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Below are Weekly Rentals with no specified number of bedrooms
Key West weekly rentals hold a special City of Key West transient license which allows these properties to be rented weekly or nightly. Most weekly rentals have a minimum stay of 3 to 5 nights and during some months require a week minimum stay.
Weekly rentals are decorated Key West island style, reflecting the unique tastes of property owners. Some are furnished luxuriously, and some more simply. All are equipped with essential amenities and conveniences of home, including internet, TV, linens, and kitchenware. Read our property descriptions to learn the details.
* PLEASE NOTE: Some properties displayed may not be available for rent due to other inquiries and pending reservations. Please contact our office to be sure of availability. info@vhkw.com or 305-294-7358 ext. 1
There are no properties available that fit all of your search options. Please contact our office if you would like assistance. info@vhkw.com or 305-294-7358 ext. 1
Admirals Gold - Private Key West Luxury Villa ~ Weekly Rental
Guaranteed Lowest Rates - Book Direct
special rates available
4 BR 3.5 Baths July 5- July 12
Weekly $5500
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Standard Rates: $5,420 - $12,570 per week
4BR 3.5BA - Sleeps 8
Located in Truman Annex Neighborhood
Waterfront Park Amphitheater
Shared Heated Pool
Short Walk to Beach
Elegant tropical luxury home with impeccable attention to detail. Situated in Key West’s prestigious gated community of Truman Annex!Short walk to Fort Zachary Taylor and Truman Waterfront. Just out the gate to downtown Old Town Key West and Duval Street.
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305-294-7358
Tropical Chill ~ Weekly Rental
Guaranteed Lowest Rates - Book Direct
special rates available
2BR 2BA July 7- July 14
July 29 - Aug 5
Weekly $2100
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Standard Rates: $2,230 - $4,260 per week
2BR 2BA - Sleeps 4
Overlooks Tropical Swimming Pool Garden
Shared Heated Pool w/ Caribbean Cabana
Truman Annex Neighborhood
Gates lead to Ft. Zachary Taylor Beach, Truman Waterfront, and Downtown Old Town Key West
If you’re looking for a place to chill-out in the tropical warmth of Key West, this cottage-style flat is a wonderful place to relax and take a breather from everyday life.
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305-294-7358
Key West Mile Zero Suite ~ Weekly Rental
Guaranteed Lowest Rates - Book Direct
special rates available
2BR 2BA May 29 - June 6 Weekly $2900
June 14 - June 30
Nightly $575
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Standard Rates: $2,580 - $6,200 per week
2BR 2BA - Sleeps 4
2nd FL Condo Suite plus private back deck on ground level
Downtown - 1 block off 500 block of Duval Street near Margaritaville
Private Heated Pool
Sun deck on ground level
When taking a selfie at the iconic Key West Mile Marker 0 just isn’t enough, now you can luxuriously live right next to this famous landmark ... in luxury and style!
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305-294-7358
Flower Power House ~ Weekly Rental
Guaranteed Lowest Rates - Book Direct
Standard Rates: $5,900 - $11,670 per week
6BR 4BA- Sleeps 12+
Attached 1BR Cottage-style Suite
Overlooks Large Tropical Garden & Large Shared Pool.
Boho style. Great value.
Easy walk to Higgs Beach
Boho beautiful, the free-spirited presence of the Key West Flower Power House has much more in common with the 'real Key West' than the shiny hotels around town. Off the beaten path but close to everything.
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305-294-7358
co*ckadoodle Cottage On Duval ~ Weekly Rental
Guaranteed Lowest Rates - Book Direct
special rates available
2BR 2BA July 7 - July 14 Nightly $475
July 20 -Aug 3
Weekly $2500
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Standard Rates: $2,095 - $4,760 per week
2BR 2BA
Sleeps 4
Great for 2 Couples or Small Family
Jacuzzi Bath Tub
On Charming Upper Duval St.
1 minute walk to South Beach.
Key West cottage architecture has been time-tested in island life and culture in this infamous little wooden 'cigar maker's' cottage located on famous Duval Street, at the 'classier upper-end.'
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305-294-7358
Island Rendezvous ~ Weekly Rental
Guaranteed Lowest Rates - Book Direct
Standard Rates: $7,830 - $17,325 per week
6BR 5BA - Sleeps 14
2 heated swimming pools
3 Cottage Compound (2-cottage villa plus a cottage).
Less than 1/2 block off Duval Street
Get together for an 'Island Rendezvous' in Key West in this Award Winning Villa and Caribbean Style Cottage side-by-sidesteps from Duval St. and 3.5 Blocks from Mallory Square.Perfect solution for a gathering of family or friends for a week in paradise.
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305-294-7358
By The Beautiful Sea ~ A Key West Beach Front Condo ~ Weekly Rental
Guaranteed Lowest Rates - Book Direct
special rates available
3BR 2BA July 13- July 24 Nightly $525
Weekly $2500
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Standard Rates: $2,580 - $5,775 per week
3BR 2BA - Sleeps up to 6
Private Ocean-View Terrace
Resort-Style Shared Pool
If you’re craving a Key West beach accommodation with a bona fide front-line view to the sea,you can instantly gratify this need with a stay in this pretty vacation rental condominium, By The Beautiful Sea.
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305-294-7358
Ocean View Luxury Villa ~ Weekly Rental
Guaranteed Lowest Rates - Book Direct
Standard Rates: $8,158 - $10,740 per week
3BR 4BA - Sleeps 6-8
Ocean View / Sun Deck
Private Heated Pool
Key West Truman Annex Neighborhood
Short Walk to Beach and Key West Waterfront Park Amphitheater
Gorgeous Old Town Key West Ocean View Luxury Home in immaculate gated neighborhood!Holding an enviable spot in Key West’s gated community of Truman Annex, this classic home offers an open water view, easy beach access, and is a short walking distance to Duval Street and downtown Old Town Key West..
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305-294-7358
Exclusive Key West Beach Front ~ Weekly Rental
Guaranteed Lowest Rates - Book Direct
special rates available
2BR 3BA July 7 - July 19 Weekly $2550
July 26 - Aug 3
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Standard Rates: $2,530 - $5,775 per week
2BR 3BA
Designer Condominium Overlooking Key West Ocean Sanctuary
You can see for miles & miles & miles ... South over the turquoise ocean, the White Street Pier stretches out in the near distance. Fresh Caribbean Breeze, great white herons wade in clear shallows below, relaxing on the balcony, southern sunrise, full moon rising ...
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305-294-7358
Old Town Caribbean Estate ~ Weekly Rental
Guaranteed Lowest Rates - Book Direct
special rates available
10BR 7.5 BA June 29 - July 2
July 27 - Aug 3
Nightly $2400
Weekly $11500
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Standard Rates: $11,800 - $25,220 per week
10 BR 7.5 BA - Sleeps 18 - 21
Heated Pool
7 BR Main House + 3 BR Guest House
Lush Tropical Gardens
Famous Historic Seaport neighborhood
Stroll to Duval St.
Spacious. Luxurious. Exotic.Old Town Caribbean Estateis amasterful combination of a classic Key West Victorian home with an exotic Caribbean-style guest house. A remarkable place for family and friends to stay together in a Key West weekly rental.
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305-294-7358
Sweet Sunshine Garden Flat ~ Weekly Rental
Guaranteed Lowest Rates - Book Direct
special rates available
2BR 1BA July 2- July 13
Weekly $1800
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Standard Rates: $1,800 - $3,675 per week
2BR 1BA - Sleeps 4
Truman Annex Neighborhood
Steps to Truman Waterfront Park
Shared Heated Pool w/ Caribbean Cabana
2 Blocks from Duval Street
10 minute walk to the waters' edge of Ft. Zachary Taylor Beach
Sweet Sunshine Garden Flatis perfectly situated for a week near the beach and downtown Old Town Key West. Looking north, you’re less than two blocks from downtown old town – looking south you’re less than two blocks from the Truman Waterfront Park and Fort Zachary Taylor State Park and Beach.
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305-294-7358
Havana Moon Over Duval ~ Weekly Rental
Guaranteed Lowest Rates - Book Direct
special rates available
2BR 2BA June 30 - July 15
Aug 2- Aug 7
Nightly $550
Weekly $2600
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Standard Rates: $2,475 - $5,820 per week
2BR 2BA - Sleeps 4
Private Swimming Pool
On Upper Duval St. - 1 min. walk to South Beach.
Great for 2 couples or small family
Originally built in the late 1800’s as a 'cigar makers’ cottage, the authentic exterior of this turn-of-the-century cottage is protected by historic preservation rules and today stands renovated to form, to be proud and handsome. But the interior of Havana Moon, is an entirely different story. Inside the owners had creative license to redesign in order to bring the cottage upscale modern vacation standards, with all the luxurious accoutrements. The cottage also has a swimming pool and large deck for lounging and sunning.Open the front door of this hand crafted Key West cottage and look south toward Havana Cuba and you'll catch a view of the ocean where the full moon rises with a soft salt southern breeze.
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305-294-7358
Truman Treasure ~ Weekly Rental
Guaranteed Lowest Rates - Book Direct
Standard Rates: $5,260 - $7,557 per week
3BR 2.5BA - Sleeps up to 5
Stroll to the Beach
Truman Annex residence with Ocean View from Bedroom Balconies
Short Walk to all Downtown Old Town Key West Features
Rent this Key West Luxury Home and Experience a Remarkable Piece of American Architectural History. A renovated 'Truman Treasure', in one of the most desirable Ocean Front Old Town Key West locations.
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305-294-7358
Villa Deja vu Key West ~ Weekly Rental
Guaranteed Lowest Rates - Book Direct
special rates available
4BR 3BA June 13 - June 22
June 28 - July 2
July 15 - July 31
Nightly $975
Weekly $5300
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Standard Rates: $5,250 - $11,075 per week
4BR 3BA - Sleeps 8-10
Heated Pool - Sun Deck
Lush Pool Garden
1/2 Block Off Duval Street
We invite you to discover that incredible experience of Déjà vu ... you know, when you enter someplace for the very first time, and instantly you get that sense that you’ve been there before. When I first walked into this house it happened to me. My mind sparked and I felt an instant kinship with the surroundings.
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305-294-7358
Private Pool Garden Villa ~ Weekly Rental
Guaranteed Lowest Rates - Book Direct
special rates available
3BR 2.5BA June 13- June 17
June 27 - July 6
July 21 - July 27
Nightly $725
Weekly $3900
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Standard Rates: $720 - $6,950 per week
3BR 2.5BA - Sleeps 6
Main House
Large Private Swimming Pool
with Spacious Outdoor Cabana
Close to Higgs Beach
Experience true tropical Key West living in this lush garden oasis home with large swimming pool and garden cabana located just one block from the beach. Easy bike ride to center of Old Town.
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305-294-7358
Tree Tops ~ Weekly Rental
Guaranteed Lowest Rates - Book Direct
Standard Rates: $2,200 - $4,170 per week
2BR 1BA - Sleeps 6
Overlooks large tropical garden with very large shared pool.
Boho style. Great value.
TheTree Tops Suitevacation rental is has a classic undying Key West charm that exudes a real down-island vacation feel. Approximately 750 square feet of living space offering an open floor plan joining the beamed ceiling living room and galley kitchen.
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305-294-7358
Classic Key West Estate ~ Weekly Rental
Guaranteed Lowest Rates - Book Direct
special rates available
7BR 5.5BA June 29 - July 2
July 27 - Aug 3
Nightly $1900
Weekly $10400
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Standard Rates: $1,080 - $19,050 per week
7 BR 5.5 BA - Sleeps 14 - 16
Heated Pool
Lush Tropical Gardens
Famous Historic Seaport neighborhood
Stroll to Duval St.
Classic Key West Estate is a grand centurion home in the Historic Seaport neighborhood. It offers a spacious two-story Victorian home and a private pool side cottage. It's ideally located two blocks from the famousHistoric Seaport.
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305-294-7358
Garden Suite ~ Weekly Rental
Guaranteed Lowest Rates - Book Direct
Standard Rates: $2,800 - $5,170 per week
3BR 2BA - Sleeps 6
Situated in Gated Tropical Garden
Expansive covered porch
Very Large Pool.
Boho Style Decor
Great value.
The allure of the bohemian styleGarden Suitevacation rental comes from its one-of-a-kind architectural design, the original wood it is built with, the fun decor, and its authentic Key West pool garden setting.Garden Suite offers over 1200 square feet of living space and features a large living room with cathedral ceilings.
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305-294-7358
Key West Wabi Sabi ~ Weekly Rental
Guaranteed Lowest Rates - Book Direct
special rates available
4BR 3.5BA June 27 - July 11 Nightly $875
July 16 - July 23
July 28 - Aug 9
Five nights $3950
Weekly $4400
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Standard Rates: $4,650 - $9,950 per week
4BR 3.5BA - Sleeps 8
Custom Interior Design
Heated Pool - Sun Deck
Steps from Duval St.
Undeniably adorable, Key West Wabi Sabi vacation rental is a celebration of authentic cottage style island living. More spacious than you may think. 2nd floor bedroom and private bath. Each bedroom has a bathroom.Built in 1930, the front of the historic wooden plank house is held to vintage form with loads of original details, complete with welcoming front porch and saw-tooth tin roof.
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305-294-7358
The Caroline House Estate ~ Weekly Rental
Guaranteed Lowest Rates - Book Direct
special rates available
5BR 3BA June 27 - July 6 Nightly $1250
Aug 1 - Aug 6
Weekly $6500
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Standard Rates: $6,645 - $13,310 per week
5BR 3BA Classic Victorian Estate
Sleeps 10
3 BR Main House plus
2.5 BR Caribbean Bungalow
Heated Pool
In-ground Jacuzzi
Large Private Garden
An exceptional degree of refinement was reserved for the sophisticated renovation and décor of this circa 1930’s Key West Victorian house plus Caribbean bungalow cottage. Displaying a perfected tropical style the architect and designer artfully intertwined a romantic look-back into architectural history with a superior eclectic cosmopolitan island charm.
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305-294-7358
Heavenly Hideout at Rainbow's End ~ Weekly Rental
Guaranteed Lowest Rates - Book Direct
special rates available
4BR 4BA July 7 - July 14
July 20 - Aug 10
Nightly $875
Weekly $4500
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Standard Rates: $4,650 - $9,950 per week
4BR 4BA - Sleeps 8
Famous Mile 0 Location
1 block off Duval Street.
Custom Interior Design
Private Heated Pool
Sun deck on ground level
Welcome to the end (and the beginning) of the road. There aren’t many places in the world where you can say you’re both beginning and ending your journey at the same time. But when you rent this Heavenly Hideout Key West penthouse, you’re spot on, and you can do exactly that.
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305-294-7358
Amelia's Hideaway ~ Weekly Rental
Guaranteed Lowest Rates - Book Direct
special rates available
4BR 4BA June 27 - July 10 Nightly $975
July 22 - Aug 1
Weekly $5300
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Standard Rates: $5,250 - $11,075 per week
4BR 4BA - Sleeps 10
Heated Pool
Expansive Roof-Top Deck
Steps from Upper Duval Street
"In-the-know" travelers who return to Key West love to choose the more elegant area of Upper Duval St. as their favorite area to stay ... "Amelia's Hideaway."
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305-294-7358
Caribbean Cottage ~ Duval Street Key West ~ Weekly Rental
Guaranteed Lowest Rates - Book Direct
special rates available
2BR 2BA June 12 - June 15
July 8 - July 18
Nightly $550
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Standard Rates: $2,445 - $5,650 per week
2BR 2BA
Sleeps 2 - 5
Charming Upper Duval Street
Private Heated Pool and Bricked Courtyard
2 min. walk to South Beach.
Great for 2 Couples or Small Family
Just steps from Duval Street, this unique Key West cottage has an authentic Caribbean ambience plus a private pool with bricked courtyard.Historic construction with original wood planked polished floors, vintage hand-hewn beams, bright blue tile kitchen and Bahama style wooden window shutters. One of the oldest houses in Key West, exudes authentic charm with all the comforts of home.
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305-294-7358
Tropical ~ Tranquility ~ Weekly Rental
Guaranteed Lowest Rates - Book Direct
special rates available
4BR 4BA June 30 - July 6 Nightly $1050
July 28 - Aug 1
6 Nights $5800
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Standard Rates: $5,420 - $12,570 per week
4BR 3.5BA - Sleeps 8
Heated Oasis Swimming Pool
Private Manicured Pool Garden
Little lane in the Heart of Old Town Key West
Few places exist where you can ride the fine line separating a secluded tranquil luxury villa, and the Heart of Old Town Key West. It may sound like a poetic abstraction, but for this masterful property with 5-Star amenities, the distinction is definitely real.
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305-294-7358
Coco's Poolside Retreat ~ Weekly Rental
Guaranteed Lowest Rates - Book Direct
Standard Rates: $2,600 - $5,390 per week
3BR 2.5BA - Sleeps 6-8
The artist-owner of this sun-lit pool-side town-home has created a delightful living space that welcomes you to an authentic tropical life-style in a unique Key West "pool garden compound."
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305-294-7358
Pavilion Villa ~ Weekly Rental
Guaranteed Lowest Rates - Book Direct
special rates available
4BR 3BA July 25 - Aug 1 Nightly $925
Weekly $4900
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Standard Rates: $5,250 - $11,075 per week
4BR 3BA - Sleeps 10
Unique 2 Cottage Design
Heated Pool - Sun Deck
Deck + Balconies
1/2 Block Off Duval Street
A Private Tropical Paradise... is the feeling you get when you enter the pavilion of this extraordinary award winning villa just a half block off Duval St. in Old Town Key West. Close to shops, restaurants, museums, Mallory Square.
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305-294-7358
Vintage Luxury Cottage On Duval ~ Weekly Rental
Guaranteed Lowest Rates - Book Direct
special rates available
1BR 1BA June 26 - June 29
July 11 - July 14
July 19 - July 25
Nightly $475
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Standard Rates: $2,390 - $5,550 per week
1BR 1BA - Sleeps 2-4
Duval Street
Heated pool in garden courtyard.
2 min. walk to South Beach. Perfect couples retreat.
Vintage Luxury Cottage on Duval.Romantic hideaway.Completely hidden from the street! Private Heated Pool in charming bricked courtyard garden. Expansive covered porches. Nothing else like this extraordinary cottage in Key West.
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305-294-7358
Duval Street Fantasy Resort Villa ~ Weekly Rental
Guaranteed Lowest Rates - Book Direct
Standard Rates: $5,250 - $10,950 per week
3BR 3BA - Sleeps 8
Just Off Upper Duval Street
Private Adjoining Cottages
with 2 Private Pools
Rare one-of-a-kind property, on Duval Street, yethidden from the street. Two cottages jointed with a bricked courtyard and swimming pool create a secret resort residence.
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305-294-7358
Down Island Digs ~ Weekly Rental
Guaranteed Lowest Rates - Book Direct
special rates available
2BR 2BA June 26 - June 29
July 6- July 18
Nightly $625
Weekly $3325
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Standard Rates: $2,580 - $6,250 per week
2BR 2BA
Sleeps 2 - 6
1/2 block off Duval Street
Traditional Key West Cottage-Style Charm
Hidden Large Back Yard Rare for Downtown Location
Private Manicured Pool-Side Garden.
Everything about "Down Island Digs" adds up to make a private precious pool- garden cottage. Sitting in the large hidden back-yard garden, you would never know you're just 1/2 block off Duval Street.
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305-294-7358
Twice as Nice on Duval Street ~ Weekly Rental
Guaranteed Lowest Rates - Book Direct
special rates available
4BR 4BA June 30 - July 15
July 19- July 22
Aug 2 _ Aug 7
Nightly $925
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Standard Rates: $5,245 - $10,500 per week
4BR 4BA Sleeps 8-10
Heated Pool
2 Sun Decks
2 Kitchens
On Upper Duval St. - 1 min. walk to South Beach
"Two is definitely better than One!" A rare set of early 1900's twin-cigar maker's cottages are both adorable and elegant and a perfect solution for a discerning group who want to lodge together in luxury but require maximum privacy.
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305-294-7358
Key West Dreamin' ~ Weekly Rental
Guaranteed Lowest Rates - Book Direct
special rates available
2BR 2BA July 4 - July 7 Nightly $650
July 12- July 18
July 27 - Aug 9
Weekly $3100
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Standard Rates: $3,035 - $7,170 per week
2BR 2BA - Sleeps 4-6
Heated Pool
Private Bricked Courtyard
Lush Landscaping
This Old Town Key West premier rental home offers all the luxury amenities, including a privateback yard pool garden. Situated in a charming Upper Duval neighborhood, a stroll through the neighborhood is to rendezvous with an important part of our island's rich cigar and rum history.
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305-294-7358