Key West Time
November 21st
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November 21st
4:43am · 75°F
View our exclusive Key West vacation rentals. Vacation Homes of Key West can help you find the perfect vacation rental for your next Key West vacation. Don't pay booking fees, save money by booking directly with VHKW today.
* 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
3 BR 3.5 Baths
Standard Rates: $12,000 - $32,960 per month
3BR 4BA
Sleeps 6 - 8
Luxury Vacation Villa
Private Pool and Spa
Located in the Heart of Old Town
Beautifully furnished, complete with modern amenities and coastal charm. Each bedroom offers ample space and privacy, with en-suite bathrooms ensuring convenience for all guests. Fully-equipped kitchen, perfect for entertaining.
2 BR 2.5 Baths
Mar 1- Mar 31
Monthly $39000
Standard Rates: $20,000 - $45,795 per month
2BR 2.5BA Sunset Key Villa
Sleeps 4-7
Private Pool
Faces West for sunset
Private beach access
Private resort island
Beautiful nautical themed resort villa on Sunset Key private island. Situated on the western shore for perfect unobstructed view for sunset. Garden gate provides direct access to a white sand private swimming beach.
Welcome to this exeptional nautical themed beach house villa on the private island of Sunset Key. Owned by a world champion sailor the curated decor is reminiscent of cruising the open sea in ultimate comfort. This 3BR 3.5BA home faces west for spectacular evening sunset viewing. It boasts a large private heated swimming pool, direct access to a private swimming beach reserved for only the neighboring few homes, covered outdoor dinint porch and true nautical Key West charm.
Standard Rates: $19,140 - $25,000 per month
2BR 2BA - Sleeps 2-4
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.
4 BR 3.5 Baths
Jan 11 - Jan 18
Weekly $6900
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.
2BR 3BA
Standard Rates: $9,900 - $21,930 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.
1 BR 2 BA
Nov 24 - Dec 24
Monthly $4900
Standard Rates: $4,900 - $9,150 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.
2 BR 2.5 BA
Monthly
Dec 1 - Dec 31
Monthly $7900
Standard Rates: $6,200 - $17,610 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.
2BR 1.5BA
Nov 25 -Jan 2
Monthly $4900
Standard Rates: $450 - $9,965 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.
Standard Rates: $8,595 - $17,910 per week
2BR 1BA
Standard Rates: $4,200 - $8,265 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.
5BR 5.5Baths
Standard Rates: $23,000 - $39,000 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.
1BR 1BA
Nov 27 - Dec 31
Monthly $3500
Standard Rates: $3,750 - $6,180 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.
2 BR 2 BA
Standard Rates: $9,900 - $21,930 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.
4BR 4BA
Monthly
$22,000
Standard Rates: $19,500 - $44,800 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.
2BR 2 Bath
Mar 1 - Mar 31
Monthly $16300
Standard Rates: $7,500 - $18,500 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.
2BR 2BA
Monthly
Monthly $
Standard Rates: $4,725 - $9,475 per month
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
You know that adage … An unexpected turn can lead to hidden treasures. If there were ever a place that meets that description, it's this 2BR 2BA Key West Poolside Loft. Cleverly tucked away, here you’re in a unique loft-style Key West cottage, with a private deck and beautiful down-look poolside view.
1BR 1BA
Standard Rates: $3,850 - $6,360 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.
3BR 3.5BA
Standard Rates: $7,500 - $17,975 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 Corazon … it 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.
Standard Rates: $28,400 - $57,500 per month
7BR 7.5BA - Sleeps up to 14
2 heated swimming pools
Premier Street in Center of Old Town
2-Story Guest House + 2-Story Main House and separate 2BR cottage
5-Star rental compound Ideal for extended families or a group of friends.Revel in luxuy while you relax, unwind, and reconnect with plenty of room to spread out. Property includes: two private swimming pool gardens and enjoy three fully equipped upscale kitchens. Grill on a unique secluded BBQ porch, workout in a private home gym, and at your fingertips is a Steinway piano! Three off-street parking spaces.Off-the-beaten path yet just three streets from mid-Duval St.
2BR 2BA
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.
2 BR 1 Bath
Standard Rates: $4,500 - $9,800 per month
2BR 1BA
Sleeps 2 - 4
Upscale Renovation
Colorful Caribbean Ambience
Adorable Curb Appeal
Most Requested Old Town Key West Neighborhood
Close to Historic Seaport
Beautiful and imaginative one-and-a-half-story shot-gun cottage ideally situated in Old Town Key West. Enchanting as can be, feng shui elements were also used in both the renovation and decorating, to achieve a calming and relaxing ambience.
2BR 2BA
Nov 12-Nov 16
Nov 23- Nov 26
Nov 29 - Dec 1
Dec 8- Dec 12
Dec 16 - Dec 22
Weekly $2400
Nightly $525
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!
3 BR 2.5 Baths
Standard Rates: $7,500 - $20,800 per month
3BR 2.5BA - Sleeps 6
Upscale renovation of Historic Home on Picturesque Lane
Private Swimming Pool w/ Sun Deck
1st & 2nd FL Covered Porches
Expansive Porch Room off Master BR
Off-Street Parking
1 Block Off Duval
Governor's Retreat is situated on a less-traveled lane that exudes sought after charm and character. Pictorial 1900’s historic home with upscale renovations and amenities. Exquisite and imaginative décor. Private pool and deck in fenced tropical garden. Multiple sitting porches in the front and back of the house. A block from the Hemingway Home and Museum.
6BR 4BA
Jan 10 - Jan 16
Nightly $800
Weekly $4900
Jan 26 - Jan 30
Nightly $1400
Weekly $6500
Standard Rates: $5,900 - $12,250 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.
2BR 2BA
Nov 22- Dec 1
Jan 4- Jan 10
Nightly $450
Weekly $1900
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.'
1BR 1BA
Standard Rates: $3,975 - $6,500 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.
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-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.
Standard Rates: $13,500 - $35,880 per month
5BR 4.5 BA - Sleeps 10
2 Heated Swimming Pools
2 Upscale Renovated Houses w/ Fenced Backyards that border each other.
1/2 Block from the Hemingway House & Museum
1 block off Duval Street
If you plan to stay with your family or friends, but treasure your own place to retreat,The Grand Marshall offers the perfect layout. A back-to-back combination of 2 upscale renovated and beautifully decorated historic homes. Around the corner from the Hemingway Home and Museum, one block off Duval St. Settle in for a month or more and become thoroughly relaxed and ‘islandized.’
3BR 2BA
Jan 3 - Jan 8
Nightly $650
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.
Standard Rates: $5,925 - $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..
2BR 3BA
Nov 28 - Dec 8
Weekly $2500
Jan 18 -Jan 25
Weekly $3900
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 ...
10BR 7.5 BA
Nov 28 - Dec 5
Dec 15 - Dec 21
Nightly $1600
Jan 25 - Feb 1
Nightly $2900
Weekly $16000
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 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.
2BR 1BA
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 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.
Standard Rates: $18,500 - $34,800 per month
3BR 4BA Sleeps 6
Epic View from the Pool to the Beach
Private Tropical Resort Island
Garden Connects with White Sandy Beaches
Epic views from the house, to the pool, to the beach. Grand traditional beach house on the private island of Sunset Key. Far enough away that life slows down. White sandy beaches, turquoise ocean, palm trees rustling, birds twittering - peacefulness. 5-Star Resort amenities at your service.
2 BR 2 BA
Standard Rates: $6,500 - $15,260 per month
2BR 2BA - Sleeps 4
Beautifully Renovated 1920 Bungalow
Private Swimming Pool & Sun Deck
Upscale Amenities
On Famous Whitehead St.
1 Block off Duval Street
On Hemingway's Rounds, is an inspired renovation of a classic circa 1920 American Bungalow redone Key West style. Private swimming pool garden and deck in the fenced back yard. Historic front porch with comfy chairs to relax and watch Key west go by. Interior design is imaginative and elegant. Less than one block from the Hemingway Home and Museum.
2BR 2.5BA
Standard Rates: $4,900 - $10,125 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.
2BR 2BA
Nov 18 - Nov 23
Jan 5 - Jan 10
Nightly $525
Weekly $2400
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.
Standard Rates: $3,900 - $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.
3BR 3BA
Monthly $
Standard Rates: $6,450 - $14,200 per month
3BR 3BA - Sleeps 6
NEW Swimming Pool Garden with Spacious Deck installed Fall 2021
Timeless Historic Features
Split-bedroom Design
Tropical Landscaping
Bricked Private Driveway
Close to Key West Beaches on the South Shore
Channeling the island spirit in oft-missed mid-town, this pool-garden home makes an enviable Key West hideaway. Timeless craftsman-colonial architecture. New swimming pool with spacious sun deck. Lush mature tropical landscaping.
Here you live removed from the hubbub, yet close enough to beaches and Old Town. With a luxuious outdoor poolside living room, you may even find yourself making new island rituals of reading, and sipping Cuban coffee or your favorite cocktail on the deck.
4BR 4BA
Jan 2 - Jan 31
Monthly $29000
Standard Rates: $18,000 - $34,800 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.
4BR 3BA
Dec 15 - Dec 19
Jan 4 - Jan 8
Nightly $925
Weekly $4900
Jan 12- Jan 21
Nightly $1200
Weekly $6400
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.
3BR 2.5BA
Nov 24 - Nov 28
Dec 18 - Dec 21
Nightly $675
Weekly $3700
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.
2 BR 1 BA
Dec 12 - Dec 24
Jan 10 - Jan 16
Nightly $450
Weekly $2100
Standard Rates: $2,200 - $4,380 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.
Standard Rates: $50,000 - $87,000 per month
5BR + Den 7BA - 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.
7BR 5.5BA
Nov 28 - Dec 5
Dec 15- Dec 21
Nightly $1500
Jan 25 - Feb 1
Nightly $2600
Weekly $13000
Standard Rates: $8,750 - $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 famous Historic Seaport.
3 BR 2 BA
Jan 10 - Jan 20
Nightly $475
Weekly $2500
Standard Rates: $2,800 - $5,430 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.
4BR 3.5BA
Nov 19 - Nov 24
Nov 30 - Dec 5
Dec 13 - Dec 15
Dec 19 - Dec 22
Nightly $725
Five nights $3400
Weekly $4200
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.
3 BR 2 BA
Standard Rates: $6,900 - $15,650 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.
5BR 3BA
Nov 30 - Dec 3
Dec 16 - Dec 20
Nightly $1000
Weekly $5900
Jan 27- Jan 31
Nightly $1425
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.
4BR 4BA
Nov 23- Nov 26
Nov 29 - Dec 1
Dec 8- Dec 12
Dec 16 - Dec 22
Nightly $775
Weekly $4400
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.
4BR 4BA
Nov 23- Nov 29
Dec 9 - Dec 12
Dec 16 - Dec 22
Nightly $925
Weekly $4650
Jan 10 - Jan 16
Nightly $1200
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."
Standard Rates: $5,150 - $9,570 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.
2BR 2BA
Nov 18 - Nov 29
Dec 14 - Dec 16
Nightly $525
Weekly $2600
Jan 27 - Jan 30
Nightly $625
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.
4BR 4BA
Dec 15 - Dec 21
Nightly $975
Jan 10 - Jan 13
Nightly $1200
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.
3BR 2.5BA
Nov 30 - Dec 17
Nightly $500
Weekly $2450
Jan 27 - Jan 30
Nightly $650
Standard Rates: $2,600 - $5,660 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."
1 1/2 BR 1BA
Standard Rates: $4,875 - $11,600 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.
4BR 3BA
Dec 19 - Dec 22
Jan 15- Jan 17
Nightly $925
Weekly $4650
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.
1BR 1BA
Dec 23 - Dec 28
Five nights $2900
Nightly $700
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.
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, yet hidden from the street. Two cottages jointed with a bricked courtyard and swimming pool create a secret resort residence.
2BR 2BA
Nov 23- Nov 27
Dec 15 - Dec 19
Nightly $525
Weekly $2400
Dec 19 - Dec 26
Weekly $3500
Nightly $800
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.
4BR 4BA
Jan 5- Jan 10
Nightly $925
Weekly $4760
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.
2BR 2BA
Dec 13 - Dec 20
Nightly $525
Weekly $2625
Jan 7 - Jan 11
Nightly $650
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.
