Key West Vacation Rentals With Pool
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info@vhkw.com
Key West Time
June 2nd
7:18pm · 84°F
 
 

Key West ~ Vacation Rentals With Pool

Key West vacation rentals with a pool offer an added element of refreshing luxury. Whether you take a quick-dip before breakfast, slip into a cool pool after a full day of fun and sun, or lounge around the deck all day, Key West rentals with a private pool can provide the ultimate amenity for relaxation.

As you browse our selection of pool-side properties, enjoy the wonderful variety of garden settings. You only need to decide if you prefer a home or Key West cottage with a private pool, or a property with shared pool and tropical resort-style grounds. Most pools can be heated, a welcome indulgence during cooler months.

* 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


vintage luxury cottage on duval
special rates available

June 14- June 20
July 18- July 25

Nightly $400
Weekly $2200

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Standard Rates: $1800 - $3950 per week

1BR 1BA - Sleeps 2-4
Duval Street
Hidden pool and courtyard.
2 min. walk to South Beach. Perfect couples retreat.

Vintage Luxury Cottage - An elegant Cottage with Private Heated Pool in hidden courtyard. "Best Kept  Key West Secret."


sweet sunshine garden flat
New
special rates available

June 20- June 27
July 4 - July 25

Weekly $1400

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Standard Rates: $1350 - $2650 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. 


key west wabi sabi
special rates available

June 7 - June 27
July 11 - July 17

Weekly $3900
Nightly $775

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Standard Rates: $3700 - $7125 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. 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.


seaport treasure estate

Standard Rates: $16000 - $26750 per month

6BR 6.5BA - Sleeps 12
Luxurious Estate ~ 2 Houses plus Guest Cottage = Private Residential Resort
Gated and Grand
Premier Historic Seaport location! Steps from the boardwalk.

A whole vacation experience for the entire family. Rent this estate and live in luxury in the most requested Historic Seaport location in Key West. Three historic dwellings are seamlessly joined to become one private luxury Key West rental estate. A combination of unique design elements impart that elusive je ne sais quoi of island architectural history. Rent the best of Key West!


island rendezvous

Standard Rates: $5700 - $12225 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.


the meeting point   key west

Standard Rates: $10725 - $21345 per week

11BR 11BA - Sleeps up to 22
2 heated swimming pools (1 with Spa Jets)
Steps from the 500 block of Duval Street
3-story historic Victorian home plus new 4 BR villa

"Let's stay together ... for a week or more." Start calling your family and make a plan. If you’re looking for luxury and plenty of room, The Meeting Point Key West is the grandest vacation rental licensed to rent weekly in Key West, both in stature and style. 7 BR 7 Full BA elegant Victorian Mansion plus 4 BR 4 Full BA luxury villa. 


key west mile zero suite

Standard Rates: $400 - $4000 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!


flower power house
special rates available

June 6 - June 17
June 24 -July 3
July 12- July 18

Weekly $5300
Nightly $1000

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Standard Rates: $4175 - $8525 per week

5-6BR (Sleeping Porch) - Sleeps 12+
Attached 1BR Cottage
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.


family reunion

Standard Rates: $8025 - $16415 per week

12BR 8 Full BA and 2 Half BA
Sleeps 28
Large swimming pool in tropical garden
Boho-beautiful main house
Two side-by-side townhouses
Walk to Higgs Beach.
Close to White Street shopping
Great value.

"Family's who play together, stay together." This is a spacious Key West rental for your family reunion vacation. Property includes: a main house and attached cottage suite decorated with a bohemian shabby chic flair, and two townhouses situated in a spacious tropical garden, and large swimming pool.


island oasis garden home

Standard Rates: $1725 - $3600 per week

2BR 2BA - Sleeps 2-4
1 Block from Duval Street
Oasis pool and hidden courtyard garden.
Private off-street parking

Just as you're inspired by an island oasis, so is this tropical island garden town home, cleverly hidden in the heart of Old Town Key West.

 

the grand marshall house ~ key west
New
special rates available

Month of Aug
available for a reduced price
Monthly $10000

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Standard Rates: $9000 - $25000 per month

4BR 3BA - Sleeps 8 - 10
Grand Luxury Estate Home
Historic Seaport Neighborhood
Heated Pool w/In-ground Jacuzzi
Propane Fireplace
Wrap-around Verandas

Entertain in grand style in the open living & formal dining room and outdoor pool-side chill-out room. Estate home built from original heart-pine wood, the interior is re-fit to be grand with polished Brazilian tigerwood floors and stunning mahogany open-beams on 12-foot ceilings. Built-in propane indoor/outdoor fireplace. Wrap around covered porches on the 1st and 2nd floor, and multi-level decks and covered porch create outdoor living spaces. 


island cosmopolitan cottage
New

Standard Rates: $5000 - $11000 per month

3 BR 2 BA
Sleeps 4 - 6
Historic Cottage
Upscale Renovation and Interior Design
Large Lap-Swimming Pool
Quiet Neighborhood close to White St.
Easy walk to Higgs Beach

An upscale renovation with elegant furnishings, this heritage cottage has all the luxuries you could want and still enjoy the ambiance of staying in an historic Key West property. Mixing a dash of contemporary style with selected cottage pieces, the designer created a unique island style cosmopolitan hide-away in the White Street Gallery district of Old Town Key West. 


oceana courtyard cottage also known as oceana suite
New

Standard Rates: $1400 - $2800 per week

1 BR 1 BA
Sleeps 2 - 4
(maximum of 2 adults and 2 children)
Secluded Free-Standing Cottage
Private Sun / Dining deck
Exclusive gated pool garden w/ 7 other cottages
10 Minute Walk to Duval Street

Whether you are looking for a secluded getaway with a central base to explore, or the perfect location for a romantic get-away, this  hidden couryard paradise will be home away from home. So, close your eyes for a few moments, and imagine tropical Key West, and this charming cottage just waiting for you.


heavenly hideout at rainbows end
special rates available

July 25- Aug 1

Weekly $3900
Nightly $775

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Standard Rates: $3700 - $7125 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.

 


ultimate key west beach house  sunset key ~ vip

Standard Rates: $16000 - $26750 per month

5BR + Den 6BA - Sleeps 10-12
Private Tropical Resort Island
Front Line Ocean Views
White Sandy Beaches
Custom Fantasy Swimming Pool w/ Waterfalls

Sit back, relax, and choose your favorite mesmerizing view from one of the magnificent private decks on this private island property, 500 yards from the ''main island' of Key West.  Unhurried sunrise, serene sunset, warm turquoise waters, and white sandy beaches – from any direction, it’s divine.


bella grand premier

Standard Rates: $10000 - $22000 per month

5BR + Den 4BA - Sleeps 12
Extraordinary swimming pool gardens
Famous Elizabeth St. in Historic Seaport Neighborhood
Stroll to Duval Street

Refined and Elegant. Displaying a perfected cosmopolitan flair, the designer has artfully intertwined a look-back into architectural history with a sophisticated contemporary Caribbean charm. Situated on renowned Elizabeth Street, in the historic seaport neighborhood of Old Town, this home is steeped in a colorful lore and seafaring history – so much so, it is sometimes referred to as “the pirate house.”


tropical chill
New

Standard Rates: $1675 - $3100 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. 


by the beautiful sea ~ a key west beach front condo
special rates available

June 28- July 1
July 8 - July 11
July 17 - July 25

Weekly $2200
Nightly $500

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Standard Rates: $1900 - $4125 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.


key west island village cottage
New

Standard Rates: $3800 - $8700 per month

2BR 1.5 BA - Sleeps 2-6
Award Winning Historic Cottage
Private Dipping Pool in Tropical Garden
Great For Small Family
Historic Seaport Neighborhood
5 Minute Walk to Seaport Docks

Story-book charm, originally built in 1860, a restoration won it the coveted Star Award by the Historic Florida Keys Foundation, in 1995. Situated on famous Southard St., in the Historic Seaport neighborhood, its unique character has so captured lovers of Key West homes and gardens, that it’s been featured in two books - Mary Emmerling’s American Country Cottages, 1993, and again in Key West Gardens and Their Stories, Frawley-Holler, 2000.


top of the house ~ near the seaport
New

Standard Rates: $3500 - $7700 per month

3BR 1 BA Sleeps 4
Historic Seaport Location
Expansive Porch overlooks Pool
Exclusive Use of Pool

A delightfully renovated three-bedroom one-bathroom hideaway, with swimming pool, that encompasses the entire 2nd floor of a historic Key West wooden house. From this location you’re only four streets from the famous wharf where the old schooners, charter boats, and luxury yachts dock. A testimony to its vintage, this charming 19th century seaport building displays an intriguing sawtooth roof - a succession of three gable roofs with valleys in between - which accentuates the historic relevance of the house.


classic key west estate

Standard Rates: $6575 - $12800 per week

7BR 5BA + 1 half BA - Sleeps 12-14
Heated Pool
Lush Tropical Gardens
Famous Historic Seaport neighborhood
Stroll to Duval St.

Classic Key West Estate is one of the few grand centurion wooden estate homes plus pool-side cottage, with private deck and swimming pool, licensed to rent weekly in the Historic Seaport neighborhood. It is located on famous Fleming St. with beautiful curb side appeal.


little red pool garden cottage

Standard Rates: $3600 - $6230 per month

2 BR 1 BA
Sleeps 2 - 4
Private Pool
Idyllic Pool-Garden Island Cottage
Close to the Beach
Quiet Neighborhood on lane less traveled

‘Heads Up’ to all of you incurable romantics who are looking for the perfect Old Town Key West garden cottage retreat close to the beach. Dream worthy and authentic, it’s a little bit like ‘Little Red Riding Hood’s cottage merges with a ‘Fantasy Island’s’ private pool garden,’ and the two are seamlessly blended.


island interlude
New

Standard Rates: $3700 - $7350 per month

2BR 2.5BR - Sleeps 6
Upscale Town home in gated bricked pool-garden courtyard
Shared Dipping pool with waterfall
Around the corner from trendy Petronia Street where you find Blue Heaven
Short Street from entrance to Fort Zachary Taylor Beach

Aspirational, luxurious, well appointed, and whimsical, are four attributes that make this courtyard townhome a lovely place to call home in Key West. Aptly named, Island Interlude, this 2-story property is situated around the corner from one of the most popular transitional urban scenes of Key West. 


designer octagon house of key west
New

Standard Rates: $20000 - $30000 per month

4BR 4.5BA - Sleeps 8
Famous Iconic Victorian Estate
Extraordinary Designer Home
Expansive Resort-Style Gardens
Large Swimming Pool
Wrap-around Verandahs

Standing prominently in the sought-after Key West Historic Seaport Neighborhood, this iconic designer octagon Victorian house is often feaured in notable architectural publilcations. Purchased and restored by superstar designer Angelo Donghia in 1976, and purchased in 1981 by famous designer Calvin Klein, it raised the bar on historic home renovation in Key West. Today is stands as a phenomenal paradise home with luxury designer decor and 5-Star amenities. Truly an amazing historic and top-of-the-line place to stay in Key West.


grande dame key west   the watson house
special rates available

June 12- June 18
July 10 - July 25

Weekly $8200
Nightly $1650

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Standard Rates: $7050 - $13700 per week

7BR 7BA - Sleeps 14
Amazing Historic Luxury Mansion
Heated Pool - Private Sun Deck
Steps from Duval St.

This award winning renovation of a 3 - story Key West mansion is by far one the rarest private estate Key West rentals offered as a single-family vacation home available by the week. Steps from Duval Street.


ocean view luxury villa

Standard Rates: $5400 - $8400 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
Pet Friendly

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..


the caroline house

Standard Rates: $4750 - $9700 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.


amelias hideaway
special rates available

June 6 - June 14
June 19 - June 23
July 13 - July 26

Weekly $4400
Nightly $800

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Standard Rates: $3850 - $7800 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."

 


truman treasure

Standard Rates: $2900 - $6300 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.


island brownstone
special rates available

June 6 - June 28
July 27- Aug 8
Weekly $1800

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Standard Rates: $1750 - $3950 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.’


caribbean cottage ~ duval street key west
special rates available

June 6 - June 27
July 4 - July 11
July 18 - July 25

Weekly $2250
Nightly $450

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Standard Rates: $1900 - $4025 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. 

 


avant garde key west luxury home

Standard Rates: $4500 - $9850 per month

2BR 2.5BA
Sleeps 4
Classic Exterior Architecture
Upscale Minimalist Interior
Premier Heart of Old Town neighborhood
Private Heated Pool

Extraordinary upscale renovation. Traditional Key West architecture is flawlessly melded with a minimalist contemporary interior. Exotic and calming, this unique home offers all the best features of classic and modern island living.


dancing palms villa
special rates available

June 6 - June 22
June 29 - Aug 1

Weekly $2100

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Standard Rates: $1800 - $3725 per week

2BR 2BA - Sleeps 4
Manicured Tropical Swimming Pool Garden
Shared Heated Pool
Walk to Duval St. in 3 minutes

Palm fronds gently dancing in the breeze, orchids hanging in the trees, manicured gardens, a pristine swimming pool set with comfortable lounge chairs. This is what you’ll experience as you make your entrance to this beautiful Bahamian ‘eyebrow’ style home, nestled away in private back corner of the small Old Town Key West gated community of Windward Park.


villa deja vu key west
special rates available

June 12 - June 27
July 5 - July 9
July 12- July 30

Weekly $4400
Nightly $800

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Standard Rates: $3850 - $7800 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.


belle maison du port

Standard Rates: $13000 - $25000 per month

3BR 3.5BA
Victorian Home + Private Guest Cottage
Situated in Private Gated Estate
Available from May through October
Large Private Heated Pool
Premier location - Hidden But Only Steps from Historic Seaport Boardwalk!

Extraordinary French Caribbean style Victorian home, Belle Maison du Port (Fine Harbor House), is available as a monthly vacation rental from May through November. Situated on the grounds of the Seaport Treasure Estate. It is comprised of a stunningly renovated 2–Story Victorian home, plus an adjoining one-bedroom guest cottage. Large private resort-style swimming pool with spacious sunning deck..


key west spa villa
special rates available

June 6 - July 3
July 9 - July 25

Weekly $4300
Nightly $750
10 Nights plus Inquire

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Standard Rates: $3850 - $7800 per week

4BR 4BA - Sleeps 8
Dipping Pool w/ Waterfall
Large Hot Tub
Sun Deck
Just off Upper Duval Street

This proud 1890's 'cigar maker's cottage, just off Duval Street, has been lovingly transformed into a stylish 4 bedroom, 4 bathroom spa villa. Captivated by the uninhibited yet wonderfully elegant Key West island life-style, the designer created a fabulous balance of opposites.


down island digs
special rates available

June 6 - July 4
July 18 - July 22

Weekly $2300
Nightly $450
10 Nights plus Inquire

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Standard Rates: $2000 - $4400 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.

 


exclusive key west beach front
special rates available

June 6- June 15
June 22- June 28
July 5- July 18

Weekly $2200
Nightly $500

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Standard Rates: $1900 - $4125 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 ...

 


tropical tranquility

Standard Rates: $3975 - $8875 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.

 


private pool garden villa
special rates available

June 6- June 20
July 12- July 22

Weekly $3500
Nightly $675

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Standard Rates: $3400 - $5300 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.


pavilion villa
special rates available

June 7 - June 19
June 23- June 27

Weekly $4400
Nightly $800

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Standard Rates: $3850 - $7800 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.


tree tops

Standard Rates: $1790 - $3075 per week

2BR 1BA - Sleeps 4-6
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.


havana moon over duval
special rates available

June 19 - June 27
July 4- July 10
July 15- July 20

Weekly $2200
Nightly $450

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Standard Rates: $1950 - $4100 per week

2BR 2BA - Sleeps 4-6
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.

 


garden suite

Standard Rates: $2090 - $3650 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.


a tropical tradition
special rates available

June 6- June 17
June 24 - July 5
July 12- July 25

Weekly $2200
Nightly $475

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Standard Rates: $1950 - $3945 per week

3BR 2.5BA - Sleeps 6

A lush private tropical garden complete with large 40' X 16' swimming pool is the main focus of this unique island setting, and this traditional Key West town-home home is situated at the "pool-side" of the garden.


duval street fantasy resort villa

Standard Rates: $3850 - $7800 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. 


twice as nice on duval street
special rates available

July 15- July 20

Nightly $800

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Standard Rates: $3850 - $7500 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.

 


foundry on the waterfront
special rates available

June 6- June 27
July 1 -July 10

Weekly $1800

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Standard Rates: $1750 - $3950 per week

2BR 2.5BA - Sleeps 4
Contemporary Interior Design Built in Historic Brick Architecture
Shared Pool in Gated Garden
Short Walk to Fort Zachary Beach
Close to Key West Water Park
Stroll to Downtown Old Town

A striking tri-level condominium situated in Key West's most historic gated Truman Annex waterfront luxury neighborhood, offers a beautiful combination of classic historic charm and refined modern ambience. Perfect location to enjoy the Truman Waterfron Park Ampitheater.

 


cocos poolside retreat
special rates available

June 6- June 17
July 11- July 17
July 21 - Aug 1

Weekly $2200
Nightly $475

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Standard Rates: $1950 - $3945 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."


the qm ~ quartermaster house key west

Standard Rates: $5500 - $10800 per month

3BR 2BA - Sleeps 6-7
Private Back Deck and garden
Shared Pool
Special Resort Amenities Gratis

Born in 1925, the Key West Quartermaster House may have found its way from the Bahamas, ‘lock stock and barrel’, during one of the most colorful points in Key West maritime history. Located in the Historic Seaport Neighborhood, today it offers all the comforts of home plus gratis resort amenities.


on hemingways rounds

Standard Rates: $4600 - $9600 per month

3BR 2BA - Sleeps 6
Private Spa Garden with Pool & Waterfall
1/2 block off Duval St.

On Hemingway's Rounds, is an inspired renovation of a classic 1930's ‘American Bungalow’ redone Key West style.  While the street side remains true to the original casual arts-and-crafts form, the interior now boasts an elegant simplicity that meets even the most discerning of modern tastes.

 


villa nouveau key west
special rates available

June 20 - June 24
July 1 - Aug 1

Weekly $4500
Nightly $850

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Standard Rates: $3850 - $7800 per week

4BR 4BA - Sleeps 8
Heated Pool
Private Sun Deck
Steps from Duval St.

A modern interior re-design has thoughtfully transformed a prosaic 'shot-gun' cottage it into the sophisticated 'L-Shape' 4 bedroom 4 bathroom pool-side courtyard Villa Nouveau. Fabulous downtown Key West location just off-Duval St. Rent separate or with Grande Dame Key West - 'The Watson House' estate.

 


key west dreamin
special rates available

June 6 - June 14
June 21 - June 26
July 3 - July 9
July 13 - July 18
July 22 - July 26

Weekly $2600
Nightly $525

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Standard Rates: $2350 - $5025 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.


amandas dream suites

Standard Rates: $3875 - $6700 per week

4-5BR (Den) 3BA - Sleeps 8-12
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.


governors retreat

Standard Rates: $5000 - $6900 per month

2BR 2BA - Sleeps 4
Serene setting - Large Lap Pool
Manicured Gardens
Old Town Key West Neighborhood -
The Meadows
Easy Stroll to Historic Seaport

A Key West luxury cottage in an idyllic retreat setting situated in a manicured garden and swimming pool. Perfectly Renovated and immaculate Key West neighborhood, known as The Meadows. Easy walk to Key West Historic Seaport. 

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