pinterest facebook instagram twitter youtube google my business
  • (305) 294-7358
info@vhkw.com
Key West Time
September 22nd
3:34am · 85°F
 
 

Vacation Rental Discounts and Special Rates

* PLEASE NOTE: The following special rates are a one time offer for the properties listed below. The rates and terms are subject to change without notice. For more information on terms and pricing please see our Rental Policies And Procedures. For faster response & more details please call 305-294-7358 ext. 1 or e-mail info@vhkw.com.

There are no special deals at this time.


seaport hideaway
special rates available

2BR 1.5BA

Sept 19 - Oct 31

Monthly $4700



Standard Rates: $4500 - $9675 per month

2BR 1.5BA
Sleeps 2 - 4
Limited Edition 2-Story Condo
2 Streets from Historic Seaport
Private Porches and Courtyard Garden
Hidden from View in Heritage Building

Magic happened when this Key West wooden heritage building was redesigned. Now offers limited-edition condominiums. A case in point is this 2BR 1.5BA Seaport Hideaway. Architecturally intriguing. Epic historic atrium stairwell. Masterfully tucked away on Fleming Street. A special residence ideally located 2 short blocks from the docks, at the Key West Historic Seaport neighborhood.

 


elegant key west tree house
special rates available

2BR 1BA

Sept 19 - Oct 31

Monthly $4500


Standard Rates: $4200 - $8025 per month

2BR 1BA
Overlooks large historic Meditation Garden
Quiet living
One Set of Stairs
Close to Higgs Beach

Discretely built back off the street to quietly overlook an historic tropical garden, this Elegant Key West Tree House, encompasses the entire 2nd floor of a beautifully renovated 1930’s building. Perched among mature tropical trees, the 1200 square foot 2nd floor flat is situated on a quiet road in the exclusive Old Town Casa Marina neighborhood. With a wide wooden covered porch spanning the front of the house, every room still has the original casement windows providing a fabulous look-down view of different garden scenes.


serenity now
New
special rates available

2 BR 2.5 BA

Monthly

Dec 1 - Dec 31

Monthly $9500


Standard Rates: $6200 - $17100 per month

2BR 2.5BA - Sleeps 4
Located in Small Gated Enclave w/in Truman Annex Neighborhood
Large Shared Heated Pool and Jacuzzi
Private Gate is Steps to Downtown Old Town
Short stroll to Truman Waterfront Park and Ft. Zacharay Taylor Beach

Close your eyes for a moment and take a deep breath ...  Now imagine yourself on an extraordinary Old Town Key West vacation. This luxury townhome vacation rental stands on a serene street, tucked in a tiny enclave called Key West Porter Court. A bit of a secret, it’s nicely hidden within the stunning neighborhood of Truman Annex where the gated grounds are park-like and immaculate. It’s as if you’re in a dream.


sunset sonnet luxury villa
New
special rates available

2BR 3BA

Nov 1- Nov 30

Monthly $10900


Standard Rates: $9500 - $21300 per month

2BR + Office 3 BA
Sleeps 4
Private Roof Top Viewing Deck
White Sandy Beaches
Garden Oasis Swimming Pool
Private Tropical Resort Island

Sunset Sonnet Luxury Villa provides an exclusive private island experience with all the amenities of resort living. A colonial - modern 2-story private luxury home. Wrap around porches overlooking pool gardens. Manicured beaches, tennis, award winning restaurant close by, 5-Star amenities. Experience the peace of  living on a tiny island with no cars. To stay on Sunset Key is to be in secluded surroundings, just a 15-minute ferry ride from downtown Key West.

 


rooftop renaissance
New
special rates available

1 BR 2 BA

Nov 5 - Dec 31

Monthly $5400


Standard Rates: $4900 - $9150 per month

1BR 2BA
Sleeps 2 - 4
Stunning 2-Story Luxury Condo
Hidden in a Heritage Victorian
Private open-air deck
Shared Zen-pool and spa
2 Streets from Historic Seaport

Rooftop Renaissance falls into a unique architectural category of Heritage Victorian - Meets Modern Luxury. This one-of-a-kind monthly rental is situated on the 2nd and 3rd level of a historic Victorian house on Caroline Street. An exquisite 1BR 2BA luxury accommodation, it was redesigned to offer all the accoutrements of a 5-Star condominium.

 


admirals gold private key west luxury villa
New
special rates available

4 BR 3.5 Baths

Sept 22 - Oct 6
Oct 13 - Oct 20
Oct 27- Nov 4
Weekly $5300

Jan 4 - Jan 11
Weekly $6900




Standard Rates: $5420 - $12570 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.


little digs key west
special rates available

1BR 1BA

Sept 19- Oct 31

Monthly $3700


Standard Rates: $3600 - $6000 per month

1 BR 1 BA
Sleeps 2 - 3
Luxury Interior Upgrades
Solares Hill Neighborhood
Center of Old Town
5 Minute Walk to Duval Street

Diminutive in size but huge in style, Little Digs Key West, authenticates how ‘big things’ really do happen in small spaces. Spacious design. A complete luxury makeover of this 1933 historic cottage. It sits in proud harmony with other historic residential cottages, on a narrow one-way lane in the middle of Old Town Key West. 


bella grand premier estate
special rates available

5BR 5.5Baths

Dec 1 - Dec 31

Monthly $26000


Standard Rates: $23000 - $38800 per month

5BR 5.5BA - Sleeps 10
Grand Luxury Estate on 7,500 Sq Ft Lot
2-Story Guest House + 2-Story Main House
Deluxe Zen-Garden Pool with Pool Bridges
Steinway Upright Piano
Premier Street in Center of Old Town
Gated and Private
5-Star Quality Experience

Deluxe Old Town Key West estate with a new twist on history. Premier custom design reflects the historic neighborhood, while reinventing the Key West luxury lifestyle. Zen-garden swimming pool, trickling tiled waterfalls and a spa. Wide stone bridges built over the pool sleekly connect the houses together. A remarkable home to experience with family and friends. 


sunset serenade
special rates available

2 BR 2 BA

Oct 1- Oct 31

Monthly $10900


Standard Rates: $9500 - $21300 per month

2BR + Office 2.5 BA
Sleeps 4 - 6
Private Roof Top Viewing Deck
White Sandy Beaches
Garden Oasis Swimming Pool
Private Tropical Resort Island

You’re one click closer to a private island paradise. Sunset Serenade can put you right there.  Here you’re softly serenaded with the sounds of the surrounding sea and rustling fronds of the palm trees, while you chill-out on your own private rooftop deck to enjoy the changing colors of the tropical sky.

 


casa bella petite le bleu
New
special rates available

2BR 2 Bath

Dec 1 - Jan 1

Monthly $8400


Standard Rates: $6000 - $18000 per month

2BR 2BA - Sleeps 4
Award Winning Historic Cottage
Gorgeous Interior Re-design
Swimming Pool

First impressions are everything. And its love at first glance with this Old Town Key West cottage. The 2BR 2BA Casa Bella Petite le Bleu is a luxurious charming pool-garden home. Situated on the quiet upper end of famous Elizabeth Street, this stylish house is filled with authentic charm. 

The impressive renovation of this 18th Century wooden cottage earned it the coveted Historic Florida Keys Foundation Preservation Award. It provides off-street bricked parking with a Tesla charging station.

An ideal cottage for 2 to 4 people, if more people decide to join you in Key West - No Problem! Right across the street is the extraordinary 5BR 5.5 BA  Bella Grand Premier Estate.

 


hidden story book cottage
special rates available

1BR 1BA

Sept 19 - Oct 31

Monthly $3,800


Standard Rates: $3700 - $6175 per month

1 BR 1 BA
Sleeps 2 - 3
Free-Standing Story-Book Cottage
Gorgeous Interior Upgrades
On a Hidden Walking Path
5 Minute Walk to Duval Street

Tucked away down a short walking path in the Center of Old Town Key West, this precious 1BR 1BA Hidden Story-Book Cottage is completely hidden from the street. Comfortable as it is adorable, it even offers a fenced in yard. Perfect for one or two people, here you can set up home and live as a local for a month or more - or settle in to work remotely.

 


villa corazon
New
special rates available

3BR 3.5BA

Sept 19 - Oct 31

Monthly $ 6850


Standard Rates: $7900 - $17500 per month

3BR 3BA
Private garden with heart-shaped pool
Luxury renovation with upscale furnishings
Private Guest Cottage in Garden
Casa Marina Neighborhood
Close to Higgs Beach

There’s lots to love about the luxurious 3BR 4BA Villa Corazonit even has a heart shaped pool. Experience ultimate resort style living in this private home retreat. A perfect pairing of a renovated Key West gingerbread cottage with an elegant free-standing cottage that are seamlessly joined with a tropical pool-garden.The interior is a harmonious sweet spot between modern aesthetics and laid-back Caribbean. 


tropical chill
special rates available

2BR 2BA

Sept 18 - Oct 11
Oct 13- Oct 20
Weekly $1900


Standard Rates: $2230 - $4260 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. 


key west mile zero suite
special rates available

2BR 2BA

Sept 18 - Oct 4

Weekly $2400
Nightly $525


Standard Rates: $2580 - $6200 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!


cockadoodle cottage on duval
special rates available

2BR 2BA

Sept 18- Oct 3
Oct 8 - Oct 18

Nightly $450
Weekly $1900

Oct 25- Oct 28
Nightly $750





Standard Rates: $2095 - $4760 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.'

 


flower power house
special rates available

6BR 4BA

Sept 18 - Oct 10
Oct 14 - Oct 20

Nightly $800
Weekly $4900


Standard Rates: $5900 - $12250 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.


butterfly garden
special rates available

1BR !BA

Sept 19 - Oct 31
Monthly $3800

Dec 1 - Jan 15
Rental $7500


Standard Rates: $3975 - $6300 per month

1BR 1BA - Sleeps 1-2
Historic meditation garden.
Quiet Living Exclusive Casa Marina neighborhood.
Close to Higgs Beach

Completely hidden from the street, this historic Butterfly Garden flat provides you with two private entrances off the large gated meditation garden. A private covered sitting porch outside your front door beckons you to sit in the freshness of the garden and watch for the butterflies.


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

3BR 2BA

Sept 21 - Sept 29

Nightly $525
Weekly $2300

Fantasy Fest Week
Weekly $3300


Standard Rates: $2580 - $5775 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.


exclusive key west beach front
special rates available

2BR 3BA

Sept 17 - Oct 5
Weekly $2500

Fantasy Fest Week
Weekly $3100
Nightly $650


Standard Rates: $2530 - $5775 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 ...

 


sweet sunshine garden flat
special rates available

2BR 1BA

Sept 18- Oct 16
Weekly $1700

Fantasy Fest
Oct 23 - Oct 30
Weekly $2500


Standard Rates: $1800 - $3675 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. 


old town caribbean estate
New
special rates available

10BR 7.5 BA

Oct 7- Oct 11
Oct 15- Oct 19
Oct 26- Oct 29
Nov 10 - Nov 13

Nightly $1600


Standard Rates: $11800 - $25220 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.


island interlude
special rates available

2BR 2.5BA


Oct 1 -Oct 31

Monthly $4900


Standard Rates: $4800 - $9825 per month

2BR 2.5BA - Sleeps 4
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. 


havana moon over duval
special rates available

2BR 2BA

Oct 8 - Oct 13
Nightly $525
Weekly $2400

Oct 25- Oct 28
Nightly $650


Standard Rates: $2475 - $5820 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.

 


key west sunset sojourn
New
special rates available

3BR 4BA

Sept 19- Oct 31

Monthly $18500


Standard Rates: $17400 - $33800 per month

4BR 4BA
Sleeps 8
Private Swimming Pool w/ fenced gardens
Private porches off each BR
Private Roof-Top Lookout Deck
White Sandy Beaches
Private Tropical Resort Island

Imagine the ultimate Key West dream home that feels like a faraway oasis - where you can watch crowning tropical sunsets from a private rooftop deck. Someplace truly extraordinary, elegant yet also comfortable – a sojourn on a private island surrounded by sparkling turquoise waters and balmy breezes. 


villa deja vu key west
special rates available

4BR 3BA

Sept 22- Oct 9
Oct 14 - Oct 19
Nightly $925
Weekly $4900


Standard Rates: $5250 - $11075 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.


private pool garden villa
special rates available

3BR 2.5BA

Sept 18- Oct 3
Oct 12 - Oct 24
Nightly $675
Weekly $3700


Standard Rates: $720 - $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.


tree tops
special rates available

2 BR 1 BA

Sept 18 - Oct 10
Oct 14 - Oct 20

Nightly $450
Weekly $2100

Fantasy Fest Week
Weekly $2900


Standard Rates: $2200 - $4380 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.


classic key west estate
special rates available

7BR 5.5BA

Oct 7- Oct 11
Oct 15- Oct 19
Oct 26- Oct 29
Nov 10 - Nov 13

Nightly $1500


Standard Rates: $1080 - $19050 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. 


garden suite
special rates available

3 BR 2 BA

Sept 18 - Oct 10
Oct 14 -Oct 22

Nightly $475
Weekly $2500


Standard Rates: $2800 - $5430 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.


key west wabi sabi
special rates available

4BR 3.5BA

Sept 28 - Oct 3
Oct 26 - Oct 30

Nightly $725
Five nights $3400
Weekly $4200


Standard Rates: $4650 - $9950 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.


island cosmopolitan cottage
special rates available

3 BR 2 BA

Sept 19 - Oct 31

Monthly $6500


Standard Rates: $6900 - $15200 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. 


the caroline house
special rates available

5BR 3BA

Oct 6 - Oct 16

Nightly $1000
Weekly $5900


Standard Rates: $6645 - $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.


heavenly hideout at rainbows end
special rates available

4BR 4BA

Sept 18- Oct 4
Oct 26 - Nov 4
Nightly $775
Weekly $4400


Standard Rates: $4650 - $9950 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.

 


amelias hideaway
special rates available

4BR 4BA

Sept 18 - Oct 9
Oct 13 - Oct 20

Nightly $925
Weekly $4650


Standard Rates: $5250 - $11075 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."

 


caribbean cottage ~ duval street key west
special rates available

2BR 2BA

Sept 18 - Sept 29
Oct 19 - Oct 22
Nightly $525
Weekly $2600


Standard Rates: $2445 - $5650 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. 

 


cocos poolside retreat
special rates available

3BR 2.5BA

Sept 18 - Oct 10
Oct 14 - Oct 20
Oct 27 - Nov 4

Nightly $500
Weekly $2450


Standard Rates: $2600 - $5660 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."


key west island village cottage
special rates available

1 1/2 BR 1BA

Monthly

Oct 1 - Oct 31
Monthly $5100


Standard Rates: $4750 - $11300 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.


pavilion villa
special rates available

4BR 3BA

Sept 18 - Oct 11
Oct 27 - Nov 3

Nightly $925
Weekly $4650



Standard Rates: $5250 - $11075 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. 


vintage luxury cottage on duval
special rates available

1BR 1BA

Sept 18- Sept 25
Oct 9 - Oct 12

Nightly $450
Weekly $2100


Standard Rates: $2390 - $5550 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.  


down island digs
special rates available

2BR 2BA

Oct 18 - Oct 20
Nightly $525
Weekly $2400


Standard Rates: $2580 - $6250 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.

 


twice as nice on duval street
special rates available

4BR 4BA

Sept 17- Sept 22
Oct 8 - Oct 13
Nightly $925
Weekly $4650

Oct 25 - Oct 28
Nightly $750


Standard Rates: $5245 - $10500 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.

 


key west dreamin
special rates available

2BR 2BA

Sept 17- Sept 25
Oct 5 - Oct 11
Nov 4 - Nov 7

Nightly $575
Weekly $2625


Standard Rates: $3035 - $7170 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.

Sort Properties


Rental Period



Vacation Rental

Rentals For
Social Distancing

rentals for social distancing

Sunset Key

sunset key

Villas

villas

Cottages

cottages

Condos

town houses and condos

Compounds

compounds

Penthouses

penthouses

Estates

estates

Truman Annex

truman annex