Key West Vacation Rentals
Guaranteed Bookings with 100% Protection
Easy Changes & Cancellation
24/7 Emergency Support
Craig M. VaycayHero Guest
"Booking with VaycayHero was easy. Any questions I had were responded to right away."
When you do not need the entire compound but still want to enjoy this magnificent property in the heart of Old Town Key West you can rent "Stars", the first level and apartment of the "Stars & Stripes" compound.
The first level offers a queen bedroom with armoire and flat screen, a full bath with claw tub and shower, and a twin room with armoire and flat screen (twins convert to a king). There is a gourmet kitchen and living room with sleeper sofa that accommodates and extra one to two guests.
The apartment is like having a separate suite for another couple as there is a small living room, kitchenette, full bath with shower tub/ combo and a queen bedroom. The apartment is located steps from the first level outside of the French door that lead to the main kitchen.
The compound's private, heated pool is shared by the other rental option called "Stripes" which includes the second and third levels of the main house. Please note, there is a cottage located behind the pool and within the grounds that is offered to other guests on a monthly basis. This cottage sleeps a maximum of four guests who also have access to the pool, grill and grounds. These guests do not have access tot he main house rental and vice versa.
Amenities include Gorgeous Renovation 2015, Gourmet Kitchen, Hardwood Floors (Level 1), Luxury Linens/ Towels, Flat Screen Tvs, Secure WiFi, Heated Pool (Shared with "Stripes" & Cottage), Washer/ Dryer, Toiletries, Starter Kit, Mitsubishi Wall, AC Units, Wall AC (Apartment), Amazing Location, Hair Dryer in all Baths, Iron/ Board, Gas Grill, Gourmet Kitchen.Key West
Perfect apartment located in Old Town in the desired Casa Marina District. Totaling one bedroom, one bathroom, plus off street parking. Enjoy a comfortable, cozy floor plan with an open kitchen and living room that flows wonderfully into the master king bedroom and outside to the pool. Enjoy the view of the pool and lush landscaping from your back porch while enjoying the sun!
Master king bedroom with two closets and a lovely view of the pool. For renters who like having visitors, there is a queen sofa bed in the living room. The kitchen is located between the master king bedroom and the living room, so it’s a perfect divider when you have company. Great for one couples with weekend guests or a family with young children.
The apartment is located inside a grand Key West home on the first floor off United Street near to the Southernmost Point of the U.S! The living room is located in the front of the unit, the kitchen in the middle, and master bedroom in the rear. The living room is painted a soft yellow color that lifts the room yet feels very relaxed. Touches of tropical décor throughout with modern accents. The kitchen is bright and open, perfect for visiting or entertaining while you cook! Kitchen is fully equipped for all of your cooking needs with beautiful, white granite counter tops and stainless steel appliances (with the exception of the microwave). The washer and dryer are also located in the kitchen, convenient and discrete. A few steps down the hallway, is a updated bathroom with a stand up shower. Plenty of storage for all of your toiletries and the vanity has nice, bright lighting for all of your “vanity” needs. Just past the bathroom, is the master king bedroom with two closets and French doors that lead to the back porch and pool. Both bedroom and living room are equipped with a flat screen.
Amenities include Off Street parking spot, Secure WiFi, Equipped Kitchen, Casa Marina District bordering Old Town Location, Granite Counters, Iron/ Board, Stainless Appliances (except microwave), Linens & Towels Provided, 1 Full Bath, Central AC, Washer/ Dryer, Coffee Maker, Flat Screen TVs, Private Porch, Heated Community Pool.Key West
This Adorable Conch Cottage is a “Stone’s Throw” from everything that Key West has to offer! Literally steps away from Duval Street, Hemingway House, Blue Heaven, Sixed Toed Cat, the Lighthouse, and the Beach. As you enter this newly refurbished two bedroom/two bath cottage, you will be greeted with fun décor and modern amenities including beautiful hardwood floors, granite countertops, stainless steel appliances, and tiled baths. Directly out from your back patio door is a beautiful pool and waterfall. Although, this area is “shared”, it seems like your own quiet piece of paradise with little to no traffic.
Main Floor: King Bedroom with bath, custom kitchen, living room, outdoor entertaining space and perfect porch! Second Floor: Queen Bedroom with in suite bath overlooking the tropical pool area. Relax in comfort with fresh, crisp hotel style linens.
Amenities include Central AC, Cable & Flat Screens, Secure Wifi, Iron/ Board, Non-Smoking, Children Welcome, Toiletries - Starter Kit, Linens & Towels, Beach Towels, Equipped Kitchen, Ceiling Fans, Alarm Clock, Heated Community Pool, Hairdryers, Viewing Balcony, Front Porch, Back Patio, Washer/ Dryer, Sound System, DVD Player, Stainless Steel Appliances, Granite Countertops, Updated Marble Baths.Key West
This property has it all! The styling of the original shot gun homes of Key West restored with a beautiful natural cypress exterior combines with the clean lines of a contemporary home. Each Twin opens to it's own semi-private deck and lounge area with steps into a large kidney shaped pool with waterfall. Inside the comfortable living room has a spiral staircase to the loft second bedroom with unique glass railing.
Large windows in the kitchen bi-fold away to allow serving directly to the pool deck and capture the warm, tropical, Key West breezes. If cooking isn't for you on your vacation, stop by the Banana Cafe Restaurant or the Coffee and Tea house right next door. Rent this property as a two bedroom/one bath or add Pete's East Cottage for a four bedroom/ two bath.
Amenities include Central Air, Air Conditioning, Ceiling Fans, High Speed Internet, Patio, Shared Pool.
Bed Configuration: Bedroom 1: Queen | Bedroom 2: Queen.
Location Distance: Camille's Restaurant: 0.07 mi | Ambrosia Sushi: 0.20 mi | Blue Heaven: 0.39 mi | Flaming Buoy Filet Co.: 0.39 mi | Santiago's Bodega: 0.43 mi | Antonia's: 0.46 mi | The Green Parrot Bar: 0.49 mi | Sarabeth's: 0.51 mi | 2 Cents: 0.52 mi | Michael's: 0.61 mi | Azur Mediterranean Cafe: 0.75 mi | Danger Charters: 0.95 mi.
Loved location, nice pool, first night air did not work, was fixed next day and we were compensated for our uncomfortable first night. Circular stairs great for younger people...very clean. If you want to be near the action this is it. Would come again.Key West
Quintessential Key West vacation home leaving nothing more to be desired. Framed by a white picket fence you will be welcomed to this classic 2 story with double porches perfect for enjoying the island breeze. Beautifully landscaped with fabulous flowering tropical foliage. Caribbean decor and a graceful open floor plan to covered porches, brick patio, lagoon shaped, heated salt water pool and outdoor dining.
Everyone will enjoy the well appointed and spacious kitchen with gourmet cooking details and gorgeous serve ware. Full en suite baths in each of the 3 bedrooms privately located on the 2nd and 3rd floor. You will simply marvel at all of the extras from decorative details, flat screen T.V.'s & IPod docking stations in each bedroom, fabulous BBQ grill, and covered off street parking. Walking distance from famous Duval Street, dining and beaches, you won't miss a thing from this central location.
The best of both worlds located directly between Historic Old Town and the Casa Marina District, just 4 short blocks from Famous Duval Street and 5 blocks from the Southernmost Point of the U.S. The White Street Gallery District is a short walk away where you will find Fausto's Food Palace, a gourmet grocery, Cuban Coffee Shops and several delightful Galleries, Cafe's and a bakery. Also within walking distance is the popular White Street Pier providing a perfect stroll to the water's edge or catch the bike and walking path that follows the perimeter of the island. There are a variety of neighborhood restaurants and waterfront dining in the area or find your way to the Historic Seaport, Old Town or Duval Street with about a 5-10 minute walk or convenient bike ride.
Amenities include Lagoon Shaped - Heated Salt Water Pool, Wireless Internet Access, Gym Equipment Available, Fully Fenced, Spacious Carport, Great Walking/Bike Area, Linens & Towels provided, Basic toiletries, Air-conditioning, Washing/Dryer, Coffee maker, Dishwasher, Iron & board, TV's, Large covered porches.Key West
When you do not need the entire compound but still want to enjoy this magnificent property in the heart of Old Town Key West you can rent "Stripes", the second and third levels of the "Stars & Stripes" compound.
The second level offers a living room, dining for eight where one four top table is located inside and the other four top table is outside on the balcony. There is a full gourmet kitchen and a large bathroom with walk-in shower. The bedrooms includes a queen room, twin room and a trundle bunk perfect for a kids room! The trundle has a twin bunk, double bottom mattress and a twin trundle so four guests can occupy this sleeping space.There is also a sleeper sofa in the living room that can accommodate an extra one to two guests.
The third floor offers a comfortable living room with flat screen and a full bath with a shower/ tub combo. The bedroom has a full-sized mattress on the left and a twin bed on the right. The couch in the living room turns into a sleeper sofa for an extra one to two guests.
The compound's private, heated pool is shared by the other rental option called "Stars" which includes the first level of the main house and the apartment. Please note, there is a cottage located behind the pool and within the grounds that is offered to other guests on a monthly basis. This cottage sleeps a maximum of four guests who also have access to the pool, grill and grounds. These guests do not have access tot he main house rental and vice versa.
Amenities include Full Kitchen, Hardwood Floors, Luxury Linens/ Towels, Flat Screen TVs, Secure WiFi, Heated Pool (Shared with "Stars"), Washer/ Dryer, Toiletries Starter Kit, Mitsubishi Wall AC Units, Amazing Location, Hair Dryer in all Baths, Iron/ Board, Gas Grill.Key West
This two bedroom condo is close to the airport, beaches, restaurants and minutes away from Duval. Warm and welcoming condominium in a quiet gated waterfront community. The open floor plan overlooks the lush gardens with sliding glass doors leading to the expansive patio surrounded by lush tropical landscape with a hint of ocean view in the distance.
This nautical home has all the quaint decor suited for a life at sea. Perfect for a family getaway in this cozy condo. The glass dining room table can seat six and the two comfortable couches are great for watching a movie or playing a board game. King bedroom and guest room with a queen size bed. Family room has a queen sized pull out couch. Perfect setting for families, or couples traveling with friends.
Two spacious bedrooms and two full baths including a sunken tub with jets and dressing vanity offer plenty of room for everyone. There is a comfortable, queen-sized sleeper sofa for extra guests, a well equipped eat-in kitchen with seating for 4, bright and airy dining room and outdoor dining under the stars.
Balmy ocean breezes and sounds of the sea surround you at this great oceanfront condo. Community amenities include a private beach, swimming pool and tennis courts plus your own covered parking spot in the garage.
Amenities include Cable & Flat Screens, Iron/ Board, Toiletries - Starter Kit, Elevator Access, Linens & Towels, Beach Towels, Ceiling Fans, Alarm Clocks, Large Community Pool, Hairdryers, Tile Flooring, Secure WiFi, Garage Parking Space, Additional Off-Street Parking, Well Equipped Kitchen, Great Walking/Bike Area, Basic Toiletries Starter Kit, Central AC, Washer/Dryer, Coffee Maker, Dishwasher, Covered Balcony, Lush Garden Views, Picnic Area, Beach Access, Community Grills, Community Hot Tub.Key West
Tortoise Shell II is an elegant two bedroom, 2 bath condominium one block off of famous Duval Street. Second floor unit with tree top views of lush landscape from the private balcony overlooking Caroline Street. Located in the hear of Old Town, you are steps away from the Key West Bight, Duval Street, and some of Key West's best restaurants and shopping.
Designer furnishings, hardwood floors , marble counters and antique glass windows. High ceilings and natural lighting throughout the living area and lofted bedroom. Sit on the deck and relax or head down to the common area in the back of the home. Enjoy the heated pool or lounge with a cocktail. You are just a block away from taking a sunset cruise on Sebago Watersports or setting sail on one of the historic schooners.
Amenities include Secure Wifi, Updated Kitchen & Baths, Great Walking/ Bike Area, Granite Counters, Hardwood Floors, Designer Decorated, Twins Convert to King, Heated Community Pool, Linens & Towels, Central AC, Washer/ Dryer, Coffee maker, Flat Screen TVs,
Large Covered Porch.Key West
Private one bedroom cottage on Simonton Street one block from Duval. Totaling one bedroom, one bathroom with an open kitchen & dining area, plus a living room. This home is perfect for one or two couples. Sit on the front porch and watch the people flow by and enjoy the morning sun or an evening cocktail.
Peaceful colors throughout with nautical décor add a nice tropical feel to the cottage. Feel like your relaxed and in the tropics whether indoors or out. Although this is a one-bedroom cottage, it feels spacious due to the beautiful wood vaulted ceilings in the living room and kitchen, and nice high ceilings in the bedroom. Hardwood floors throughout and plenty of windows for natural sunlight. There is a fully equipped kitchen that is open to the dining room, great for visiting while cooking and a beautiful, newly renovated full bath with stand up shower conveniently located in the middle of the home.
Queen bedroom in the front of the cottage beyond the living area with it’s own private entrance. Sleeper sofa in the living room also with it’s own private entrance to accommodate the second couple or overnight guests. This home is perfect for a couple’s getaway that may have visitors or 2 couples sharing.
Amenities include Walking Distance to Duval, Cable & Flat Screen TVs, Secure Wifi, Iron/ Board, Non-Smoking, Sleeper Sofa, Children Welcome, Pets Considered, Washer/ Dryer Outside, Toiletries - Starter Kit, Linens & Towels, Beach Towels, Equipped Kitchen, Ceiling Fans, Hairdryer, Hardwood Flooring, Tiled Bath - Stand-Up Shower.
Great Location just one block from Duval. Nicely decorated historical home, everything you need to make your stay feel at home. Definitely would recommend highly! JanKey West
This newly renovated two bedroom condo is located in The Shipyard, a neighborhood of Truman Annex in the heart of Old Town Key West! Colorful, fun patterns fill the rental with life while the furnishings provide a comfortable gathering space for your group. The sunny deck overlooks the distance views of the ocean through the lush trees but can also be a shady retreat with the help of the adjustable awning.
The Quarterdeck’s open floor plan and ample seating provides the perfect space for your group to enjoy together. Curl up on the couch and watch a movie on the flat screen, gather around the dining table to play a game or cook together in the fully equipped kitchen!
Both guest rooms have a comfortable queen bed with extra drawers built into the bed frames for maximum storage space! Each room has a closet with lots of hanging space a flat screen TV, and new carpet and paint for a fresh, clean feel. The living room offers a sleeper sofa that can accommodate an additional two guests.
Open the French doors to the back deck letting in the great breezes and sunrays that fill the space throughout the day. This wonderful extension to the living space has a table for two where you can have your morning coffee or enjoy a cocktail after a long day of exploring. On hot summer days pull out the awning to push back the sun so you can enjoy the views without sitting in the direct sunlight.
Amenities include Wifi, washer/ Dryer, Iron/ Board, Flat Screen TV, Cable, Community Pool, Linens/ Towel Provided, Equipped Kitchen, Balcony, 2nd Floor Unit, Designated Parking Spot, Gated Community, Old Town Location (The Shipyard in Truman Annex).Key West
When only the best will do! The Seashell is the classic Old Town Key West home. Perfect setting for your dream island vacation. This beautifully landscaped home with gracious sitting porch awaits you and your family. Newly renovated master bedroom and bath are located on the main floor as well as a guest room with bath. A spacious great room that flows to the porches, pool and great outdoor space allows for family gatherings and hours of entertaining.
Updated kitchen looks over Sawyer Lane and opens to the pool area for easy outdoor dining.
Lovely Dade County Pine floors throughout and plenty of natural Key West sunshine from the many windows and doors. The second floor has a bonus room featuring bedroom, bath, office and rooftop sun deck.
Amenities include Covered Porches, Driveway 1-2 Vehicles, Main floor Master Suite, Premier Old Town Location, Heated Pool with Waterfall Feature, Multiple Zone Sonos Sound System, Secure Wifi, Flat Screens in all Bedrooms, Granite, Tile and Stainless, Spacious Office, Widows Walk, Alarm System, Linens & Towels Provided.Key West
This ground floor unit is conveniently located near the sunny swimming pool and offers a private covered patio framed with bright bougainvillea. Upon entering you are greeted by a wave of calm turquoise amidst chic beach decor and soaring ceilings.
Dine in the spacious, open living / dining area with seating for 6 at the dining table or well appointed kitchen with stainless appliance package and bar offering additional seating.
Slumber in the downstairs cheerful coral master bedroom with a sparkling white en suite bath and glass enclosed shower or upstairs in the lofted bamboo bedroom with soothing natural light and clever architectural details. Play like a child on summer vacation in this home equipped with all you will need to unwind plus off street parking for one car at your back door.
Amenities include Hardwood Floors, Updated Kitchen & Baths, Well Equipped Kitchen, Close to Duval Street, Kurig Coffee/ Tea Maker, Great walking/Bike Area, Assigned Parking, Secured Wi-Fi, Linens & Towels, Basic toiletries, Air-conditioning, Washing/ Dryer, Coffee maker, Dish Washer, Iron & board, TVs, Private Patio, Heated Community Pool.Key West
This private, two bedroom cottage is the perfect place to unwind for a couple or a small family. Sliding glass doors create a serene indoor-outdoor living space where you can listen to the fountain feature and the songs of the birds. The Meadows is a quiet neighborhood with peaceful streets, great for taking long walks to view the beautiful homes and tropical foliage.
Parrtodise has a completely updated interior offering a custom, modern décor blended with comfortable furnishings and soothing tropical colors. Downstairs you will find a master suite that faces the front porch and overlooks the garden. The suite features a king bed with luxury linens, a flat screen TV and an en suite bath. The master bath has sleek, hidden cabinets offering great storage for hanging clothes, towels and toiletries. Wind up the spiral staircase to the guest suite, equipped with two twin beds, a flat screen TV, en suite bath and viewing balcony that overlooks the backyard garden. This space welcomes your guests and children age fifteen and older.
An open floor plan brings you together to relax, cook or dine in the great room which is saturated with natural light flowing through the large glass windows that open up to the back garden. Guests who enjoy cooking will love the custom kitchen designed by the owner. The sleek, gray cabinetry is fraught with all the cooking essentials you might need. You can spread out your ingredients on the spacious quartz counter tops and let the quality, stainless steel appliances assist in your culinary pursuits.
The “icing” on this tropical treat is the details: wood floors, tiled baths and comfortable island-style furniture harmonizing the home’s décor. A secure Wifi connection, local home phone line, and multiple flat screen TVs offer our guests the technology they need to stay in touch with the ‘real world’ while they enjoy island life! Parking is always scarce in Key West, but the Meadow’s quiet streets are separated from the busy, tourist areas and provide ample street parking!
Escape to the back porch where you can unwind and leave the stresses of life behind. Sunbathe on the lounge chair while listening to the trickling water from the fountain and the breeze flowing through the palms. This open space lets the sunrays in while lush, tropical plants surround the area with privacy. A dining table for four provides a beautiful place to share meals together or play cards.
Amenities include Cable, Internet, Wi-Fi, Flat Screens, Washer/Dryer, Stainless Appliances, Wood Floors, Front Porch, Back Patio with Fountain Feature.Key West
This pet friendly Old Town Key West home is just steps from the award winning restaurants and charming boutiques of Petronia Street in historic Bahama Village. The Village Rooster greets you with a charming front porch and quaint entry.
Village Rooster boasts an open living area and spacious kitchen plus two bedrooms and 2 fulls baths. The spacious back deck is a perfect place to read a book and relax in one of the lounge chairs. Or you can easily entertain and grill under the covered porch. End the evening with a dip in the hot tub.
This property is truly walking distance to anything Old Town has to offer. You are just around the corner from the famous Southernmost Point, Hemingway House, Duval Street, Lighthouse Museum, Beaches, amazing restaurants and local boutiques.
Amenities include Air Conditioning, Cable & Flat Screens, Secure Wifi, Non-Smoking, Iron/ Board, Children Welcome, Toiletries - Starter Kit, Linens & Towels, Beach Towels, Equipped Kitchen, Parking - 1 Compact, Ceiling Fans, Alarm Clock, Hot Tub, Hairdryer, Porch/ Lanai/ Balcony, Washer/ Dryer, Hardwood Flooring, Pet Friendly.Key West