Vacation Rentals By Owner In Key West, FL

$192.25

A Conch Escape at The Truman Annex in Key West

Key West, Florida, United States

Location, location, adorable two bedroom, one bath second floor condo overlooking the Truman Waterfront Park is the perfect Key West getaway!brRecently updated kitchen includes stainless steel appliances, tons of cooking and serving and prep utensils, everything you will need to dine in!brThe living room and dining rooms are combined with lovely views through the rear French doors to the rear private porch which is the perfect place to enjoy your morning coffee or an evening beverage. brOne bedroom features a queen bed, while the other bedroom has twin beds that can also be converted to a king at your request. There is a beautiful full bathroom which is convenient to both bedrooms and right across from the laundry center.brThis terrific property also offers an assigned off street parking space, central ac and all towels and linens, including beach towels.brCome and enjoy Key West in this little gem soon!brPlease note: This property is monthly rental - the minimum rental period is 28 nights

2

Bed

1

Bath

4

Sleeps

$195.08

/ Nightly

Condo

Ocean Oasis at Sunset Marina-2 bed 2 bath oceanfront condo w/boat slip rental

Key West, Florida, United States

AGE REQUIREMENT:brEveryone must be 25 years or older. Families are welcome as long as children are accompanied with their parents and primary renters are 25 years or older. We do not accommodate bachelor parties, bachelorette parties, student groups or construction workers-NO EXCEPTIONSbrbrThis property is a 28 night minimum. Boat slips available for rent! Inquire with us. brbrFEATURES:brBedrooms: 2 (1 king and 1 queen)brBathrooms: 2brLocation: Sunset Marina Gated CommunitybrSquare Feet: 1171brParking: 1 assigned covered parking space (NO ELECTRIC VEHICLES/SCOOTERS/BIKES ALLOWED)brAmenities: Wifi, TVs, in-unit laundry, balcony, shared pool, near the golf course, boat slip availablebrbrbrTHINGS TO KNOW: brRestrictions/Rules: No smoking. No Pets.brbrCheck in: 4PM - We do not guarantee an early check in request will be granted because we need to give the housekeepers time to ready the units for check-in, however, should your unit be ready early, we will notify you from this number that you can check-in. No units will be able to accommodate a check-in earlier than 12pm. brbrCheck out: 10AM - We do not accommodate late check outs. brbrItems provided: All linens, bath towels and beach towels are provided for your convenience. You are provided an initial supply of bath soap, dish washing liquid, toilet paper, laundry detergent and paper towels. Additional supplies are the responsibility of the renter, or once the initial supply is used.

Bed

Bath

Sleeps

$1504.94

/ Nightly

Private Vacation Home

Tropical Tranquility - 4BR Luxury Villa In Old Town Key West w Pool

Key West, Florida, United States

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. Extraordinarily secluded and completely hidden from view on a sleepy artist's lane, Tropical ~ Tranquility vacation rental is a special slice of Key West you would never find on your own. While most of the colorful cottages along this charming Old Town lane face right up to the curb, commanding immediate attention, the gated entrance to this authentic Caribbean resort-style property is set back off the lane and masterfully camouflaged.brbrGrounds: From the moment you step inside the property gate you'll feel as though you've entered a world all your own. All human senses are immediately redirected to a different perception and the winding down to island-time begins. First the meandering brick path, lined with mature tropical landscaping, comes to view and leads through an impressive manicured garden. Visuals become simultaneously dramatic and tranquil with the spacious free-form black bottom pool that possesses the prettiest elements of a peaceful natural lagoon. Next you are treated to the serene sound of a trickling waterfall that gently spills to the pool. Walk past the lagoon, and the brick pathway widens way out to become an open spacious courtyard where you enjoy more tropical trees and flowers which, depending on the time of year, produce a sensual floral fragrance. At this point the stresses of everyday life seem to gently float away and you know you're in your own little piece of paradise.brbrInterior Layout: Your focus now naturally turns to the house itself which displays the most authentic and romantic elements of Key West's historic architecture while simultaneously offering all of the most tranquil attributes of a traditional Caribbean resort-style villa. In order to enlarge the house and create the privacy he envisioned, the owner began by purchasing and annexing the next door property thereby lending ample room for the spacious garden and new lagoon swimming pool. A tall fence built across the front of the property served to camouflage the house and also created off-street parking for two cars. The next task was to repair and then re-define the original shot-gun cottage so as to incorporate it into the visualization designs of a spacious villa.brbrBedrooms and Bathrooms: In its grand new form as a villa most of the original little cottage structure was re-invented as the master bedroom. Located at the far left of the villa (as you face it) it is situated to offer maximum privacy and now stands with a vaulted cathedral ceiling, wood flooring, a spacious en-suite master bathroom, and double French doors leading to a charming private deck and garden ideal for sipping morning coffee and evening champagne. Furnishings are soft and sophisticated and it is beautifully appointed with original artwork and a king size bed.brbrA light-filled hallway off the master bedroom serves as a wing connecting three of the bedrooms to the rest of the villa. Skylights and transom lights over the bedroom doors invite the sunshine into the long hallway which leads the way to bedrooms two and three, the second bathroom, and the laundry center; bedrooms and full bathroom are on one side of the hall and the laundry center on the other.brbrMoving up the hall, the next room is the second bedroom which is filled with window light and a view of the pool garden. This room offers pretty tropical bamboo furnishings, original wall art work, and a queen size bed. Just past this room up the hall is a full bathroom that is conveniently situated between the second and third bedrooms and serves as their shared bath.brbrThe next room up the hall is bedroom number three. Furnished and appointed in a similar pretty d ecor as the second bedroom, this room offers two twin beds (which can be pushed together to make a king size bed). This light filled room also offers beautiful pool garden views. As you continue up the hallway you find a conveniently located power room (half-bath) just to your left.brbrKitchen / Dining / Living Room: At the end of the long hallway French doors seamlessly adjoin a pavilion style building that was created to house an elegant Scandinavian style cooking center. Light pickled wood walls, white counter tops, open kitchen shelving, and vaulted ceilings with elegant lighting make a beautiful statement. Situated at the center of the home this kitchen really is the hub of the house and the natural place to gather. A wide center cook's island with a gas cook top is placed on the side of the island closest to kitchen sink. Bar stools are set on the other side of the cook's island so friends and family can chat with the cook during meal preparation. A round dining table is set in a pavilion style loggia that is joined to the garden with more French doors so as to facilitate the pleasure of indoor-outdoor dining to the maximum. Like the kitchen this beautiful dining area has dramatic vaulted ceilings just lightly pickled to show the wood grain. The unique round marble top dining table is a unique piece the owner purchased in Bali.brbrAt this point in the villa, both the indoor cooking center and pavilion dining area intersect with the expansive and elegant living room / music room. Graceful furnishings are a European and sophisticated Caribbean blend and are thoughtfully placed to invite guests to lounge and visit, curl up with a good read, sit and play the piano, or watch TV. Light wood floors, vaulted ceilings, and multiple windows invite in the light and French doors open up to the pool garden to bring the outdoors in with an effortless style. An expansive covered wooden porch is trimmed with capital-topped porch posts and appointed with stylized recessed ceiling lighting. Teak chairs and a porch swing entice everyone to sit outside and take in the pool garden ambience.brbrPrivate Guest Cottage: As we complete our tour of this phenomenal villa we finally arrive to the private free-standing Caribbean design guest cottage. This building is situated just within a few feet of the living room, close but completely separate. This cottage serves as the fourth bedroom to the villa. It has a king size bed and offers the most privacy of all. The front entrance to the private guest cottage is turned to face the brick courtyard so the lagoon pool is always in view and just steps away. Ceilings are vaulted up to meet the hip-roof line to optimize air flow. When the French doors are opened the tropical breezes easily flow through to maximize open-air island living. The cottage has its own private covered sitting porch that mirrors the style of the next door living room porch described above. Consistent with the rest of the home the beautiful furnishings for this free-standing cottage are soft, elegant, and sophisticated and the walls are decorated with original art work. A private spacious en-suite bathroom is set to the left side of the cottage as you face the front.brbrUltimate International Island Resort Home: The overall style and design of the Tropical ~ Tranquility villa reflect the unique vision of the worldly Scandinavian artist-owner to create the ultimate Key West - Caribbean - European villa that flawlessly blends the indoors with the garden. French doors leading to covered porches, soaring vaulted ceilings, and ceiling fans make it comfortable to enjoy the open air island green life style. While the villa does have two central a/c units, the forward thinking environmental design of this home allows you to enjoy life without a/c on most days.brbrAn original art collection from local Key West artists and Scandinavian artists graces every room. Furniture and wall colors are soft and neutral to enhance the tranquil feel of the home; most of the color is provided from bright tropical flowers in the garden.brbrAmenities: Large lagoon style swimming pool with trickling waterfall, expansive bricked courtyard with mature palm garden and manicured tropical garden, privacy fences. Fully equipped kitchen, a/c, telephone, piano, TV, stereo, washer / dryer. Linens and towels are provided.brbrParking: Private off street parking for one to two cars maximum. From this location you do not need a car. Enjoy walking or biking everywhere-you'll see more that way.brbrActivities: Heart of Old Town Key West in designated historic district. Walk to all old town features, no need for a car. Close to shopping, art galleries, and variety of national and international restaurants, coffee shops. Sailing, boating, diving, museums, nightlife are within easy walking distance. Just a short walk to the charmingLittle Pearl restaurant at Elizabeth and Olivia Streets. Explore the fascinating Historic Key West Cemetary, just one block over. And check out the legendary Grotto at Saint Mary's Basillica one block in the other direction.brbrRestrictions: Smoke free house. Smoking permitted outside only. Absolutely no pets please. We do not accept guests less than 25 years of age unless accompanied by a family group or guardian.brbrNotes: The elegance and design of this home make it ideal for sophisticated individuals with discerning tastes and is best suited for a family or executive group looking for the very finest Key West has to offer in a truly authentic home with 5-Star Quality amenities. It should never be considered as an option for travelers looking to stage a party or any kind of event.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.brPARKING: There is parking for 2 cars maximum at Tropical Tranquility, at 824 Johnson Lane. Parking is on a bricked parking space in front of the tall wooden fence. Please do not park more than two vehicles

Bed

Bath

Sleeps

$350.04

/ Nightly

Private Vacation Home

Luxurious monthly rental in mid-town

Key West, Florida, United States

28 Day minimum Rental: Secured behind a contemporary privacy fence and an attractive cobblestone driveway is this hidden jewel of a 3 bedroom, 3 bathroom home in mid-town Key West. Located just a few short blocks from the beach and not far from Duval Street, this home is the perfect spot for your extended vacation.brbrAs you enter, the wide-open living space is calm and inviting, offering a clear view to the back garden. The open, well-appointed kitchen is accented with blonde wood cabinets and modern granite countertops. Recessed lighting, colorful artwork and a dramatic tray-ceiling compliment the inviting living area. Open the sliding doors wide to experience true Key West indoor-outdoor living.brbrThe master bedroom features a large ensuite bathroom and sliding doors that lead out to the pool and hot tub. Luxuriate in the large, private outdoor shower just outside the door. Two additional bedrooms feature queen sized beds and baths of their own.brbrOutside, the large, turquoise pool and raised hot tub beckon you to relax and unwind. Lush landscaping and large, mature palm trees sway overhead in the tropical breeze as you lay back and enjoy your extended vacation in paradise.brbrBedding: 2 King, 1 QueensbrOff Street Parking

Bed

Bath

Sleeps

$450.76

/ Nightly

Condo

A Sunset & Harbour View at The Truman Annex in Key West

Key West, Florida, United States

Exceptional accommodations, spectacular location and first class amenities await you and your group! This two bedroom, two bath condo boasts of views of passing ships and sunsets from your own deck or balcony in the Truman Annex's most prestigious building, the former U.S. Naval Administration Building in Key West. Take in the sunshine from the lap pool overlooking the ever-changing waterfront. Stroll out the private gates and you're at the harbor, just steps from the sights and sounds of Mallory Square, downtown tourist attractions, Key West's best beaches, and Old Town's fabulous restaurants. This condo features a 60; HDTV in the living room, washer/dryer, pots, pans, towels, linens, and central air conditioning. Covered off street parking for one vehicle is provided.brPlease note: This property has a 28 night minimum stay

Bed

Bath

Sleeps

$1935.04

/ Nightly

Private Vacation Home

Southern Palms - Steps to Duval with Private Pool

Key West, Florida, United States

Summary:brbrWelcome to Southern Palms, the ultimate home base for your Key West adventure! Perfect for couples, friends, or large groups, this versatile property is made up of three separate units, Coconut Palm, Traveler's Palm, and Royal Palm.brbrbrbrWith its own private pool, hot tub, BBQ grill, five bedrooms, and four bathrooms, Southern Palms is your tropical oasis. The lush backyard is perfect for relaxing between excursions, while its prime location on Whitehead Street puts you just steps from the excitement of Duval Street.brbrbrbrFrom world-class bars and restaurants to Key West’s iconic attractions, everything you want to explore is right at your doorstep. Southern Palms offers exceptional value, comfort, and convenience for those who prioritize adventure and unforgettable experiences in paradise!brbrbrbrThe Space:brbrThe whole property allows for a maximum occupancy of 16, the bed layout is as follows:brbrCoconut Palm: brbrBedroom 1: QueenbrbrBedroom 2: Queen with attached living area & queen pullout couchbrbrBedroom 3: King with en suite bathroombrbrbrbrTraveler's Palm: brbrStudio: 2 Kings & a queen pullout couch in the living room brbrbrbrRoyal Palm: brbrStudio: King BedbrbrbrbrCoconut Palm has three bedrooms, a fully equipped kitchen, and a spacious backyard with a BBQ grill. The bedrooms include 1 king, 2 queens, and a pullout couch attached to the king bedroom, sleeping up to 8 guests.brbrbrbrTraveler's Palm is a separate studio located upstairs from Coconut Palm. It has its own private entrance, a large balcony with a hammock and a kitchenette. This unit includes 2 king size beds and a pullout couch, sleeping up to 6 guests.brbrbrbrRoyal Palm is located on the other side of the backyard. It is a cozy studio with its own patio, kitchenette and hot tub. This unit features a king size bed sleeping 2 guests.brbrbrbrGuest Access:brbrOur contactless check-in procedure makes check-in easy. Guests will receive a personalized access code prior to check-in to enter the unit.brbrbrbrThe Neighborhood:brbrLocated on Whitehead St which is 1 block from world famous Duval St, Southern Palms is walking distance to nearly everything you will want to experience during your escape to Key West. Walk to popular spots like The Southernmost Point, Key West Lighthouse, Blue Heaven, Firefly, Green Parrot and the Ernest Hemingway Home which are all just right down the street. Want to hit the beach Head down to Ft Zach State Park & Beach and enjoy the crystal clear waters and beautiful quiet beaches for a small admission fee.brbrbrbrGetting Around:brbrParking Information: If you reserve all three units in Southern Palms (including: Coconut Palm, Travelers Palm & Royal Palm), there is space for two compact cars in the gated driveway. Please note, you may need to tuck in your side mirrors to enter the driveway.brbrbrbrThere are a variety of great ways to explore Key West including by bicycle, pedi-cab, Moke, scooter, golf cart, Uber, Taxi, or by feet. As this unit is located in downtown Key West, many attractions are within walking distance. Feel free to ask us for recommendations!brbrbrbrOther Things to Note:brbr- There are 2 washer/dryers on site: one located just off of the back deck and one in the driveway.brbr- Pets are welcome! Our requirements are as follows: brbr•40lb maximum per petbrbr•$250/per staybrbr•2 pet maximumbrbrPlease let us know if you plan on bringing your pet.brbr- If you are within 90 days of your check in date: you can reserve the compound properties individually (Coconut Palm, Travelers Palm & Royal Palm)

Bed

Bath

Sleeps

$167.21

/ Nightly

Private Vacation Home

ANCHORS AWAY ~ Cheerful 1 BR, 1 Ba Condo with Private Hot Tub in The Meadows!

Key West, Florida, United States

CLASSIC AND COZY...brExhale your worries away as you approach this delightful condo, one of four that are situated inside the Mahogany House, surrounded by the shade of Spanish lime trees and classic balustrades that confirm you've finally arrived in Key West. Located on a quiet corner of The Meadows community, you are within biking and walking distance to all of Old Town as well as the Garrison Bight waterfront for exciting boating adventures.br***GUESTS MUST BE 25 YEARS OF AGE OR OLDERbrbrDETAILS AND AMENITIES…brEnter through your private entrance into this open and inviting pied a terre. Sink down into the comfortable furnishings of the living area and enjoy your favorite movie on the large wall-mounted TV or fall asleep reading your favorite novel as the sultry sunshine warms you through the large French doors that lead to your backyard oasis. The living area opens to the spacious and well-appointed kitchen, equipped with butcher block counters, stainless appliances and all of the culinary tools you need to create a fabulous meal. A table for 4 in the spacious kitchen invites you and your loved ones to dine in cozy comfort. Wash the day off in the renovated bathroom with a double sink vanity and glass-door shower. A separate laundry room with built-in cabinetry offers additional storage space for your essentials. A separate 108 square foot cottage lies in the backyard for your al fresco enjoyment (it is not air-conditioned), and has a sofa. brbrSLEEPING ARRANGEMENTS…brThe charming king bedroom will soothe your senses, inviting you to rest after your day of fun and frivolity. Two large windows allow abundant tropical sunshine to brighten your mood and wake you for another day in paradise. A large wall-mounted TV tempts you to nestle down in your plush bedding for bingeworthy tv viewing. A sofa sleeper resides in the living area so you can invite friends or family to join you. brbrOUTDOOR LIVING…brCarry your iced and crafted cocktail out to your private backyard hideaway with ample outdoor seating and lush landscaping. This outdoor gem comes complete with an outdoor fire table, hot tub and open-air shower. Let the swaying palms and cooling breezes carry you away from the real world. You'll want to stay a while at this small but mighty jewel!brbrPARKING...brThis home does not have designated parking but there is on street parking in the surrounding neighborhood. Please refrain from parking in spots marked “residential”. Guests may also park at the Old Town Parking Garage which allows daily and monthly rates.brbrPETS...brDogs are considered at 45 lb. or less and a maximum of 2 per the HOA of the property. A pet fee is required. Please make sure to check the box that you are bringing a pet when booking, and include size, breed, and age of the pet in Comments/Special Requests.brbrMULTI MONTH RESERVATIONS... brFor monthly reservations, the following fees will be added PER MONTH: brMid-stay cleanbrPool/hot tub heating fee (if applicable)brPet fee (if applicable)brbrBOOKING DATES...brThis home is only available as a monthly rental (28 night minimum). We prefer to book by the calendar month (first day of the month to the last). We may consider alternate dates if the calendar allows or if the owner will make an exception.brbrCONCIERGE SERVICES...brEnjoy our concierge service to assist you with planning activities for your trip. They can also have your fridge stocked with all the necessities in advance of your arrival!brbrCANCELLATION...brBookings canceled at least 90 days before the start of stay will receive a 100% refund. brbrCancellations inside of 90 days may receive a refund if we are able to re-rent any or all of the dates of the stay. The refund amount is dependent upon the rate of the new reservation. For multi-month reservations for January through March, a refund will only be offered in the event we are able to re-rent. The refund amount is dependent upon the rate of the new reservation(s).brbrYOU DESERVE TO BE HERE...

1

Bed

1

Bath

4

Sleeps

$1026.38

/ Nightly

Private Vacation Home

LOST SHAKER OF SALT ~ 3 Bed, 2 Bath Pet Friendly with 40' Private Heated Pool

Key West, Florida, United States

THE HEART OF OLD TOWN...brCharming Old Town home in the heart of Key West. Located on Southard Street just steps from Duval's many restaurants and bars. You are in walking distance to museums, shopping, and Fort Zachary Taylor beach. Relax on the front porch and watch the people walk by while sipping a cocktail or reading a book.br***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGEbrbrSLEEPING ARRANGEMENTS AND FURNISHINGS...brThis home has a beautiful, large master suite with king size bed just off the front porch with an adjoining spacious bath that offers a shower and a hanging closet. Although the room is surrounded by windows that fills the room with soft, natural light, there are also blinds that offer privacy and shade for guests. There is a flat screen and dresser for your convenience. Youtube TV service is available in this home. brbrWalk up the spiral staircase to find 2 twins beds in a quiet loft, that can convert to a king, overlooking the kitchen and sitting area which has a pull out couch for two additional guests. The updated private guest bathroom is located just off the renovated kitchen and has a glass tile shower. The kitchen is fully equipped for meal preparation and serving and has a breakfast bar for 2, stainless steel appliances, and custom cabinetry. The first floor guest room has a queen size bed with a hanging closet, luggage rack, flat screen TV and a dresser. brbrPOOL AND OUTDOOR LIVING...brFrench doors open to the private 40' heated pool with a back deck and four lounge chairs where you can spend the day in peace and quiet under the tropical landscaping. The back deck also has a grill and table that are ideal for dining Al Fresco. Your best friend can enjoy the fully fenced yard in this pet friendly home as well.brbrPARKING...brThis home does not have designated parking but there is on street parking in the surrounding neighborhood. Please refrain from parking in spots marked “residential”. Guests may also park at the cash lot just a block away (800 block of Southard) for $15/day. brbrPETS... brPets are considered and a pet fee is required. Please include the size/breed when inquiring.brbrSimonton Beach is 0.16 mi.brFort Zachary Taylor Beach is 1.1 mi.brSouth Beach is 0.8 mi.brHiggs Beach is 1.2 mi.brSmathers Beach is 2.3 mi.brbrCONCIERGE SERVICES...brEnjoy our concierge service to assist you with planning activities for your trip, from bike/scooter/golf cart rentals to any excursion you can think of including snorkeling and sunset cruises, jet ski rentals, parasailing, kayaking, fishing, paddle boarding and much more. They can also have your fridge stocked with all the necessities in advance of your arrival!brbrCANCELLATION...brBookings canceled at least 30 days before the start of stay will receive a 100% refund. Bookings canceled at least 14 days before the start of stay will receive a 50% refund.brbrLIVE LIKE A LOCAL!

3

Bed

2

Bath

8

Sleeps

$366.41

/ Nightly

Private Vacation Home

CORAL CABANA ~ Lush Porch Views of the Pool & Gardens, near Golf Course!

Key West, Florida, United States

WELCOME BOATING AND GOLFING ENTHUSIASTS..brLocated just off Key West at mile marker 5, the gated community of Coral Hammock on Stock Island is a stunning and peaceful retreat with a gorgeous resort style giant pool, luxurious clubhouse and fully equipped fitness area. You are close enough to all the excitement of downtown Key West without being right on top of the nightlife. br***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGEbrbrDETAILS AND AMENITIES...brTake a deep breath and exhale as you step into this delightful three bedroom three bath townhome, boasting inviting indoor/outdoor living space. The open concept kitchen, dining and living area offers optimal flow for function and comfort. Delight your loved ones with delicious meals crafted in the modern and fully stocked kitchen with top of the line cookware. Entertain, play games and enjoy your favorite shows on the plush living area furnishingsbrbrSLEEPING ARRANGEMENTS.....brThis home has three full bedrooms each with TVs as well as three full bathrooms, comfortably sleeping 6 - 8 people so it is ideal for families with seniors or couples traveling together. The primary suite features a king with an en suite bathroom with a conventional tub/shower combination. The 1st floor bedroom has a queen size bed & full bathroom with tiled shower. The 2nd floor bedroom has two twin size beds (which can be converted to a king) and a full en suite bathroom with soaking tub and separate shower. There is also a custom Carolina Chair queen size sleeper sofa in the living room and a pack and play available.brbrOUTDOOR LIVING...brA tranquil pool view can be easily appreciated by relaxing on either the upper or lower balconies. With its gated entryway and lush landscaped grounds this home boasts panoramic tropical garden views and a convenient pool side location. The resort sized heated swimming pool invites you to soak up the sun while enjoying our island’s warm breeze. The Key West Golf Course is just a stone’s throw away. For the boaters out there, Coral Cabana is also centrally located to 3 different marinas.brbrPARKING...brParking for 2 vehicles. brbrPETS...brThis is not a pet-friendly home.brbrCONCIERGE SERVICES...brEnjoy our concierge service to assist you with planning activities for your trip, from bike/scooter/golf cart rentals to any excursion you can think of including snorkeling and sunset cruises, jet ski rentals, parasailing, kayaking, fishing, paddle boarding and much more. They can also have your fridge stocked with all the necessities in advance of your arrival!brbrCoral Hammock HOA-Rules & Regulations:br· No boats, trailers, wave runners, motor homes, campers and/or buses allowed on site. (You must make other arrangements in advance at a local marina, etc)br· Vehicles may park only in designated parking spaces and may not park in the following areas of the association property: designated “fire lanes” or driveways.br· Boats, buses, campers, trailers, motor homes, recreation vehicles, mobile homes and commercial vehicles shall not be parked on the association property.brbrCANCELLATION...brBookings canceled at least 30 days before the start of stay will receive a 100% refund. Bookings canceled at least 14 days before the start of stay will receive a 50% refund.brbrSPOIL YOURSELF IN PARADISE...

3

Bed

3

Bath

8

Sleeps

$1,073

/ Nightly

Private Vacation Home

CAPTAIN'S QUARTERS ~ A Vintage Key West Retreat that is full of Charm!!

Key West, Florida, United States

HISTORIC OLD-WORLD CHARM WITH MODERN AMENITIES AND A LAGOON-STYLE POOL....brOnce you step through the threshold of this Old Town home you feel enveloped in vintage Key West. Dade County wood surfaces, nautical accents plus appealing and comfortable decor make this a true Captain's Quarters. Hang out in the living room with flat screen TV. br***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGEbrbrSLEEPING ARRANGEMENTS...brYou will have many sleeping options while staying in this stunning home as it comfortably sleeps 8-10 guests. There are three bedrooms located in the main house and a one bedroom cottage off the rear deck by the pool. As you enter the main hallway, there are two queen guest bedrooms immediately to your left and right. They each have TVs, storage for clothing and the option of using the hall or rear bathrooms. The master bedroom is fitted with a king size bed, flat screen, closet and has an interior door that leads to a full bathroom. You will find a cast iron clawfoot tub with rain shower as well as a vintage pedestal sink. The rear bathroom off the family room has a tiled shower with glass door and a pedestal sink. There is a powder room off the kitchen that houses the washer and dryer. It has a door to the rear deck that can double for cottage use. The cottage is your fourth bedroom with a queen size bed, pedestal sink, dresser and flat screen with a view of the pool! If you have one or two more guests they can use the sleeper sofa in the family room. brbrAMENITIES...brCaptains' Quarters had updates completed in the spacious homes layout and decor in 2015. Impressively rich Dade County pine and high ceilings make this property a real stand out. The kitchen is fully equipped to meet your cooking needs and has a formal dining room steps away. Your family can dine together at the table for six or use the space to play games or cards. brbrOUTDOOR LIVING...brLush tropical landscaping greets you at the front gate and wraps around the property. Once inside, you will find a covered porch with a swing and seating area perfect for your morning coffee or to curl up with a book. A winding path will take you around the side yard to a real gem; the lagoon-style pool! The large private, heated pool is situated in the rear yard surrounded by a composite deck with plenty of seating. There is a gas grill and outdoor table covered with a large umbrella meant for six to dine al fresco and grill your fresh catch of the day. If you are a sun worshiper you can kick back and relax on one of the five lounge chairs that surround the pool. Enjoy an outdoor shower to rinse off and head into town!brbrPARKING...brThis home does not have designated parking but there is on street parking in the surrounding neighborhood. Please refrain from parking in spots marked “residential permit”. brbrDISTANCES TO BEACHES...brHiggs Beach is 0.8 mibrSouth Beach is 0.9 mibrSmathers Beach is 1.7 mibrFort Zachary Taylor Beach is 1.7 mbrbrCONCIERGE SERVICES...brEnjoy our concierge service to assist you with planning activities for your trip, from bike/scooter/golf cart rentals to any excursion you can think of including snorkeling and sunset cruises, jet ski rentals, parasailing, kayaking, fishing, paddle boarding and much more. They can also have your fridge stocked with all the necessities in advance of your arrival!brbrCANCELLATION...brBookings canceled at least 30 days before the start of stay will receive a 100% refund. Bookings canceled at least 14 days before the start of stay will receive a 50% refund.brbrISLAND TIME AWAITS...

4

Bed

2

Bath

10

Sleeps

$433.96

/ Nightly

Apartment

RIPTIDES ~Stylish Studio Located in a Central Location Near All the Action!

Key West, Florida, United States

STYLISH STUDIO ONE BLOCK FROM DUVAL…brPrivate studio apartment on Simonton Street one block from Duval. This home is located at the rear of the property and is perfect for a couple who wants to be near all the action. br***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGEbrbrSLEEPING ARRANGEMENTS & FURNISHINGS…brThis quaint studio offers a queen size bed, kitchenette with a Keurig coffee maker, table for 2, and separate bathroom. Perfect for a couple’s no-frills getaway. brbrDETAILS AND AMENITIES…brLocated a few doors down is Better Than Sex, Duffy's and Pisces restaurants. It is the perfect location for anywhere you would like to go in Key West, and most importantly, it is one block from Duval. brbrDISTANCES TO LOCAL BEACHES...brSimonton Beach: 0.7 milesbrFort Zachary Taylor Beach: 1.1 milesbrSouth Beach: 0.5 milesbrHiggs Beach: 1.1 milesbrSmathers Beach: 2.5 milesbrbrPARKING...brThis home does not have designated parking but there is on street parking in the surrounding neighborhood. Please refrain from parking in spots marked “residential”. Guests may also park at the Old Town Parking Garage which allows daily and monthly rates.brbrCONCIERGE SERVICES...brEnjoy our concierge service to assist you with planning activities for your trip, from bike/scooter/golf cart rentals to any excursion you can think of including snorkeling and sunset cruises, jet ski rentals, parasailing, kayaking, fishing, paddle boarding and much more. They can also have your fridge stocked with all the necessities in advance of your arrival!brbrCANCELLATION...brBookings canceled at least 30 days before the start of stay will receive a 100% refund. Bookings canceled at least 14 days before the start of stay will receive a 50% refund.brbrCOME JOIN US AND LIVE LIKE A LOCAL…

1

Bed

1

Bath

2

Sleeps

$340.82

/ Nightly

Private Vacation Home

AN ISLAND SIESTA: 2 BR, 2 BA Townhouse in Key West, Sleeps 6

Key West, Florida, United States

This lovely, fully furnished, townhouse has two bedrooms that sleeps up to 6 and two full baths . The spacious upstairs bedrooms offer one King bed in the master with dressers, and closet areas and a shared full bath. One full bath with shower and den/single bedroom are conveniently located downstairs. Screened porches overlooking the golf course and pond offer tranquil nature and wildlife views. This home has a well equipped kitchen with dishwasher and microwave. Flat screen Smart TVs in the living room and each bedroom with streaming Direct TV content live TV. Complimentary Wi-Fi service is provided as well. The upstairs bedrooms have privacy shades for napping/sleeping in on lazy mornings. The screened in back porch from the living room is furnished with table and chairs for al fresco dining to enjoy the tropical breezes. The newly pavered back yard offers lush, tropical landscaping and a propane grill to cook your catch. Additional outdoor seating is located on the front porch. This home is located within the Key West Golf Club Community and offers a private gated entrance with 24 hour security services providing a safe environment for an evening neighborhood walk or use of the large waterfall pool and the exercise room/gym. These complimentary amenities are located just a short walk from your porch. An additional pool is located across the street from the home. Both pool locations offer complimentary open Wi-Fi access. This home provides a serene vacation setting when a tropical rest and relaxation private escape is needed but still just moments away from the sights and entertainment of Historic Duval Street in downtown Cayo Hueso.

2

Bed

2

Bath

6

Sleeps

$435.38

/ Nightly

Guest House

Nassau suite-2 bedroom 2 bath, a block off Duval St w/pool, parking

Key West, Florida, United States

AGE REQUIREMENT: brALL guests staying at the property MUST be 25 years of age or older at this property- NO EXCEPTIONSbrbrPARKING: brAvailable on a first-come, first-served basis each day with three tandem parking spots allocated for the four units in the building. You may park only ONE vehicle per unit if you secure a spot. brbrRESTRICTIONS: brWe do not accommodate bachelor parties, bachelorette parties, student groups or construction workers-NO EXCEPTIONSbrThe pool closes at 11PMbrNo smoking on the propertybrNo petsbrbrFEATURES:brThis unit is a 2nd story unit.brBedrooms: 2 (2 king beds)brBathrooms: 2brLocation: One block off DuvalbrAmenities: Shared heated pool, outdoor dining area with BBQ grill, TVs, WifibrbrTHINGS TO KNOW: brCheck in: 4PM - We do not guarantee an early check in request will be granted because we need to give the housekeepers time to ready the units for check-in, however, should your unit be ready early, we will notify you from this number that you can check-in. No units will be able to accommodate a check-in earlier than 12pm. brbrCheck out: 10AM - We do not accommodate late check outs. brbrItems provided: All linens, bath towels and beach towels are provided for your convenience. You are provided an initial supply of bath soap, dish washing liquid, toilet paper, laundry detergent and paper towels. Additional supplies are the responsibility of the renter, or once the initial supply is used.

2

Bed

2

Bath

6

Sleeps

$622.46

/ Nightly

Guest House

Grand Bahama suite-3 bedroom 2 bath, a block off Duval St w/pool, parking

Key West, Florida, United States

AGE REQUIREMENT: brALL guests staying at the property MUST be 25 years of age or older at this property- NO EXCEPTIONSbrbrPARKING: brAvailable on a first-come, first-served basis each day with three tandem parking spots allocated for the four units in the building. You may park only ONE vehicle per unit if you secure a spot. brbrRESTRICTIONS: brWe do not accommodate bachelor parties, bachelorette parties, student groups or construction workers-NO EXCEPTIONSbrThe pool closes at 11PMbrNo smoking on the propertybrNo petsbrbrFEATURES:brThis unit is a 2nd story unit.brBedrooms: 3 (one bedroom has a king other bedrooms have queens)brBathrooms: 2brLocation: One block off DuvalbrAmenities: Shared heated pool, outdoor dining area with BBQ grill, TVs, WifibrbrTHINGS TO KNOW: brCheck in: 4PM - We do not guarantee an early check in request will be granted because we need to give the housekeepers time to ready the units for check-in, however, should your unit be ready early, we will notify you from this number that you can check-in. No units will be able to accommodate a check-in earlier than 12pm. brbrCheck out: 10AM - We do not accommodate late check outs. brbrItems provided: All linens, bath towels and beach towels are provided for your convenience. You are provided an initial supply of bath soap, dish washing liquid, toilet paper, laundry detergent and paper towels. Additional supplies are the responsibility of the renter, or once the initial supply is used.

Bed

Bath

Sleeps

$293.49

/ Nightly

Private Vacation Home

ABSOLUTE KEY WEST in the Truman Annex >>Charming home with a European flair!

Key West, Florida, United States

This Private home is located in the historic award-winning gated community of the Truman Annex in Old Town Key West, brYou can get away from it all while being near the best that Key West has to offer. Shared heated pool and off-street parking. Of course, as with all of our units in the Truman Annex, this home comes fully furnished with all the linens, kitchen accessories, central air and heat, and an ambiance that can't be beat. 2 Bedroom 2 Bath Plus Den, Single Family Home with Shared Pool. brbrPlease note: This property is monthly rental -This property has a 27 night minimum stay

Bed

Bath

Sleeps

$464.33

/ Nightly

Private Vacation Home

Queen Emma at the Truman Annex in Key West

Key West, Florida, United States

This beautifully finished and decorated four bedroom, three bath home has classic Key West architecture and is located on a charming tree lined street in the Truman Annex. The custom designed two story home has an open floor plan on the main level with separate living and dining areas including a full bath and guest bedroom. The huge porch, perfect for entertaining, overlooks the large rear yard with heated pool and is accessed from the living area through two sets of French doors. Upstairs the spacious master suite opens to a private porch and the two guest rooms share a bath and porches. brbrPlease note: This property is monthly rental -This property has a 27 night minimum stay

Bed

Bath

Sleeps

$448.82

/ Nightly

Condo

Tropical Executive at The Truman Annex in Key West

Key West, Florida, United States

This Harbour Place condominium is in Key West's most prestigious community of Truman Annex offering breath taking water and sunset views from your own private deck. This beautifully decorated stately Condo has wonderful views along the length of the new Truman Waterfront Park. This property features a king, and 2 twins or 2 twins as a king and a convenient sleeper sofa. | This community is located 2 blocks from Duval Street and all of the Old Town Key West attractions. The properties are also located close to Fort Zachary Taylor State Park and Beach. This unique property is outfitted with washer/dryer, pots & pans, towels & linens, central air conditioning, covered off street parking and waterfront pool.brbrPlease note: This property has a 28 night minimum stay

2

Bed

2

Bath

6

Sleeps

$406.1

/ Nightly

Guest House

Paradise Island suite-2 bedroom 1 bath, a block off Duval St w/pool, parking

Key West, Florida, United States

AGE REQUIREMENT: brALL guests staying at the property MUST be 25 years of age or older at this property- NO EXCEPTIONSbrbrPARKING: brAvailable on a first-come, first-served basis each day with three tandem parking spots allocated for the four units in the building. You may park only ONE vehicle per unit if you secure a spot. brbrRESTRICTIONS: brWe do not accommodate bachelor parties, bachelorette parties, student groups or construction workers-NO EXCEPTIONSbrThe pool closes at 11PMbrNo smoking on the propertybrNo petsbrbrFEATURES:brBedrooms: 2 (1st bedroom has 1 queen, the 2nd bedroom has 2 queens)brBathrooms: 1brLocation: One block off DuvalbrAmenities: Shared heated pool, outdoor dining area with BBQ grill, TVs, WifibrbrTHINGS TO KNOW: brCheck in: 4PM - We do not guarantee an early check in request will be granted because we need to give the housekeepers time to ready the units for check-in, however, should your unit be ready early, we will notify you from this number that you can check-in. No units will be able to accommodate a check-in earlier than 12pm. brbrCheck out: 10AM - We do not accommodate late check outs. brbrItems provided: All linens, bath towels and beach towels are provided for your convenience. You are provided an initial supply of bath soap, dish washing liquid, toilet paper, laundry detergent and paper towels. Additional supplies are the responsibility of the renter, or once the initial supply is used.

2

Bed

1

Bath

6

Sleeps

$841.86

/ Nightly

Guest House

Bimini suite-3 bedroom 3 bath, a block off Duval St w/pool, parking

Key West, Florida, United States

AGE REQUIREMENT: brALL guests staying at the property MUST be 25 years of age or older at this property- NO EXCEPTIONSbrbrPARKING: brAvailable on a first-come, first-served basis each day with three tandem parking spots allocated for the four units in the building. You may park only ONE vehicle per unit if you secure a spot. brbrRESTRICTIONS: brWe do not accommodate bachelor parties, bachelorette parties, student groups or construction workers-NO EXCEPTIONSbrThe pool closes at 11PMbrNo smoking on the propertybrNo petsbrbrFEATURES:brBedrooms: 3 (1 king, 2 queens)brBathrooms: 3brLocation: One block off DuvalbrAmenities: Shared heated pool, outdoor dining area with BBQ grill, TVs, WifibrbrTHINGS TO KNOW: brCheck in: 4PM - We do not guarantee an early check in request will be granted because we need to give the housekeepers time to ready the units for check-in, however, should your unit be ready early, we will notify you from this number that you can check-in. No units will be able to accommodate a check-in earlier than 12pm. brbrCheck out: 10AM - We do not accommodate late check outs. brbrItems provided: All linens, bath towels and beach towels are provided for your convenience. You are provided an initial supply of bath soap, dish washing liquid, toilet paper, laundry detergent and paper towels. Additional supplies are the responsibility of the renter, or once the initial supply is used.

Bed

Bath

Sleeps

$443.59

/ Nightly

Private Vacation Home

Our Piece of Paradise-

Key West, Florida, United States

Welcome to your ideal Key West getaway!brPerfect for families and ideally situated between Old Town, New Town, and Duval Street. We're near Garrison Bight Marina, great for boat lovers. Chill in the heated pool, freshen up in the outdoor shower, and unwind on the covered patio. Our home is air-conditioned and pet-friendly, blending comfort with authentic island charm. All the ingredients for an unforgettable vacation are here, wrapped in a warm, inviting atmosphere. Come make yourself at home!

3

Bed

3

Bath

6

Sleeps

Vacation Rentals By Owner In Key West, FL

$192.25

$195.08

$1504.94

$350.04

$450.76

$1935.04

$167.21

$1026.38

$366.41

$1,073

$433.96

$340.82

$435.38

$622.46

$293.49

$464.33

$448.82

$406.1

$841.86

$443.59

Rent a place that suits your needs

Most popular vacation rentals in Key West

$2168.85

$2433.36

$2377.08

$2193.75

$2179.76

$2078.34

$2059.55

$2072.19

$2489.04

$2144.26

Most Popular Cities in Florida