into the cit ...
From $278 per night (USD)
Expedia
From $461 per night (USD)
VRBO
MAJESTIC PARADISE II Luxury living in Truman Annex. Downtown, pool, 2 blks
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Featured in The Key West Citizen Home of the Week. Perfect location, and newly renovated with fresh paint, new kitchen w ...
From $461 per night (USD)
VRBO
From $943 per night (USD)
Expedia
**JASMINE JEWEL @ THE ANNEX** Lush Private Home & Pool + LAST KEY SERVICES…
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Hidden amongs ...
From $943 per night (USD)
Expedia
From $615 per night (USD)
VRBO
ADMIRAL'S PARADISE in Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Newly renovated town home located on a charming lane in the Truman Annex. The generous open floor plan features 10 foot ...
From $615 per night (USD)
VRBO
From $416 per night (USD)
Expedia
Waterfront Property - Marina Access - Spacious - Excellent Key West Condo
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Located just two miles from picturesque Smathers Beach, this well appointed two bedroom, two bath condo is ideally situa ...
From $416 per night (USD)
Expedia
From $847 per night (USD)
VRBO
Key West's Crown Jewel
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Key West's Crown Jewel is a penthouse condominium at 1800 Atlantic Condominium development with two-bedroom, two-bath wi ...
From $847 per night (USD)
VRBO
Click For Pricing
Expedia
Beautiful & Relaxing 2 bed 2 bath condo
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This is a large 2 bed 2 bath condo with a separate living room, kitchen, and private balcony at the Hyatt Resort. It off ...
Click For Pricing
Expedia
From $484 per night (USD)
VRBO
The Dancing Rooster: 2 Blocks from Duval in Old Town.
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Located just 2 short blocks from Duval and in the center of downtown, the Southernmost Retreat is a recently renovated a ...
From $484 per night (USD)
VRBO
From $341 per night (USD)
Expedia
**SEAPORT SENSATION @ OLD TOWN VILLAS** Condo & Pool + LAST KEY SERVICES...
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! It is not so ...
From $341 per night (USD)
Expedia
From $451 per night (USD)
VRBO
**COASTAL LOVING @ OLD TOWN** Chic 4BR Home & Pool + LAST KEY SERVICES...
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! If you’re loo ...
From $451 per night (USD)
VRBO
From $613 per night (USD)
Expedia
Flirty Flamingo Key West
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Flirty Flamingo is luxurious and in a prime Key West location. Built in 1998 and meticulously cared for this spacious 3 ...
From $613 per night (USD)
Expedia
From $332 per night (USD)
VRBO
Runaway Bills | 3 Bed, 1 Bath
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
This stylish Conch Home is tucked away on a quiet lane in Old Town Key West. Surrounded by distinctive neighborhoods thi ...
From $332 per night (USD)
VRBO
From $531 per night (USD)
Expedia
Henry's Piece of Paradise on the Ocean in Key West - Weekly / Nightly
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Thirteen-hundred-fifty square feet of fabulous living space located on the second floor with garden and partial ocean vi ...
From $531 per night (USD)
Expedia
From $374 per night (USD)
VRBO
First Floor; 2 Bedroom 1 Bath Condo at Bayfront Suites & Marina
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Bayfront Suites offers incredibly spacious, meticulously designed homes for a variety of guests. In this specific proper ...
From $374 per night (USD)
VRBO
From $433 per night (USD)
Expedia
Sunset views at the Galleon
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
You will be back year after year! Unit features full kitchen with Master King, Guest Twin Beds, and Pull out Sleeper Sof ...
From $433 per night (USD)
Expedia
From $897 per night (USD)
VRBO
Waterfront 4 Bed, 4-Bath Condo @ Bayfront Suites & Marina
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Bayfront Suites offers incredibly spacious, meticulously designed homes for a variety of guests. In this specific proper ...
From $897 per night (USD)
VRBO
From $219 per night (USD)
Expedia
Upscale Townhome w/ Golf, Garden & Lake Views, Shared Pool, WiFi - Dogs OK
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
The Tipsy Mermaid at Key West Golf Club Our calendar is updated in real-time & our nightly rates are accurately display ...
From $219 per night (USD)
Expedia
From $575 per night (USD)
VRBO
~HORSE CONCH~ Amazing location with shared pool and covered balcony!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
THE PROPERTY: Enjoy your stay in the tropics at Horse Conch, part of the highly touted "Queen Conch" complex, which incl ...
From $575 per night (USD)
VRBO
From $569 per night (USD)
Expedia
3-Bedroom 3-Bath Condo at Bayfront Suites & Marina
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Bayfront Suites offers incredibly spacious, meticulously designed homes for a variety of guests. In this specific proper ...
From $569 per night (USD)
Expedia
From $799 per night (USD)
VRBO
Waterfront 4-Bed, 4-Bath Condo at Bayfront Suites & Marina
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Bayfront Suites offers incredibly spacious, meticulously designed homes for a variety of guests. In this specific proper ...
From $799 per night (USD)
VRBO
From $834 per night (USD)
Expedia
4-Bed 4.5 Bath Condo @ Bayfront Suites & Marina Non-Waterfront
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Bayfront Suites offers incredibly spacious, meticulously designed homes for a variety of guests. In this specific proper ...
From $834 per night (USD)
Expedia
From $639 per night (USD)
VRBO
3 Bedroom Condo at Bayfront Suites & Marina - Non-Waterfront
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Bayfront Suites offers incredibly spacious, meticulously designed homes for a variety of guests. In this specific proper ...
From $639 per night (USD)
VRBO
From $986 per night (USD)
Expedia
4-Bed, 3-Bath Waterfront Condo at Bayfront Suites & Marina
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Bayfront Suites offers incredibly spacious, meticulously designed homes for a variety of guests. In this specific proper ...
From $986 per night (USD)
Expedia
From $884 per night (USD)
VRBO
4-Bed, 4.5 Bath Condo at Bayfront Suites & Marina Non-Waterfront
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Bayfront Suites offers incredibly spacious, meticulously designed homes for a variety of guests. In this specific proper ...
From $884 per night (USD)
VRBO
From $641 per night (USD)
Expedia
Waterfront 3-Bedroom Condo at Bayfront Suites & Marina
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Bayfront Suites offers incredibly spacious, meticulously designed homes for a variety of guests. In this specific proper ...
From $641 per night (USD)
Expedia
From $203 per night (USD)
VRBO
coral stone
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Our apartment offers all the comforts of home, 120 paces to Duval Street - shopping, restaurants and nightlife. Near Hem ...
From $203 per night (USD)
VRBO
From $697 per night (USD)
Expedia
~Serene Lily~ Luxurious 2 bed, 2.5 bath home in the upscale Truman Annex
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
WEEKLY RENTAL: This property has a 7 night minimum stay. **Beginning January, 2026, Fair Winds will be a MONTHLY (28 ni ...
From $697 per night (USD)
Expedia
From $179 per night (USD)
VRBO
Paradise found at the Key West Golf Club!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
We selected the best of everything to create paradise in Key West. Enjoy tropical breezes as you sip your morning coffee ...
From $179 per night (USD)
VRBO
From $515 per night (USD)
Expedia
SUMMER ISN'T OVER YET - PROCES REDUCED FOR OPEN NIGHTS!!!!
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
City of Key West Business License # 28224 We hope you will enjoy this home where Ernest Hemingway and Jimmy Buffet memo ...
From $515 per night (USD)
Expedia
From $203 per night (USD)
VRBO
Lush Gardens-Pool-Jacuzzi-No Contact Check-In
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
This 3 bedroom home is located one block from where Tennessee Williams home was located. The home has a true historic fl ...
From $203 per night (USD)
VRBO
Click For Pricing
Expedia
FANTASY WEEK
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Set along the Atlantic Ocean, Hyatt Windward Pointe Resort blends the laid-back Key West style with a modern, upscale re ...
Click For Pricing
Expedia
From $1010 per night (USD)
VRBO
Historic Old Town Key West - Turtle House, Sleeps 6
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
OVERVIEW The Turtle House is a 100+ year old recently completely renovated “Conch” house. The house can be described as ...
From $1010 per night (USD)
VRBO
From $291 per night (USD)
VRBO
Seaport Walkabout- the best location in town
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Open to annual rental at lower rate Two hundred yards from Schooner Wharf and the seaport and steps from Pepe’s in the ...
From $291 per night (USD)
VRBO
From $534 per night (USD)
VRBO
**COLORS OF THE KEYS @ THE FOUNDRY** Villa Near Duval & Beach + LAST KEY SERVICE
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! COLORS OF THE ...
From $534 per night (USD)
VRBO
From $250 per night (USD)
Expedia
Hidden Paradise-2bed 2bath condo w/ ocean views, dock space, pool
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
AGE REQUIREMENT: Everyone must be 25 years or older. Families are welcome as long as children are accompanied with their ...
From $250 per night (USD)
Expedia
From $535 per night (USD)
VRBO
Key West On My Mind, Ocean Views, Renovated Kitchen, Last minute deals
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
CONSTRUCTION NOTICE- Balcony Restoration Project – 1800 Atlantic Start Date: May 2025-Estimated Completion: Spring 2026 ...
From $535 per night (USD)
VRBO
From $493 per night (USD)
Expedia
Premier Ocean views, expansive balcony, renovated kitchen & bath 2024
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
CONSTRUCTION NOTICE- Balcony Restoration Project – 1800 Atlantic Start Date: May 2025-Estimated Completion: Spring 2026 ...
From $493 per night (USD)
Expedia
From $820 per night (USD)
VRBO
Casa Papa Del Mar Ocean Front 1800 Atlantic spectacular view and Island charm
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
CONSTRUCTION NOTICE - There will be concrete restoration project happening at 1800 Atlantic Starting in May 2025 through ...
From $820 per night (USD)
VRBO
From $541 per night (USD)
Expedia
Moonlight Paradise Upgraded Family oasis Tropical views expansive balcony
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
CONSTRUCTION NOTICE- Balcony Restoration Project – 1800 Atlantic Start Date: May 2025-Estimated Completion: Spring 2026 ...
From $541 per night (USD)
Expedia
From $218 per night (USD)
VRBO
Charming Oceanfront Escape in Key West’s Historic District
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
CONSTRUCTION NOTICE - There will be concrete restoration project happening at 1800 Atlantic Starting in May 2025 through ...
From $218 per night (USD)
VRBO
From $350 per night (USD)
Expedia
Key West Paradise, Conch Hideaway, Island Vibrations, Balmy Ocean Breezes KWF
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
This property features an extra large floor plan from the popular B building at 1800 Atlantic. Enjoy the flow through br ...
From $350 per night (USD)
Expedia
From $373 per night (USD)
VRBO
~POINCIANA GARDEN~ Casual 1st floor duplex 2 blocks from Duval Street!
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
THE PROPERTY: Located on a teeny tiny quiet lane, this comfortably furnished first-floor duplex home comes with Key West ...
From $373 per night (USD)
VRBO
From $224 per night (USD)
Expedia
Monthly historic old town rental Key West
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Historic 2-Bedroom Cigar Maker’s Cottage – A Key West Gem! Step back in time and experience Old Key West charm in this ...
From $224 per night (USD)
Expedia
From $562 per night (USD)
VRBO
Key West Beachfront Luxury 2/2 Condo A212
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Sale on for June thru Aug construction by the pool. This Luxury unit is 1375 sq ft of breath taking beachfront living sp ...
From $562 per night (USD)
VRBO
From $213 per night (USD)
Expedia
Vibrant Island retreat, Expansive private balcony, Enjoy the Coastal Breezes
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
CONSTRUCTION NOTICE - There will be concrete restoration project happening at 1800 Atlantic Starting in May 2025 through ...
From $213 per night (USD)
Expedia
From $389 per night (USD)
VRBO
Key West Salty Sea Breezes, Exquisite Morning Sunrises, Luxurious Condo
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
CONSTRUCTION NOTICE- Balcony Restoration Project – 1800 Atlantic Start Date: May 2025-Estimated Completion: Spring 2026 ...
From $389 per night (USD)
VRBO
From $214 per night (USD)
Expedia
Casa Coastal East – Morning Sunrises, Evening Vibes, Island Home in Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
CONSTRUCTION NOTICE- Balcony Restoration Project – 1800 Atlantic Start Date: May 2025-Estimated Completion: Spring 2026 ...
From $214 per night (USD)
Expedia
From $790 per night (USD)
VRBO
Amazingly Transformed in 2022 Luxurious renovation Fantastic Ocean View
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
CONSTRUCTION NOTICE - There will be concrete restoration project happening at 1800 Atlantic Starting in May 2025 through ...
From $790 per night (USD)
VRBO
From $632 per night (USD)
Expedia
Key Wes't Best- Upgraded condo 5 mins to Smathers Beach Fantastic value
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
CONSTRUCTION NOTICE- Balcony Restoration Project – 1800 Atlantic Start Date: May 2025-Estimated Completion: Spring 2026 ...
From $632 per night (USD)
Expedia
From $435 per night (USD)
VRBO
Paradise Found in Key West upgrades throughout 5 minutes to Smathers Beach
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
CONSTRUCTION NOTICE- Balcony Restoration Project – 1800 Atlantic Start Date: May 2025-Estimated Completion: Spring 2026 ...
From $435 per night (USD)
VRBO
From $234 per night (USD)
Expedia
Carolina to Keys Ocean view dream Monthly pricing Best pool on the Island
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
CONSTRUCTION NOTICE - There will be concrete restoration project happening at 1800 Atlantic Starting in May 2025 through ...
From $234 per night (USD)
Expedia
From $617 per night (USD)
VRBO
Anchor Drop modern elegance upgrades throughout views of Atlantic Ocean
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
CONSTRUCTION NOTICE- Balcony Restoration Project – 1800 Atlantic Start Date: May 2025-Estimated Completion: Spring 2026 ...
From $617 per night (USD)
VRBO
From $531 per night (USD)
Expedia
Tropical Paradise Key West - Upgraded Master Bath - Best Value Discounts
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
CONSTRUCTION NOTICE- Balcony Restoration Project – 1800 Atlantic Start Date: May 2025-Estimated Completion: Spring 2026 ...
From $531 per night (USD)
Expedia
From $242 per night (USD)
VRBO
Stunning Oceanfront Retreat with Panoramic Views & Private Balcony
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
CONSTRUCTION NOTICE- Balcony Restoration Project – 1800 Atlantic Start Date: May 2025-Estimated Completion: Spring 2026 ...
From $242 per night (USD)
VRBO
From $196 per night (USD)
Expedia
Sea La Vie, Elegant Key West 2BR/2BA | Renovated Condo at 1800 Atlantic
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
CONSTRUCTION NOTICE- Balcony Restoration Project – 1800 Atlantic Start Date: May 2025-Estimated Completion: Spring 2026 ...
From $196 per night (USD)
Expedia
From $1297 per night (USD)
VRBO
~ Chick-A-Pea Cottage ~ Enjoy Key West’s charisma, with a pool, and parking!
Bedrooms:
2
Bathrooms:
4
Sleeps:
7
THE PROPERTY: Come enjoy the Key West cottage lifestyle where you can people watch from your front porch or take a dip ...
From $1297 per night (USD)
VRBO
From $197 per night (USD)
Expedia
Key West Getaway – Island Style Living with Ocean Views & Sunrises
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
CONSTRUCTION NOTICE - There will be concrete restoration project happening at 1800 Atlantic Starting in May 2025 through ...
From $197 per night (USD)
Expedia
From $575 per night (USD)
VRBO
Thirsty Mermaid - Large 4/3 Pool Home
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Thirsty Mermaid is located in the Casa Marina area just minutes from the Atlantic Ocean. This beautiful property has 2 f ...
From $575 per night (USD)
VRBO
From $227 per night (USD)
Expedia
Old Town! Spacious Condo in Historic Home w/Pool!
Bedrooms:
2
Bathrooms:
1
Sleeps:
4
Tony's Conch Retreat is a spacious updated condo is located in a historic home on William Street that was converted into ...
From $227 per night (USD)
Expedia
From $553 per night (USD)
VRBO
**VILLA CUBANA @ OLD TOWN** Comfy Cottage Near Duval + LAST KEY SERVICES...
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! This colorful ...
From $553 per night (USD)
VRBO
From $503 per night (USD)
Expedia
**MAISON TROPICALE @ OLD TOWN** Historic Home + LAST KEY SERVICES...
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! Imagine a tra ...
From $503 per night (USD)
Expedia
From $1028 per night (USD)
VRBO
**BRISA FRESCA @ THE ANNEX** Airy Home by Duval & Beach + LAST KEY SERVICES...
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! A trip to Key ...
From $1028 per night (USD)
VRBO
From $642 per night (USD)
Expedia
**VILLA OLIVIETTA @ SOLARES HILL** Upscale Home & Pool + LAST KEY SERVICES...
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! This ultimate ...
From $642 per night (USD)
Expedia
From $571 per night (USD)
VRBO
**SMOOTH SAILING @ THE BEACH** Ocean Condo / Pool & Tennis + LAST KEY SERVICES..
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
CONSTRUCTION NOTICE - 25% off!!! - 25% off any stay through summer 2026 due to construction at the complex! 25% discount ...
From $571 per night (USD)
VRBO
From $549 per night (USD)
Expedia
**VILLA BAHAMA @ THE ANNEX** Villa Near Duval & Beach + LAST KEY SERVICES...
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! VILLA BAHAMA ...
From $549 per night (USD)
Expedia
From $1056 per night (USD)
VRBO
**THE CONTENTED CRANE @ OLD TOWN** Home & Pool Near Duval + LAST KEY SERVICES...
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Traveling to ...
From $1056 per night (USD)
VRBO
From $1880 per night (USD)
Expedia
**THE ROYAL COMPOUND @ THE ANNEX** Lush Estate & Pool + LAST KEY SERVICES...
Bedrooms:
4
Bathrooms:
5
Sleeps:
8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Located in th ...
From $1880 per night (USD)
Expedia
From $2175 per night (USD)
VRBO
**SOUTHERNMOST HOSPITALITY VII** 7BR/7BA & Pool + LAST KEY SERVICES...
Bedrooms:
7
Bathrooms:
7
Sleeps:
16
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! SOUTHERNMOST ...
From $2175 per night (USD)
VRBO
From $626 per night (USD)
Expedia
**GULFSIDE VISTAS @ THE ANNEX** Condo & Pool + LAST KEY SERVICES...
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! GULFSIDE VIST ...
From $626 per night (USD)
Expedia
From $2072 per night (USD)
VRBO
**STAR OF THE SEAPORT @ OLD TOWN** Huge Home & Pool + LAST KEY SERVICES...
Bedrooms:
5
Bathrooms:
5
Sleeps:
12
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! For a truly o ...
From $2072 per night (USD)
VRBO
From $816 per night (USD)
Expedia
**CASA OLIVIANA @ SOLARES HILL** Grand Home & Pool + LAST KEY SERVICES...
Bedrooms:
5
Bathrooms:
6
Sleeps:
12
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! Finally, a la ...
From $816 per night (USD)
Expedia
From $537 per night (USD)
VRBO
**CONCH IN THE TREETOPS @ 1800 ATLANTIC** Beach Condo / Pool + LAST KEY SERVICES
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
CONSTRUCTION NOTICE - 25% off!!! - 25% off any stay through summer 2026 due to construction at the complex! 25% discount ...
From $537 per night (USD)
VRBO
From $476 per night (USD)
VRBO
COLONY CALYPSO - A quaint 1 Bedroom Cottage just two blocks to Duval
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Part of a small collection of cottages known as The Colony, this quaint cottage sits to the back of the property and is ...
From $476 per night (USD)
VRBO
From $464 per night (USD)
VRBO
Quaint, Quiet & Convenient - CasaBianca is The Perfect Old Town Sanctuary
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Welcome to CasaBianca! Here you'll find the character & charm of Old Town blended perfectly with all the modern amenitie ...
From $464 per night (USD)
VRBO
From $572 per night (USD)
Expedia
**CASA SUITE CASA @ CASA MARINA** Lush Home / Pool + LAST KEY SERVICE...
Bedrooms:
1
Bathrooms:
4
Sleeps:
8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! Imagine your ...
From $572 per night (USD)
Expedia
From $1834 per night (USD)
VRBO
**SOUTHERNMOST HOSPITALITY V** 5BR/5BA & Pool + LAST KEY SERVICES...
Bedrooms:
5
Bathrooms:
5
Sleeps:
12
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! SOUTHERNMOST ...
From $1834 per night (USD)
VRBO
From $593 per night (USD)
Expedia
Our Nautical Home Key West prime location & amenities. Last minute specials.
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
CONSTRUCTION NOTICE- Balcony Restoration Project – 1800 Atlantic Start Date: May 2025-Estimated Completion: Spring 2026 ...
From $593 per night (USD)
Expedia
From $441 per night (USD)
VRBO
**CAYO CALYPSO @ HIGGS BEACH** Modern Home / Pool + LAST KEY SERVICES...
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! Upscale islan ...
From $441 per night (USD)
VRBO
From $538 per night (USD)
Expedia
Poolside Breeze Retreat Key West – Your Tropical Getaway Awaits
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
CONSTRUCTION NOTICE- Balcony Restoration Project – 1800 Atlantic Start Date: May 2025-Estimated Completion: Spring 2026 ...
From $538 per night (USD)
Expedia

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