Vacation Home Rentals By Owner In Key West, FL

Three bedroom (all queens sizes beds) and three full bathroom two story home in a gated community within walking distance to several great restaurants, convenience stores, liquor and marina's with boat ramps. This property has a club house for additional rental use for parties or receptions as well as, an exercise room, and large pool. Grill located on back porch. Well stocked kitchen. Finally, all the little extra's for light packing and more time to have fun.

Tropical Key West out of the way

Key West, Florida, United States

Bed

Bath

Sleeps

$387.4

NEW PROPERTY!!!brbrExperience the best of Key West from this stunning modern island retreat, perfectly situated in the heart of Old Town’s vibrant cultural district. Built in 2019, this luxurious home blends contemporary comfort with classic Key West charm—just a short stroll from Duval Street, Fort Zachary Taylor Beach, and the Truman Waterfront Amphitheater.brbrStep inside to find a bright, open living space where the gourmet kitchen, dining area, and living room flow seamlessly together—ideal for gathering with family or friends. Oversized glass doors open to your private backyard oasis, featuring a sparkling heated pool with a cascading waterfall, sun-filled patio, and lush tropical landscaping.brbrAfter a day of exploring, retreat to spacious bedrooms with spa-inspired bathrooms, or relax on one of several covered porches to enjoy the island breeze. Every detail has been thoughtfully designed for your comfort—from hardwood floors and impact windows to custom finishes and modern furnishings throughout.brbrEnjoy off-street parking, above-flood elevation, and all the conveniences of home in a location that truly has it all—steps from Key West’s best restaurants, galleries, and nightlife, yet tucked away in a peaceful residential setting.brbrWhether you’re here for sun-soaked days or lively evenings, this property offers the perfect blend of modern luxury and authentic Key West living.

Bahama Village Sanctuary - Family & Dog Friendly

Key West, Florida, United States

Bed

Bath

Sleeps

$366.86

Starr`s Suite features a King Pillow-Top Memory Foam mattress. Renovated in 2010, it features a tumbled marble shower, granite counter-tops in kitchen with dishwasher and vanity. Tommy Bahama bath amenities are provided, as well as coffee, creamer and sugar. 56” Smart TV (bring UN/PW for Netflix, Amazon, etc. to watch your favorite shows). Private Solana spa in your private courtyard. Daily housekeeping is provided. Use of 2 heated pools.brbrStarr`s Suite is in Abbey Road, a gated compound shared with Harrison`s Hideaway, McCartney`s Manor and Lennon`s Lodge. It features ceiling fans and Mitsubishi split AC/Heat for year round comfort. The common area features a Weber grill, W/D, bicycle lock-up, 2nd story dining area with ice maker and seating. Next door is the heated Family pool and across the lane is the heated Adults Only.brbrCommon areas and two pools. Upstairs deck with table/chairs, ice-maker, BBQ grill, bike lock-up, W/D at Abbey Road.brbrI stop by most days but housekeeping and groundsman/maintenance are there daily.brbrQuiet 2 block street between Simonton and Duval. A bicycle/moped rental is on the corner. Across Truman is a CVS, Subway, Doctor`s office. Restaurants/bars abound within a few blocks.brbrWalk, bike, moped, electric car. There is also a bus around Old-town and there is a map of all the stops in your in-room information book. Stops are just around the corner from us!brbrWe are located on a nice quite lane, only 2 blocks long yet only 1/2 block off Duval Street and US1.brRegistered guest must be 25 or older during March/April (Spring Break). Keep noise to a minimum after 10 pm at the Family pool, other guests may have an early morning trip.

Apartment

Starr`s Suite - 2 person K Suite w/Private Spa!

Key West, Florida, United States

Bed

Bath

Sleeps

$205.01

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 EXCEPTIONSbrbrFEATURES:brThis unit is a 30 night minimum. This is a 2 story unit.brBedrooms: 2brBathrooms: 2brLocation: Front StbrSquare Feet: 904brParking: One assigned parking space in lotbrAmenities: Shared heated pool, TVs, Wifi, walkable to shops & restaurants downtownbrbrTHINGS TO KNOW: brRestrictions/Rules: No smoking. No commercial vehicles permitted in the parking lot.brPet Policy: One pet under 25 lbs. allowed with approval prior to booking and a non-refundable pet fee.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.

Banyan Court downtown condo- 2 bedroom, 2 bath, walkable, parking, pool

Key West, Florida, United States

Bed

Bath

Sleeps

$270.53

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 30 night minimum. brbrFEATURES:brBedrooms: 4 (1 king, 1 king, 1 queen, 1 double)brBathrooms: 3.5brLocation: Key HavenbrSquare Feet: 2097brParking: Off street parking in drivewaybrAmenities: Wifi, TVs, in-unit laundry, boat dock space, jacuzzi, enclosed patiobrbrbrTHINGS 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.

Waters Edge-Key Haven 4bedroom 3.5bath canal front home w/jacuzzi, dock space

Key West, Florida, United States

Bed

Bath

Sleeps

$300.35

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 30 night minimum. brbrFEATURES:brBedrooms: 4 (1 king, 1 queen, 1 queen, 2 doubles)brBathrooms: 3brLocation: Key HavenbrSquare Feet: 1804brParking: Off street parking behind gated driveway and parking along fencebrAmenities: Wifi, TVs, in-unit laundry, boat trailer parking, dock space for 1 boat, private pool, outdoor bar areabrbrbrTHINGS 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.brbrPool heating is $100 per week and must be requested in advance

Key Haven Retreat-4 bedroom 3 bath canal front home w/private pool, boat dock

Key West, Florida, United States

Bed

Bath

Sleeps

$335.3

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 EXCEPTIONSbrbrBOAT SLIP INFORMATION:brOne boat slip is included with this Retreat. Each Retreat can only accommodate one boat; no exceptions. Trailer parking is not available on property. Trailer parking and additional boat slips are available across the harbor at the City of Key West Marina. Please contact the dock master’s office to make arrangements for trailer storage and/or additional boat slips atbrbrFEATURES:brBedrooms: 2 ( 1 king, 2 queens in 2nd bedroom) brBathrooms: 2 en suitesbrLocation: Garrison Bight Marina off Eisenhower DrbrSquare Feet: 1215brParking: 2 parking spaces includedbrAmenities: Wifi, TVs, in-unit laundry, 1 complimentary boat slip, water viewsbrbrTHINGS 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.

Bermuda Retreat-waterfront 2BR 2BA condo w/ pool & boat slip

Key West, Florida, United States

Bed

Bath

Sleeps

$235.4

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 EXCEPTIONSbrbrFEATURES:brBedrooms: 2 (1 king and 2 twins-can be converted to a king, Sleeper Sofa)brBathrooms: 2brLocation: Truman Annex - Shipyard CondosbrSquare Feet: 646brParking: 1 assigned parking space in gated lotbrAmenities: Wifi, TVs, in-unit laundry, patio area, shared pool, walkable to downtown shops & restaurants brbrbrTHINGS 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.

Shipyard 297-Condo in Truman Annex-2 bedroom 2 bath, close to Duval w/ pool

Key West, Florida, United States

Bed

Bath

Sleeps

$503.74

Duval Square is a charming community with shops and restaurants downstairs and secure, quiet, private residences, pool and pavilion upstairs. Although the condo includes one assigned parking space in the gated garage, you can stroll anywhere from this conveniently located condo. All of the shops, galleries, restaurants, and attractions on and around Duval Street and nearby beaches are just a leisurely stroll away. brbrWhen you enter the home you will find a fully equipped kitchen, dining area, spacious living room and a convenient half bath. French doors let in the natural sunshine and open to the private back deck with dining table and chairs perfect for outdoor entertaining. brbrOn the second floor, you will find 2 bedroom suites, each with their own private bathroom and an additional private balcony off the main suite.brbrBedding: 1 king, 1 queen, queen sleeper sofa.brbrElevator access from ground level to the first floor of the condos. Stairs to the unit's second floor bedrooms.brbr**Construction Disclaimer** From mid May through the month of June, 2026, the pool area will be under construction. This will create noise and dust that could impact your stay and may lead to pool closure as well.

ARTIST'S CONDO @ Duval Square by Rent Key West Vacations - Located on Duval

Key West, Florida, United States

Bed

Bath

Sleeps

$368.71

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 EXCEPTIONSbrbrBOAT SLIP INFORMATION:brOne boat slip is included with this Retreat. Each Retreat can only accommodate one boat; no exceptions. Trailer parking is not available on property. Trailer parking and additional boat slips are available across the harbor at the City of Key West Marina. Please contact the dock master’s office to make arrangements for trailer storage and/or additional boat slips atbrbrFEATURES:brBedrooms: 2 ( 1 king, 2 queens in 2nd bedroom)- THE SLEEPER SOFA IS NOT RECOMMENDED FOR ADULTSbrBathrooms: 2 en suitesbrLocation: Garrison Bight Marina off Eisenhower DrbrSquare Feet: 1215brParking: 2 parking spaces includedbrAmenities: Wifi, TVs, in-unit laundry, 1 complimentary boat slip, water viewsbrbrTHINGS 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.

Flamingo Retreat-waterfront 2BR 2BA condo w/ pool & boat slip

Key West, Florida, United States

Bed

Bath

8

Sleeps

$615.94

Tom's Oceanfront PenthousebrbrExperience coastal luxury at Tom's Oceanfront Penthouse, a stunning 3-bedroom, 2-bathroom unit ideally located in a prime spot within the complex. Just steps from the elevator, this expansive 2,000 sq. ft. penthouse offers the ultimate in comfort and convenience, including secure, covered garage parking for vehicles under 6 feet 4 inches in height.brbrEach of the three bedrooms and the spacious living room features sliding glass doors that lead out to a private 60-foot wraparound balcony—perfect for enjoying sweeping ocean views and fresh sea breezes.brbr Master Bedroom: King-size bedbr Guest Bedroom: Queen-size bedbr Third Bedroom: Two twin bedsbrbrCondominium Amenities:brbr Olympic-size swimming poolbr 20-person spabr Saunabr Fitness areabr Librarybr Tennis courtsbrbrWhether you're lounging on the balcony, relaxing in the spa, or enjoying a game of tennis, this penthouse provides everything you need for an unforgettable oceanfront retreat.brbrElevator Upgrade project taking place from June - September 2026 - Please note there will still be one working elevator in both the East and West building while this project is underway.

Tom's Spectacular OceanFront 3 Bdrm Endless Atlantic view, Key West Amazing

Key West, Florida, United States

Bed

Bath

Sleeps

$1702.94

This gorgeous classical Key West Estate property is quite possibly the most stylish blend of historic Victorian-Caribbean with stunning island-modern that we have seen. An exceptional degree of refinement was reserved for the sophisticated renovation and décor of this circa 1930’s Key West Victorian house plus Caribbean bungalow cottage. brbrLocated in Key West’s famous Old Town Historic Seaport neighborhood on two full lots, The Caroline House Estate vacation rental is comprised of two dwellings – a classic 2-story Key West Victorian house, and a hidden 1 ½ story Caribbean bungalow. brbrTHE CAROLINE HOUSE (Main Victorian House)brbrINTERIOR LAY OUT:br(Downstairs)brbrEntrance: The arts-and-crafts staircase defines the luxurious entrance to the house and leads to the 2nd floor straight ahead, where the three bedrooms in the main house are found. The expansive runs of original heart pine wood that make the interior walls of the house have been painted with absolutely brilliant tropical colors you find on the feathers of a scarlet macaw parrot. brDownstairs - left side (as you face the house): Immediately to your left of the staircase is a spacious entrance hall, fit to receive the most discerning guest. Take an immediate left again to find the fabulous Victorian sitting room with yellow-gold painted walls and styled in eclectic tropical modern fashion. Cushy floral barrel chairs surround a round bamboo and glass coffee table and prints of colorful parrots the sitting room walls.brbrA square arch leads directly to the next room, a bright red dining room furnished with an oversized round mahogany dining table and chairs. The interior decorator has perfectly placed a long mahogany side board that runs the entire length of the dining room under the sash windows. A striking bouquet of red coral is placed in the middle, and then framed with a pair of clear designer lamps topped with coral red shades to match.brbrAnother square arch flows directly from the dining room to the spacious living room where a designer sofa and chairs have been chosen for comfort and style. The large wicker sofa with nautical striped upholstery is flanked by an oversized ottoman that doubles as a lounge table. A pair of khaki print occasional chairs and an antique side table is set to the side. A large flat-screen TV is prominently placed in the living room for group enjoyment, and mounted above the TV is an impressive taxidermy of a sword fish.brbrStraight ahead is yet a third square arch that melds into the left side of the spacious kitchen, where a double set of French doors lead to the spacious deck and swimming pool. But before we consider details of the kitchen and the pool grounds let’s look at the right side of the downstairs starting from the front.brbrDownstairs – right side (as you face the house): The classic hard wood front entrance hall points all the way to the back of the house where your senses are ultimately treated to a remarkable blend of a Key West historical kitchen with contemporary culinary luxury. But first, on the way to the kitchen, you pass through a beautiful office kiosk that is set with a wooden desk large enough for two. Folk-art prints from Mario Sanchez and a rustic shutter create a charming Key West office décor. Continue through to the other end of the office to the right side of the living room, and then a final interior passage joins the living room with the kitchen.brbrThe spacious sunlit kitchen is spectacular. It encompasses most of the back of the house and feels even grander with the 12 foot high ceilings, and pendulum designer lighting that show it all off. One entire wall, from floor to ceiling, is tiled with a period correct blue and white Spanish design pattern. Against the traditional tiled wall is the contrasting modern bright white cabinets and glistening stainless steel chef’s kitchen. A large dark wooden table creates an elegant dining area for in-kitchen meals, and is joined via French doors with the back sun deck and swimming pool. Finally, at the very back of the house, off the kitchen, is a walk-in laundry room and a half-bath. There is an outdoor shower just outside the door near the laundry room and downstairs bathroom.brbrUpstairs - Back to the front door entrance of the main house, the staircase leads to the 2nd floor where you find three beautifully appointed bedrooms off the hallway. The first bedroom is the master suite. Luxuriously styled in tropical gold walls and bedding of soft shades of tropical pink and green, it’s set toward the back of the house and furnished with a traditional king size four-poster mahogany bed, upscale matching Caribbean style furnishings, original art, and a 42” flat screen TV. The completely modernized en-suite bathroom for this bedroom is done vintage style with mahogany vanity and double size walk in shower with dual shower heads.brbrNext in line down the hallway is the 2nd bedroom. Situated in the middle of the hall, it is very comfortable and offers a 27” flat screen TV. Providing two twin beds and sweetly decorated in pretty shades of coral pink and white with sea-grass headboards, it is possible to push the beds together to make a king size bed.brbrThe 3rd bedroom is at the end of the hall at the front of the main house. Shown in our slide show with a blue and white comforter, walls painted sun yellow create a striking contrast for the queen size mahogany pencil poster bed and matching wood and wicker furnishings. This bedroom also provides a 27” flat screen TV.brbrBoth the 2nd and 3rd bedrooms share a large luxury bathroom with soak tub and in-tub shower that is located at the end of the hall near the top of the stairs. brbrTHE CAROLINE COTTAGE (Caribbean Bungalow Cottage)brINTERIOR LAYOUT:brbrSet on the lot next door to the main house on the other side of the pool garden, is the 1930’s free-standing Caribbean bungalow cottage. A brass plaque on the outside announces you have arrived at ‘The Caroline Cottage.’ From the outside, it maintains it’s traditional historic cottage charm, but inside is a completely different story. brbrAs with the main house, the staircase in the cottage defines the entrance and is also the center piece for the entire interior. The architect made a dramatic statement by taking the ceiling line clear up to the roof timbers. Then the builder hand-crafted an outrageous wooden winding staircase to reach the 2nd floor sleeping loft that was made possible with the extreme vaulted ceiling. The sleeping loft is cozy and feels a bit like a secret hiding place when you’re up there. brbrThe compact yet well designed and fully equipped kitchen lines one corner of the cottage and is ideally set to serve as a preparation kitchen for entertaining guests. Beautiful tropical furnishings and soft goods fill every room. A 52” TV is placed for easy viewing throughout the main room.brbrThe master bedroom, located directly off the living room space, provides a chocolate color wicker king size bed that makes a stunning contrast against the flamingo pink walls. On the wall directly opposite the bed is a flat screen TV. The entire cottage is finished with beautiful hard wood floors that compliment the staircase. The cottage provides one full beautiful bathroom on the main floor with a bath tub and in-tub shower.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 off-street parking for a maximum of 2 vehicles at The Caroline House Estate. Park in the driveway is to the left of the main house on Caroline Street, one vehicle in front of the other.brbrParking is challenging in Old Town Key West and parking meters and parking lots are relatively expensive. Since this part of the island was developed before there were cars, this should be expected. It is best to park your car, remove your valuables, lock it, and forget about it when you are here. Enjoy your location and walk or bike everywhere if possible.

The Caroline House Estate - 1 Block off Duval & Key West Historic Seaport

Key West, Florida, United States

Bed

Bath

Sleeps

$223.25

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 EXCEPTIONSbrbrbrFEATURES:brBedrooms: 2 (1 king and 1 queen)brBathrooms: 1brLocation: Truman Annex - Shipyard CondosbrSquare Feet: 600brParking: 1 assigned parking space in gated lotbrAmenities: Wifi, TVs, in-unit laundry, patio area, shared pool, walkable to downtown shops & restaurants brbrbrTHINGS 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.

Shipyard 197-Condo in Truman Annex-2 bedroom 1 bath, close to Duval w/ pool

Key West, Florida, United States

Bed

Bath

Sleeps

$686.47

Summary:brbrRelax and unwind in this spacious waterfront condo in downtown Key West. Ideal for families and groups, enjoy a full kitchen, open living space, and a private balcony overlooking the marina and pool. Dockage available with a fish cleaning station and ice maker, perfect for boating and fishing. Located about 1 mile from Duval Street, restaurants, and nightlife, and just 10 minutes from EYW airport. Amenities include a heated pool, tiki area, BBQ grills, free parking, elevator, and secure entry.brbrbrbrThe Space:brbrWELCOME TO DOMINICA YOUR WATERFRONT RETREAT IN KEY WESTbrbrbrbrLocated in the desirable Pelican Landing waterfront community, Dominica is a beautifully appointed 2 bedroom, 2 bath condo offering a spacious layout and comfortable coastal feel, ideal for families, couples, or small groups. Comfortably sleeps up to 6 guests, with a maximum occupancy of 8.brbrbrbrDesigned for comfort and easy living, this waterfront home features a bright, open layout, a fully equipped kitchen, and a large private balcony overlooking the marina and pool. Whether you are here for boating, exploring downtown Key West, or simply unwinding by the water, it’s an ideal place to relax and enjoy your stay.brbrbrbr✨ THE SPACEbrbr Primary Suite: King bed, marina views, private balcony access, ensuite bathroom, walk-in closet, and flat-screen TVbrbr ️ Second Bedroom: Two Queen beds, ensuite bathroom, and flat-screen TVbrbr ️ Living and Dining Area: Spacious open layout with comfortable seating, perfect for relaxing, dining, or gathering after a day on the waterbrbr ️ Kitchen: Fully stocked with cookware and essentials, ready for meals at homebrbr Laundry: Full-size washer and dryer for added conveniencebrbr Balcony: Large private balcony overlooking Garrison Bight Marina and the pool, ideal for morning coffee, boat watching, or sunset drinks. Includes direct stair access to the pool and docksbrbrbrbr DOCKAGE INCLUDEDbrbrA private boat slip is available for your stay, complete with water and a covered fish cleaning station. A commercial ice maker is available on-site, perfect for boating, fishing, and easy days on the water.brbrbrbr ️ EXTRAS AND AMENITIESbrbrPet-friendlybrbrFree on-site parkingbrbrHigh-speed WiFibrbrPrivate building elevatorbrbrbrbr COMMUNITY AMENITIES PELICAN LANDINGbrbr Heated poolbrbr Waterfront setting on Garrison Bight, located near Charter Row where many captains offer pickup directly from the dockbrbr Fish cleaning stationbrbr Private dock access for guests and ownersbrbr Tiki area and BBQ grillsbrbrbrbr LOCATION HIGHLIGHTSbrbr Bayview Park is adjacent with tennis courts and open green spacebrbr Fausto’s Food Palace 0.4 miles and Publix grocery store 1.4 milesbrbr ️ Higgs Beach 1.2 miles, Smathers Beach 1.5 miles, Fort Zachary Taylor Beach 2 milesbrbr✈️ Key West Airport about 10 minutesbrbrbrbr INSIDER TIPSbrbr Mac’s Place is right next door, a local favorite for casual food and drinksbrbr☕ Sandy’s Cafe 0.3 miles, known for Cuban coffee and breakfastbrbr Charter fishing, sandbars, and sunset cruises depart nearby from Garrison Bightbrbr Easy access to downtown, Duval Street, and the Historic Seaport, about 1 mile awaybrbrbrbrGuest Access:brbrGuests have full, private access to the entire 1,200 sq ft condo, including both bedrooms, two bathrooms, a fully equipped kitchen, and open living and dining areas. Enjoy the private balcony overlooking the marina and heated pool, along with direct access to the pool and dock area. You will also have access to the heated pool, tiki area, BBQ grills, and a private boat slip reserved for your stay. Free on-site parking is included, and a private building elevator provides easy access to the unit. Guests may also enjoy the adjacent park with tennis courts.brbrbrbrThis home is professionally managed by Keys Time Vacation Rentals, operated by hosts Jenny and Kim. Anthony, our on-site team member, is available during normal business hours if needed.brbrbrbrOur team is available 24/7 for any questions or maintenance needs to ensure a smooth and comfortable stay.brbrbrbrThe Neighborhood:brbrLocated in the downtown area of Key West, this waterfront condo offers easy access to everything the island is known for, while still providing a more relaxed setting just outside the busiest streets. Duval Street, the Historic Seaport, restaurants, bars, and nightlife are all about 1 mile away.brbrbrbrKey West is famous for its vibrant atmosphere, with live music, over 200 restaurants and bars, and nightly sunset celebrations. From beaches and boating to historic landmarks like the Hemingway House and Southernmost Point, everything is within easy reach. Bayview Park is right next door with tennis courts and open green space.brbrbrbrThe property overlooks Garrison Bight Marina, a hub for boating, fishing, and charter excursions. Located near Charter Row, many captains offer convenient pickup directly from the dock, making it an ideal location for guests planning time on the water.brbrbrbrGetting Around:brbrOur location is ideal for exploring Key West by foot or bicycle—everything is close by! Many guests also enjoy renting electric carts, which are widely available on the island, and we can accommodate plug-in access if needed. You really won’t need a car unless you're driving down Route 1 from mainland Florida. Lyft and Uber are also readily available throughout the area for added convenience. brbrbrbrOther Things to Note:brbr⏰ CHECK-IN AND CHECK-OUTbrbrCheck-in is 4 PM and check-out is 10 AM. The base rate includes up to 6 guests, with a maximum occupancy of 8. Guests 7 and 8 are $100 per person per night and must be included on the reservation prior to arrival.brbrbrbr PETSbrbrOne dog up to 25 lbs is welcome with a $200 non-refundable pet fee.brbrbrbr PARKINGbrbrFree on-site parking is available for one vehicle or golf cart.brbrbrbr DOCKAGE DETAILSbrbrMaximum boat length 40 ft, maximum beam 13 ft, with an 18 ft fixed bridge clearance into the marina. Overnight stays on boats are not permitted.brbrbrbr AGE REQUIREMENTbrbrAll guests must be at least 25 years of age unless accompanied by a parent. Please reach out with any questions.brbrbrbr TROPICAL ENVIRONMENTbrbrOur home is treated regularly by professional pest control. Due to the tropical climate, occasional insects may be present. If needed, we will promptly arrange service during your stay.brbrbrbrInteraction with Guests:brbrThis home is professionally managed by Keys Time Vacation Rentals, operated by hosts Jenny and Kim. Anthony, our on-site team member, is available during normal business hours if needed.brbrbrbrCheck-in is simple with keyless entry. You will receive access codes for the building at least 24 hours prior to arrival and your condo access code on the day of arrival.brbrbrbrOur team is available 24/7 for any questions or maintenance needs to ensure a smooth and comfortable stay.

Waterfront Dock Pool Downtown Near Duval Pet

Key West, Florida, United States

Bed

Bath

Sleeps

$1509.53

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival!brbrIf your idea of a vacation includes pampering yourself and indulging in the finer things in life, then a stay at the DUCHESS OF CATHERINE will be your cup of tea. This newly built, professionally designed home is fit for a King and offers plenty of space for all the members of your court. Located on Catherine Street, just steps from Duval Street, you couldn’t ask for a more centrally-located vacation rental. The spacious interior includes five suites (each with an en-suite bathroom) and a versatile Media Room. Outside, the private backyard features a splendid, heated pool and enough space for everyone to spread out or come together for a poolside BBQ. Your stay at DUCHESS OF CATHERINE also includes Last Key Realty's Five-Star Guest Services & Complimentary Concierge, ensuring you’ll feel like royalty.brbrTHE LOCATION…brbrIf you decide to pull yourself away from this beautiful home, you’ll realize that the best Key West restaurants, live entertainment, and attractions are all within a few blocks of your front door. While you won’t need a car to get around from this fabulous location, there is off-street parking in the driveway for one vehicle if you decide to bring one. If you don’t have a vehicle but want to explore the island in a fun way, Last Key Realty’s concierge service can assist with a golf cart, scooters or bike rentals.brbrTHE LIVING AREA & KITCHEN…brbrDUCHESS OF CATHERINE was designed and furnished with comfort in mind. The open living area is ideal for gearing up to head out on the town or for unwinding after a day full of adventure on the water. The spacious living room has a large flat-screen Samsung Frame TV that can be enjoyed from the two plush sofas or chairs. The fully equipped kitchen is next to the living room, with every appliance and tool needed to prepare a meal at home. The extra-large dining table seats 10 and there’s additional seating at the kitchen bar.brbrTHE PRIVATE POOL…brbrNo royal vacation is complete without a private pool to spend your days relaxing in. The fully fenced private pool area gets equal amounts of sun and shade throughout the day. Your private saltwater pool can be heated in the cooler months upon request. Kick back poolside in the chaise lounges or gather the group for an outdoor BBQ using the propane grill and outdoor dining set.brbrTHE ACCOMMODATIONS…brbr** Florida Suite: Located on the First Floor with a King bed, a flat-screen TV, a built-in armoire, and an en-suite bathroom with a walk-in shower.brbr** Paddleboard Suite: Located on the First Floor with Two Twins OR One King bed, a flat-screen TV, a closet, and an en-suite bathroom with a walk-in shower.brbr** Media Room: Located on the First Floor with a sofa that pulls out into a Queen to accommodate extra guests and a flat-screen TV.brbr** Whale Suite: Located on the Second Floor with Two Twins OR One King bed, a flat-screen TV, a built-in armoire, and an en-suite bathroom with a walk-in shower.brbr** Flamingo Suite: Located on the Second Floor with Two Twins OR One King bed, a flat-screen TV, a closet, and an en-suite bathroom with a walk-in shower.brbr** Aviary Suite: Located on the Second Floor with a King bed, a flat-screen TV, a closet, a trundle bed with two twin mattresses, and an en-suite bathroom with a walk-in shower.brbrALL LAST KEY VACATION HOMES INCLUDE:brbr** Washer & Dryerbr** Central Heat and A/Cbr** Ceiling Fansbr** Flat Screen Cable 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 and full cable is includedbr** Full Time Concierge ServicebrbrIn addition, this fully stocked home also includes, but is not limited to the amenities on this list:brbr** Fully Fenced Yardbr** Private Saltwater Pool (with Pool Heat for $30/day)br** Propane BBQ Grillbr** Off-Street Parking for 1 Vehiclebr** Queen Sleeper SofabrbrOther notes:brbr** Interim housekeeping provided upon requestbr** This property will accommodate up to 14 adultsbr** Max of 2 Pets Allowed with Additional Fee of $200 per petbr** Last Key Realty vacation homes are rented to family groups and responsible adult groups only. Groups who expect they may cause after hours noise will not be a good fit for this home and should be aware they may incur additional penalties when in residence for violations. There will be a $500 charge for after-hours dispatch of our staff in response to calls resulting from verified noise complaints for violations by our guests in residence.

**DUCHESS OF CATHERINE @ DUVAL** Brand New Home & Pool + LAST KEY SERVICES…

Key West, Florida, United States

6

Bed

5

Bath

14

Sleeps

$2831.25

Discover the beauty of Key West from this spacious property. The property is perfect for hosting conventions.brThis would be an excellent property to use as a screen for an action movie.brThere is lots of free parking available and it is right next to Bernstein Park.

Serene 3-bedroom house with AC in charming Key West + private, small house

Key West, Florida, United States

Bed

Bath

Sleeps

$334.17

Rum Cay offers a quiet alternative to the downtown area of Key West. This modern condo is located a short 10-minute ride away from the nightlife, shopping, restaurants, and attractions near world-famous Duval Street. Rum Cay is a condo offering spacious bedrooms, a common area with a large screen TV, a murphy bed, plus a dining area and updated kitchen with stainless steel appliances.brbrThe condo is nestled on the edge of a nature preserve offering a quiet surrounding. There is a community pool, ample parking, and an elevator. Rum Cay offers a beautiful view of the estuary and views of the island and the water. brbrThe primary bedroom has a king bed, a large walk-in closet, and an updated bathroom offering a glass shower with rain showerhead. The primary bedroom has a flat screen TV and large dresser. The second bedroom offers a queen bed and flat screen TV. It has access to the second bathroom which is also accessible from the kitchen area.brbrThe living room and kitchen area are spacious with vibrant colors. A comfortable leather couch and two chairs offers space to unwind after a busy day around the island. Extra guests can utilize the murphy bed that folds out with a very comfortable memory foam mattress. The living room offers a large flat screen TV and there are sliding glass doors out to your own private balcony with a table and seating for four people. The kitchen is a great use of space with a larger table and four chairs. Everything you need to cook a meal at home is available. brbrRum Cay is the perfect place for a family or for friends who want to enjoy the quieter side of Key West.

Retreat to RUM CAY @ Sunrise Suites

Key West, Florida, United States

Bed

Bath

Sleeps

$291.04

Poolside Paradise is a cozy, 1930s-era pool cottage lovingly renovated into a 1B/1BA suite. The sage-green exterior blends Caribbean, Victorian, and contemporary influences: crisp white trim and sky-blue Bermuda shutters. brbrThis intimate, poolside cottage is set back from the street and shaded by gardens, mature palms, and gumbo limbo trees in a quiet, upscale, gated courtyard community of five historic Old Key West vacation rentals. The spacious pea-gravel courtyards boast tropical landscaping, coral and rock hardscaping, and walkways leading to the shared pool area. The central common area, with a pool, picnic tables, and gas grill, is shared by guests of this upscale, gated enclave of six historic Old Key West vacation rentals. There’s also a shared laundry area with commercial washers & dryers.brbrPoolside Paradise was once the guest suite/pool cottage of Toon Hall. Toon Hall was owned (and aptly named) by Jeff MacNelly (1947-2000), lauded as one of the most brilliant political cartoonists. brbrIn 1977, MacNelly launched his comic strip Shoe, characterized by wit, wry humor, and cynicism. He became The Chicago Tribune’s syndicated editorial cartoonist. Newsweek Magazine described MacNelly’s style as “goofy gracefulness.” In his lifetime, MacNelly received three Pulitzers and two Reuben Awards, the highest honor of the National Cartoonists Society. Since Jeff MacNelly’s death in 2000, the Shoe comic strip has been kept alive by Chris Cassatt, Gary Brookins, and Susie MacNelly. brJeff MacNelly and his wife Susie cherished the vibrant Key West arts scene as a wintertime retreat. Today, Poolside Paradise offers a cozy island suite beside the pool and courtyard in a gated enclave of elegant vacation properties.brSip Cafe Cubano at the covered, alfresco dining table as Caribbean breezes rustle the palm fronds, or relax poolside with a Margarita. Prepare a light tropical meal in the kitchenette. Dine alfresco when nights are fragrant with jasmine and frangipani. Stroll to great seafood, fine dining, beaches, and iconic attractions like the KW Butterfly & Nature Museum, Southernmost Point, Higgs Beach, and West Martello Tower. brbrStreet parking is available out front. Poolside Paradise has one King Bed, ideal for couples or solo travelers. The home has an all-new water filtration system. brAre you interested to learn more about the life and work of Jeff MacNelly Pop into The Gallery on the Greene, the exclusive KW gallery representing MacNelly. Cartoons, pen and ink drawings, and original canvases are on display. brbrLiving:brPoolside Paradise is a bright, airy, one-room living space with tile floors, large windows, raised ceilings, exposed beams, a ceiling fan, and an interior color palette of crisp white and earthy neutrals. A built-in desk/TV stand boasts a Smart TV with Roku. Stream your favorite shows or movies. French doors open to a covered alfresco dining area with rattan benches. Enjoy easy-breezy indoor/outdoor living space. brbrKitchen/Dining:brThe sunny kitchenette has tile floors, abundant cabinets, and Formica countertops. Appliances include a compact fridge, microwave, farmhouse-style sink, coffee maker, and toaster. Prepare sandwiches or a light island-style meal after a day at the beach! The kitchenette has a dinette with seating for two. French doors from the kitchen lead directly to covered alfresco dining and to the pool deck, making for seamless indoor/outdoor entertaining.brbrBedrooms/Baths:brPoolside Paradise has one air-conditioned bedroom and one bathroom. There is one King bed. Matching rattan-style bedside tables have reading lamps. A built-in TV stand/desk boasts a Smart TV.brbrThe sparkling-clean, remodeled bathroom has a single-sink vanity, a walk-in glass door shower, a water-saving toilet, toiletries, and a hair dryer. brbrBedroom Overview:brPrimary: King Bed, Ensuite bath w/ walk-in shower brbrOutdoor Amenities:brA tall exterior fence, lush gardens, and mature trees provide privacy, security, shade, and a peaceful, tropical ambiance. Enjoy a private dining space on your fenced patio. This dining space seats two. The whitewashed fence buffers your private space from the central common area. brbrCool off in the sparkling blue swimming pool, or doze poolside on a cushioned lounge chair. This swimming pool will delight families, children, the very young, and the young at heart. (The common pool area is shared by guests of this upscale, gated enclave of six historic, Old Key West vacation rentals.) The poolside deck features a gas grill and two wrought-iron picnic tables with seating for eight or more. Gather for an afternoon cookout in paradise! Mature palms, mango trees, and vibrant bougainvillea shade the pool deck.brSince laundry never sleeps (even when you're on vacation), the common area offers a laundry shed with two commercial washers and two commercial dryers. brbrDiscover the ultimate amenity: stroll just two blocks to Higgs Beach. Dip your toes in the emerald ocean. Collect seashells and savor serene Caribbean sunsets in pink, violet, and gold hues. Park your car in shaded street parking spots out front. Stroll or bike to attractions.brbrThe Neighborhood:brbrThe proximity of Toon Hall to the Casa Marina Hotel and the beautiful beaches adds to the appeal, making it a perfect blend of history, culture, and coastal living. Picturesque south island streets are lined with beautifully preserved Conch-style homes, each exuding character and charm. Lush, tropical landscaping adds to the serene atmosphere, making every walk or bike ride a delightful experience. brbrA car is not necessary on the island. Make the green choice. Park out front or along shaded side streets and enjoy the island on foot, by bicycle, scooter, trolley, or bus. The island trolley stop is one block away. The Duval Loop City bus stop is four blocks away. brbrStroll .07 miles to The Ernest Hemingway Home and Museum, which offers a fascinating glimpse into the life of one of America's greatest writers. Enjoy the diverse culinary scene with various restaurants, cafes, and bars offering everything from fresh seafood to classic Cuban cuisine. Local favorites such as Blue Heaven, Louie’s Backyard, and Sloppy Joe’s are within easy reach, providing unforgettable dining experiences. brbrDon't miss the chance to explore West Martello Tower during your stay! Just a 10-minute walk or a quick 3-minute bike ride from Toon Hall, this hidden gem is a tropical garden paradise on the site of a historic Civil War fort. The gardens, maintained by the Key West Garden Club, are open to the public. brbrHiggs Beach, approximately 0.5 miles (a 10-minute walk or a 3-minute bike ride), is the closest beach to Southern Cross. Enjoy crystal-clear waters, perfect for swimming or snorkeling. The nearby White Street Pier offers panoramic sea views and excellent fishing opportunities. brbrApproximately 1.5 miles away, Smathers Beach is Key West’s largest public beach. This two-mile stretch of sugary sand is ideal for sunbathing, beach volleyball, and water sports such as kayaking, paddleboarding, and windsurfing. brbrFort Zachary Taylor Historic State Park Beach, approximately 2 miles away, offers natural beauty and historical intrigue. Visitors and locals gather here and at Mallory Square to celebrate each and every exquisite island sunset. brbrSeeking family-friendly activities or rainy-day excursions Check out the Key West Aquarium, the Butterfly and Nature Conservatory, The Shipwreck Treasure Museum, and the Lighthouse and Keepers Quarters Museum. Nightlife and live music abound in Key West! Take in a show at the Tropic Cinema. Catch a live band at the Green Parrot.brbrIf you’ve been charmed by the magic of Toon Hall and wish to learn more about the life and work of Jeff MacNelly, tour the island art galleries and pay a visit to Gallery on the Greene, the exclusive gallery representing MacNelly. While cartooning was MacNelly’s livelihood, he was skilled in many media, including oil, acrylic, and clay (sculpture). Today, The Community Foundation of the Florida Keys honors the legacy of Jeff MacNelly with a youth scholarship, The Jeff MacNelly Memorial Scholarship Award, which helps students in Monroe County to further their art careers.

Apartment

Tropical Village: Poolside Paradise by RENT KEY WEST VACATIONS

Key West, Florida, United States

Bed

Bath

Sleeps

$357.18

Sunrise Suite 203 is a quiet alternative to the bustling noise of downtown Key West. Located just a 10-minute drive from all of the nightlife, shopping, restaurants, and activities of world-famous Duval Street, Sunrise Suite is your own private condo in our island paradise. You will enjoy the conveniences of a hotel with the comforts and space of home.brbrThis comfortable, non-smoking, reasonably-priced two-bedroom/two-bath unit offers everything that will make your vacation memorable. Enjoy nightly sunsets from your private balcony overlooking the pool. Go for a dip in the shared lagoon-style pool or pull up a lounge chair and enjoy the Florida sun. You also can relax in the outdoor spa surrounded by the lush tropical foliage.brbrThe primary bedroom has a king bed with walk-in closet and ensuite bath that includes a tub, shower, large vanity sink, and plenty of towels. The second bedroom has a queen bed with adjoining bathroom. There is also a queen-sized sleeper sofa in the living room.brbrThe kitchen is open to the living room with bar counter seating and is fully-equipped with full a stove, refrigerator with ice maker, dishwasher, microwave, small appliances, and sink disposal. All glassware, dishes, utensils, and cookware are there whether you choose to cook at home or heat up leftovers after dining out at one of the fantastic eateries in Key West.brbrThe resort also features tennis courts, gym facilities, and free parking. Nearby activities include jet skiing, sailing, snorkeling, diving, boating, fishing, kayaking, parasailing, windsurfing, sightseeing, golf, biking, and walking. Movie theaters, museums, and live theater also are nearby. Our concierges can always be counted on to help you plan your day or evening. Or just take in the sunrise while walking the Atlantic oceanfront down the street and enjoy the morning coolness. A 15-minute walk away is Smathers Beach, where you can play in the sun with your toes in the sand.brbrThe individual making the reservation must be 25 years or older with proper identification and be an occupant of the property. The maximum number of people allowed in this property is 6. If there are more than 6 people are in your party upon arrival, your party will be asked to leave without compensation. Violation of ANY house rules will result in your party being asked to leave without compensation.

Stay at SUNRISE SUITES 203!

Key West, Florida, United States

Bed