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| List of All Our Vacation Homes |
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| Vacation Villas | ||||||||||
 Amelia's Hideaway (#3714) ... locate on map |
4BR 3.5BA Sleeps 8-10 |
"In-the-know" travelers who return to Key West love to choose the more elegant area of Upper Duval St. as their favorite area to stay... "Amelia's Hideaway." | ||||||||
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 Pavilion Villa (#5222) ... locate on map |
4BR 3BA Sleeps 10 |
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. | ||||||||
 A Duval Duet (#1223) ... locate on map |
5BR 4.5BA Sleeps 10-12 |
Exquisitely Key West yet exotically Cuban, this classy compendium of an elegant casa grande plus vintage casita is ideally located in the fascinating Upper South End of Duval Street. | ||||||||
 Tropical ~ Tranquility (#8248) ... locate on map |
4BR 3.5BA Sleeps 8 |
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. | ||||||||
 Viva On Duval (#1224) ... locate on map |
3BR 2.5BA Sleeps 8 |
Displaying the most romantic elements of neoclassicism design this inspired home has a special fairy-tale charm. At long last this splendid 5-Star home of fine distinction and testimony to our Key West - Cuban architectural history lives again! | ||||||||
 By The Beautiful Sea (#1002) ... locate on map |
3-4BR (*Den) 3BA Sleeps 6-8 |
You've just discovered a private Key West house with a beautiful sea view that's next to Key West's Fort Zachary Taylor Beach, and just a few short walking streets from the heart of downtown. | ||||||||
 Key West Dreamin' (#522) ... locate on map |
2BR 2BA Sleeps 4-6 |
This private rental home offers all the luxury amenities. A stroll through this charming Upper Duval neighborhood is to rendezvous with an important part of our island's rich cigar and rum history. | ||||||||
 Fantasy Resort Villa (#1613) ... locate on map |
3-4BR (*Den) 2.5BA Sleeps 8 |
This one-of-a-kind island villa perfectly blends two charming historic cottages right into a little bit of Old Town Key West island heaven. Your own private tropical resort is the feeling you get when you enter the bricked courtyard. | ||||||||
 Abaco Dreams (#1017) ... locate on map |
3BR 2BA Sleeps 5-6 |
Authentic "old-world" charm meets modern tropical luxury in this wonderful historic island home. Built of original glistening heart pine from floor to ceiling, the interior rooms radiate a warm and magical feel. | ||||||||
 Private Pool Garden Villa (#1307) ... locate on map |
3BR 2.5BA Sleeps 6 |
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. | ||||||||
 Lazy Iguana  (#1308) ... locate on map |
4BR 3.5BA Sleeps 8 |
During the months of June through November this genuine Key West combo of our "Private Pool Garden Villa" plus a classy private studio cottage that adjoins the property can be your very own get-away. | ||||||||
 Louisa's Private Courtyard (#805) ... locate on map |
3BR 3BA Sleeps 6-8 |
Some days it will be all you can do to resist the temptation to just stay at this private tropical courtyard villa and lounge around the pool all day. It simply exudes Caribbean Charm. | ||||||||
 Amanda's Dream Suites (#1306) ... locate on map |
5BR 3BA Sleeps 8-10 |
Originally built in the 1940's, this charming large wooden home has two full stories with deep porches which overlook the garden and pool. A renovation of the home redesigned the floor plan so it can also be utilized as two separate units. | ||||||||
 The Watson House (#524) ... locate on map |
6BR 6BA Sleeps up to 12 |
The Watson House is a one-of-a-kind award-winning Victorian home in the heart of Old Town Key West. Just half a block from Duval Street you can easily walk everywhere in the island village. | ||||||||
 Twice as Nice (#1228) ... locate on map |
4BR 4BA Sleeps 8 |
"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. | ||||||||
 Island Interlude (#812) ... locate on map |
4BR 4BA Sleeps 8-10 |
This spectacular Key West villa has maintained its historic residential authenticity, while being redesigned as two separate wooden structures joined by a Caribbean-style covered wooden walkway-porch. | ||||||||
 Port Side Perfection (#318) ... locate on map |
2BR 2BA Sleeps 2-4 |
A celebration of island style is made imminent throughout the interior of the cottage with soft modern tropical furnishings and a beautiful display of tropical artwork by local artists. | ||||||||
 Key West~Indies (#5251) ... locate on map |
4BR 3BA Sleeps 4-8 |
Neatly situated between a fashionably narrow island street and a hidden lane, this "house-plus-guest-cottage" villa displays a West Indies design that smoothly melds a sophisticated British Colonial gracefulness with a carefree Caribbean flare. The overall effect both warms the heart and tickles the soul with a fanciful-folly-of-charm. | ||||||||
 Hidden Botanical Oasis (#1006) ... locate on map |
4BR 2BA Sleeps 6-8 |
Like inspired fantasy island art this splendid Key West botanical-oasis home stands in a class all in its own. | ||||||||
 Spanish Villa (#4796) ... locate on map |
2BR 2BA Sleeps 6 |
Spanish-style Private Luxury Villa right in the Heart of Old Town Key West. Originally built in 1938, this fully renovated luxury home is a spectacular show piece and one of the most creative designs in Key West. | ||||||||
 Southern Comfort (#1111) ... locate on map |
1BR 2BA Sleeps 2-4 |
Island living is made easy and beautiful in this adorable one bedroom, 2-story Key West "mini manor." Designed classical style, this charming rental home is appointed in front with a romantic gingerbread Juliet-style 2nd floor balcony and two symmetrically placed full-size Palladian windows on either side of the front door. | ||||||||
 Governor's Retreat (#6169) ... locate on map |
2BR 2BA Sleeps 4 |
Gentle Retreat in the Key West Meadows. Perfectly Renovated and Immaculate Neighborhood. | ||||||||
 Island Elegance (#639) ... locate on map |
2BR 2BA Sleeps 4+ |
A unique flare of island elegance is achieved when Caribbean cottage architecture is at once dressed with a blend of traditional and sophisticated island furnishings. | ||||||||
 Villa On Story-Book-Lane (#704) ... locate on map |
3BR 3BA Sleeps 6-7 |
You'll only wish you could live right here... "happily ever after" in this absolutely perfect island dream home hidden deep in the heart of Key West on one particular charming story-book lane. | ||||||||
 Mediterranean Caribbean Villa (#1214) ... locate on map |
3BR 2.5BA Sleeps 6 |
Tucked behind a breathtaking tropical garden wall and located along one of Key West's most desirable residential streets, this spectacular home reflects a dynamic blend of contemporary Mediterranean and Caribbean architectural design. | ||||||||
 Avant-Garde - Modernistic Luxury Home (#1205) ... locate on map |
3BR 3BA Sleeps 7 |
Designed by a well known Key West abstract artist and a landscape architect this unique art deco living space is at once daring, serene, and comfortable. | ||||||||
 Luxurious Manor (#4121) ... locate on map |
3BR 3BA Sleeps 6-7 |
Live in the lap of luxury in this stunningly renovated Key West classic "Eyebrow House." An esteemed Key West renovation builder assembled a creative team of elite woodworkers, masons, local craftspeople, and an internationally known traveling artist sailor to execute his plans. | ||||||||
 Dancing Palms Villa (#415) ... locate on map |
3BR 2BA Sleeps 6-8 |
An untold variety of exotic palm trees thrive on the island of Key West, nourished by the tropical sun. Literally dozens of palms join limbs and fronds to gently surround this wonderful villa, creating a living wall of tropical privacy. | ||||||||
| Key West Penthouses | ||||||||||
 Penthouse On Duval (#718) ... locate on map |
4BR 4BA Sleeps 8 |
Perfectly staged on Duval Street Key West, this gorgeous downtown Key West rental received a major upscale renovation to become the premium "Penthouse On Duval." Close to Mallory Square and the beach. | ||||||||
 Top of the House (#6164) ... locate on map |
2BR 2BA Sleeps 2-4 |
"Top of the House" is a stunning 5-Star suite located in Key West's Historic Seaport. Upscale amenities and an enviable "story-book view" of famous Caroline Street below make this one hard to resist. | ||||||||
 Caroline Street Quartet (#6168) ... locate on map |
4BR 6BA Sleeps 8+ |
Encompassing in the entire 2nd storey and 1/2 of a Victorian Key West vacation home, this property provides our most discriminating guests with four spacious bedrooms in the most requested Historic Seaport Key West location. | ||||||||
| Bungalows & Cottages | ||||||||||
 Vintage Luxury Cottage (#4532) ... locate on map |
1BR 1BA Sleeps 4 |
"Vintage Luxury Cottage" - Just off Upper Duval Street. This is an elegant Cottage with Private Heated Pool. "Best Kept Key West Secret." | ||||||||
 Down Island Digs (#508) ... locate on map |
2BR 2BA Sleeps 2-6 |
Everything about "Down Island Digs" adds up to make a precious private garden cottage. Sitting in the mature tropical tree garden in the hidden back yard, you would never know you're just 1/2 block off Duval Street. | ||||||||
 Carriage Cottage (Sea Shell Cottage) (#1304) ... locate on map |
1BR 1BA Sleeps 2-4 |
An artist-owner's delightful design and renovation of a carriage house has created an adorable intimate two-story, one bedroom fantasy island sea-shell cottage. | ||||||||
 Secret Courtyard Cottage (#512) ... locate on map |
2BR 1BA Sleeps 2-5 |
Welcome to a little piece of hidden paradise you never knew existed. Once you're nestled into this hideaway, you'll never know you're right in the center of Old Town Key West. | ||||||||
 Caribbean Cottage (#506) ... locate on map |
2BR (*Spa) 1.5BA Sleeps 2-6 |
Just steps from Duval Street, this unique Key West cottage has an authentic Caribbean feel, with original wood planked polished floors, vintage hand-hewned beams, bright blue tile and Bahama style wooden window shutters. | ||||||||
 Island Village Cottage (#1103) ... locate on map |
2BR 2BA Sleeps 2-6 |
Ideally situated in the Historic Seaport side of Key West, this one-and-one-half-story Classic Revival shotgun island cottage stands in one of the most charming and interesting Old Town residential neighborhoods. | ||||||||
 Havana Moon (#1227) ... locate on map |
2BR 2BA Sleeps 4-6 |
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. | ||||||||
 Cockadoodle Cottage (#1229) ... locate on map |
2BR 2BA Sleeps 4-6 |
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." | ||||||||
 Deco Vibe (#527) ... locate on map |
1BR 1BA Sleeps 2 |
"Deco Vibe" cottage is beautifully set on the perimeter of the historic Key West Grande Dame Estate property. Located on Simonton Street you are just 1 short block from Duval Street. | ||||||||
 Butterfly Garden (#1693) ... locate on map |
1BR 1BA Sleeps 1-4 |
Completely hidden from the street, this recently redecorated historic garden flat provides you with two private entrances off the large gated garden. An private sitting porch outside your front door beckons you to sit in the freshness of the garden and watch for the butterflies. | ||||||||
 Romantic Garden Cottage (#4007) ... locate on map |
2BR 1BA Sleeps 4-6 |
From the outside this adorable Key West garden cottage almost resembles a big toy house, it's diminutive scale belying a surprisingly spacious interior in which every ship shape square inch delivers. | ||||||||
 Sweet Sunshine Garden Cottage (#1317) ... locate on map |
2BR 2BA Sleeps up to 6 |
Everyone dreams of a sun drenched Caribbean style cottage, like this one, tucked away behind a tall picket privacy fence where flowers drape over the weathered slats. Here you live the authentic Key West lifestyle. | ||||||||
 Tropical Chill (#13172) ... locate on map |
2BR 2BA Sleeps 2-4 |
A designers dream to creatively transform a tropical garden hideaway into an intimate contemporary island retreat was the inspiration of the owner-designer of this upscale modern luxury cottage. | ||||||||
| Town Houses & Condos | ||||||||||
 Private Key West Sunset (#316) ... locate on map |
3BR 3BA Sleeps 6 |
Holding a perfect perch overlooking the entrance to the Key West Harbor, this spacious luxury condominium is situated in a revered waterfront position in Old Town Key West’s up-scale gated community named “Truman Annex”. | ||||||||
 Exclusive Key West Beach Front (#1500) ... locate on map |
2BR 3BA Sleeps up to 6 |
Rare, one-of-a kind designer luxury suite located in an exclusive gated beachfront property with ocean views. | ||||||||
 Island Oasis Garden Home (#6055) ... locate on map |
2BR 2BA Sleeps 2-4 |
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. | ||||||||
 Island Brownstone (#2002) ... locate on map |
2BR 2.5BA Sleeps 4-6 |
An exclusive island style brownstone perfectly nestled in Key West's most prominent gated waterfront neighborhood known as "Truman Annex." | ||||||||
 A Tropical Tradition (Gallup Arms) (#1311) ... locate on map |
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. | ||||||||
 Foundry on the Waterfront (#5005) ... locate on map |
2BR 2.5BA Sleeps 2-6 |
A striking tri-level condominium situated in Key West's most historic gated waterfront luxury neighborhood offers a beautiful combination of classic historic charm and refined modern ambience. | ||||||||
 Coco's Poolside Retreat (#1310) ... locate on map |
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." | ||||||||
 Suite Home Key West (#819) ... locate on map |
2BR 2BA Sleeps 2-6 |
This pretty tri-level two bedroom two bath condominium is at once fun, spacious, and comfortable and offers beautiful resort amenities right in the heart of Old Town Key West. | ||||||||
 Good Day Sunshine (#3039) ... locate on map |
2BR 2BA Sleeps 2-4 |
Proving that there is sophisticated style in Key West beyond the Old Town Historic District, this relatively unknown modern European-style resort complex is on the extreme southern or "quiet" end of the island of Key West. | ||||||||
 Executive Retreat By The Sea (#807) ... locate on map |
3BR 3.5BA Sleeps 6 |
This spacious custom built 3-story town home is set around a serene Zen-garden courtyard garden Complete with dipping pool, soothing waterfall, and private lounging deck. | ||||||||
 Twin Palms Suite (#6161) ... locate on map |
1BR 1BA Sleeps 2-4 |
Perfectly set within Key West's Historic Seaport neighborhood, "Twin Palms Suite" offers a gorgeous home away from home. This one bedroom luxury accommodation provides 5-Star resort amenities plus an idyllic front porch where you can idle away the time and watch the 'world of Key West' pass you by. | ||||||||
 Suite Mandarin (#6162) ... locate on map |
1BR 1BA Sleeps 2-4 |
A classically elegant upscale condominium with a "twist of Zen" offers 5-Star amenities generally reserved for a luxury resort accommodation. Situated in an ideal location in Old Town Key West's famous Historic Seaport district on Caroline Street, this luxury property offers all a couple could want in a tropical home away from home. | ||||||||
 Suite Ginger (#6163) ... locate on map |
1BR 1BA Sleeps 2-4 |
An artistic fusion of "past meets present" provides a decidedly refreshing and modern interpretation of a classic Key West style. And if the two-of-you are looking to stay awhile in one of the loveliest up-scale escapes in Old Town Key West, then this could be your perfect spot. | ||||||||
 Bird's Eye View (#6166) ... locate on map |
1BR 2BA Sleeps 2-4 |
Key West's original and distinctive Old Town Historic Seaport finds its residential heart on Caroline Street. This one bedroom - 2 bathroom luxury condominium suite is located on gracious Caroline Street, offers 5-Star amenities generally reserved for a luxury resort accommodation, and is just a minute walk from Key West's "Harbor Walk at the Historic Seaport" and lower Duval Street. | ||||||||
 Rooftop Renaissance (#6165) ... locate on map |
1BR 2BA Sleeps 2-4 |
"Rooftop Renaissance" falls right into the exceptional category of "charming historic-meets modern luxury" and has been made over to become an absolutely stunning 5-Star luxury condominium suite. This unique 2-story one bedroom - two bathroom accommodation offers a charming skyline view of Old Town Key West classic tin rooftops and overlooks a peaceful Zen-pool garden below. | ||||||||
| Key West Suites | ||||||||||
 City Island View (#7181) ... locate on map |
2BR 2.5BA Sleeps 4 |
Perched just above the fun and frolic of Duval Street you're sure to capture the "island beat" that stirs this tiny tropical island of Key West, Florida. Close to Mallory Square and the beach. | ||||||||
 Topsail Suite (#425A) ... locate on map |
2BR 1BA Sleeps 2-4 |
"Topsail Suite" is a spacious 2 bedroom, 1 bathroom hideaway that encompasses the entire second floor of our Classic Revival Key West Bahamian Estate. | ||||||||
 Starlight Siesta (#7182) ... locate on map |
2BR 2.5BA Sleeps 4 |
Perfectly staged in the island's city center, this spectacular downtown Key West rental received a major upscale just completed in June, 2009. Close to Mallory Square and the beach. | ||||||||
 Green Turtle Suite (#425B) ... locate on map |
1BR 1BA Sleeps 2-4 |
Situated in the heart of the Key West Historic Seaport District, the "Green Turtle Suite" offers a sun filled spacious accommodation on the first-floor front of the Key West Bahamian Estate. | ||||||||
 Abaco Suite (#425C) ... locate on map |
2BR 2BA Sleeps 2-6 |
Completely hidden from the street, "Abaco Suite" encompasses the back two-thirds of the first floor of our Classic Revival Key West Bahamian Estate. | ||||||||
 Exquisite Victorian Suite (#525A) ... locate on map |
2BR 2BA Sleeps 2-4 |
If you are looking for something spectacular and unique, we invite you to celebrate the era of romance in this beautiful and lavishly styled Victorian suite. | ||||||||
 Balcony Terrace Suites (#525B) ... locate on map |
4BR 4BA Sleeps 6-8 |
Situated in the heart of Old Town Key West on historic Simonton Street, this spectacular suite property encompasses the entire 2nd and 3rd floors of the large Victorian home in the Grande Dame Estate property. | ||||||||
 Tree Tops (#1306A) ... locate on map |
2BR 1BA Sleeps 4 |
Tree Tops Suite provides approximately 750 square feet of living space offering an open floor plan joining the beamed ceiling living room and galley kitchen. | ||||||||
 Garden Suite (#1306B) ... locate on map |
2.5BR 2BA Sleeps 6 |
Garden Suite offers over 1200 square feet of living space and features a large living room with cathedral ceilings. | ||||||||
 Tree Garden Courtyard (#3051) ... locate on map |
1BR 1BA Sleeps 2-4 |
A perfect retreat for a couple or single who want to experience Key West as the locals love and live it. | ||||||||
| Key West Resort Properties | ||||||||||
| Good Day Sunshine (#3039) ... locate on map |
2BR 2BA Sleeps 2-4 |
Proving that there is sophisticated style in Key West beyond the Old Town Historic District, this relatively unknown modern European-style resort complex is on the extreme southern or "quiet" end of the island of Key West. | ||||||||
| Key West Compounds | ||||||||||
 Island Rendezvous (#5730) ... locate on map |
6BR 5BA Sleeps 12 |
An Award Winning Villa and Caribbean Style Cottage side-by-side just 3.5 Blocks from Mallory Square. | ||||||||
 Family Reunion (#2616) ... locate on map |
12BR 6.5BA Sleeps 22-28 |
This is a perfect spacious Key West rental for your family reunion vacation. Why not gather in a three home complex, plus private cottage, grand garden, and large swimming pool - all your own! | ||||||||
| Key West Estates | ||||||||||
 Caroline Zen ~ A Private Inn Residence (#6167) ... locate on map |
7BR 9BA Sleeps 14-20 |
An extraordinary Victorian Estate in the Historic Seaport Key West neighborhood with 7 bedrooms, 9 baths, and 6 kitchens. This private Key West rental has all the up-scale amenities that you can possibly want. | ||||||||
 Grande Dame Key West (#525) ... locate on map |
7BR 7BA Sleeps 16 |
This award winning renovation of a 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. | ||||||||
 Classic Key West Estate (#428) ... locate on map |
7BR 5BA Sleeps 10-14 |
"Classic Key West Estate" is a meticulously maintained grand wooden estate home available as a weekly Key West vacation rental. It is located on Fleming Street in the Historic Seaport Key West neighborhood. | ||||||||
 South Point Selection (#2541) ... locate on map |
7BR 6.5BA Sleeps 14-16 |
A gorgeous collection of 3 historic residences combines a grand neo-classic home and 2 delightful cottages to create your own private estate. Right on Duval Street, this property is available as a weekly Key West rental. | ||||||||
 The Grand Marshall Key West - Bahama Estate (#425) ... locate on map |
5+BR 4BA Sleeps 12-14 |
This Grand Marshall is a beautiful representation Key West - Bahamian architecture. Built as a 19th century single family, a refit restored the original exterior of the house and modernized the interior to become three spacious vacation rental suites. | ||||||||
 Bella Grande Premier (#513) ... locate on map |
5BR 5BA Sleeps 10 |
"Bella Grand Premier" is an exquisite private Victorian estate home offering 5- Star Resort Quality Amenities generally reserved for a resort. No Detail in this Key West rental has been overlooked. | ||||||||
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