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$Comfortable Home with Private Pool, Central AC, WiFi, and Private Washer\/Dryer$
From $266 per night (USD)
VRBO
Comfortable Home with Private Pool, Central AC, WiFi, and Private Washer\/Dryer
Bedrooms:
2
Bathrooms:
4
Sleeps:
6
Flagler Station Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $266 per night (USD)
VRBO
From $332 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 $332 per night (USD)
Expedia
From $390 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 $390 per night (USD)
VRBO
$~DREAMING ON DUVAL~ Grand 5 bedroom, 4.5 bath home with private pool\/parking$
From $2406 per night (USD)
Expedia
~DREAMING ON DUVAL~ Grand 5 bedroom, 4.5 bath home with private pool\/parking
Bedrooms:
5
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 $2406 per night (USD)
Expedia
$Henry's Penthouse on the Ocean in Key West - weekly \/ nightly rentals$
From $528 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 $528 per night (USD)
VRBO
$**OLD TOWN OASIS @ THE ANNEX** Oceanside 2BR\/2BA Condo & Pool + LAST KEY SERVICE$
From $662 per night (USD)
Expedia
**OLD TOWN OASIS @ THE ANNEX** Oceanside 2BR\/2BA Condo & Pool + 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! OLD TOWN OASI ...
From $662 per night (USD)
Expedia
From $366 per night (USD)
VRBO
Craig & Cindy Key West Truman Annex Shipyard Condo with a deck at Mile Marker 0!
Bedrooms:
1
Bathrooms:
3
Sleeps:
4
Partial list of rental amenities at Craig & Cindy's Truman Annex Shipyard Condos include: 2 bedrooms 1 bath {queen and ...
From $366 per night (USD)
VRBO
From $503 per night (USD)
Expedia
Craig & Cindy Truman Annex Foundry Townhouse 2 bedrooms 2.5 baths
Bedrooms:
3
Bathrooms:
3
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 $503 per night (USD)
Expedia
From $238 per night (USD)
VRBO
COCONUT Adorable cottage in Old Town
Bedrooms:
1
Bathrooms:
2
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 $238 per night (USD)
VRBO
From $405 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 $405 per night (USD)
Expedia
From $402 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 $402 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 $662 per night (USD)
VRBO
Heart of Key West - 2BR Waterfront at the Galleon Resort
Bedrooms:
2
Bathrooms:
3
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 $662 per night (USD)
VRBO
From $360 per night (USD)
Expedia
Welcome to the Shady Palms - Private Pool - RealKeyWest
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
Step into this beautifully restored and redecorated 1933 Key West home. This first-floor home has Bahama shutters throug ...
From $360 per night (USD)
Expedia
From $714 per night (USD)
VRBO
**ENVY OF THE ISLAND @ OLD TOWN** Pristine Home & Pool + LAST KEY SERVICES...
Bedrooms:
7
Bathrooms:
5
Sleeps:
10
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! While Old Tow ...
From $714 per night (USD)
VRBO
From $166 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 $166 per night (USD)
Expedia
From $469 per night (USD)
VRBO
SOUTHERNMOST SWIM AND SOCIAL CLUB
Bedrooms:
2
Bathrooms:
4
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 $469 per night (USD)
VRBO
$Treasure Cove- 2BDR\/2.5BA | 2 Bed, 2.5 Bath$
From $623 per night (USD)
Expedia
Treasure Cove- 2BDR\/2.5BA | 2 Bed, 2.5 Bath
Bedrooms:
3
Bathrooms:
3
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 $183 per night (USD)
VRBO
Quiet Lane in the Heart of Old Town, Sleeps 4 + 🐶🐾
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Unbeatable location just 1 block from the iconic Green Parrot Bar and 2 blocks from world famous Duval Street. Blue Heav ...
From $183 per night (USD)
VRBO
$ISLAND TIME - 5 Bed\/3 Bath OldTown Complex - MONTHLY - Private pool$
From $792 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 $792 per night (USD)
Expedia
From $348 per night (USD)
VRBO
TROPICAL PROPERTIES VACATION RENTAL - KEY WEST
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
****This property requires a minimum stay of 28 nights in the same calendar month**** ***Brand New Pool with waterfall, ...
From $348 per night (USD)
VRBO
$Tropical Jewel: Historic Seaport Oldtown - 2BR\/2BA - Pool - RealKeyWest$
From $273 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 $273 per night (USD)
Expedia
From $470 per night (USD)
VRBO
MAJESTIC PARADISE II Luxury living in Truman Annex. Downtown, pool, 2 blks
Bedrooms:
3
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 $470 per night (USD)
VRBO
From $1199 per night (USD)
Expedia
**JASMINE JEWEL @ THE ANNEX** Lush Private Home & Pool + LAST KEY SERVICES…
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Hidden amongs ...
From $1199 per night (USD)
Expedia
$Getaway in Key West: Tranquil Room w\/ Balcony | Resort w\/ Pool Access$
From $1025 per night (USD)
VRBO
Getaway in Key West: Tranquil Room w\/ Balcony | Resort w\/ Pool Access
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Unwind in Key West's vibrant heart, where every step brings you closer to adventure. Just moments from Duval Street, the ...
From $1025 per night (USD)
VRBO
$Old Town Key West Family Retreat | Spacious Room w\/ Balcony | Parking Onsite$
From $964 per night (USD)
VRBO
Old Town Key West Family Retreat | Spacious Room w\/ Balcony | Parking Onsite
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Unwind in Key West's vibrant heart, where every step brings you closer to adventure. Just moments from Duval Street, the ...
From $964 per night (USD)
VRBO
From $575 per night (USD)
VRBO
ADMIRAL'S PARADISE in Key West
Bedrooms:
3
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 $575 per night (USD)
VRBO
From $1436 per night (USD)
Expedia
Balcony - Sky Suites Retreat, on Duval
Bedrooms:
5
Bathrooms:
6
Sleeps:
12
Summary: This elegant, elevated 2nd story loft with vaulted ceilings has been designed for your next dream Key West geta ...
From $1436 per night (USD)
Expedia
From $519 per night (USD)
VRBO
Balcony, Pool, & Pet Friendly - Tortuga Suite
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Summary: Welcome to Sunrise Suites, a peaceful community on Key West's southeast side. Just 1 mile from the beach and 10 ...
From $519 per night (USD)
VRBO
From $355 per night (USD)
Expedia
Waterfront Property - Marina Access - Spacious - Excellent Key West Condo
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Located just two miles from picturesque Smathers Beach, this well appointed two bedroom, two bath condo is ideally situa ...
From $355 per night (USD)
Expedia
From $563 per night (USD)
VRBO
Key West's Crown Jewel
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Key West's Crown Jewel is a penthouse condominium at 1800 Atlantic Condominium development with two-bedroom, two-bath wi ...
From $563 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 $761 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 $761 per night (USD)
VRBO
From $475 per night (USD)
Expedia
Casa Verde - Perfection in a monthly rental - private pool - RealKeyWest
Bedrooms:
4
Bathrooms:
3
Sleeps:
6
As you step through the door, you are enveloped in a serene atmosphere highlighted by soothing tropical colors and impre ...
From $475 per night (USD)
Expedia
From $409 per night (USD)
VRBO
**SEAPORT SENSATION @ OLD TOWN VILLAS** Condo & Pool + LAST KEY SERVICES...
Bedrooms:
4
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 $409 per night (USD)
VRBO
From $450 per night (USD)
Expedia
**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 $450 per night (USD)
Expedia
From $810 per night (USD)
VRBO
Flirty Flamingo Key West
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Flirty Flamingo is luxurious and in a prime Key West location. Built in 1998 and meticulously cared for this spacious 3 ...
From $810 per night (USD)
VRBO
From $265 per night (USD)
Expedia
Runaway Bills | 3 Bed, 1 Bath
Bedrooms:
1
Bathrooms:
4
Sleeps:
6
This stylish Conch Home is tucked away on a quiet lane in Old Town Key West. Surrounded by distinctive neighborhoods thi ...
From $265 per night (USD)
Expedia
$Henry's Piece of Paradise on the Ocean in Key West - Weekly \/ Nightly$
From $477 per night (USD)
VRBO
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 $477 per night (USD)
VRBO
From $492 per night (USD)
Expedia
Sunset South: 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 $492 per night (USD)
Expedia
From $433 per night (USD)
VRBO
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)
VRBO
From $991 per night (USD)
Expedia
Upper Bayview North: Waterfront 4 Bedroom 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 $991 per night (USD)
Expedia
$Upscale Townhome w\/ Golf, Garden & Lake Views, Shared Pool, WiFi - Dogs OK$
From $232 per night (USD)
VRBO
Upscale Townhome w\/ Golf, Garden & Lake Views, Shared Pool, WiFi - Dogs OK
Bedrooms:
3
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 $232 per night (USD)
VRBO
From $504 per night (USD)
Expedia
~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 $504 per night (USD)
Expedia
From $1030 per night (USD)
VRBO
Upper Bayview South: Waterfront 4 Bedroom 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 $1030 per night (USD)
VRBO
From $875 per night (USD)
Expedia
Middle Sunset: 3 Bedroom 3 Bath Luxury 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 $875 per night (USD)
Expedia
From $1047 per night (USD)
VRBO
Bayview North One: Waterfront 4 Bedroom 4 Bath Condo at Bayfront Suites
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Bayfront Suites offers incredibly spacious, meticulously designed homes for a variety of guests. In this specific proper ...
From $1047 per night (USD)
VRBO
From $977 per night (USD)
Expedia
Sunset North: Luxury 4 Bedroom 4.5 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 $977 per night (USD)
Expedia
From $881 per night (USD)
VRBO
Upper Sunset South: Luxury 3 Bedroom 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 $881 per night (USD)
VRBO
From $955 per night (USD)
Expedia
Bayview South: 4 Bedroom 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 $955 per night (USD)
Expedia
From $983 per night (USD)
VRBO
Upper Sunset North: Luxury 4 Bedroom Condo at Bayfront Suites & Marina
Bedrooms:
5
Bathrooms:
4
Sleeps:
8
Bayfront Suites offers incredibly spacious, meticulously designed homes for a variety of guests. In this specific proper ...
From $983 per night (USD)
VRBO
From $923 per night (USD)
Expedia
Bayview Middle: 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 $923 per night (USD)
Expedia
From $187 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 $187 per night (USD)
VRBO
From $751 per night (USD)
Expedia
~Serene Lily~ Luxurious 2 bed, 2.5 bath home in the upscale Truman Annex
Bedrooms:
3
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 $751 per night (USD)
Expedia
From $175 per night (USD)
VRBO
Paradise found at the Key West Golf Club!
Bedrooms:
2
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 $175 per night (USD)
VRBO
From $513 per night (USD)
Expedia
BOOKING SMOKING HOT 2025 DEALS 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 $513 per night (USD)
Expedia
From $210 per night (USD)
VRBO
Lush Gardens-Pool-Jacuzzi-No Contact Check-In
Bedrooms:
1
Bathrooms:
1
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 $210 per night (USD)
VRBO
Click For Pricing
Expedia
FANTASY WEEK
Bedrooms:
2
Bathrooms:
4
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 $151 per night (USD)
VRBO
Petite Pearl! Spacious 1 Bedroom, 1 Bath Pool Condo- RealKeyWest
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Welcome to Petite Pearl, your hidden gem nestled in the heart of the coveted Meadows district in Key West. A stone's thr ...
From $151 per night (USD)
VRBO
From $955 per night (USD)
Expedia
Historic Old Town Key West - Turtle House, Sleeps 6
Bedrooms:
1
Bathrooms:
3
Sleeps:
5
OVERVIEW The Turtle House is a 100+ year old recently completely renovated “Conch” house. The house can be described as ...
From $955 per night (USD)
Expedia
From $332 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 $332 per night (USD)
VRBO
From $394 per night (USD)
Expedia
The Sylvia Gwynn, Key West Southernmost Point monthly vacation rental
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Just 1 block from the action of Duval Street lies our newest space located at 1307 Whitehead Street. The Sylvia Gwynn is ...
From $394 per night (USD)
Expedia
From $682 per night (USD)
VRBO
**COLORS OF THE KEYS @ THE FOUNDRY** Villa Near Duval & Beach + LAST KEY SERVICE
Bedrooms:
3
Bathrooms:
1
Sleeps:
6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! COLORS OF THE ...
From $682 per night (USD)
VRBO
From $480 per night (USD)
VRBO
The Key West Bougain Villa, a Monthly Vacation Rental
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
The Bougain Villa is found on Whitehead Street. Reserve a stay in this home located in the heart of historic Old Town Ke ...
From $480 per night (USD)
VRBO
$Hidden Paradise-2bed 2bath condo w\/ ocean views, dock space, pool$
From $220 per night (USD)
VRBO
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 $220 per night (USD)
VRBO
From $535 per night (USD)
Expedia
Key West On My Mind, Ocean Views, Renovated Kitchen, Last minute deals
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
CONSTRUCTION NOTICE - There will be concrete restoration project happening at 1800 Atlantic Starting in May 2025 through ...
From $535 per night (USD)
Expedia
From $543 per night (USD)
VRBO
Premier Ocean views, expansive balcony, renovated kitchen & bath 2024
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
CONSTRUCTION NOTICE - There will be concrete restoration project happening at 1800 Atlantic Starting in May 2025 through ...
From $543 per night (USD)
VRBO
From $701 per night (USD)
Expedia
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 $701 per night (USD)
Expedia
From $496 per night (USD)
VRBO
Moonlight Paradise Upgraded Family oasis Tropical views expansive balcony
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
CONSTRUCTION NOTICE - There will be concrete restoration project happening at 1800 Atlantic Starting in May 2025 through ...
From $496 per night (USD)
VRBO
From $229 per night (USD)
Expedia
Ocean Front Key West Oasis Island Tones Charming Historical Downtown area
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
CONSTRUCTION NOTICE - There will be concrete restoration project happening at 1800 Atlantic Starting in May 2025 through ...
From $229 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 $430 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 $430 per night (USD)
Expedia
From $172 per night (USD)
VRBO
Best Downtown Location Monthly Rental open March 7th 2025 Great deal
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
This delightful 2 Bedroom Cigar Maker's Cottage at 1008 Whitehead was built in the 1880's, where there was once a Cigar ...
From $172 per night (USD)
VRBO
$Key West Beachfront Luxury 2\/2 Condo A212$
From $571 per night (USD)
Expedia
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 $571 per night (USD)
Expedia
From $167 per night (USD)
VRBO
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 $167 per night (USD)
VRBO
From $315 per night (USD)
Expedia
Salty Sea Breezes, Exquisite Morning Sunrises, Luxurious Condo. Fall Specials
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
CONSTRUCTION NOTICE - There will be concrete restoration project happening at 1800 Atlantic Starting in May 2025 through ...
From $315 per night (USD)
Expedia
From $212 per night (USD)
VRBO
Casa Coastal East, Morning sunrises, Evening night time vibes An Island home.
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
CONSTRUCTION NOTICE - There will be concrete restoration project happening at 1800 Atlantic Starting in May 2025 through ...
From $212 per night (USD)
VRBO
From $667 per night (USD)
Expedia
Amazingly Transformed in 2022 Luxurious renovation Fantastic Ocean View
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
CONSTRUCTION NOTICE - There will be concrete restoration project happening at 1800 Atlantic Starting in May 2025 through ...
From $667 per night (USD)
Expedia
From $633 per night (USD)
VRBO
Key Wes't Best- Upgraded condo 5 mins to Smathers Beach Fantastic value
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
CONSTRUCTION NOTICE - There will be concrete restoration project happening at 1800 Atlantic Starting in May 2025 through ...
From $633 per night (USD)
VRBO
From $566 per night (USD)
Expedia
Paradise Found in Key West upgrades throughout 5 minutes to Smathers Beach
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
CONSTRUCTION NOTICE - There will be concrete restoration project happening at 1800 Atlantic Starting in May 2025 through ...
From $566 per night (USD)
Expedia
From $196 per night (USD)
VRBO
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 $196 per night (USD)
VRBO
From $638 per night (USD)
Expedia
Anchor Drop modern elegance upgrades throughout views of Atlantic Ocean
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
CONSTRUCTION NOTICE - There will be concrete restoration project happening at 1800 Atlantic Starting in May 2025 through ...
From $638 per night (USD)
Expedia
From $551 per night (USD)
VRBO
Tropical Paradise Key West - Upgraded Master Bath - Best Value Discounts
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
CONSTRUCTION NOTICE - There will be concrete restoration project happening at 1800 Atlantic Starting in May 2025 through ...
From $551 per night (USD)
VRBO
Click For Pricing
Expedia
Key West Morning reflections, Balmy Ocean Breezes, Downtown family fun
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
This beautifully renovated 2-bedroom, 2-bath penthouse offers stunning views of the Atlantic Ocean and Smathers Beach. T ...
Click For Pricing
Expedia
From $242 per night (USD)
VRBO
Oceanfront Overlook in open for March of 2025 - Key West's Finest
Bedrooms:
2
Bathrooms:
3
Sleeps:
4
Oceanfront Overlook is a unique unit with an amazing view of the Atlantic Ocean, your perfect home away from home, equip ...
From $242 per night (USD)
VRBO
From $212 per night (USD)
Expedia
Sea La Vie, Island Breezes, Morning Sunrises & Key West Island days.
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
CONSTRUCTION NOTICE - There will be concrete restoration project happening at 1800 Atlantic Starting in May 2025 through ...
From $212 per night (USD)
Expedia
From $1603 per night (USD)
VRBO
~ Chick-A-Pea Cottage ~ Enjoy Key West’s charisma, with a pool, and parking!
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
THE PROPERTY: Come enjoy the Key West cottage lifestyle where you can people watch from your front porch or take a dip ...
From $1603 per night (USD)
VRBO
From $196 per night (USD)
Expedia
Island Style, Morning Sunrises, Salty Ocean Breezes & Downtown Key West days.
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
CONSTRUCTION NOTICE - There will be concrete restoration project happening at 1800 Atlantic Starting in May 2025 through ...
From $196 per night (USD)
Expedia
$Thirsty Mermaid - Large 4\/3 Pool Home$
From $409 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 $409 per night (USD)
VRBO
$Old Town! Spacious Condo in Historic Home w\/Pool!$
From $222 per night (USD)
Expedia
Old Town! Spacious Condo in Historic Home w\/Pool!
Bedrooms:
2
Bathrooms:
2
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 $222 per night (USD)
Expedia
From $669 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 $669 per night (USD)
VRBO
From $359 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 $359 per night (USD)
Expedia
From $1289 per night (USD)
VRBO
**BRISA FRESCA @ THE ANNEX** Airy Home by Duval & Beach + LAST KEY SERVICES...
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! A trip to Key ...
From $1289 per night (USD)
VRBO
From $408 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 $408 per night (USD)
Expedia
$**SMOOTH SAILING @ THE BEACH** Ocean Condo \/ Pool & Tennis + LAST KEY SERVICES..$
From $775 per night (USD)
VRBO
**SMOOTH SAILING @ THE BEACH** Ocean Condo \/ Pool & Tennis + LAST KEY SERVICES..
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
CONSTRUCTION NOTICE - There will be concrete restoration happening in this complex through Summer 2026. This constructio ...
From $775 per night (USD)
VRBO
From $634 per night (USD)
Expedia
**VILLA BAHAMA @ THE ANNEX** Villa Near Duval & Beach + LAST KEY SERVICES...
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! VILLA BAHAMA ...
From $634 per night (USD)
Expedia
From $1196 per night (USD)
VRBO
**THE CONTENTED CRANE @ OLD TOWN** Home & Pool Near Duval + LAST KEY SERVICES...
Bedrooms:
4
Bathrooms:
3
Sleeps:
8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Traveling to ...
From $1196 per night (USD)
VRBO
From $2276 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 $2276 per night (USD)
Expedia
$**SOUTHERNMOST HOSPITALITY VII** 7BR\/7BA & Pool + LAST KEY SERVICES...$
From $2572 per night (USD)
VRBO
**SOUTHERNMOST HOSPITALITY VII** 7BR\/7BA & Pool + LAST KEY SERVICES...
Bedrooms:
8
Bathrooms:
7
Sleeps:
16
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! SOUTHERNMOST ...
From $2572 per night (USD)
VRBO
From $839 per night (USD)
Expedia
**GULFSIDE VISTAS @ THE ANNEX** Condo & Pool + LAST KEY SERVICES...
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! GULFSIDE VIST ...
From $839 per night (USD)
Expedia

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