Vacation Homes
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| List of All Our Vacation Homes |
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Click on Vacation Home Name to read details, rates, and make a reservation. |
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| Vacation Villas | |||||||||
 Amelia's Hideaway (#3714) ... locate on map |
4BR 3BA Sleeps 6-10 |
'Hidden Courtyard Villa' with Pool Steps off Upper Duval St. in Historic Old Town Keywest Location! Location! Most Desired Old Town Setting. | |||||||
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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. | |||||||
 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. Truly a home of fine distinction, that now offers 5-Star resort quality amenities, at long last this splendid piece of Key West - Cuban architectural history lives again! | |||||||
 Key West Dreamin' (#522) ... locate on map |
2BR 2BA Sleeps 4-6 |
This private historic home is beautifully furnished and offers all the amenities of a luxury accommodation situated in a genuine Old Town Key West location. 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) 2½BA Sleeps 8 |
This one-of-a-kind island villa perfectly blends two charming historic cottages right into a little bit of island heaven. Your own private tropical resort is the feeling you get when you enter the bricked courtyard of this extraordinary property just off Upper Duval St. in Old Town Key West. | |||||||
 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 clear heart pine from floor to ceiling, the interior rooms radiate a warm and magical feel that would be nearly impossible to replicate by modern builders. | |||||||
 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 pool located just one block from the sea. Easy bike ride to center of Old Town. | |||||||
 Louisa’s Private Courtyard (#805) ... locate on map |
3BR 3BA Sleeps 6-8 |
Set in a private tropical courtyard completely hidden from view this unique Old Town Key West villa exudes Caribbean charm and offers all the amenities for true indoor-outdoor isle-style living. Some days it will be all you can do to resist the temptation to just stay at the villa and lounge around the pool all day. | |||||||
 Amanda's Dream Suites (#1306) ... locate on map |
5BR 3BA Sleeps 8-10 |
A renovation of this home in the early 1990's redesigned the floor plan so the home can also be utilized as two separate units. | |||||||
 Victorian Mansion (#4379) ... locate on map |
5BR 3BA Sleeps 10 |
Key West Victorian Estate. A Hidden Legendary Gingerbread Mansion Estate in Old Town Key West. | |||||||
 The Watson House (#524) ... locate on map |
6BR 6BA Sleeps up to 12 |
The Watson House is a one-of-a-kind award-winning centurion Victorian home located in the heart of Old Town Key West in the 500 block of Simonton Street. From here you can easily walk to all features in the historic island village. | |||||||
 New Wave Oasis (#3011) ... locate on map |
2BR 2BA Sleeps 2-4 |
A daring designer renovation by an extraordinary Key West based artist-designer, this artful award-winning home is no less than remarkable in its setting and composition. | |||||||
 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. | |||||||
 Spanish Villa (#4796) ... locate on map |
2BR 2BA Sleeps 6 |
Spanish-style Private Luxury Villa right in the Heart of Old Town Key West. | |||||||
 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 2½BA 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. | |||||||
| Bungalows & Cottages | |||||||||
 Vintage Luxury Cottage (#4532) ... locate on map |
1BR 1BA Sleeps 4 |
'Vintage Luxury Cottage' - Just off Upper Duval Street. Elegant Cottage with Private Heated Pool. "Best Kept Key West Secret". | |||||||
 Down Island Digs (#508) ... locate on map |
2BR 2BA Sleeps 2-6 |
The focus of this property is definitely the Key West quintessential indoor / outdoor living that makes island life so relaxing and wonderful. | |||||||
 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 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 1½ (+Spa)BA Sleeps 2-6 |
Recently restored, this historic cottage has an authentic Caribbean feel, with original wood planked polished floors, vintage hand-hewned beams, bright blue tile (accented with marble), 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 is located in one of the most charming and interesting Old Town residential neighborhoods. | |||||||
 Havana Moon (#1227) ... locate on map |
2BR 2BA Sleeps 2 - 6 |
Open the front door of this hand crafted Key West cottage, step from the porch, and look south toward Havana Cuba and . . . . mmmm . . . you’ll catch a view of the ocean where the full moon rises with a soft salt southern breeze. | |||||||
 Private Estate Guest Cottage (#527) ... locate on map |
1BR 1BA Sleeps 2-4 |
Beautifully set on the perimeter of the historic Grande Dame Estate property is this very special tropical island guest cottage. | |||||||
 Butterfly Garden (#1693) ... locate on map |
1BR 1BA Sleeps 1-4 |
Tropical Butterfly Garden Flat Near the Beach. | |||||||
 Gingerbread Cottage Flat (#900) ... locate on map |
1BR 1BA Sleeps 1-4 |
If you're looking for a nicely styled updated charming Key West retreat for a month or more , be sure to consider our Gingerbread Cottage Flat. | |||||||
 Romantic Garden Cottage (#4007) ... locate on map |
2BR 1BA Sleeps 4-6 |
Romantic Renovated Turn-of-the-century Garden Cottage. Private Jacuzzi in Tropical Garden. | |||||||
 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. | |||||||
 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 | |||||||||
 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. | |||||||
 Southern Sunrise (#3685) ... locate on map |
2BR 2BA Sleeps 4-6 |
If your desire is a beautiful Key West property with stylish resort amenities, but you're looking for an affordably priced option, this may be your choice. | |||||||
 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 |
Nestled in one of Key West's original gated 'mini-compounds,' this spacious 1990's three-story Key West town home provides an island living experience in a traditional tropical' style - both inside and out. A lush private tropical garden complete with large 40' X 16' swimming pool is the main focus of this unique island setting. | |||||||
 Foundry on the Waterfront (#5005) ... locate on map |
2BR 2½BA Sleeps 2 - 4 |
Creatively renovated in the 1990's by a local private developer, this beautiful Historic Foundry structure was re-designed as mid-rise condominium residences in what is now known as the residential neighborhood of 'Truman Annex'. | |||||||
 Ocean View Luxury (#208) ... locate on map |
3BR 2BA Sleeps up to 6 |
You'll be carried away by the stunning ocean views from this luxurious Key West condominium. | |||||||
 Coco's Poolside Retreat (#1310) ... locate on map |
3BR 2½BA Sleeps 6-8 |
This three story, poolside town home was built in the 1990's and was designed to compliment the architecture of the original two-story wooden home. | |||||||
 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. | |||||||
| Key West Suites | |||||||||
 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. | |||||||
 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 |
2½BR 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. | |||||||
 Island Cosmopolitan (#1005) ... locate on map |
3BR 2BA Sleeps 2-6 |
Completely renovated and newly furnished in May 2005, this island court-style property has all the creature comforts you could want and still enjoy the ambiance of staying in an historic property. | |||||||
| Key West Resort Properties | |||||||||
| Southern Sunrise (#3685) ... locate on map |
2BR 2BA Sleeps 4-6 |
If your desire is a beautiful Key West property with stylish resort amenities, but you're looking for an affordably priced option, this may be your choice. | |||||||
| 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 |
9BR 6½BA Sleeps 18-22 |
Two home complex, plus private cottage, grand garden, and large swimming pool. | |||||||
| Key West Estates | |||||||||
 Grande Dame Key West (#525) ... locate on map |
7BR 7BA Sleeps 16 |
This award winning renovation of a grand Key West mansion is by far one the rarest and most exclusive private estate residences in Key West offered as a licensed single-family vacation home. | |||||||
 Classic Key West Estate (#428) ... locate on map |
6BR 4BA Sleeps 12-14 |
The timeless charm of this distinguished Classic Revival mansion is at once authentic and magnificent. If you have ever had the opportunity to stroll the historic residential streets of Old Town of Key West, you have experienced first hand the type of incredible architectural history this home embodies. | |||||||
 South Point Selection (#2541) ... locate on map |
5BR 4.5BA Sleeps 12 |
Located within view of Key West South Beach and around the corner from the Southern Most Point of the United States sits a unique and very special combination of two privately owned historic residences bearing a proud Key West - Cuban architectural history. | |||||||
 The Grand Marshall Key West - Bahama Estate (#425) ... locate on map |
5+BR 4BA Sleeps 12-14 |
This Spectacular large estate home is a beautiful representation Key West - Bahamian architecture, and a center piece of this Old Town Key West neighborhood. Built as a 19th century single family, a recent renovation completely restored the original exterior of the house and modernized the interior to divide it into 3 spacious upscale suites. | |||||||
 Bella Grande Premier (#513) ... locate on map |
5BR 5BA Sleeps 10 |
An exquisite private Victorian estate home offering “5- Star Resort Quality Amenities generally reserved for an exclusive Resort. No Detail has been overlooked!” | |||||||
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