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From $430 per night (USD)
VRBO
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 $430 per night (USD)
VRBO
From $305 per night (USD)
Expedia
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 $305 per night (USD)
Expedia
From $1952 per night (USD)
VRBO
~DREAMING ON DUVAL~ 5 bedroom, 4.5 bath home with private pool and 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 $1952 per night (USD)
VRBO
From $707 per night (USD)
Expedia
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 $707 per night (USD)
Expedia
From $438 per night (USD)
VRBO
**SET SAIL @ COCONUT MALLORY** Condo + Last Key White Glove Service...
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 $438 per night (USD)
VRBO
From $515 per night (USD)
VRBO
Prime Waterfront! Steps to Duval & Sunset Pier! 2BR with Pool & Tiki Bar at 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 $515 per night (USD)
VRBO
From $391 per night (USD)
VRBO
Shady Palms | Historic Charm Private Pool & Effortless Island Style 2BD/2.5BA
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Welcome to Shady Palms, a polished private retreat where historic Key West character meets relaxed island luxury. Though ...
From $391 per night (USD)
VRBO
From $266 per night (USD)
Expedia
It's a Salt Life After All at the Golf Club in Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This 2 bedroom 2 bath town-home is just what you are looking for. The amenities include two community pools, a gym, and ...
From $266 per night (USD)
Expedia
From $242 per night (USD)
VRBO
Quiet Lane in the Heart of Old Town, Sleeps 4, Dog Friendly
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to our Key West retreat — a home we cherish and live in part of the year, now open for guests who appreciate com ...
From $242 per night (USD)
VRBO
From $480 per night (USD)
Expedia
SOUTHERNMOST SWIM AND SOCIAL CLUB
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Your Home Away from Home in Beautiful Key West Welcome to Southernmost Swim & Social Club — where you and your loved on ...
From $480 per night (USD)
Expedia
From $413 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 $413 per night (USD)
VRBO
Click For Pricing
Expedia
Tropical Jewel - Stay Where The Vacation Never Ends- 2BD/2Bath - Private Pool
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 city ...
Click For Pricing
Expedia
From $396 per night (USD)
VRBO
**JASMINE JEWEL @ THE ANNEX** Lush Home & Pool + Last Key White Glove Service...
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! Hidden amongs ...
From $396 per night (USD)
VRBO
From $1335 per night (USD)
Expedia
Sky Suites Retreat - Balcony Overlooking Duval
Bedrooms:
4
Bathrooms:
4
Sleeps:
12
Summary: This elegant, elevated 2nd story loft with vaulted ceilings has been designed for your next dream Key West get ...
From $1335 per night (USD)
Expedia
From $516 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 $516 per night (USD)
VRBO
From $409 per night (USD)
Expedia
The Tortuga at Sunrise Suites - Balcony & Pool
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Summary: Welcome to Sunrise Suites, a peaceful community on Key West's southeast side. Just 1 mile from the beach and 1 ...
From $409 per night (USD)
Expedia
From $596 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 $596 per night (USD)
VRBO
From $548 per night (USD)
Expedia
**SEAPORT SENSATION @ OLD TOWN** Condo & Pool + Last Key White Glove Service...
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 $548 per night (USD)
Expedia
From $602 per night (USD)
VRBO
**COASTAL LOVING @ OLD TOWN** 4BR Home & Pool + Last Key White Glove Service...
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 $602 per night (USD)
VRBO
From $449 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 $449 per night (USD)
Expedia
From $265 per night (USD)
VRBO
Runaway Bills
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Summary: Runaway Bills- 2 BDR Main house with 1 BDR Cottage and pool in the Key West downtown. The Space: This char ...
From $265 per night (USD)
VRBO
From $596 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 $596 per night (USD)
Expedia
From $750 per night (USD)
VRBO
Waterfront 4 Bed, 4-Bath Condo @ Bayfront Suites - CLEANING FEE INCLUDED
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Bayfront Suites offers incredibly spacious, meticulously designed homes for a variety of guests. In this specific proper ...
From $750 per night (USD)
VRBO
From $408 per night (USD)
Expedia
2 Bedroom 1 Bath Condo at Bayfront Suites & Marina - CLEANING FEE INCLUDED
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Bayfront Suites offers incredibly spacious, meticulously designed homes for a variety of guests. In this specific proper ...
From $408 per night (USD)
Expedia
From $443 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 $443 per night (USD)
VRBO
From $730 per night (USD)
Expedia
Waterfront 4-Bed 3-Bath Condo @ Bayfront Suites - CLEANING FEE INCLUDED
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Bayfront Suites offers incredibly spacious, meticulously designed homes for a variety of guests. In this specific proper ...
From $730 per night (USD)
Expedia
From $674 per night (USD)
VRBO
3-Bedroom 3-Bath Condo at Bayfront Suites & Marina - CLEANING FEE INCLUDED
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Bayfront Suites offers incredibly spacious, meticulously designed homes for a variety of guests. In this specific proper ...
From $674 per night (USD)
VRBO
From $734 per night (USD)
Expedia
Waterfront 4-Bed, 4-Bath Condo at Bayfront Suites - CLEANING FEE INCLUDED
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Bayfront Suites offers incredibly spacious, meticulously designed homes for a variety of guests. In this specific proper ...
From $734 per night (USD)
Expedia
From $750 per night (USD)
VRBO
4-Bed 4.5 Bath Condo @ Bayfront Suites - CLEANING FEE INCLUDED 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 $750 per night (USD)
VRBO
From $669 per night (USD)
Expedia
3 Bed 3 Bath Condo @ Bayfront Suites - CLEANING FEE INCLUDED (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 $669 per night (USD)
Expedia
From $679 per night (USD)
VRBO
4-Bed, 3-Bath Waterfront Condo at Bayfront Suites -CLEANING FEE INCLUDED
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Bayfront Suites offers incredibly spacious, meticulously designed homes for a variety of guests. In this specific proper ...
From $679 per night (USD)
VRBO
From $740 per night (USD)
Expedia
4-Bed, 4.5 Bath Condo & Bayfront Suites-non waterfront CLEANING FEE INCLUDED
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Bayfront Suites offers incredibly spacious, meticulously designed homes for a variety of guests. In this specific proper ...
From $740 per night (USD)
Expedia
From $597 per night (USD)
VRBO
Waterfront 3-Bedroom Condo at Bayfront Suites & Marina- CLEANING FEE INCLUDED
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Bayfront Suites offers incredibly spacious, meticulously designed homes for a variety of guests. In this specific proper ...
From $597 per night (USD)
VRBO
From $303 per night (USD)
Expedia
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 $303 per night (USD)
Expedia
From $522 per night (USD)
VRBO
Summer is here! Don't wait- book your dream stay now.
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 $522 per night (USD)
VRBO
From $214 per night (USD)
Expedia
coral stone 28 day minimum rental
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 $214 per night (USD)
Expedia
From $233 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 $233 per night (USD)
VRBO
From $289 per night (USD)
Expedia
**COLORS OF THE KEYS** Villa Near Duval + Last Key White Glove Service...
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! COLORS OF THE ...
From $289 per night (USD)
Expedia
From $255 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 $255 per night (USD)
VRBO
From $217 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 $217 per night (USD)
Expedia
From $958 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 $958 per night (USD)
VRBO
From $492 per night (USD)
Expedia
Key West On My Mind, Ocean Views, Renovated Kitchen, Last minute deals
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Stunning 2-Bedroom Ocean-View Oasis at 1800 Atlantic – Key West Welcome to your perfect tropical escape! This beautiful ...
From $492 per night (USD)
Expedia
From $527 per night (USD)
VRBO
Premier Ocean views, expansive balcony, renovated kitchen & bath 2024
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Penthouse property with vaulted ceilings at the famous 1800 Atlantic. Both bedrooms and the living room have access to y ...
From $527 per night (USD)
VRBO
From $573 per night (USD)
Expedia
Casa Papa Del Mar Ocean Front 1800 Atlantic spectacular view and Island charm
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Casa Papa Del Mar Two Bedroom Premiere Ocean View With a complete 2023 renovation, the décor is inspired by the life and ...
From $573 per night (USD)
Expedia
From $492 per night (USD)
VRBO
Moonlight Paradise Upgraded Family oasis Tropical views expansive balcony
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to Moonlight Luxury Beachfront Condo in Key West Your Private Oasis on the Beach Escape to paradise at Moonlig ...
From $492 per night (USD)
VRBO
From $220 per night (USD)
Expedia
Charming 2 Bdrm Oceanfront Oasis Key West Beach access Old Town Bike ride.
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Spacious 2-Bedroom Condo with Ocean Views & Island Comforts This beautiful 2-bedroom, 2-bath condo offers a lovely view ...
From $220 per night (USD)
Expedia
Click For Pricing
VRBO
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 ...
Click For Pricing
VRBO
From $408 per night (USD)
Expedia
~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 $408 per night (USD)
Expedia
From $587 per night (USD)
VRBO
Key West Beachfront Luxury 2/2 Condo A212
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This Luxury unit is 1375 sq ft of breath taking beachfront living space in this tropical complex. Great views from the 4 ...
From $587 per night (USD)
VRBO
From $184 per night (USD)
Expedia
Vibrant Island retreat, Expansive private balcony, Enjoy the Coastal Breezes
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Fabulous top floor ocean-view penthouse condo. Available during the Spring/Summer Season. Enjoy the Ocean-breeze's from ...
From $184 per night (USD)
Expedia
From $362 per night (USD)
VRBO
Key West Salty Sea Breezes, Exquisite Morning Sunrises, Luxurious Condo
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Keys to Paradise: A 5-Star Beachside Retreat in Key West Welcome to Keys to Paradise, a luxurious 3-bedroom, 2-bath co ...
From $362 per night (USD)
VRBO
From $362 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 $362 per night (USD)
Expedia
From $610 per night (USD)
VRBO
Amazingly Transformed in 2022 Luxurious renovation Fantastic Ocean View
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
The Grand Vista - 2 bedroom suite - Totally renovated in 2022 - pictures coming soon. 2 Bedroom 2 bath suite, some re ...
From $610 per night (USD)
VRBO
From $408 per night (USD)
Expedia
Key Wes't Best- Upgraded condo 5 mins to Smathers Beach Fantastic value
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Ocean View Condo at 1800 Atlantic – Your Perfect Key West Retreat Experience stunning ocean views and modern comfort in ...
From $408 per night (USD)
Expedia
From $538 per night (USD)
VRBO
Paradise Found in Key West upgrades throughout 5 minutes to Smathers Beach
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
2 Bedroom, 2 Bath Garden View Condo – 1800 Atlantic, Key West Escape to paradise in this beautifully renovated garden-v ...
From $538 per night (USD)
VRBO
From $527 per night (USD)
Expedia
Anchor Drop modern elegance upgrades throughout views of Atlantic Ocean
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Anchor Drop – Oceanfront Escape in Key West Welcome to Anchor Drop, a beautifully renovated two-bedroom condo in the ex ...
From $527 per night (USD)
Expedia
From $469 per night (USD)
VRBO
Tropical Paradise Key West - Upgraded Master Bath - Best Value Discounts
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Tropical Luxury in Key West – 2-Bedroom, 2-Bath Oasis Welcome to your beautifully decorated two-bedroom, two-bath retre ...
From $469 per night (USD)
VRBO
From $365 per night (USD)
Expedia
Oceanfront Overlook 2 Bdrm premiere monthly keys style with resort amenities
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Oceanfront Overlook – Your Perfect Island Retreat Welcome to Oceanfront Overlook, a one-of-a-kind unit offering an unpa ...
From $365 per night (USD)
Expedia
From $267 per night (USD)
VRBO
Sea La Vie, Elegant Key West 2BR/2BA | Renovated Condo at 1800 Atlantic
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Beautifully Renovated 2nd Floor Condo with Ocean & Preserve Views – 28-Day Minimum Stay Welcome to your home away from ...
From $267 per night (USD)
VRBO
From $213 per night (USD)
Expedia
2 Bdrm Monthly ocean view, expansive porch ,renovated unit Key West Fabulous
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Spacious 3rd-Floor Condo with Partial Ocean View & 50-Foot Balcony – Key West Paradise Escape to your island retreat in ...
From $213 per night (USD)
Expedia
From $343 per night (USD)
VRBO
Old Town! Spacious Condo in Historic Home w/Pool!
Bedrooms:
2
Bathrooms:
1
Sleeps:
2
Tony's Conch Retreat is a spacious updated condo is located in a historic home on William Street that was converted into ...
From $343 per night (USD)
VRBO
From $251 per night (USD)
Expedia
Monthly historic old town rental Key West quaint 1 block to Duval
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 $251 per night (USD)
Expedia
From $514 per night (USD)
VRBO
**VILLA CUBANA @ OLD TOWN** Cottage Near Duval + Last Key White Glove Service...
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 $514 per night (USD)
VRBO
From $759 per night (USD)
Expedia
**MAISON TROPICALE @ OLD TOWN** Historic Home + Last Key White Glove Service...
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 $759 per night (USD)
Expedia
From $524 per night (USD)
VRBO
**BRISA FRESCA @ THE ANNEX** Airy Home + Last Key White Glove Service...
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! A trip to Key ...
From $524 per night (USD)
VRBO
From $1036 per night (USD)
Expedia
**VILLA OLIVIETTA @ SOLARES HILL** Home & Pool + Last Key White Glove Service...
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 $1036 per night (USD)
Expedia
From $495 per night (USD)
VRBO
**SMOOTH SAILING** Ocean Condo / Pool & Tennis + Last Key White Glove Service...
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Formerly La B ...
From $495 per night (USD)
VRBO
From $345 per night (USD)
Expedia
**VILLA BAHAMA @ THE ANNEX** Villa Near Beach + Last Key White Glove Service...
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! VILLA BAHAMA ...
From $345 per night (USD)
Expedia
From $790 per night (USD)
VRBO
**THE CONTENTED CRANE @ OLD TOWN** Home & Pool + Last Key White Glove Service...
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 $790 per night (USD)
VRBO
From $1896 per night (USD)
Expedia
**THE ROYAL COMPOUND @ THE ANNEX** Pool + Last Key White Glove Service...
Bedrooms:
4
Bathrooms:
5
Sleeps:
8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! Located in th ...
From $1896 per night (USD)
Expedia
From $1783 per night (USD)
VRBO
**SOUTHERNMOST HOSPITALITY VII** 7BR & Pool + Last Key White Glove Service...
Bedrooms:
7
Bathrooms:
7
Sleeps:
16
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! SOUTHERNMOST ...
From $1783 per night (USD)
VRBO
From $352 per night (USD)
Expedia
**GULFSIDE VISTAS @ THE ANNEX** Condo & Pool + Last Key White Glove Service...
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 $352 per night (USD)
Expedia
From $2027 per night (USD)
VRBO
**STAR OF THE SEAPORT @ OLD TOWN** Pool + Last Key White Glove Service......
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 $2027 per night (USD)
VRBO
From $1207 per night (USD)
Expedia
**CASA OLIVIANA @ SOLARES HILL** Home & Pool + Last Key White Glove Service...
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 $1207 per night (USD)
Expedia
From $459 per night (USD)
VRBO
**CONCH IN THE TREETOPS** Beach Condo / Pool + Last Key White Glove Service...
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! This freshly ...
From $459 per night (USD)
VRBO
From $1119 per night (USD)
Expedia
**AMERICANA TROPICALE @ OLD TOWN** Home & Pool + Last Key White Glove Service...
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! For the ultim ...
From $1119 per night (USD)
Expedia
From $492 per night (USD)
VRBO
**SHANG-RI-LA** Oceanview Condo/ Pool & Tennis + Last Key White Glove Service...
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! SHANG-RI-LA i ...
From $492 per night (USD)
VRBO
From $597 per night (USD)
Expedia
**ATLANTIC REFLECTIONS @ THE BEACH** Penthouse + Last Key White Glove Service...
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
ATLANTIC REFLECTIONS is a newly renovated water view condo that has been meticulously furnished with a modern tropical f ...
From $597 per night (USD)
Expedia
From $2083 per night (USD)
VRBO
**THE IBIS & THE CRANE @ OLD TOWN** Compound + Last Key White Glove Service...
Bedrooms:
7
Bathrooms:
6
Sleeps:
16
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Dreaming of a ...
From $2083 per night (USD)
VRBO
From $494 per night (USD)
Expedia
Botanical Island Delight Key West fantastic discounts for Summer & Fall
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
This unit has a king in both bedrooms. 1800 Atlantic is directly on the Atlantic ocean in Key West, adjacent to Smather ...
From $494 per night (USD)
Expedia
From $247 per night (USD)
VRBO
**SALTWATER HARMONY @ THE ANNEX** Condo & Pool + Last Key White Glove Service...
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! SALTWATER HAR ...
From $247 per night (USD)
VRBO
From $538 per night (USD)
Expedia
Atlantic Paradise Found modern luxury Best pool in Key West fine finishes
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Atlantic Paradise Found C232 at 1800 Atlantic Condominiums is a beautifully appointed spacious condominium with a lovely ...
From $538 per night (USD)
Expedia
From $247 per night (USD)
VRBO
**LA PETITE PENTHOUSE** Elegant Condo & Pool + Last Key White Glove Service...
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! LA PETITE PEN ...
From $247 per night (USD)
VRBO
From $1659 per night (USD)
Expedia
**CONCH CASA GRANDE** Home+ Pool near Duval + Last Key White Glove Service...
Bedrooms:
6
Bathrooms:
5
Sleeps:
8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! CONCH CASA GR ...
From $1659 per night (USD)
Expedia
From $722 per night (USD)
VRBO
**RIVIERA AMERICANA @ THE BEACH** Ocean Views + Last Key White Glove Service...
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! A stay in Key ...
From $722 per night (USD)
VRBO
From $537 per night (USD)
Expedia
**PROMENADE TO PARADISE** Ocean Condo & Pool + Last Key White Glove Service...
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! If you dream ...
From $537 per night (USD)
Expedia
From $511 per night (USD)
VRBO
**CASA SUITE CASA @ CASA MARINA** Home / Pool + Last Key White Glove Service...
Bedrooms:
5
Bathrooms:
4
Sleeps:
8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! Imagine your ...
From $511 per night (USD)
VRBO
From $1562 per night (USD)
Expedia
**SOUTHERNMOST HOSPITALITY V** 5BR/5BA & Pool + Last Key White Glove Service...
Bedrooms:
5
Bathrooms:
5
Sleeps:
12
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! SOUTHERNMOST ...
From $1562 per night (USD)
Expedia
From $469 per night (USD)
VRBO
Our Nautical Home Key West prime location & amenities. Last minute specials.
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Escape to paradise in this spacious first-floor garden-view condo in beautiful Key West — the perfect setting for a rela ...
From $469 per night (USD)
VRBO
From $350 per night (USD)
Expedia
**CAYO CALYPSO @ HIGGS BEACH** Home / Pool + Last Key White Glove Service...
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 $350 per night (USD)
Expedia
From $492 per night (USD)
VRBO
Poolside Breeze Retreat, Tropical flare, Key West spectacular getaway.
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Poolside Breeze is a nicely decorated two bedroom 1st floor condominium with an excellent location very close to the poo ...
From $492 per night (USD)
VRBO
From $454 per night (USD)
Expedia
Top floor Ocean Views, Spacious 2 Bedroom Condo, Views from every room
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Top floor penthouse ocean-view condominium at 1800 Atlantic in the highly desirable B building. This unit has recently b ...
From $454 per night (USD)
Expedia
From $309 per night (USD)
VRBO
**SUNSET POINT @ SUNSET MARINA** Condo / Pool + Last Key White Glove Service...
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! SUNSET POINT ...
From $309 per night (USD)
VRBO
From $513 per night (USD)
Expedia
**SEA CAPTAIN'S HAVEN** Luxury Villa & Pool + Last Key White Glove Service...
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! SEA CAPTAIN'S ...
From $513 per night (USD)
Expedia
From $496 per night (USD)
VRBO
**THE MELLOW MACAW** Cozy Condo Near Duval + Last Key White Glove Service...
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! This colorful ...
From $496 per night (USD)
VRBO
From $515 per night (USD)
Expedia
Hemingways Atlantic Retreat overlooks Smathers Beach upgrades galore Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
**About...** Hemingway Atlantic Retreat is a two-bedroom condo conveniently located near beaches and restaurants, just ...
From $515 per night (USD)
Expedia
From $651 per night (USD)
VRBO
**NEPTUNE'S PENTHOUSE** Oceanside Condo / Pool + Last Key White Glove Service...
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! As Neptune wa ...
From $651 per night (USD)
VRBO
From $517 per night (USD)
Expedia
**CASITA ANGELITA @ OLD TOWN** Condo by Duval + Last Key White Glove Service...
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! This Old Town ...
From $517 per night (USD)
Expedia
From $274 per night (USD)
VRBO
**SUNSET DREAMS @ SUNSET MARINA** Condo / Pool + Last Key White Glove Service...
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! SUNSET DREAMS ...
From $274 per night (USD)
VRBO
From $229 per night (USD)
Expedia
Truman Annex Gem Shipyard 2BR C Walk to Beach & Bars, Best of Old Town
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Shipyard Pool Closure The Shipyard Pool will be closed starting August 1, 2026, for the Pool Deck Replacement Project. W ...
From $229 per night (USD)
Expedia

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