Key West ~ Vacation Rentals With Pool

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.  

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.

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.

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.

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.

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.

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.

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 2BR 2.5BA 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.

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.

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. 

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.

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.

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.

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.

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. 

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. 

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.

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!

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.

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.  

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.

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.

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.’

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 ...

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..

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. 

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.

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.

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

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. 

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. 

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

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.

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.

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. 

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.

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.

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.

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.

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. 

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.

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.

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. 

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.

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.

"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."

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. 

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."

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.

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.

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. 

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. 

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.

"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.

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.