Vacation Villa Rentals By Owner In Key West, FL

Welcome to Admirals Gold, a luxurious weekly vacation rental nestled in the prestigious Truman Annex neighborhood. This 4-bedroom, 3.5-bathroom home is the perfect destination for those seeking a spacious and luxurious escape for the entire family. Quintessential Key West architecture provides an authentic lifestyle experience with a charming covered front porch, tin roof, clapboard siding, and white picket fences.brbrInside, this entire 3-Story home is filled with natural light. Light wood flooring, wide crown molding, fashionable lighting, and colonial window shutters set the stage for a beautiful fusion of tropical furnishings. During sunset time diffused window light bathes the rooms in a golden glow, setting the tone to relax and unwind island style. A private garden patio adjoining the great room is set for outdoor lounging and dining. brbrWhen you`re not basking in the comfort of this admirable home, you’re just a short stroll away from some of Key West`s most desirable Old Town attractions. Plan to visit the Truman Little Whitehouse museum, explore the one-of-a-kind Truman Waterfront Park and revel in the stunning ocean views and entertainment it offers. A favorite destination is the Key West Amphitheater, featuring both local and world-famous music performances. Kids in your party will love the playground with fountain Splash Pad. And when you`re in the mood for beachside bliss, Fort Zachary Taylor Beach, considered the best beach on the island, awaits you just moments away.brbrInterior LayoutbrbrWith its sophisticated design and impeccable attention to detail, the 3-story Admirals Gold - Private Key West Luxury Villa promises a dream worthy stay. The open floor plan of this 2,500 Sq ft vacation rental seamlessly blends indoor and outdoor living spaces, allowing guests to fully immerse themselves in the beauty of the surroundings. Expansive windows and glass French doors provide unobstructed views of the private gardens, capturing the classical tone that envelopes Truman Annex. The interior design was thoughtfully chosen to complement the island setting and create an atmosphere of casual refinement.brbrEntrance:brbrA hidden walkway lined with manicured tropical leads to the front entrance. Before you step up onto the front porch, take a moment to enjoy the rooster sculpture standing proudly in the garden. According to lore, the rooster is a symbol of good luck and prosperity. And beyond that, the rooster is the unofficial mascot of Key West, where gypsy chickens are legally protected due to their significance to the islands colorful culture.brbr1st Floor: As you enter the front door the expansive great room captivates your senses. The entire great room is painted in a soothing sand color and trimmed with bright white wainscoting. Artwork reflects your whereabouts with a map of the Caribbean and a luminous rooster painting. brbrTo your right, the newly renovated kitchen dips back into the front of the house. The kitchen is fully equipped with upscale appliances, and complete dining, cooking, and hosting sets. Displaying classic bright white cabinets with glass front doors, the ceiling is adorned with a fanciful metal sculpture chandelier. Finished with stylish quartz marble countertops the breakfast bar is fitted with artful hand-carved wooden chairs.brbrA bamboo bentwood dining table and chairs, topped with an elaborate seashell chandelier, is situated behind the breakfast bar. The dining room sets a tropical tone and creates a natural division between the kitchen and the living room.brbrTo your left, conveniently located beneath the staircase, you’ll find a powder room with sink and commode. The cultivated design incorporates grass reed wallpaper that is appointed with a round gold mirror and gilt palm tree wall sconces.brbrReturning to the great room, kick back in style in the elegant and comfortable living room. A soft textured matching sofa and loveseat is paired with a soft print armchair. The seating area is finished with bamboo side tables with reading lamps, and perfectly complimented with a mango wood credenza plus teak and metal coffee table. A 72-inch TV is mounted on the wall for easy viewing from anywhere in the great room.brbrTwo sets of single-pane glass French doors comprise the rear of the first floor. The doors provide a great view and seamless indoor/outdoor connection during the cooler months and access to the private tranquil sitting patio.brbr2nd Floor: A wooden staircase on the wall opposite the dining area, leads upstairs. Steps topped with dark wood treads and fronted with bright white risers, varnished wood railing, and capital topped posts reflect a timeless Key West design. At the top of the stairs, a bedroom hallway leads to the master suite and guest bedroom.brbrBoth bedrooms feature a Tommy Bahama style décor, creating an opulent Caribbean/British Colonial feel. Dark wood, woven rattan, and carved bureaus reflect the essence of sophisticated island living. Floors are covered with wall-to-wall seagrass carpet, and palm leaf ceiling fans complete the upscale décor.brbrGuest Bedroom One – Directly to your right at the stair landing, lies the guest bedroom. Sunshine yellow walls seem to glow against the dark furnishings. The king size bed features carved bamboo posts, and the matching armoire features Chippendale inspired cutouts and woven rattan panels. Bedside tables on either side offer woven base reading lamps. A double sash window provides a beautiful view of the treetops.brbrJust outside this guest room is the guest bathroom. The effervescent green mosaic tile with round portal window is reminiscent of the tropical rainforest the Truman Annex neighborhood so closely shares its climate with. A single sink vanity is topped with a gold tone mirror and faucet to match the fixtures in the shower. Back in the bedroom hallway, at the front of the house is the master suite.brbrMaster Suite – A sumptuous king size bed of dark wood, woven rattan, and pineapple posts and matching bedside tables and lamps elevates the bedroom to a luxurious exotic retreat. Grass reed wallpaper adds to the sophisticated aesthetic. Three sets of sash windows stream in natural light and a full-length mirror reflects the twilight glow. Connecting with the bedroom is the private master bath.brbrThe master bathroom is made exquisite with a quartz marble countertop finished with sunken double sinks and gold tone bath fixtures. A counter to ceiling mirror above the vanity provides the perfect place to primp. The oversize shower, with ceiling rain shower, features a stunning Caribbean blue mosaic tile wall.brbrLaundry Closet – Step back into the hallway, you’ll appreciate the convenient location of the laundry closet. The stacked washer/dryer are kept hidden behind a closet door. At the opposite end of the hall, the staircase switches back to the 3rd floor where we find two more guest bedrooms.brbr3rd Floor: On opposite ends of the third floor lie guest room two and three. Both bedrooms are similarly appointed with two queen size beds placed on either side of a sash window. The front bedroom is shown with the white bedside table and bold colorful rug. The bedroom toward the back of the house is shown with the grass woven bedside table and the round blue and white rug.brbrThe full bathroom is located just outside the front bedroom. It offers a single shower and is nicely finished with a marble topped single sink and wooden shelves to place your toiletries. Back in the hall, across from the bathroom door, a bench has been placed to drop your personal things or take off your shoes.brbrGuests who nestle on the 3rd floor can enjoy elevated treetop views. And when the sunsets, it’s great to be up high when the magical glow of sunset seeps through the windows.brbrGrounds:brbrThroughout the day, guests can enjoy the property`s outdoor spaces, designed for relaxation and enjoyment. A private courtyard garden, adorned with lush vegetation and comfortable seagrass sofa seating and teak dining table with wicker chairs, becomes a sanctuary in which to unwind and absorb the enchanting atmosphere.brbrWhether sipping coffee, a refreshing cocktail or engaging in conversation with loved ones, the serene beauty adds an extra layer of tranquility and luxury to these outdoor spaces. Additionally, you have access to a shared pool, exclusive for residents, allowing you to cool off and relax in the refreshing water after a day of exploring.brbrStep outside the gates of the Truman Annex community, and you’re at the waterfront or in the vibrant heart of downtown Old Town Key West. Immerse yourself in the island`s famous bars, indulge in exquisite dining experiences at the wonderful restaurants, catch a captivating theater performance, or witness the lively energy of Mallory Square.brbrAmenities: Private back garden patio, shared pool, lush tropical landscaping. Quartz marble countertops, upscale steel appliances, fully equipped kitchen, washer and dryer, central air conditioning, Wi-Fi, 76-inch TV.brbrActivities: Short walk to all Old Town Key West features. 10-to-15-minute stroll to Mallory Square Sunset Celebration. Just a few short streets from Duval St. Short walk to Fort Zachary Taylor State Park and Beach, Truman Waterfront Park, the Key West Amphitheater, and the Truman Little Whitehouse Museum. Close to boutique shopping, art galleries, and a variety of national and international restaurants, coffee shops. Close to the beach. You can get everywhere in the Old Town on foot in a short time (remember - it takes 3 to 4 Key West streets to make a city block). Colorful and historic Bahama Village is just outside the main front gate, and home to a delightful variety of cool and funky cafes and restaurants.brbrPAYMENT: Payment for the rental will be processed outside of VRBO according to the terms of your rental agreement (sent for review upon reservation). Payments by credit card are subject to an additional 2.95% merchant processing fee.

Admirals Gold Key West - Truman Annex Villa - Close to Beach and Duval w Parking and Pool Access

Key West, Florida, United States

4

Bed

Bath

8

Sleeps

$701.11

• Luxury 2nd & 3rd floor Penthouse br• 3 Bedrooms with private porches & 2 1/2 Bathsbr• 2200 square feet of living spacebr• Over 2000 square feet of porches and decksbr• Backyard with tropical landscaping, pool & waterfallbr• Huge roof top sun deck overlooking Duval Streetbr• off-street parkingbrbrOne of a kind! Located in the heart of Old Town Key West on famous Duval St. just steps from restaurants, shops and theatres, this very unique Duval Street Luxury Residence offers a discerning traveler the best of Key West. brbrBrand new and beautiful, this sprawling two-story penthouse has three bedrooms, each with private terraces, a huge roof top sun deck overlooking the action of Duval St., and a private tropical garden with pool and gorgeous waterfall to relax by. brbrFine furnishings and art, top of the line Viking kitchen, fabulous bathrooms, and endless outdoor entertaining & sun worshiping areas make this a very special Key West retreat. brbrKeywords: Penthouse

Downtown Duval Street Penthouse- Private Pool-Parking-Roof Deck- Walk Everywhere

Key West, Florida, United States

Bed

Bath

Sleeps

$684.05

Welcome to Coral Villa by AvantStay!brbrSpacious, beautifully decorated, and rare in all the right ways — Coral Villa offers 3 bedrooms, 3 bathrooms, and off-street parking for two vehicles, a genuine luxury in Key West. Tucked inside the gated community of Coral Hammock just off U.S. 1, this townhome sits directly across from the Key West Golf Course and puts you minutes from the local-favorite restaurants, marinas, Smathers Beach, and the airport.brbrStep inside to an easy, open first floor where the living and dining areas flow into a fully stocked kitchen ready for family breakfasts, sunset cocktails, and everything in between. A main-floor bedroom with a full bathroom sits just off the living space, opening to a back patio and balcony made for morning coffee or a quiet nightcap.brbrUpstairs, the primary suite and a second guest bedroom each come with their own en-suite bathroom — ideal for families or friends traveling together. Soft earth tones carry through every room, creating a calm, grounded feel that makes it easy to settle in. The home comfortably sleeps up to 8.brbrWhen you're ready to cool off, the community pool and clubhouse are just a short walk away. And when you want the energy of downtown Key West and Duval Street, you're only about 3 miles from the action — close enough to dip in whenever the mood strikes, far enough to retreat to your own private corner of the island when it's time to unwind.brbrKey West is the place to visit the lively nightlife and relax in the historic charm, flamboyance, and conch-style architecture that early Bahamian settlers made famous. It embodies a clash of the past and the present, and every building (including this rental) in Key West reflects this eclectic ambiance!brbrAvantStay provides a personalized hospitality experience to elevate your stay. With our Concierge Service, guests have access to our tech-enabled services like fridge stocking, private chefs, massages, transportation, special occasion celebrations, baby gear rentals, ski gear, beach gear, and more. For anything you need, we’re at your fingertips!brbr*Home Truths:*br- This home has access to a shared pool.br- We allow service animals at this home. If undisclosed pets are brought into the home without AvantStay's approval there is a fine of $500 per pet.br- Any reservations 28 days or longer will require additional clean/cleans to be scheduled. Additional payment will be collected and the amount of cleans will depend on the length of your stay.br- All bookings 28 days or longer require a security deposit to be charged after booking.br- This home is on a monthly pest control schedule. The area of Key West is home to many insects such as termites, no-see-ums, and mosquitos. Pest control can not eliminate these insects during the swarming season. You may also encounter geckos, lizards, iguanas, frogs, and chickens during your stay in the area.br- Key West is a resort island where renovation of existing historic properties, new construction, and road repair sometimes occur without forewarning. AvantStay is not liable for any guest inconveniences caused due to construction in the area.br- Please note that if requested, the two twin beds can be converted into one king bed with bedding for a fee of $75. Please ensure you make this request at least 48 hours in advance.br- This home offers a sleeper sofa for additional sleeping arrangements.br- Please note that max occupancy includes infants.br- Please be advised that documentation may be necessary for ESA/service animals to gain entry.brbrParking Details:brOff-street parking for 2 cars.brBoats, Jet Skis, buses, campers, trailers, motor homes, recreating vehicles, mobile homes, and commercial vehicles are notbrallowed to park on the association property (except for deliveries).brbr---brbrThe room configuration is as follows:brbrPrimary Bedroom / King bed brBedroom 2 / Queen bedbrBedroom 3 / Two twin bedsbrSleeper sofabrbr---brbrThis is a smoke-free property. Violation of the no-smoking policy will result in forfeiture of the security deposit, a $300 smoking fee, and liability for any fire or property damage costs.brbrAs part of our commitment to being good neighbors, occupancy limits and quiet hours (9pm-8am) are strictly enforced. No speakers or sound systems will be provided for use in our properties. Violation of any noise ordinances will be subject to fines that can reach up to $10,000 per violation. brbrEvents or parties are not allowed without prior written approval and an additional fee. Any unauthorized parties or events will be shut down and a fine will be assessed. Please inquire for more information about our event policies and fees. brbrThere is nothing more important to us at AvantStay than the health, safety, and experience of our guests & staff. We've enhanced our cleaning and sanitation protocols and are taking extra care to disinfect all surfaces between reservations with hospital-grade disinfecting solutions.brbrAs a reminder, we do work with 3rd party vendors to maintain the property, and although we adhere to the strictest CDC guidelines and advise all contractors to wear PPE equipment, we can not always enforce. We strongly advise guests to please deny access if any vendors fail to meet and adhere to these standards.brbrIDs will be requested for verification after booking. brbrWe report and prosecute all Credit Card Fraud.

Coral Villa by AvantStay | Close 2 DT Key West | Shared Pool & Patio!

Key West, Florida, United States

Bed

Bath

Sleeps

$622.35

Coral Palm is a lovely 3 bedroom, 3 bathroom, 2 story townhome located in the private gated community of Coral Hammock on Stock Island. The property is less than 5 miles from downtown Key West allowing you to live in a quiet tropical paradise while still being close to all that Key West has to offer.brbrEntering the property you will feel immediately at home. The first floor has an elegant living space with a dining table for six and a vibrant living room. The french doors open up to the private porch overlooking the palms with an additional outdoor dining space. There is a guest bedroom off of the main living area with two twin beds and a full bathroom just down the hall. The full kitchen is equipped with updated appliances and everything you will need for your gourmet meals.brbrBoth bedrooms on the second floor have a king bed with an en suite full bathroom. The french doors in the master bedroom open to a spacious balcony overlooking the property. The washer and dryer set in the upstairs hall also add to the convenience of the home.brbrCoral Palm is conveniently located just down the street from Hurricane Hole Restaurant and Marina where you can explore kayaking, paddle boarding, and fishing excursions. Walk to some of Key West's best restaurants including Roostica, Hog Fish Bar and Grill, Chico’s Cantina, El Siboney, Croissant De France Bakery, and The Dolphin Deli.brbrKey West is the place to visit the lively nightlife and relax in the historic charm, flamboyance, and conch-style architecture that early Bahamian settlers made famous. It embodies a clash of the past and the present, and every building (including this rental) in Key West reflects this eclectic ambiance!brbrAvantStay provides a personalized hospitality experience to elevate your stay. With our Concierge Service, guests have access to our tech-enabled services like fridge stocking, private chefs, massages, transportation, special occasion celebrations, baby gear rentals, ski gear, beach gear, and more. For anything you need, we’re at your fingertips!brbr*Home Truths:*br- Pool heat is not available between 4/1 and 10/1.br- This home has access to a shared pool and is part of a gated community.br- This home also features a sleeper sofa in the downstairs living room.br- Any reservations 28 days or longer will require additional clean/cleans to be scheduled. Additional payment will be collected and the amount of cleans will depend on the length of your stay.br- All bookings 28 days or longer require a security deposit to be charged after booking.br- This home is on a monthly pest control schedule. The area of Key West is home to many insects such as termites, no-see-ums, and mosquitos. Pest control can not eliminate these insects during the swarming season. You may also encounter geckos, lizards, iguanas, frogs, and chickens during your stay in the area.br- Key West is a resort island where renovation of existing historic properties, new construction, and road repair sometimes occur without forewarning. AvantStay is not liable for any guest inconveniences caused due to construction in the area.br- Please note that if requested, the two twin beds can be converted into one king bed with bedding for a fee of $75. Please ensure you make this request at least 48 hours in advance.br- Please note that max occupancy includes infants.br- Please be advised that documentation may be necessary for ESA/service animals to gain entry.brbrPets:br- This home allows pets for a fee. If undisclosed pets are brought into the home without AvantStay's approval there is a fine of $500 per pet. br- We LOVE pets, however- Certain breeds typically have to have an additional owner or HOA approval. If your pet falls under any typical breed restrictions (breed, size, weight) please let us know so that we can confirm!brbrParking Details:brOff-street parking is available.brBoats, Jet Skis, buses, campers, trailers, motor homes, recreating vehicles, mobile homes, and commercial vehicles are notbrallowed to park on the association property (except for deliveries).brbr---brbrThe room configuration is as follows:brbrPrimary Bedroom / King bed brBedroom 2 / King bedbrBedroom 3 / Two twin bedsbrSleeper sofabrbr---brbrThis is a smoke-free property. Violation of the no-smoking policy will result in forfeiture of the security deposit, a $300 smoking fee, and liability for any fire or property damage costs.brbrAs part of our commitment to being good neighbors, occupancy limits and quiet hours (9pm-8am) are strictly enforced. No speakers or sound systems will be provided for use in our properties. Violation of any noise ordinances will be subject to fines that can reach up to $10,000 per violation. brbrEvents or parties are not allowed without prior written approval and an additional fee. Any unauthorized parties or events will be shut down and a fine will be assessed. Please inquire for more information about our event policies and fees. brbrThere is nothing more important to us at AvantStay than the health, safety, and experience of our guests & staff. We've enhanced our cleaning and sanitation protocols and are taking extra care to disinfect all surfaces between reservations with hospital-grade disinfecting solutions.brbrAs a reminder, we do work with 3rd party vendors to maintain the property, and although we adhere to the strictest CDC guidelines and advise all contractors to wear PPE equipment, we can not always enforce. We strongly advise guests to please deny access if any vendors fail to meet and adhere to these standards.brbrIDs will be requested for verification after booking. brbrWe report and prosecute all Credit Card Fraud.

Coral Palm by AvantStay | Key West Walkable| Gated Community & Shared Pool

Key West, Florida, United States

Bed

Bath

Sleeps

$748.14

Sunday to Sunday WEEK available to book. Limited Boat Slip available onsite. Must be reserved in advance after reservation is secured. $15. Daily Fee paid directly to Resort.brbrWelcome to your own private sanctuary, complete with old-fashioned screen-enclosed porches, gardens bursting with tropical flowers and crystal clear water views. All residences capture the light, airy look and feel of old Key West and come equipped with superior amenities and unmatched Hyatt service. With Key West’s famous galleries and restaurants just a short distance away, you can enjoy as much raucous celebration—or restful seclusion—as your heart desires.brbrBeachfront Beauty - Enjoy the privacy and privilege of your own white sandy beach, furnished with thick-cushioned chairs, picnic tables and barbeque grills. Soak up the sun or relax under a lush tropical palm tree and savor the warm breeze.brbrService Amenities - Complimentary parking; concierge services; in-room washer and dryer; child care; cribs and high chairs upon requestbrbrResidence Amenities - Luxurious 2-bedroom residences with private balcony; king-sized beds and spa tub in master suite; queen sized beds in guest bedroom; Wi-Fi and premium electronics throughout; fully equipped kitchen and dining area; sleeper sofa and much morebrbrResort Amenities - Beautiful plantation-style design creates an environment of relaxation and restoration; outdoor lagoon pool and spa tub; complimentary Wi-Fi throughout; privileges at nearby Hyatt Key West Resort & SpabrbrRecreation Amenities - Access Key West’s finest golf club, outdoor excursions and water activities. Your concierge will be happy to help you plan the perfect adventure.brbr*** The Coronavirus is considered a foreseeable risk. Covid Travel Insurance HIGHLY Recommended for your own protection and trip investment. Simply google Covid Travel Insurance for current available options ***

Hyatt Beach House Resort. Key West. 2 Bedroom. 2 Bathroom WEEK Stay.

Key West, Florida, United States

Bed

Bath

Sleeps

$325.13

The Poolside Studio Villa is a stand-alone Key West vacation rental that features full kitchen appliances and a sitting and sleeping area for two people. The privacy of our Villas, our thoughtful amenities, and our convenient location near Duval Street makes Key West Villas a refreshing alternative to run-of-the-mill hotels. Make your getaway to Key West, Florida!brbr* 1 Queen Bedbr* Sleeps up to 2 Peoplebr* Full Kitchen Appliancesbr* Shared Pool Deckbr* Flat Screen TV with Cablebr* Shared Heated Poolbr* Continental Breakfast Includedbr* Parking by Reservation ($15/night plus tax)br* 200 Feet from Duval Street

Poolside Studio Villa Steps from Duval!

Key West, Florida, United States

Bed

Bath

Sleeps

$617.63

We have the perfect accommodation for a family vacation or friends getaway in Old Town Key West, Florida. Our Two-Bedroom Poolside Villa has two bathrooms and features Dade County pine interior walls and floors with a gracious kitchen, dining area, and living room. This spacious vacation rental can accommodate up to six people, two in each of its two bedrooms and two additional people on a convertible sofa in the living room.brbr* 1 King, 1 Queen, 1 Queen Sleeper Sofabr* 2 Full Bathroomsbr* Sleeps up to 6 Peoplebr* Full Kitchen with Dining Areabr* Flat Screen TV with Cablebr* Shared Heated Poolbr* Continental Breakfast Includedbr* Parking by Reservation ($15/night plus tax)br* 200 Feet from Duval Street

Two Bedroom Two Bath Poolside Villa Steps from Duval!

Key West, Florida, United States

Bed

Bath

Sleeps

$617.63

The Two Bedroom Balcony Villa is a gracious two story Key West rental decorated in a tropical style with a living room, dining area, a luxurious kitchen, and two bathrooms. It can accommodate up to six people, two in each of its two bedrooms and two additional persons on a convertible sofa in the living room. Book a Key West getaway today!brbr* 1 King, 1 Queen, 1 Queen Sleeper Sofabr* 2 Full Bathroomsbr* Sleeps up to 6 Peoplebr* Continental Breakfast Includedbr* Full Kitchen with Dining Areabr* Shared Pool Deck and Private Balconybr* Flat Screen TV with Cablebr* Parking by Reservation ($15/night plus tax)br* 200 Feet from Duval Street

Two Bedroom Two Bath Balcony Villa Steps from Duval!

Key West, Florida, United States

Bed

Bath

6

Sleeps

Select Dates for Price

Hyatt Vacation Club at Windward Pointe!!! Located in Key West, this villa is a dream. With two cozy bedrooms featuring a king and a queen bed, guests can enjoy restful nights. The villa includes two bathrooms, one with a relaxing jetted bathtub. A nice living room offers a sofa bed, perfect for extra guests or lounging. Comfort is key here, with heating and air conditioning to keep the temperature just right. Whether you’re unwinding after a day of exploring or spending time with loved ones, this superb villa provides a perfect home base. We think our place will help you experience everything Key West has to offer.

Gorgeous 2-bedroom villa with AC in vibrant Key West

Key West, Florida, United States

Bed

Bath

6

Sleeps

$489.21

Experience modern island living at its most refined in this sleek two-bedroom villa on exclusive Sunset Key--a private island retreat designed for those who appreciate elegance, privacy, and comfort.brbrThe contemporary residence blends clean architectural lines with warm coastal sophistication. The open-concept first floor features cool tile floors, a full equipped modern kitchen, and a spacious living area designed for both relaxation and connection. Natural light floods the interior, while sliding glass doors open to multiple outdoor seating areas--perfect for morning coffee, sunset cocktails, or al fresco dining surrounded by lush tropical landscaping.brbrUpstairs, two well-appointed suites offer both comfort and privacy. The primary suite features a king bed, en suite bath, and direct access to the wraparound second-floor porch, where ocean breezes and palm views create an atmosphere of calm. The guest suite includes two queen beds, its own en suite bath, and shared access to the same panoramic porch--ideal for visiting family or friends. brbrLocated just steps from the resort's large pool, the villa offers all the conveniences of a world-class designation with the intimacy of a private residence. Whether you're hosting clients, working remotely, or taking time to recharge, you'll find every detail curation for elevated living: high-speed WiFi, a designated workstation with printer, and serene surroundings that inspire focus and creativity. brbrWith easy ferry access to Key West, yet the peace of a private island, this Sunset Key executive villa delivers the best of both worlds--a discreet escape where you can work brilliantly, live beautifully, and experience the rare luxury of true balance.brbr**Monthly rentals only. brbrAmenities:brbrExclusive Sunset Key Location--private island living just a 6-minute resort ferry ride from vibrant Key West.brbr24-Hour Island Ferry Access -- seamless, on-demand transportation to and from Key West for dining entertainment, or travel connections.brbrSleek Modern Design -- contemporary architecture with clean lines and open spaces.brbrTwo Luxury Bedroom Suites: the Primary Suite has a king bed, en suite bath and direct access to wraparound porch. The Guest Suite has two queen beds, private bath, and shared porch access.brbrExpansive Wraparound Porch--elegant second-floor veranda with ocean breezes and tropical views.brbrFully Equipped Gourmet Kitchen--includes double oven, side-by-side refrigerator, and full suite of modern appliances.brbrPropane Grill & Outdoor Dining Area--perfect for relaxed island evenings and entertaining guests.brbrSpacious Open-Concept Living Area--tiled floors, comfortable seating, and natural light throughout. Carpeted stairs and bedrooms for safety and noise control.brbrMultiple Outdoor Seating Spaces--shaded and sunlit options surrounded by lush landscaping.brbrSteps from the Resort Pool--enjoy access to a large resort-style pool just moments from your door.brbrHigh Speed WiFi and Dedicated Workspace with Printer--designed for executives who wish to stay connected while away.brbrResort Amenities--Access to private beaches and on-island dining.brbrOpal Key Resorts requires that a contract be signed for any island rentals. We will be happy to send you a contract prior to booking.

Modern Luxury Meets Island Privacy: Executive Villa on Exclusive Sunset Key

Key West, Florida, United States

Bed

Bath

Sleeps

$571.46

★Excellent Key West Location - Oceanside Resort - Two Bedroom - Two Bath - Sleeps 6br★Very Clean - Very Nice Property.brbrThis Oceanside two-bedroom condo features a primary bedroom with a king size bed, and adjoining bathroom with a walk-in shower and a relaxing jetted tub. The guest bedroom features a queen size bed and access to full guest bathroom. There is a living room with a sleeper sofa, TV and wi-fi access. The unit can accommodate up to six people. It features a full kitchen with granite countertops and appliances, including a full size refrigerator, stove-top burners, a microwave, a sink, a coffee maker, and a toaster. The condo also features a washer and dryer, for convenience.brbrCome and enjoy the outdoor accommodations, from sparkling infinity edge pool and jacuzzi, a shuffleboard court, pool, ping pong, foosball tables, a beach volleyball court, a restaurant, and concierge services right on site.brbrEnjoy the white sands of the world-famous Smathers Beach. Only 3 miles away is the famous Southernmost Point, old town Key West, and all the fun of Duval street. Just minutes away guests will find the Fort East Martello Museum, the Key West Aquarium, Mallory Square, world class fishing, and excellent restaurants.brbrROOM AMENITIES INCLUDE:br- Entertainment with complimentary Wi-Fi, phone, and premium TV channels, alarm clockbr- Kitchen with refrigerator, microwave, stove-top, oven, coffee/tea maker, toaster, sink, cookware, dishware, and utensilsbr- Shower; Jetted tubbr- In room climate control (air conditioning)br- Hair dryerbr- Iron/ironing boardbr- Separate sitting areabr- In room safebr- Sleeper sofabr- Portable cribs/pack 'n plays (available upon request)brbrPROPERTY AMENITIES INCLUDE:br- Luggage storagebr- Elevatorbr- ATMbr- Front deskbr- Pool and pool chairsbr- Laundry facilities in unitbr- Complimentary Wi-Fibr- Outdoor infinity-edge poolbr- Outdoor jacuzzibrbrProperty offers complimentary self parking.brNo recreational vehicle parking is permitted.brbrUnits are assigned at check-in. The unit's location, decor and view may vary. Room views need to be discussed ahead of booking. Room moves may be required with multiple week stays.brbr- Resort fee of $22.50/per day will be charged at check-in, along with a refundable $100 security deposit for incidentals (subject to change).brbrA split week fee of approximately $125 may apply for reservations shorter than one week. (Subject to Change).brbrThe resort will be undergoing an enhancement project from May 2026 to August 2026. During this time, guests may experience limited-view obstructions if located in building under renovation. Additionally, anticipate minor construction noise between the hours of 9AM to 5PM.brbrPlease note, there is no cash available at this resort and credit cards are the only acceptable form of payment.brbrWe do not accept liability for any inconveniences beyond our control including but not limited to temporary defects or outage of utilities, closures of resort amenities, or limitation of any other service. We will not provide refunds, reimbursements, or compensation for inconvenience or interruption of utilities, resort amenities, or any other service.

Oceanfront Property - 2BR/2BA - Near Smather's Beach - Poolside Bar and Grill

Key West, Florida, United States

Bed

Bath

Sleeps

$285.32

READ ADDITIONAL REVIEWS -Old Town -Whitehead St- BEST LOCATION -On Whitehead St. -Steps to Duval -Any discounts offered will be taken off price shown-will send special offer that you can accept or decline…Sleeps 7 Walk to new Truman Annex water park & Ft Zach Beach or FREE community pool 7-8 blocks..OUTSIDE SHOWER.. As seen in the March 2015 issue of Island Jane Magazine, this Hemingway inspired Villa sits on the Old Samaritan Hall site where they held lots of weddings! Such a good vibe! ( James Brown played here!!) This unique home w/ 10 ft ceilings offers lush private gardens on double lot, & plenty of off street parking. Hemingway's house, Lighthouse, mm0, Southernmost Pt, & Mallory Sq are all located right here! Duval is one block, Ft Zach beach is 2 blks- Water park and playground 2 blocks away near Coastguard Ship. Large free community pool blocks away. It is never crowded and overlooks the ocean. It is a monthly rental since we do not have a transient license to rent it out for less than 28 nights. ( 4 weeks) You can go in on the house with friends and family for the entire month and share the house. Please inquire if you have any questions. Thanks for considering staying at the Little Hemingway House! We look forward to accommodating you! brbrSee below for additional reviews. ( copied & pasted because guest reviews after 3 years are hidden) We especially love our repeat guests! (however they don’t leave additional reviews each year -but here’s what some had to say) brbr 5/5brGreat house & location can't be beat!brWe had a great time staying at the Little Hemingway House! The location is fantastic, so close to everything and yet still in a quiet section. We adopted a family of chickens out front - Mamma and her babies stayed with us almost the entire time. Brenda was super easy to work with, and answered every question we had lightning fast. We wouldn't hesitate to rent again - thanks so much for everything! Megan Pbrbrbr 5/5brExceeded Expectations...A lotbrLocation and Privacy. What a gem, located in the heart of everything Key West. One block from Blue Heaven restaurant, half a block off Duval and a short walk to Mallory Square. And amazingly the house is completely private with three off street parking spots two of which are behind a private gate solely for the house. Great gardens enable guests to have coffee and people watch while remaining secluded. Decorated with fantastic touch. We liked the house better and better each day and didn't want to leave. Finally 'little' is misrepresentative, the house has plenty of room with the two master suites and downstairs bedroom. You'll pinch yourself if you’re lucky enough to rent the Little Hemingway House. Can you tell we loved it ! Zach M

Villa 3 Bdrms/3 baths/close to everything/off st prking/Old Town/15% off Aug

Key West, Florida, United States

Bed

Bath

Sleeps

$1237.5

- Secret Villa II - brbrA Newly Renovated, Private Sanctuary, Centrally Located off of Duval Street with your very own private pool. Secret Villa II is available for rent exclusively on VRBO and HomeAway. We have recently completed a total update of the pool deck to match the beauty and size of her sister property, Secret Villa I. Please Note there is a Security Camera On the Front porch. Please Contact the Property Manager To Have It Disconnected if you Wish brbrSecret Villa II is the perfect vacation rental for discerning, upscale clientele. The property is a newly renovated 3BR, 3BA home with a heated pool situated in the heart of old town on a quiet and private lane. The fenced-in private pool is surrounded by lush gardens, natural vegetation, and tropical canopies, providing our guests with the privacy and intimacy that Key West visitors are looking for. Newly renovated inside and out so that you and your party experience Key West in a clean & comfortable environment where everything is just right.brbrIf you are looking for additional accommodations our sister property Secret Villa I is available in the same compound. Please see our VRBO listing #754594 for availability. br- The Location - brbrSVII is just 1.5 blocks from Key West's most famous party area - Duval Street! Enjoy the hustle and bustle of live music and world renowned restaurants, then you and your party can retire to SVII's private, fence enclosed sanctuary. brbrSVII is conveniently located on a private lane just off Simonton, between Southard and Fleming (just behind the Marquesa Hotel). It’s an extremely unique location for such a large Villa. SVII provides the convenience of being within walking distance to all the action Old Town has to offer, while still allowing guests to retreat to the sanctuary, a much more tranquil atmosphere that only a home on a quiet Key West lane can provide. Although a driveway is provided, most guests find they leave the keys at home and instead walk or bike to local attractions - fine dining, bars, galleries, nightlife, shopping, museums, and much, much more! And although the heated pool may encourage you to relax and sunbathe at home, three of the most popular Key West beaches are within a minute's bike ride.brbrPlease note - one mid-sized car or small SUV can comfortably fit in the driveway.brbr- Secret Villa II is a Healthy Environment Experience -brbrAnyone who has traveled in the tropics knows humidity is the enemy, quickly turning even elegant venues into musty unhealthy experiences. No matter how much a place is cleaned or overly scented with perfumes to hide the problem, the only way to have a healthy house is to address humidity and air quality head on!brbrAt Secret Villa II, the entire structure has been renovated including the air quality and air handling equipment. All furniture, draperies, mattresses, pillows and linens are clean and new. All duct work was either replaced or cleaned with eco-friendly antimicrobial agents. The HVAC system includes HEPA filtration and whole house dehumidification. The house has hurricane impact windows and doors that seal in the low humidity and HEPA-clean air making it pleasant throughout the entire house.brbrAlso while guests may smoke their Havana cigars out by the pool, we have a “No Smoking” policy inside the house. The result is an extraordinarily healthy environment where guests wake up feeling refreshed, energized, and ready to meet the day!brbr- The Accommodations -brbrAll SVII rooms are large and comfortable making the house a perfect getaway for 2 to 3 couples. The 2nd floor has 2 master bedrooms each with an en suite bathroom - one with a California King bed and the other with a King bed. The upstairs bedrooms share a large outside porch where guests can enjoy a late night glass of wine while watching the night sky and taking in a cool evening breeze. The first floor bedroom shares a bath with the living room and comes furnished with a Queen sized bed. The first floor bedroom is perfect for in-laws or grandparents that may be part of your vacation party.brbrAll beds have recently been updated with double pillow tops, ultra luxurious, extra firm mattresses. All bedrooms include extra soft, high thread count sheets with 6 pillows, a comforter, extra sheets, blankets, towels, dark make-up removing towels, a ceiling fan, black-out curtains, smoke detector, safe, and flat screen TV. Every convenience has been thought-of and added, including even small conveniences such as powerstrips with USB connections on both sides of the bed. Although designed for 3 couples, the living room also includes a full-sized pullout bed.brbr- The Private Pool -brbrOne of the highlights of this home is the private pool area. Fully fenced and surrounded by lush tropical greenery for safety and complete privacy, this will undoubtedly be a primary gathering place for your group. The comfortable chaise lounges can be pulled into the sun or the shade right beside the pool. Sun bathing can be on the upper terrace or poolside, and multiple pool towels are provided. brbrThe pool area includes a propane grill for an outdoor BBQ by the pool. Enjoy the view from the upper terrace that overlooks the rooftops and the trees of Old Town, or mix-up some much-deserved cocktails in the blender as you watch the rest of your group play in the pool and the burgers cook on the grill. br br- The Living Area & Kitchen - brbrSecret Villa II boasts an extra large living room with high ceilings and luxurious modern furnishings including a 60” LED HDTV with Disney+, Hulu, and ESPN. Secure high-speed internet with wifi is available throughout the property. Floor to ceiling double french doors allow natural light to pour into the first floor all day while blackout curtains provide privacy at night. A full complement of games are located in the credenza under the living room TV (i.e. Poker chip set and playing cards, Clue, Monopoly, Cards Against Humanity, Yahtzee, Scrabble, etc.). brbrAmateur and master chefs alike will love their cooking experience in the fully equipped and spacious kitchen. If you enjoy staying in and creating your own meals, every high-end modern kitchen appliance can be found right in the comfort of your vacation home. The kitchen includes state of the art appliances and all of the tools and utensils you will need to prepare a meal at home when taking a break from the restaurant options of Key West. Open shelving allows guests to easily select the right wine, beer, or cocktail glass for your own happy hour (blender provided!). The outdoor patio, accessible from either the kitchen or living room, has seating for eight. brbrConveniently located at the end of the kitchen is a state-of-the-art, over-sized washer and dryer, making laundry tasks quick, easy, and finished while you’re out and about enjoying the town. brbr- Summary -brbrSVII is more than fantastic – instead it’s actually JUST RIGHT! Newly renovated, clean, comfortable, spacious, private, lush, and centrally located. brbrSecret Villas Key West is proud to represent this paradise home and to provide you with the vacation experience you’ve always wanted and deserved.

Secret Villa II @ Old Town: with Private Pool, close to Duval!

Key West, Florida, United States

Bed

Bath

6

Sleeps

$1260.0

- Secret Villa I - brbrA Newly Renovated, Private Sanctuary, Centrally Located off of Duval Street with your very own private pool. Secret Villa I is available for rent exclusively on VRBO and HomeAway. We have recently completed a total update of the Secret Villa I kitchen and bathrooms to match the beauty of her sister property, Secret Villa II. Please Note there is a Security Camera On the Front porch. Please Contact the Property Manager To Have It Disconnected if you Wish brbrSecret Villa I is the perfect vacation rental for discerning, upscale clientele. The property is a newly renovated 3BR, 3BA home with a heated pool situated in the heart of old town on a quiet and private lane. The fenced-in private pool is surrounded by lush gardens, natural vegetation, and tropical canopies, providing our guests with the privacy and intimacy that Key West visitors are looking for. Newly renovated inside and out so that you and your party experience Key West in a clean & comfortable environment where everything is just right.brbrIf you are looking for additional accommodations our sister property Secret Villa II is available in the same compound. Please see our VRBO listing #692758 for availability. brbr- The Location - brbrSVI is just 1.5 blocks from Key West's most famous party area - Duval Street! Enjoy the hustle and bustle of live music and world renowned restaurants, then you and your party can retire to SVI's private, fence enclosed sanctuary. brbrSVI is conveniently located on a private lane just off Simonton, between Southard and Fleming (just behind the Marquesa Hotel). It’s an extremely unique location for such a large Villa. SVI provides the convenience of being within walking distance to all the action Old Town has to offer, while still allowing guests to retreat to the sanctuary, a much more tranquil atmosphere that only a home on a quiet Key West lane can provide. Although a driveway is provided, most guests find they leave the keys at home and instead walk or bike to local attractions - fine dining, bars, galleries, nightlife, shopping, museums, and much, much more! And although the heated pool may encourage you to relax and sunbathe at home, three of the most popular Key West beaches are within a minute's bike ride.brbrPlease note - one mid-sized car or small SUV can comfortably fit in the driveway. brbr- Secret Villa I is a Healthy Environment Experience -brbrAnyone who has traveled in the tropics knows humidity is the enemy, quickly turning even elegant venues into musty unhealthy experiences. No matter how much a place is cleaned or overly scented with perfumes to hide the problem, the only way to have a healthy house is to address humidity and air quality head on!brbrAt Secret Villa I, the entire structure has been renovated including the air quality and air handling equipment. All furniture, draperies, mattresses, pillows and linens are clean and new. All duct work was either replaced or cleaned with eco-friendly antimicrobial agents. The HVAC system includes HEPA filtration and whole house dehumidification. The house has hurricane impact windows and doors that seal in the low humidity and HEPA-clean air making it pleasant throughout the entire house.brbrAlso while guests may smoke their Havana cigars out by the pool, we have a “No Smoking” policy inside the house. The result is an extraordinarily healthy environment where guests wake up feeling refreshed, energized, and ready to meet the day!brbr- The Accommodations -brbrAll SVI rooms are large and comfortable making the house a perfect getaway for 2 to 3 couples. The 2nd floor has 2 master bedrooms each with an en suite bathroom - one with a California King bed and the other with a King bed. The upstairs bedrooms share a large outside porch where guests can enjoy a late night glass of wine while watching the night sky and taking in a cool evening breeze. The first floor bedroom shares a bath with the living room and comes furnished with a Queen sized bed. The first floor bedroom is perfect for in-laws or grandparents that may be part of your vacation party.brbrAll beds have recently been updated with double pillow tops, ultra luxurious, extra firm mattresses. All bedrooms include extra soft, high thread count sheets with 6 pillows, a comforter, extra sheets, blankets, towels, dark make-up removing towels, a ceiling fan, black-out curtains, smoke detector, safe, and flat screen TV. Every convenience has been thought-of and added, including even small conveniences such as powerstrips with USB connections on both sides of the bed. Although designed for 3 couples, the living room also includes a full-sized pullout bed.brbr- The Private Pool -brbrOne of the highlights of this home is the private pool area. Fully fenced and surrounded by lush tropical greenery for safety and complete privacy, this will undoubtedly be a primary gathering place for your group. The comfortable chaise lounges can be pulled into the sun or the shade right beside the pool. Sun bathing can be on the upper terrace or poolside, and multiple pool towels are provided. brbrThe pool area includes a propane grill for an outdoor BBQ by the pool. Enjoy the view from the upper terrace that overlooks the rooftops and the trees of Old Town, or mix-up some much-deserved cocktails in the blender as you watch the rest of your group play in the pool and the burgers cook on the grill. br br- The Living Area & Kitchen - brbrSecret Villa I boasts an extra large living room with high ceilings and luxurious modern furnishings including a 60” LED HDTV with Disney+, Hulu, and ESPN. Secure high-speed internet with wifi is available throughout the property. Floor to ceiling double french doors allow natural light to pour into the first floor all day while blackout curtains provide privacy at night. A full complement of games are located in the credenza under the living room TV (i.e. Poker chip set and playing cards, Clue, Monopoly, Cards Against Humanity, Yahtzee, Scrabble, etc.). brbrAmateur and master chefs alike will love their cooking experience in the fully equipped and spacious kitchen. If you enjoy staying in and creating your own meals, every high-end modern kitchen appliance can be found right in the comfort of your vacation home. The kitchen includes state of the art appliances and all of the tools and utensils you will need to prepare a meal at home when taking a break from the restaurant options of Key West. Open shelving allows guests to easily select the right wine, beer, or cocktail glass for your own happy hour (blender provided!). The outdoor patio, accessible from either the kitchen or living room, has seating for eight. brbrConveniently located at the end of the kitchen is a state-of-the-art, over-sized washer and dryer, making laundry tasks quick, easy, and finished while you’re out and about enjoying the town. brbr- Summary -brbrSVI is more than fantastic – instead it’s actually JUST RIGHT! Newly renovated, clean, comfortable, spacious, private, lush, and centrally located. brbrSecret Villas Key West is proud to represent this paradise home and to provide you with the vacation experience you’ve always wanted and deserved.

Secret Villa I @ Old Town with Private Pool, close to Duval!

Key West, Florida, United States

Bed

Bath

Sleeps

$379.38

Looking for where to stay in Key West, Florida Look no further! Our One Bedroom Loft Villa features a queen bed downstairs and a cozy lofted bedroom with another queen bed, a full kitchen with dining area, and a private porch. The Loft Villa can accommodate a total of four persons: two in the front room and two additional persons in the loft reached by a ships ladder. This villa is great for a Key West family vacation.brbr* Two Queen Bedsbr* Sleeps up to 4 Peoplebr* Full Kitchen with Dining Areabr* Private Porchbr* Shared Heated Poolbr* Continental Breakfast Included Dailybr* Flat Screen TV with Cablebr* Parking by Reservation ($15/night plus tax)br* 200 Feet from Duval Street

Loft Villa Steps from Duval!

Key West, Florida, United States

Bed

Bath

Sleeps

$417.13

Enjoy a wonderful Key West accommodation. brOur One Bedroom Deck Villa features a living room, a separate bedroom with king-sized bed, and a private deck. The unit also has a full kitchen with a separate dining area. It can accommodate a total of four persons: two in the private bedroom and two additional persons on a convertible sofa in the living room. Enjoy a fun filled Key West family vacation with us.brbr* 1 King Bed, 1 Queen Sleeper Sofabr* Sleeps up to 4 Peoplebr* Full Kitchen with Dining Areabr* Porch with Outdoor Seatingbr* Flat Screen TV with Cablebr* Shared Heated Poolbr* Continental Breakfast Includedbr* Parking by Reservation ($15/night plus tax)br* 200 feet from Duval Street

One Bedroom Deck Villa Steps from Duval!

Key West, Florida, United States

Bed

Bath

Sleeps

$316.13

The Poolside King Room is a hotel-style room adjacent to the pool. It can sleep up to four persons, two in the king-sized bed and an additional two on a convertible sofa. Our many Key West, FL vacation villas offer something for everyone!brbr* 1 King Bed, 1 Queen Sofa Sleeperbr* Sleeps up to 4 Peoplebr* Flat Screen TV with Cablebr* Shared Heated Poolbr* Continental Breakfast Includedbr* Parking by Reservation ($15/night plus tax)br* 200 Feet From Duval Street

Poolside King Room Steps from Duval!

Key West, Florida, United States

Bed

Bath

Sleeps

$284.63

The Poolside Queen Room is a hotel-style bedroom and bath unit that offers the amenities of our Key West villas for those travelers who do not need a suite or kitchen. With one queen-size bed, this accommodation is perfect for romantic vacations and weekend getaways for two.brbr* 1 Queen Bedbr* Sleeps up to 2 Peoplebr* Flat Screen TV with Cablebr* Shared Heated Poolbr* Continental Breakfast Includedbr* Parking by Reservation ($15/night plus tax)br* 200 Feet from Duval Street

Poolside Queen Room Steps from Duval!

Key West, Florida, United States

Bed

Bath

Sleeps

$1047.35

Zen Villa - A Luxe Retreat in the Heart of Old Key West! Tucked away on a quiet lane just steps from the vibrant heartbeat of Old Town, Zen Villa is where modern luxury meets island tranquility. Designed for those who crave both exhilaration and escape, this stunning contemporary retreat offers an effortless blend of indoor-outdoor living, lush tropical beauty, and refined elegance. Step inside to soaring 20-foot cathedral ceilings and an inviting lounge complete with a sleek wet bar, granite countertops, beverage cooler, and ice maker—because every great escape deserves a proper welcome. The open-concept living and dining areas flow seamlessly to multiple outdoor sanctuaries, framed by expansive sliding glass doors that invite Key West's natural beauty inside. Outside, the lush tropical landscape and Craig Reynolds-designed heated dipping pool with a cascading water feature, ambient lighting, and a refreshing outdoor shower set the scene for pure relaxation. Whether you're hosting under the stars or stealing a quiet moment in the sun, this tropical oasis delivers serenity at every turn. The first-floor primary suite is a spa-like haven, boasting a marble-clad en suite and indulgent steam shower. Upstairs, the second primary suite offers a private retreat with wide-plank hardwood floors, an en suite, and sliding glass doors leading to a covered porch and outdoor shower—the perfect spot for a slow morning or a sunset wind-down. A third (guest) bedroom features a day bed, soaking tub and a covered patio, ideal for unwinding in blissful solitude. All this, just moments from World-Famous Duval Street, the island's best restaurants, central shopping, and buzzing nightlife, as well as the sun-soaked shores of Fort Zachary Taylor Beach and Truman Waterfront Park. Zen Villa is more than a home—it's a lifestyle experience. A tranquil reprieve amidst the city's energy, waiting to welcome you in.

Zen Villa - A Luxurious 3-bedroom Sanctuary with WiFi & a Pool in Old Key West

Key West, Florida, United States