Vacation Rentals By Owner In Key West, FL

Welcome to Casa Tranquila! This 2-bedroom townhome is perfect for your escape to Key West. Located in Old Town just five blocks off of Duval, it boasts 3 total queen beds, 2 fully renovated en-suite bathrooms with showers, huge new smart TV's, PRIVATE HOT TUB, grill, fire pit, laundry, and all-new finishes inside and out. This beautiful rental has everything you need for a comfortable stay in a super convenient location whether you're heading to Duval, the beaches or the marina. Tons of extras including a starter set of toiletries and paper products, a fully stocked kitchen with all of the essentials for cooking and grilling your own meals, an additional wine fridge and drink fridge in addition to all brand-new appliances in the kitchen, and multiple sets of bed and bath linens. You'll never want to leave!brbrParking for one vehicle or golf cart on street in front of townhome.brbrThis home is available for monthly rental (minimum of 28-days). Owners will consider dates other than an entire same-month booking - please feel free inquire before reserving your dates if you'd like.

Casa Tranquila - Fully-Renovated 2-bedroom Townhome in Old Town Key West

Key West, Florida, United States

Bed

Bath

Sleeps

$170.12

pJust a short distance from the sea, this pet-friendly apartment lets you experience it all. There's convenient onsite parking, so you can leave your vehicle behind and let your feet make short work of the 9-minute walk to Westerland Beach or the 8-minute walk to Friedrichstraße. If you're looking to expand your horizons and see other nearby locales, you can catch a train at Westerland (Sylt) Station, located within a 5-minute walk of your stay. /ppThe kitchen is equipped with a stovetop, a refrigerator, and a dishwasher, as well as a coffee maker and a microwave. Enjoy the WiFi, TV, and stereo. And you can even pack a bit lighter because there's a washer and dryer. /p

Apartment

App. Stadtoase, Haus Nordland

Westerland, Schleswig-Holstein, Germany

Bed

Bath

Sleeps

Select Dates for Price

Relax in style at the Hyatt Windward Pointe Resort. This is the best location within the resort: Top floor, end unit. Located on the Atlantic Ocean. Enjoy beautiful sunrises from your own private balcony and sunsets from the shared balconies facing west. This unit has two-bedrooms and 2 full baths, 1 is a master suite with king-size bed, TV, adjoining bath with walk-in shower and jetted tub. 2nd bedroom with queen-size bed and full bath. There is a full kitchen, dining area, living room with couch that coverts to a bed for 2, TV, stereo CD player, washer, dryer, furnished balcony and wireless Internet. The grounds include a pool, hot tub, staffed tiki bar, bbq grills, hammocks, workout and game rooms. Easy walk just across the street to Smathers Beach. Please check the Hyatt Windward Pointe website for additional amenities, features and photos. Available February 22-March 1. brAccess to the nearby Hyatt Centric Key West Resort & Spa. Concierge service.

Luxurious top floor, end unit, within premier resort on the Atlantic Ocean.

Key West, Florida, United States

Bed

Bath

Sleeps

$571.27

This Modern & Spacious 2 story Apartment is located directly in the center of the Famous Duval Street. Enjoy Dining, Shopping, and Entertainment in the heart of Key West. Ones you enter the property through your private entrance you would be captivated by its modern clean design. First floor has open floor plan living room, dining room and chefs kitchen. Comfortable couches and a flat-screen TV will help you relax after all day playing. A full size bathroom and a walk-in closet are also located on the first floor. Tastefully decorated 2 bedrooms are at the second floor and have a Queen and a Full-size bed. Second half bathroom is on the second floor. Plush towels and high -end linens are provided for our most discerning guests. brbrFor those who love to entertain and cook, we offer fully equipped Chefs kitchen with new stainless steel appliances, quarts countertop, and a dining table. brbrEnjoy people watching while sipping tropical cocktails in the privacy of your balcony.brbrBedrooms- Both bedrooms are located on the second floor.br*Master bedroom- Queen size bed, make-up vanity, Flat-screen smart TV. br*Guest bedroom- Full size bed, Smart flat screen TV, Plenty of storage. brbrAdditional features:brStarter supply paper productsbrStarter set cleaning productsbrLinens, bath and pool towelsbrKitchen cookware, dishes, flatware, glasswarebrWireless high-speed internetbrAT&T Uverse cable, smart TV capable thru-outbrFully fenced yardbrbrFree parking availablebrbrHousekeeping services availablebrbrbrbrbrbrbrbrbrbrbrbrbrbr

Luxury two floor apartment in prime location of famous Duval Street

Key West, Florida, United States

Bed

Bath

Sleeps

$333.17

28 DAY MINIMUM RENTALbrbrWalk the historic streets of Key West, live in Old Town in a quiet residential neighborhood. Just two blocks from Duval Street, it is a quick walk or bike ride to all of Key West's attractions, including it's close proximity to the Historic Seaport area. This is a lovingly restored eyebrow 3 bedroom house and is listed on the Key West's Historic House Registry. The house has one bedroom on the ground floor with king bed and full bath, upstairs there are two bedrooms, one with a queen bed and the other with twin beds. The large pool with waterfall enhance your island experience, the ambient background sound of falling water and the neighboring tropical birds at Nancy's Secret Garden make this a delightful island getaway. The large deck surrounding the pool has a glorious, private outdoor shower. You can also lounge and dine al fresco around the pool. French doors lead back inside to a dining room and open kitchen. Bedding: 1 king, 1 queen, 2 twin

Elizabeth Retreat: A three bedroom historic home in Old Town

Key West, Florida, United States

Bed

Bath

Sleeps

$5009.35

This private four (4) house compound accommodates (20) guests and is has a private 10′ x 25′ heated pool including a 5’ x 10’ heated Jacuzzi. In addition, there is a private 8′ x 10′ heated Jacuzzi, Starlink high speed wi-fi network, and CCTV in the common elements (garden (2), pools (2), and property perimeters (3). There are brick walkways, and a 10′ x 40′ sun deck, including a stainless steel propane barbecue, chaise lounges for sunbathing and relaxing; and tables and chairs for dining. The design of the property lends itself perfectly for large gatherings with friends and family. This is a very unique Key West property for guests looking for a private,, authentic Key West experience.brbr1. MAIN HOUSEbrbrOverviewbrThe Main House is a two (2) story 100+ year old, recently completely renovated “Conch” house. The house has an open downstairs floor plan, and four (4) private bedrooms upstairs. There is a downstairs wraparound porch, and a complimenting upstairs wrap around balcony, both of which overlook the pool, sundeck and Thomas Street. All window, door and floor trim is turn of the century style, and all windows are 6 / 6 double-hung sash.brbrThe house has a Starlink high speed wi-fi network, streaming internet TV, and four (4) SMART HDTVs ((2) 40 Samsung SMART HDTVs, (1) 40 Sony SMART HDTV, and (1) 32 Samsung SMART HDTV). The house has five (5) tons of central air conditioning, and six (6) 52″ Hunter ceiling fans; there is a full size Whirlpool washer and dryer located at the rear of the house. There is a propane barbecue located on the pool deck.brbrThe house can comfortably accommodate a maximum of eight (8) guests.brbrAll linens and towels are furnished.brbrThere are two (2) off-street parking spaces on the property.brbrFirst FloorbrThe kitchen, dining room, living room are located on the first floor. Located off the living room is a half bathroom, which has a pedestal sink. The downstairs floor is a Golden Oak Pergo, and the downstairs ceiling is 9’ high.brbrKitchenbrThe contemporary galley kitchen is new with maple cabinets, Corian countertops, and a double compartment, integrated Corian sink. Kitchen equipment includes a GE range, GE microwave, GE dishwasher, garbage disposal, Samsung side-by-side refrigerator with icemaker and serve through ice and water dispenser, coffee maker, toaster, dishes, flatware, glasses (service for 8), pots, pans, and all basic cooking utensils. There is a set of two (2) French doors providing access from the kitchen to side porch, pool, and sundeck.brbrDining RoombrThe dining room has a wood Parson's dining room table with seating for eight (8). There is a ceiling fan in the dining room.brbrLiving RoombrThe living room has a sectional sofa with a queen sleeper and a lounge seat, a reading chair, an entertainment center, and a 40 Samsung SMART HDTV. The living room has recessed lighting, and a 52 Hunter ceiling fan.brbrSecond FloorbrThe second floor has four (4) private bedrooms – (2) queen beds and two (2) full beds. Each bedroom has a ceiling fan, and there is a 40 Samsung SMART HDTV in one bedroom, a 40 Sony SMART HDTV in another bedroom, and a 32 Samsung SMART HDTV in another bedroom. One bedroom provides access to the 275 square foot wrap around balcony, which overlooks the pool and sundeck, and Thomas Street. The second floor is carpeted, and there is a new full bathroom located on the second floor.brbr2. TURTLE HOUSEbrbrOverviewbrThe Turtle House is a 100+ year old recently completely renovated “Conch” house. The house can be described as having “an open, crisp, private space”. The house has two (2) gabled ceilings, which creates a contemporary, spacious living environment. The downstairs floor is Golden Oak Pergo. All window, door, and floor trim is turn of the century style, and all windows are 6/6 double-hung sash. All linens and towels are furnished.brbrThe house has a Starlink highspeed Wi-Fi network, a 43 Samsung SMART HDTV, and two (2) 26 Samsung 26″ SMART HDTVs. The house has central air conditioning, a ceiling fan, and access to a stacked washer and dryer. There is a stainless steel propane barbecue located on the pool deck.brbrThe house can comfortably accommodate a maximum of five (5) guests – who are comfortable sharing an open living environment.brbrFirst FloorbrThe kitchen, dining, living, and bathroom are located on the first floor. An architectural beam containing halogen lighting extends the entire length of the house. The bathroom, located off the living room, is completely new and has recessed LED lighting, a full shower, and sink. There are two (2) sets of French doors providing access to the rear courtyard where the 8’x10′ heated Jacuzzi is located.brbrKitchenbrThe contemporary galley kitchen is new with maple cabinets, black Zimbabwe granite countertops, stainless steel single compartment sink, and the ceiling has recessed LED lighting. Kitchen equipment includes an under the counter GE refrigerator, an under the counter Sub-Zero freezer with icemaker, a stainless steel electric range, garbage disposal, Quasar microwave, and Braun coffee maker, Krupps toaster, dishes, flatware, glasses (service for 6), pots, pans, and basic cooking utensils.brbrDining RoombrThe dining room has a wood Parson's dining room table with seating for six (6), and a maple with black Zimbabwe granite service credenza – complete with wine rack.brbrLiving RoombrThe living room has one (1) queen sleeper sofa, a queen bed, a relaxing chair, a 43 Samsung SMART HDTV, and an Onkyo receiver.brbrMaster Loft Sleeping AreabrA staircase is used to access the master loft sleeping area. The loft has a queen size bed and a 26 Samsung SMART HDTV.brbrGuest Loft Sleeping AreabrA staircase is used to access the guest loft sleeping area. The loft has a full size bed and a 26 Samsung SMART HDTV.brbr3. CIGAR HOUSEbrbrOverviewbrThe Cigar House is a 100+ year old “Cigar maker’s house”. The recently completely renovated house is charming, spacious, secluded and private. The cottage has a raised vaulted wood ceiling, creating a rustic, Caribbean ambiance. The downstairs floor is the original Dade County Pine. All window, door, and floor trim is turn of the century style, and all windows are 6/6 double-hung sash. All linens and towels are furnished.brbrThe house has a Starlink high speed wi-fi network, a 32 Sony SMART HDTV, and a 26 Sony SMART HDTV. The house has central air conditioning, a ceiling fan, and a stacked LP washer and dryer. There is a stainless steel propane barbecue located on the pool deck.brbrThe cottage can comfortably accommodate a maximum of four (4) guests – who are comfortable sharing an open social living environment.brbrFirst FloorbrThe kitchen, living, dining, sitting, and bathroom are located on the first floor. The living room has a queen sleeper sofa/daybed, a 32 Sony SMART HDTV. The bathroom, located off the living room, has been recently completely renovated and has a vaulted ceiling and full sized marble walk-in shower.brbrKitchenbrThe kitchen is new and contemporary with mahogany cabinets, white Corian countertops, and integrated Corian sink, and serve thru access to the dining room. The ceiling is vaulted with architectural beams and LED lighting. The kitchen has a pantry, refrigerator, electric range, garbage disposal, microwave, and Braun coffee maker, Krupps toaster, dishes, flatware, glasses (service for 6), pots, pans, and all the basic cooking utensils. There is a French door providing access to the rear deck where the washer and dryer are located.brbrLoft Sleeping AreabrA ladder is used to access the loft sleeping area. The loft has a full size bed, and a 26 Sony SMART HDTV.brbr4. CONCH HOUSEbrbrOverviewbrThe Conch House is a 100+ year old “Cigarmaker’s house. The house is recently renovated, charming, spacious, secluded and private. The raised vaulted ceiling creates an open living environment. The downstairs floor is the original Dade County Pine. All window, door, and floor trim is turn of the century style, and all windows are 6/6 double hung sash. All linens and towels are furnished.brbrThe house has a secured Starlink wi-fi network, a 32 Sony SMART HDTV, and a 26 Samsung SMART HDTV. The house has central air conditioning, a ceiling fan, and a stacked LP washer and dryer. There is a stainless steel propane barbecue located on the pool deck.brbrThe house can comfortably accommodate a maximum of five (5) guests – who are comfortable sharing an open sociable living environment.brbrFirst FloorbrThe kitchen, living/dining room, a small bedroom, and a full bathroom. There is a queen sleeper sofa/day bed and a 32 Sony SMART HDTV in the living room. There is a full bed in the small bedroom located between the kitchen and the living room. The bathroom, located off the small bedroom, has been recently completely renovated – it has a vaulted ceiling, recessed lighting, oak cabinets, and black granite vanity top.brbrKitchenbrThe kitchen has serve thru access to the dining/living room. The kitchen ceiling is vaulted with recessed LED lighting. There is a stainless steel gas range, a stainless steel refrigerator, microwave, Braun coffee maker, garbage disposal, Krupps toaster, pots & pans, all basic cooking utensils; and dishes, flatware, glasses (service for 6). There are (2) French doors providing access to the rear deck where the washer and dryer are located.brbrLoft Sleeping AreabrA ship's ladder is used to access the loft sleeping area. The loft has a full size bed, and a Samsung 26″ HDTV.brbrCHICKENS & ROOSTERSbrThe City of Key West protects chickens and roosters, and considers them as part of the history and charm of Key West. As a result, Key West and many of the islands throughout the Florida Keys have free-range chickens and roosters. You will definitely see and hear chickens and roosters during your stay in Key West. Some visitors to Key West love them, and some visitors hate them - personally, I enjoy them best roasted, with plantains, and black beans and rice!

Historic Old Town Key West Rental Compound - 11 Beds, 4 Sleeper Sofas, 20 Guests

Key West, Florida, United States

11

Bed

5

Bath

20

Sleeps

$887.09

JUST OFF DUVAL...brPrivate single family home with three bedrooms and three bathrooms. Open the rear French doors to a private backyard oasis with a heated pool and spacious deck for sunbathing, outdoor dining and grilling your fresh catch. Located a short walk from restaurants, bars and fun attractions.br***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGEbrbrDETAILS and AMENITIES...brComfortable furnishings give this home a modern island feel. Beautiful designer decor bring the atmosphere of the Keys right inside the door. Flat screen TVs are located in all bedrooms as well as the living area. The modern updates include a fully-equipped kitchen with granite counters and stainless steel appliances. brbrSLEEPING ARRANGEMENTS.....brTwo bedrooms and two baths reside on the first floor. The first guest bedroom has a king size bed and an en-suite bath. The second bedroom has a king size bed with access to the guest bath. The third bedroom is located up the spiral staircase in the loft and has two twin beds which can be converted to a king bed and a full bathroom with a shower. The sofa in the front living area features a pull-out accommodating 1-2 guests (full size bed).brbrPOOL AND OUTDOOR LIVING...brSwim in the pool or chill with a cocktail on the large rear deck. Dine under the stars or enjoy a good book at the outdoor seating. Venture out the front door with your morning coffee to the front porch seating.brbrPETS...brNo pets please! 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.brbrDISTANCES TO BEACHES...brSouth Beach is 0.2 mibrHiggs Beach is 0.8 mibrSmathers Beach is 2 mibrFort Zachary Taylor Beach Is 1.4 mibrAll beaches have beach chair and umbrella rentals.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.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!brbrPARADISE AWAITS...

SUNKISSED ~ Come Enjoy this Charming 3 Bedroom Home When Location Is Key!

Key West, Florida, United States

Bed

Bath

Sleeps

$730.83

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival!brbrLike many highlights of Key West, THE ADMIRAL'S ESTATE celebrates a rich history of the island while embracing a modern restoration. THE ADMIRAL'S ESTATE is a true historic Key West home, originally built for a high-ranking Naval Officer in the early 1900s. This impressive estate is armed with two living areas, a top-of-the-line gourmet kitchen, classic front double porches, and a beautiful backyard retreat. Ideal for entertaining and enjoying time together with your entire fleet, THE ADMIRAL'S ESTATE combined with Last Key Realty's Five-Star Guest Services is sure to make your month in America's Paradise a memorable one.brbrTHE GATED COMMUNITY...brbrTruman Annex is the most exclusive residential community in Old Town. Located just off the main drag of Duval Street, Truman Annex is an oasis of calm, quiet streets lined with palm trees and beautiful Floridian homes. Within Truman Annex, the home is accessed via Admiral's Lane, which is even further tucked away down a small cul-de-sac. Fort Zachary Taylor State Park beach is just a few short blocks away. You won't need a car to get around, however the home does have two off-street parking spots.brbrCompliance with Truman Annex Community Rules & Regulations is expected of all Last Key guests. This includes “Quiet Time” in all outdoor areas, public and private, after 10PM.brbrTHE MAIN FLOOR...brbrAlthough THE ADMIRAL'S ESTATE faces Whitehead Street, the most commonly used entrance is via Admiral's Lane. Upon entering, you'll be greeted by a welcoming foyer that is accessible to the kitchen and the formal dining room. The fully equipped kitchen has premium appliances and all of the tools needed to prepare a meal at home. The kitchen bar seating is perfect for a quick bite or keeping the cooks company. For more formal meals, there is a full formal dining room with seating for 8.brbrNavigate your way through the kitchen to reach the two living rooms. The first living room has a large flat screen TV and multiple seating options, including a plush sofa. The second living room is located across the hall and is equipped with a soothing fireplace and plenty of comfortable seating. Both living areas have classic saloon doors that open up to the spacious porch that graces the façade of the home.brbrTHE LANAI & PRIVATE POOL...brbrLead the troops outside to experience outdoor island living at its' finest. The covered lanai has a large outdoor TV and comfy outdoor furniture. From the lanai, step down to the private pool area for some fun in the sun. The saltwater pool is perfect for cooling off on a hot day or can be heated in the cooler months. Relax in the chaises located on the pool's deck or enjoy a poolside meal using the BBQ grill and outdoor dining table.brbrTHE ACCOMMODATIONS...brbr** First Master Suite: Located in the Guest House with a Queen bed and an en-suite bathroom with double vanities and a walk-in shower.brbr** Second Master Suite: Located on the Second Floor with a King bed and en-suite bathroom with two pedestal sinks and a walk-in shower.brbr** Third Bedroom: Located on the Second Floor with a Queen bed and en-suite bathroom with a walk-in shower. brbr** Fourth Bedroom: Located on the Second Floor with Two Twins OR One King bed and an en-suite bathroom with a walk-in shower.brbrALL LAST KEY VACATION HOMES INCLUDE:brbr** Washer and Dryerbr** Central Heat and A/Cbr** Ceiling Fansbr** Flat Screen TVs in Living Room & All Bedroomsbr** Fully Equipped Kitchenbr** Basic stock of spicesbr** Starter supply of paper productsbr** Starter set of cleaning productsbr** Linens and Towels providedbr** Wireless high-speed Internet access & full cable includedbrbrIn addition, this fully stocked home also includes, but is not limited to the amenities on this list:brbr** Fully Fenced & Lushly Landscaped Private Yard br** Private Heated Poolbr** Off-Street Parking in Private Carportbr** Propane BBQ GrillbrbrOther notes:brbr** All monthly rentals include a mandatory interim clean. Multi-month stays require 1 interim clean per month.br** Additional interim cleanings availablebr** This property will accommodate up to 8 adultsbr** Pets Not Allowed

**THE ADMIRAL'S ESTATE** Grand Home & Pool + LAST KEY SERVICES...

Key West, Florida, United States

Bed

Bath

Sleeps

$205.32

PLEASE BE AWARE:brThis community is currently undergoing balcony repair property-wide potentially through May 2026. A 12 person crew will be working section-by-section from 8am-6pm, 5 days a week, and Saturdays will be weather make-up days as-needed. Please understand there will most likely be some amount of noise heard throughout the community. Your specific unit's balcony repair is currently scheduled for 12/11/25 -2/6/26. This is subject to change depending on how the project progresses. Our rentals have been priced to offset noise issues or any other inconvenience due to the construction project.brbrUNWIND IN PARADISE…brLet you worries wash away in this peaceful retreat located within the 1800 Atlantic community offering endless amenities. This 2 bedroom, 2 bathroom gem is the ideal setting to take advantage of your time in Paradise while having every luxury at your fingertips!br***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGEbrbrDETAILS & AMENITIES…brGreeted by an open space filled with comfortable furnishings with nautical décor, this charming abode pulls you into your alternate reality. Enjoy a large, fully equipped kitchen with stainless steel appliances for meal prep that can be enjoyed at the dining table for 4. Occupy the living area for movie and card night as you continue to create your Key West story together. The unit is accessible by an elevator or the stairs. brbrSLEEPING ARRANGEMENTS…brSleep comfortably in a cozy queen bedroom with a TV and hallway bathroom with a shower tub combination. The primary king suite comes with a TV and en suite bathroom with a walk in shower and ample closet space. Both rooms conveniently open up to a balcony overlooking a lush, vibrant courtyard with a sliver of the sparkling ocean from the distance. Enjoy a sofa sleeper to accommodate visiting guests in town.brbrOUTDOOR LIVING…brTake advantage of the sweet island breeze as you craft up your 5 o’clock cocktail on the balcony with blissful views beyond. A heated, saltwater community pool is equipped with plenty of loungers and views of the sparkling ocean. Tennis courts reside on property as well as a community grill and fitness center. Enjoy being located in these peaceful surroundings with just a short ride into town! brbrPARKING...brDesignated garage parking space included as well as overflow parking in front lots (first come first serve). brbrBOOKING DATES...brThis home is offered only 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. brbrPETS...brThis is not a pet-friendly home.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)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 90 days before the start of stay will receive a 100% refundbrbrCancellations 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). brbrCOME GET ON ISLAND TIME…

Condo

ALMOST HEAVEN ~ Stunning 2 Bedroom, 2 Bathroom Condo with Community Pool!

Key West, Florida, United States

Bed

Bath

Sleeps

$286.22

28 DAY MINIMUM RENTAL brbrFrom the owners of South of Frances, here is another beautiful, historic restoration project. This lovingly restored home is ready for guests following a complete redo! The attention to detail and master craftsmanship can be seen everywhere in this beautiful home.brbrThe first floor of the home features a den/TV room with a built-in queen size Murphy bed highlighting the original Dade county pine walls. The living room/dining area opens with French doors to a bricked courtyard and pool area. Upstairs has two bedrooms with baths ensuite. Each have their own private porches for enjoying a morning cup of coffee.brbrA beautiful home to relax and enjoy Key West, whether you stay for a month... or more!brbrParking: on-street neighborhood.brbrBedding: 2 queens, 1 queen Murphy bed

Ashe Splashe: A beautiful restoration of a historic Key West property

Key West, Florida, United States

Bed

3

Bath

Sleeps

$210.52

Summary:brbrUnder the Palms is a bright, modern 2 bedroom, 2 bath second floor condo ideal for comfortable 28 night plus stays in Key West. This sun filled corner unit offers extra privacy and natural light with two serene bedrooms. Located in Old Town, near dining, beaches, it sits within a quiet gated community featuring a shared heated pool, private parking, and space for bikes to explore at your own pace.brbrbrbrThe Space:brbrFully renovated in Summer 2024, the condo features an open concept living area and a modern kitchen with new countertops, stainless steel appliances, and all home cooking essentials. High speed WiFi makes it ideal for extended stays and remote work. Outside, relax by the shared heated pool, shared with only three other units, or unwind in the grill and lounge area surrounded by swaying palms and bright Key West skies.brbrbrbrSleeping ArrangementsbrbrBedroom 1: King bed with en suite bathroombrbrBedroom 2: King bed with en suite bathroom, convertible to two twins if neededbrbrbrbrFrom waterfront walks to unforgettable sunsets, Under the Palms offers the perfect balance of comfort, convenience, and peaceful island living.brbrbrbrGuest Access:brbrEnjoy a smooth, contactless check in experience with a personalized access code provided prior to arrival. Guests also have access to the community pool, complete with lounge chairs for relaxing and sunbathing. Please note the condo is located on the second floor and is accessible by stairs only.brbrbrbrThe Neighborhood:brbrExplore all that Key West has to offer, including a beautiful waterfront park and pier overlooking the Gulf. On Thursdays, catch the sunset farmers market or bring the kids to the splash pad for a fun-filled waterpark adventure. Just a 3-block stroll from the world-famous Duval Street, Under the Palms is within walking distance of endless shopping and dining options, including local favorites Santiago’s and Café Sole.brbrbrbrGetting Around:brbrParking Information: There is assigned parking provided for 1 vehicle. We can provide you with recommendations for parking additional vehicles upon request.brbrbrbrThere are a variety of great ways to explore Key West including by bicycle, pedi-cab, scooter, golf cart, Uber, Taxi, or by feet. As this unit is located in downtown Key West, many attractions are within walking distance.brbrbrbrOther Things to Note:brbr- In unit washer & dryerbrbr- This home has a 28-night minimumbrbr- Shared Grilled brbr- Mid-stay cleans are required

Apartment

Under the Palms - Relaxing Condo, Shared Pool & Parking

Key West, Florida, United States

Bed

Bath

4

Sleeps

$407.81

Experience Key West like a local in this 3-bedroom waterfront unobstructed open water view home with heated and chilled pool. The space features a king bedroom ensuite with jacuzzi tub, 2nd bedroom with queen bed , and 3rd bedroom also with queen bed. With 2.5 bathrooms, guests enjoy convenience and privacy throughout their stay. The house offers a soothing atmosphere where you can relax after a day of exploring around the island or on the water out your back door. The backyard heated pool has chaise lounges , couches and chairs. Use our four house bikes and enjoy all what Key West has to offer with a stay at Casa Cayo. With advance notice we can accommodate your personal or rented boat (2’ draft or less ) up to 27’ on our private dock. Relax on your private dock watching the sunset over the Historic Seaplane Basin where the first Pan Am flight took off on the first international commercial flight to Cuba. By City Ordinance it is a minimum of 28 night stay. One dog may be allowed on a case by case basis with non-refundable deposit. The open kitchen is fully equipped with full complement cookware, utensils, dishes, glassware, and outdoor grill. Wireless blue tooth speakers and an old school record player with a small collection of vinyl. Casa Cayo is beautifully decorated with quality furniture , bedding, and original Key West artwork by Sandford. Casa Cayo is located within the gated Gulfview Point community. We are newly back in the monthly rentals after a 5 year hiatus and willing to discount extended stay in the off and should seasons. Let us show you a wonderful stay in the Conch Republic.

Rare Key West Waterfront Dock for Lobster Season - Min 28 days

Key West, Florida, United States

3

Bed

3

Bath

Sleeps

$2025.0

Discover this relaxing oasis in the heart of Key West's famed Old Town. Lush, verdant foliage surrounds the grounds and beautiful contemporary design creates an environment of relaxation and restoration. Guests are encouraged to slow down and relax, to dip into the outdoor pool and whirlpool hot tub while soaking up some famed Floridian rays.brbrGuests will also receive privileges at the adjacent Hyatt Key West Resort and Marina, offering even more ways to keep occupied even on your off days. brbrThe right size, the perfect view and the must-have amenities... Hyatt Sunset Harbor Resort's residences become the perfect home-away-from-home during your stay in Key West! Classic studios offer a king-size bed, casual living area, TV and DVD player. The one-bedroom tropical-style residence features a deluxe queen bed, fully-equipped kitchen, dining area, ceiling fans, seating area with TV, stereo, DVD player and private balcony. The beautiful two-bedroom residence is even more luxe, and includes a master suite with king-sized bed, adjoining bath and spa tub, a guest suite with queen bed and full bathroom. In addition, enjoy a fully-equipped kitchen, seating area, TV, DVD player and balcony!brbrHyatt Sunset Harbor isn’t just another Key West property - it’s in the heart of Old Town, the heart and soul of one of America’s most treasured vacation destinations. Nearby, you can also enjoy Duval Street shopping or nightlife and Mallory Square. Of course, if you're looking for more natural pursuits, you have plenty of options - Key West is a haven for fishers, and the unique ecosystem is well-suited to those seeking to explore by foot or bike. Plenty of unique attractions await those looking for a change of pace - check out the The Harry S. Truman Little White House, Key West Aquarium, Key West Lighthouse Museum and Mel Fisher Maritime Heritage Museum!brbrA few things to note.... The resorts require a credit card at check-in to cover incidentals. Please note parking fees may apply and are not included in the price quoted here. The room view and bed may vary and is not guaranteed here unless agreed upon before booking. If you would like an upgrade to a specific view or bed please let me know and if available I can do that, additional fees may be required. Additionally some resorts have various towers/buildings and may vary, please check with us in advance to discuss the view/building/unit and. Finally, Tourist Accommodation Taxes must be paid directly to the resort; this is standard procedure for resorts.brbrResort policies and rules Resort will provide the information

2 Sunset Harbor Resort Key West, Hot Tub, Pool!

Key West, Florida, United States

Bed

Bath

Sleeps

$2475.0

Overlooking the shimmering span of Gulf of Mexico in historic Old Town, The Galleon Resort puts you in an ideal spot to enjoy the countless charms of Key West. Mingle with friends new and old at the Tiki Bar, or relax and unwind in the swimming pool. The resort's observation deck guarantees a stunning view from sunrise to sunset, and even to gaze at the stars.brbrRent a boat for a private viewing of the Keys or take a jetski for a spin right from the resort's marina. Work up a sweat at the on-site exercise room and afterwards, relax your body and mind in the sauna. brbrThe Galleon Resort offers a multitude of accommodations in studio, one-bedroom and two-bedroom configurations. Studios house two people and are equipped with a small refrigerator, coffee maker and microwave oven. One-bedroom suites sleep up to four while most two-bedroom suites sleep up to six, while both include a full kitchen, dining area and decked out living area. Each is lovingly furnished with sandy earth tones, rattan furniture and tropical prints that perfectly set the mood for your stay in Key West.brbrThe Galleon Resort is perfectly positioned, sitting only two blocks from Duval Street - a legendary road that boasts top-notch restaurants, dazzling nightlife and non-stop soirees. Party until dawn at a carnival, swing by a cuban cigar stand or bring your camera to the exotic butterfly conservatory, all located on this versatile street that's earned its reputation. At the northwest end of Duval Street lies Mallory Square, a plaza which is famous for its Sunset Celebration - tourists gaze at the sunset while arts and crafts displays and entertainers amuse the gatherers. Key West's oldest attraction, the Key West Aquarium is a hit with families - everyone will enjoy scoping out the menagerie of rainbow-hued fish.brbrA few things to note.... The resorts require a credit card at check-in to cover incidentals. Please note parking fees may apply and are not included in the price quoted here. The room view and bed may vary and is not guaranteed here unless agreed upon before booking. If you would like an upgrade to a specific view or bed please let me know and if available I can do that, additional fees may be required. Additionally some resorts have various towers/buildings and may vary, please check with us in advance to discuss the view/building/unit and. Finally, Tourist Accommodation Taxes must be paid directly to the resort; this is standard procedure for resorts.brbrResort policies and rules

Studio Galleon Resort, Hot Tub, Pool, Marina, Gym

Key West, Florida, United States

Bed

Bath

4

Sleeps

$2475.0

Overlooking the shimmering span of Gulf of Mexico in historic Old Town, The Galleon Resort puts you in an ideal spot to enjoy the countless charms of Key West. Mingle with friends new and old at the Tiki Bar, or relax and unwind in the swimming pool. The resort's observation deck guarantees a stunning view from sunrise to sunset, and even to gaze at the stars.brbrRent a boat for a private viewing of the Keys or take a jetski for a spin right from the resort's marina. Work up a sweat at the on-site exercise room and afterwards, relax your body and mind in the sauna. brbrThe Galleon Resort offers a multitude of accommodations in studio, one-bedroom and two-bedroom configurations. Studios house two people and are equipped with a small refrigerator, coffee maker and microwave oven. One-bedroom suites sleep up to four while most two-bedroom suites sleep up to six, while both include a full kitchen, dining area and decked out living area. Each is lovingly furnished with sandy earth tones, rattan furniture and tropical prints that perfectly set the mood for your stay in Key West.brbrThe Galleon Resort is perfectly positioned, sitting only two blocks from Duval Street - a legendary road that boasts top-notch restaurants, dazzling nightlife and non-stop soirees. Party until dawn at a carnival, swing by a cuban cigar stand or bring your camera to the exotic butterfly conservatory, all located on this versatile street that's earned its reputation. At the northwest end of Duval Street lies Mallory Square, a plaza which is famous for its Sunset Celebration - tourists gaze at the sunset while arts and crafts displays and entertainers amuse the gatherers. Key West's oldest attraction, the Key West Aquarium is a hit with families - everyone will enjoy scoping out the menagerie of rainbow-hued fish.brbrA few things to note.... The resorts require a credit card at check-in to cover incidentals. Please note parking fees may apply and are not included in the price quoted here. The room view and bed may vary and is not guaranteed here unless agreed upon before booking. If you would like an upgrade to a specific view or bed please let me know and if available I can do that, additional fees may be required. Additionally some resorts have various towers/buildings and may vary, please check with us in advance to discuss the view/building/unit and. Finally, Tourist Accommodation Taxes must be paid directly to the resort; this is standard procedure for resorts.brbrResort policies and rules

1/1 Galleon Resort, Hot Tub, Pool, Marina, Gym

Key West, Florida, United States

Bed

Bath

4

Sleeps

$11248.88

Discover this relaxing oasis in the heart of Key West's famed Old Town. Lush, verdant foliage surrounds the grounds and beautiful contemporary design creates an environment of relaxation and restoration. Guests are encouraged to slow down and relax, to dip into the outdoor pool and whirlpool hot tub while soaking up some famed Floridian rays.brbrGuests will also receive privileges at the adjacent Hyatt Key West Resort and Marina, offering even more ways to keep occupied even on your off days. brbrThe right size, the perfect view and the must-have amenities... Hyatt Sunset Harbor Resort's residences become the perfect home-away-from-home during your stay in Key West! Classic studios offer a king-size bed, casual living area, TV and DVD player. The one-bedroom tropical-style residence features a deluxe queen bed, fully-equipped kitchen, dining area, ceiling fans, seating area with TV, stereo, DVD player and private balcony. The beautiful two-bedroom residence is even more luxe, and includes a master suite with king-sized bed, adjoining bath and spa tub, a guest suite with queen bed and full bathroom. In addition, enjoy a fully-equipped kitchen, seating area, TV, DVD player and balcony!brbrHyatt Sunset Harbor isn’t just another Key West property - it’s in the heart of Old Town, the heart and soul of one of America’s most treasured vacation destinations. Nearby, you can also enjoy Duval Street shopping or nightlife and Mallory Square. Of course, if you're looking for more natural pursuits, you have plenty of options - Key West is a haven for fishers, and the unique ecosystem is well-suited to those seeking to explore by foot or bike. Plenty of unique attractions await those looking for a change of pace - check out the The Harry S. Truman Little White House, Key West Aquarium, Key West Lighthouse Museum and Mel Fisher Maritime Heritage Museum!brbrA few things to note.... The resorts require a credit card at check-in to cover incidentals. Please note parking fees may apply and are not included in the price quoted here. The room view and bed may vary and is not guaranteed here unless agreed upon before booking. If you would like an upgrade to a specific view or bed please let me know and if available I can do that, additional fees may be required. Additionally some resorts have various towers/buildings and may vary, please check with us in advance to discuss the view/building/unit and. Finally, Tourist Accommodation Taxes must be paid directly to the resort; this is standard procedure for resorts.brbrResort policies and rules Resort will provide the information

2 Sunset Harbor Resort Key West Florida

Key West, Florida, United States

Bed

Bath

Sleeps

$782.65

Welcome to La Margarita, a newly renovated home with coastal charm only blocks away from Duval Street, the Historic Seaport Boardwalk and steps away from several highly rated well-known local restaurants. brbrThis spectacular and cozy home includes:br• Spacious open living and dining room areasbr• Fully stocked large kitchen with modern stainless-steel appliances and ample counter space with cabinet storagebr• Cable & Hi Speed Internetbr• 82-inch flat screen TV in living roombr• All bedrooms include 55-inch flat screen TV's, name brand memory foam mattresses and ceiling fansbr• Double headed shower heads in several bathrooms and hand-held shower wands in every bathroombr• Newly installed central A/C with commercial grade UV/ionization air purification systembr• Walk into a hotel like scented home with a continuous hypoallergenic air diffuser systembr• Newly installed high capacity washer and dryerbr• Enjoy your morning coffee as you people watch on the outdoor bistro set

Newly Renovated Luxury Coastal Home in the Heart of Old Town Key West

Key West, Florida, United States

Bed

Bath

Sleeps

$549.34

TIME TO CREATE LIFELONG MEMORIES…brYour long-awaited island retreat is sure to have all expectations exceeded within this grand, historic 4 bedroom, 4.5 bathroom gem capturing a dreamy setting with modern luxuries. Spend your days tooling around in this vibrant neighborhood boasting endless charm and character with just minutes to all the fun loving Key West attractions on Duval St. br***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGEbrbrDETAILS & AMENITIES…brThis welcoming home provides the ultimate privacy and comfort making your time in Paradise hard to leave. Admire rich Dade County Pine walls, Brazilian cherry floors with high ceilings and hand crafted finishings all around. A fully equipped chef’s kitchen provides a desirable space for creating meals together which can be enjoyed in the formal dining room or casually on the bar top seating area. The kitchen includes a desk area and opens up to a large living room with comfortable furnishings for movie nights with mesmerizing views of the outdoor oasis from all around. An additional sunny seating room lies on the 1st level which is a great space to reminisce about all your island adventures together. brbrSLEEPING ARRANGEMENTS…brTake advantage of a restful night’s sleep within one of the 3 large king (one that could be converted to twins if desired) 2nd floor guest rooms all equipped with en suite bathrooms, storage space and TVs. The primary suite includes a clawfoot tub and shower as well as a private balcony overlooking the pool area. The 3rd floor is a private apartment with dramatic dormered ceilings and accessed by an outside stairwell. It includes two twin beds (that can be converted to a king upon request), a bathroom with a shower/tub combination, TV, kitchenette and seating. An additional powder room occupies the 1st level of the home. brbrOUTDOOR LIVING…brThe epitome of island living is achieved through the incredible indoor/outdoor space this home provides on any of the wrap around balconies and out in the backyard area as you perch the French doors open. A large pool with a dining table allows for endless entertaining. Rinse off in the outdoor shower/foot wash and lounge in the island breeze as you grill up your fresh catch of the day! brbrPARKING...brA compact parking spot is available although being just a short stroll away from all the downtown fun. brbrPETS...brPets are not considered at this home.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, 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 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). brbrCOME LIVE ON ISLAND TIME…

SERENDIPITY ~ Grand 4 Bedroom/4.5 Bathroom Home in Heart of Key West!

Key West, Florida, United States

Bed

Bath

Sleeps

$750.69

OLD TOWN LOCATION...brA beautifully furnished and comfortable home, located just 5 short blocks to Duval Street. Have bikes delivered and you will rarely need your vehicle to get around the Island if at all! br***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGEbrbrFURNISHINGS...brUpdated furnishings throughout this charming 2 bedroom home. The living room features vaulted ceilings and has several French doors which open to the deck and pool. The kitchen is located off the living room and is fully equipped to meet all your cooking needs. There are ceiling fans and flat screen TVs located in each bedroom as well as closets to store all your belongings.brbrSLEEPING ARRANGEMENTS...brThe master bedroom is located on the second floor and is outfitted with a comfortable king size bed and full tiled bathroom en suite. The guest bedroom in on the first floor and has two twin beds which can be conveniently converted to a king to meet your needs. There is also a full bath located next to the guest bedroom. There is also a queen size sofa bed located in the living room for additional guest sleeping.brbrPOOL AND OUTDOOR LIVING...brOpen the rear French doors and step out to a private small heated pool where you can cool off. The deck is equipped with two loungers and a small table for two. Enjoy grilling up your fresh catch on the propane grill!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, and is 3 blocks away.brbrPETS... brOne dog is considered at this home. A pet fee is required.brbrDISTANCES TO BEACHES...brSimonton Beach: 0.9 milesbrFort Zachary Taylor Beach: 1.6 milesbrSouth Beach: 1.3 milesbrHiggs Beach: 1.2 milesbrSmathers Beach: 1.8 milesbrbrCONCIERGE 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.brbrENJOY PARADISE!

CONCH HEAVEN ~ Stylish 2B/2Ba, Sleeps 6 in Old Town w/ Heated Cocktail Pool!

Key West, Florida, United States

Bed

Bath