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Key West Time
October 3rd
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Key West ~ Weekly Vacation Rentals

Your Search Results:
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


tropical chill
special rates available

2BR 2BA

Sept 29- Oct 10
Oct 31 - Nov 16

Weekly $2100

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Standard Rates: $2165 - $4140 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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key west mile zero suite
special rates available

2BR 2BA

Sept 21 - Oct 10

Nightly $500
Weekly $2575

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Standard Rates: $2230 - $6030 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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flower power house
special rates available

6BR 4BA

Oct 1- Oct 5
Oct 8 - Oct 12
Oct 16- Oct 21
Oct 28 - Nov 5
Weekly $4900
Nightly $900


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Standard Rates: $4750 - $11670 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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cockadoodle cottage on duval
special rates available

2BR 2BA

Sept 26 - Oct 20
Nightly $450
Weekly $1900

Oct 27 - Oct 31
Nightly $675

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Standard Rates: $1895 - $4640 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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island rendezvous

Standard Rates: $7830 - $16680 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-side steps 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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by the beautiful sea ~ a key west beach front condo
special rates available

3BR 2BA

Sept 24 - Oct 10

Nightly $550
Weekly $2400

Oct 25 - Oct 30
Fantasy Fest
Nightly $635

Oct 30 - Nov 6
Nightly $550
Weekly $2400

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Standard Rates: $2580 - $5625 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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ocean view luxury villa

Standard Rates: $6970 - $10740 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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exclusive key west beach front
special rates available

2BR 3BA

Sept 21 - Oct 7
Oct 30 - Nov 6
Weekly $2500

Oct 21- Oct 29
Fantasy Fest
Weekly $3500

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Standard Rates: $2530 - $5625 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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old town caribbean estate
New
special rates available

10BR 7.5 BA

Oct 6 - Oct 14
Nov 11 - Nov 18
Nightly $1900
Weekly $8900

Oct 28 - Nov 4
Fantasy Fest
Nightly $2200
Weekly $11000

Dec 23- Dec 27
Four nights $12900

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Standard Rates: $10080 - $23420 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 Estate is a masterful 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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sweet sunshine garden flat
special rates available

2BR 1BA

Sept 21 - Oct 9
Weekly $1700

Oct 25 - Nov 1
Fantasy Fest
Weekly $2600

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Standard Rates: $1485 - $3575 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 Flat is 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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havana moon over duval
special rates available

2BR 2BA

Oct 2- Oct 6
Weekly $2200
Nightly $550

Oct 27 - Nov 1
Nightly $750

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Standard Rates: $2190 - $5600 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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truman treasure

Standard Rates: $3745 - $8130 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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island brownstone
special rates available

2BR 2BA

Oct 16 - Oct 23

Weekly $2350

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Standard Rates: $2500 - $5520 per week

2BR 2.5BA - Sleeps 4-6
Stroll to downtown Old Town Key West
Short walk to Fort Zachary Taylor Park and beach

An exclusive island style brownstone town home offers a dramatic and spacious layout with features and details that include extra high ceilings, artistic crown molding, lots of windows and French doors. It is perfectly nestled in Key West’s most prominent gated waterfront neighborhood known as ‘Truman Annex.’

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villa deja vu key west
special rates available

4BR 3BA

Sept 28- Oct 14
Oct 17 - Oct 22
Oct 30 - Nov 6
Nightly $950
Weekly $4900

Oct 22- Oct 30
Fantasy Fest
Nightly $1250
Weekly $6400

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Standard Rates: $5250 - $10650 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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private pool garden villa
special rates available

3BR 2.5BA

Oct 8 - Oct 13
Oct 20 - Oct 23
Oct 30 - Nov 8
Nightly $725
Weekly $3900

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Standard Rates: $4245 - $6950 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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tree tops
special rates available

2BR 2BA

Oct 1- Oct 5
Oct 8 - Oct 12
Oct 16-Oct 21

Nightly $450
Weekly $1900

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Standard Rates: $2060 - $4170 per week

2BR 1BA - Sleeps 6
Overlooks large tropical garden with very large shared pool.
Boho style. Great value.

The Tree Tops Suite vacation 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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classic key west estate
special rates available

7BR 5.5BA

Oct 6 - Oct 14
Nov 11 - Nov 18
Nightly $1700
Weekly $7900

Oct 28 - Nov 4
Fantasy Fest
Nightly $1800
Weekly $9000

Dec 23- Dec 27
Four nights $12000

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Standard Rates: $7310 - $20100 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 famous Historic Seaport. 

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garden suite
special rates available

3BR 2BA

Oct 1- Oct 5
Oct 8 - Oct 12
Oct 16-Oct 21

Weekly $2550
Nightly $500

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Standard Rates: $2375 - $5170 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 style Garden Suite vacation 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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key west wabi sabi
special rates available

4BR 3.5BA

Sept 26 - Oct 11
Oct 15 - Oct 20
Nightly $775
Weekly $4500

Nov 19 - Nov 27
Nightly $985
Weekly $5500

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Standard Rates: $4195 - $9700 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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the caroline house
special rates available

5BR 3BA

Oct 1- Oct 7
Oct 14 - Oct 23

Nightly $1175
Weekly $5950

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Standard Rates: $5345 - $13310 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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heavenly hideout at rainbows end
special rates available

4BR 4BA

Sept 28 - Oct 10
Weekly $4500
Nightly $775

Nov 6 - Nov 17
Nov 20 - Nov 27
Nightly $985
Weekly $5500

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Standard Rates: $4195 - $9700 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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amelias hideaway
special rates available

4BR 4BA

Sept 28 - Oct 3
Oct 17 - Oct 22
Nightly $875
Weekly $4900

Oct 27 - Nov 5
Fantasy Fest
Nightly $1025
Weekly $5900

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Standard Rates: $4345 - $10650 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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amandas dream suites

Standard Rates: $4430 - $9115 per week

5BR (Den) 3BA - Sleeps 10-12
Bohemian Design and Decor
Large Shared Pool in Tropical Garden
Expansive Porches
Easy Walk to Higgs Beach

Originally built in 1938, this charming large wooden home has two full stories with deep porches which overlook the garden and shared swimming pool. The floor plan was redesigned with an exterior staircase so it can also be utilized as two separate units.

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caribbean cottage ~ duval street key west
special rates available

2BR 2BA

Sept 30 - Oct 7
Oct 15 - Oct 22
Oct 29 - Nov 6
Nightly $525
Weekly $2375

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Standard Rates: $2190 - $5500 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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tropical tranquility
special rates available

4BR 4BA

Dec 16 - Dec 21
Five Nights $4500
Nightly $1025

Jan 12- Jan 15
Nightly $1375

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Standard Rates: $4490 - $12170 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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cocos poolside retreat
special rates available

3BR 2.5BA

Sept 30 - Oct 4
Oct 16- Oct 22
Oct 29 - Nov 5

Nightly $525
Weekly $2500

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Standard Rates: $2265 - $5390 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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pavilion villa
special rates available

4BR 3BA

Sept 30 - Oct 5

Nightly $875
Weekly $4900

Dec 23- Dec 26
Nightly $1325

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Standard Rates: $4345 - $10650 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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vintage luxury cottage on duval
special rates available

1BR 1BA

Oct 21-Oct 29
Fantasy Fest
Weekly $3500
Nightly $685

Oct 30 - Nov 4
Nightly $525

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Standard Rates: $1970 - $5400 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 DuvalRomantic 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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duval street fantasy resort villa

Standard Rates: $4350 - $10650 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, yet hidden from the street. Two cottages jointed with a bricked courtyard and swimming pool create a secret resort residence. 

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down island digs
special rates available

2BR 2BA

Sept 30 - Oct 6
Oct 17 - Oct 21

Nightly $525
Weekly $2375

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Standard Rates: $2230 - $6030 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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twice as nice on duval street
special rates available

4BR 4BA

Oct 27 - Nov 1
Nightly $1475

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Standard Rates: $4400 - $10150 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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key west dreamin
special rates available

2BR 2BA

Sept 30 - Oct 4
Nov 20 - Nov 24

Nightly $600
Weekly $2875

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Standard Rates: $2600 - $6900 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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