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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 $430 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 $430 per night (USD)
Expedia
From $435 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 $435 per night (USD)
VRBO
From $2234 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 $2234 per night (USD)
Expedia
From $605 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 $605 per night (USD)
VRBO
From $667 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 $667 per night (USD)
Expedia
From $350 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 $350 per night (USD)
VRBO
From $434 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 $434 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 $311 per night (USD)
VRBO
Villa Nomade at Shipyard Condominiums
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Relax at Villa Nomade in luxurious surroundings. Featuring a fully equipped kitchen with bar seating and dining area. Th ...
From $311 per night (USD)
VRBO
From $650 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 $650 per night (USD)
VRBO
From $574 per night (USD)
VRBO
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 $574 per night (USD)
VRBO
From $875 per night (USD)
Expedia
**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 $875 per night (USD)
Expedia
From $549 per night (USD)
VRBO
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 $549 per night (USD)
VRBO
From $365 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 $365 per night (USD)
VRBO
From $784 per night (USD)
VRBO
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)
VRBO
From $587 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 $587 per night (USD)
VRBO
From $278 per night (USD)
VRBO
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)
VRBO
From $578 per night (USD)
Expedia
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 $578 per night (USD)
Expedia
From $1060 per night (USD)
VRBO
**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 $1060 per night (USD)
VRBO
From $731 per night (USD)
Expedia
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 $731 per night (USD)
Expedia
From $1591 per night (USD)
VRBO
Balcony - Sky Suites Retreat, on 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 geta ...
From $1591 per night (USD)
VRBO
From $626 per night (USD)
Expedia
Pet Friendly, Pool, Private Balcony-Tortuga Suite
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 10 ...
From $626 per night (USD)
Expedia
From $380 per night (USD)
VRBO
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 $380 per night (USD)
VRBO
From $861 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 $861 per night (USD)
VRBO
Click For Pricing
VRBO
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
VRBO
From $686 per night (USD)
Expedia
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 $686 per night (USD)
Expedia
From $511 per night (USD)
VRBO
**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 $511 per night (USD)
VRBO
From $586 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 $586 per night (USD)
Expedia
From $669 per night (USD)
VRBO
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 $669 per night (USD)
VRBO
From $322 per night (USD)
Expedia
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 $322 per night (USD)
Expedia
From $577 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 $577 per night (USD)
VRBO
From $463 per night (USD)
Expedia
2 Bedroom 1 Bath Condo at Bayfront Suites & Marina - NO CLEANING FEE
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Bayfront Suites offers incredibly spacious, meticulously designed homes for a variety of guests. In this specific proper ...
From $463 per night (USD)
Expedia
Click For Pricing
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 ...
Click For Pricing
VRBO
From $1216 per night (USD)
Expedia
Waterfront 4 Bed, 4-Bath Condo @ Bayfront Suites & Marina - NO CLEANING FEE
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Bayfront Suites offers incredibly spacious, meticulously designed homes for a variety of guests. In this specific proper ...
From $1216 per night (USD)
Expedia
From $219 per night (USD)
VRBO
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)
VRBO
From $572 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 $572 per night (USD)
Expedia
From $912 per night (USD)
VRBO
3-Bedroom 3-Bath Condo at Bayfront Suites & Marina - NO CLEANING FEE
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Bayfront Suites offers incredibly spacious, meticulously designed homes for a variety of guests. In this specific proper ...
From $912 per night (USD)
VRBO
From $1047 per night (USD)
Expedia
Waterfront 4-Bed, 4-Bath Condo at Bayfront Suites & Marina - NO CLEANING FEE
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)
Expedia
From $1090 per night (USD)
VRBO
4-Bed 4.5 Bath Condo @ Bayfront Suites - NO CLEANING FEE (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 $1090 per night (USD)
VRBO
From $746 per night (USD)
Expedia
3 Bed 3 Bath Condo @ Bayfront Suites - NO CLEANING FEE (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 $746 per night (USD)
Expedia
From $1055 per night (USD)
VRBO
4-Bed, 3-Bath Waterfront Condo at Bayfront Suites & Marina - NO CLEANING FEE
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Bayfront Suites offers incredibly spacious, meticulously designed homes for a variety of guests. In this specific proper ...
From $1055 per night (USD)
VRBO
From $1190 per night (USD)
Expedia
4-Bed, 4.5 Bath Condo & Bayfront Suites - NO CLEANING FEE (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 $1190 per night (USD)
Expedia
From $771 per night (USD)
VRBO
Waterfront 3-Bedroom Condo at Bayfront Suites & Marina - NO CLEANING FEE
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Bayfront Suites offers incredibly spacious, meticulously designed homes for a variety of guests. In this specific proper ...
From $771 per night (USD)
VRBO
From $203 per night (USD)
Expedia
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)
Expedia
From $727 per night (USD)
VRBO
~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 $727 per night (USD)
VRBO
From $193 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 $193 per night (USD)
Expedia
From $634 per night (USD)
VRBO
Fantastic Fall Special Rates.
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 $634 per night (USD)
VRBO
From $215 per night (USD)
Expedia
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 $215 per night (USD)
Expedia
Click For Pricing
VRBO
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
VRBO
From $1057 per night (USD)
Expedia
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 $1057 per night (USD)
Expedia
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 $529 per night (USD)
Expedia
LOVE LANDING ~ Charming 3 Bedroom, 3 Bathroom Home w/ Pool and Parking!
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
MARITIME-INSPIRED LIVING… Come unwind in this desirable retreat, tucked in a quiet and private lane just a stone's throw ...
From $529 per night (USD)
Expedia
$The Hollinsed House \Victorian Delights\ - Large 1 Bedroom$
From $327 per night (USD)
VRBO
The Hollinsed House \"Victorian Delights\" - Large 1 Bedroom
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Mingle with other guests around the tropical gardens surrounding the heated pool and sundeck creating the perfect settin ...
From $327 per night (USD)
VRBO
From $275 per night (USD)
Expedia
BAREFOOT BUNGALOW~2 Bedroom, 2 Bathroom Home w/ Office, Pool and Tiki Hut!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
IMAGINE PARADISE… Picture your very own tropical estate enhanced with luxurious perks to include an expansive outdoor oa ...
From $275 per night (USD)
Expedia
From $516 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 $516 per night (USD)
VRBO
From $372 per night (USD)
Expedia
ORCHID ESCAPE~ 2 bedroom 2 bath set in Old Town with private dip pool!
Bedrooms:
2
Bathrooms:
2
Sleeps:
7
CLASSIC OLD KEY WEST HOME... This home is boasting a rare combination of location and character. A mix of historic detai ...
From $372 per night (USD)
Expedia
From $253 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 $253 per night (USD)
VRBO
From $845 per night (USD)
Expedia
By the Beautiful Sea - Key West Beach Front Condo - w Pool Access
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
If you're craving a Key West beach front accommodation with a bone fide front-line view to the sea, you know that Key We ...
From $845 per night (USD)
Expedia
From $516 per night (USD)
VRBO
Rose Lane Villas - Villa Alta - 1 bedroom - Sleeps 4 - Downtown Key West
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Nestled on a quiet lane in the heart of Old Town Key West, Rose Lane Villas is as close to the action as you'll get wit ...
From $516 per night (USD)
VRBO
From $904 per night (USD)
VRBO
Hyatt Sunset Harbour Resort-Prime location on Key West!!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
All rentals will be in seven-night increments with a Friday through Sunday for check-in. Thank you for choosing Dash R ...
From $904 per night (USD)
VRBO
From $489 per night (USD)
VRBO
WANDERLUST ~ Stunning 3 Bed, 3 Bath Retreat in Peaceful Neighborhood w/ Pool!
Bedrooms:
3
Bathrooms:
3
Sleeps:
9
STUNNING KEY WEST RETREAT… Just renovated, this island gem exudes the utmost island spirit with authentic historic chara ...
From $489 per night (USD)
VRBO
From $343 per night (USD)
VRBO
Cozy Piece of Key West History
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
PERFECTLY located, 100 y-o "Conch" House, w AAA+ front-porch, and 3 full baths to go w 3 BRs... brand-new kitchen, compl ...
From $343 per night (USD)
VRBO
From $1880 per night (USD)
VRBO
~CHAVEZ HOUSE~ The private pool and lanai are a Key West dream come true!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
** Chavez House is available for 28 night minimum for the month of August ONLY. Live like a local! THE PROPERTY: By br ...
From $1880 per night (USD)
VRBO
From $501 per night (USD)
VRBO
~ SOLARIS COTTAGE ~ Live like a local in this bright and cozy retreat.
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
THE PROPERTY: This one bedroom, one bath, first-floor duplex is conveniently located in Old Town. Walkable to so many Ke ...
From $501 per night (USD)
VRBO
From $511 per night (USD)
VRBO
~ SEA VISTA ~ A waterfront dream with private heated pool and boat launch.
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
MONTHLY RENTAL: Requires a minimum stay of 28 nights occurring within the same month. Stay a month and live like a local ...
From $511 per night (USD)
VRBO
From $1473 per night (USD)
VRBO
~ SOUTHARD COMFORT ~ Feel the Key West vibe in Old Town with a private pool.
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
THE PROPERTY: Nancy & Carl invite you to share their love of the island in their enchanted 3-bedroom home. Live like a l ...
From $1473 per night (USD)
VRBO
From $801 per night (USD)
VRBO
~ PETITE MAISON ~ 2 king ensuite bedrooms on a quiet lane near Duval Street.
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
THE PROPERTY: An open staircase leading to the second floor is where your vacation begins! The reverse floor plan, tres ...
From $801 per night (USD)
VRBO
From $542 per night (USD)
Expedia
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 $542 per night (USD)
Expedia
From $713 per night (USD)
VRBO
~ CASABLANCA TOO ~Chicly updated home with hot tub in a quiet location.
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
**This home is available in August only as a monthly rental (28 nights in the same month).** Come and live like a local! ...
From $713 per night (USD)
VRBO
From $674 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 $674 per night (USD)
Expedia
From $912 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 $912 per night (USD)
VRBO
From $562 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 $562 per night (USD)
Expedia
From $227 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 $227 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 $461 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 $461 per night (USD)
VRBO
From $490 per night (USD)
VRBO
~TROPICAL DREAM~Sun deck, pool, and parking adorn this home in Old Town.
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
MONTHLY RENTAL: Requires a minimum stay of 28 nights occurring within the same month. Stay a month and live like a local ...
From $490 per night (USD)
VRBO
From $281 per night (USD)
VRBO
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 $281 per night (USD)
VRBO
From $560 per night (USD)
VRBO
~ SOLARIS GARDEN ~ Relax and enjoy this Bohemian dream on a quaint lane.
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
THE PROPERTY: Bohemian bits indoors and lush landscaping outdoors will give you that tropical island feeling you are loo ...
From $560 per night (USD)
VRBO
From $623 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 $623 per night (USD)
VRBO
From $185 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 $185 per night (USD)
Expedia
From $550 per night (USD)
VRBO
THE OLD SAPODILLA HOUSE ~ Pet Friendly Home in Historic Bahama Village
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
PERFECT GETAWAY JUST STEPS FROM DUVAL... Private family home with poolside cottage totals three bedrooms and three full ...
From $550 per night (USD)
VRBO
From $340 per night (USD)
VRBO
~ THE PINK HOUSE ~ Saline pool, lush privacy and 2 ensuites with balconies.
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
MONTHLY RENTAL: Requires a minimum stay of 28 nights occurring within the same month. Stay a month and live like a local ...
From $340 per night (USD)
VRBO
From $380 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 $380 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 $967 per night (USD)
VRBO
~ CASABLANCA ~ Fabulous home w/ private pool/parking, in a quiet location.
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
THE PROPERTY: Between the welcoming front porch and the private pool, you will be sure to enjoy fresh air and sunshine d ...
From $967 per night (USD)
VRBO
From $590 per night (USD)
VRBO
~FAIR WINDS @ THE FOUNDRY~ Frolic on Duval St then unwind in the shared pool!
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 n ...
From $590 per night (USD)
VRBO
From $785 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 $785 per night (USD)
VRBO
From $598 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 $598 per night (USD)
Expedia
From $568 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 $568 per night (USD)
VRBO
From $2281 per night (USD)
VRBO
~ CLOUD 9 ~ It's heaven on earth in this 3B/3BA lavish home with pool/parking
Bedrooms:
3
Bathrooms:
3
Sleeps:
7
THE PROPERTY: If you are looking for a peaceful retreat that is close to everything, this is the ultimate home for you. ...
From $2281 per night (USD)
VRBO
From $229 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 $229 per night (USD)
VRBO
From $1398 per night (USD)
VRBO
~POTTER'S COTTAGE~ Key West charmer in great location with private pool!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
THE PROPERTY: Enjoy the walkable location of this charming property. As you enter the home from its covered rocking chai ...
From $1398 per night (USD)
VRBO
From $2271 per night (USD)
VRBO
~ GRAND MAISON ~ Spacious home on Duval St with pool and 4 ensuite bedrooms.
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
THE PROPERTY: This home’s Key West charm and modern amenities make for a wonderful stay. From the Adirondack chair front ...
From $2271 per night (USD)
VRBO
From $592 per night (USD)
Expedia
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 $592 per night (USD)
Expedia
From $657 per night (USD)
VRBO
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 $657 per night (USD)
VRBO
From $239 per night (USD)
Expedia
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 $239 per night (USD)
Expedia
From $208 per night (USD)
VRBO
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 $208 per night (USD)
VRBO
From $411 per night (USD)
VRBO
~ POINCIANA TREETOP ~ Casual second 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 second-floor duplex home comes with Key Wes ...
From $411 per night (USD)
VRBO

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