Vacation Villa Rentals By Owner In Key West, FL

Escape to your own private paradise at Oasis on 18th, a luxurious three-bedroom, three-bathroom haven nestled within the prestigious gated Key West Golf Club.brbrThis meticulously maintained home, which happens to be the largest in the Key West Golf Club, offers the ultimate in comfort and relaxation. As you enter, you'll be greeted by the spacious living area, adorned with tasteful furnishings and elegant decor. The open floor plan seamlessly connects the living room, dining area, and kitchen, creating an inviting space for gatherings and relaxation. Adjacent to the living area is a separate sitting room, providing additional space for relaxation and entertainment, complete with a pull-out sofa bed for overnight guests.br brThe kitchen is a chef's dream, equipped with modern appliances and featuring a spacious bar, two wine coolers and an extra beverage cooler, perfect for unwinding with your favorite vintage after a day of exploration. br brAscend the stairs to the upper level of this remarkable home to discover the primary en-suite bedroom, a refuge of comfort and tranquility. Adjoined to this elegant retreat is in the palm trees level Hemmingway sitting room, offering a whimsical escape amidst the canopy of palms with unparalleled views. Step out onto the second-floor balcony and soak in the beauty of the surrounding tropical landscape. Each of the other two bedrooms also boasts a shared balcony, offering private outdoor spaces to soak up the sunshine, tropical breeze and enjoy the fresh air. Additionally, guests will find themselves greeted by the comforts of home, with both bedrooms furnished with a Keurig coffee machine, ensuring that every morning begins with the perfect cup of coffee.brbrNestled in a quiet location within the privately gated Sanctuary of the Key West Golf Club, Oasis on 18th offers peace and tranquility while still being just a short 3 Mile distance away from the bustling energy of the famous Duval Street. Explore the vibrant shops, five-star restaurants, exciting attractions, golf and world class fishing, as well as fantastic opportunities for sightseeing, diving and boating before returning to your private oasis. In addition, just a short drive away you can be enjoying either Smathers Beach, Higgs Beach or Fort Zachary Taylor Historic State Park!br brOutdoor living is a dream at Oasis on 18th. Relax by the large PRIVATE HEATED POOL, surrounded by a charming herringbone brick patio. Fire up the new Weber Genesis four-burner gas grill for a barbecue, dine al fresco at the spacious dining table on the fully screened lanai, or unwind in the comfortable seating area – the choice is all yours.brbrSurrounded by lush manicured landscaping and overlooking a tranquil pond on the 18th hole, this home offers breathtaking views and unparalleled privacy. The private fenced yard adds an extra layer of seclusion, perfect for enjoying quiet moments in nature.br brAs part of the highly esteemed Key West Golf Club community, guests enjoy exclusive access to a wealth of amenities designed to elevate their stay. With not just one, but two pools, at their disposal, guests can choose between lounging in the tranquil ambience of the large resort-style pool or engaging in invigorating laps in the lap pool. The state-of-the-art gym caters to fitness enthusiasts. And for avid golfers, the crowning jewel of the community is the renowned Reese Jones Designed Golf Course, ensuring there's something for everyone to enjoy during their stay.brbrWith a private driveway and carport, parking is convenient and secure, allowing you to come and go as you please.brbrKey West Golf Club Amenities you may enjoy while staying at Oasis on 18th:br* 24/7 Security and Gated Entry br* Parking for 2 Vehicles br* 24 hr Fitness Centerbr* 2 Additional Pools, one being a Resort Style Pool & one being a Lap Style Poolbr* 1 Mid-Stay Cleaning is included in your staybrbrDon't miss the opportunity to experience the ultimate Key West getaway at Oasis on 18th. Book your stay today and make memories that will last a lifetime! We look forward to hosting you soon at Oasis on 18th!br brOther Things to Know:br* Guests must use their own logins for streaming services.brSecurity Camera -br* There is one active Ring Doorbell Camera located on the Front Door facing the street.br* Pet Friendly - 1 to 2 dogs allowed with a total weight of 50 lbs for both - restrictions on dogs may apply. br** Pet Fee of $500 per dog.br**Minimum Age to rent is 25 - Due to local laws or HOA requirements, guests must be at least 25 years of age to book. Guests under 25 must be accompanied by a parent or legal guardian for the duration of the reservation.

Escape to Oasis on 18th w/ PRIVATE HEATED Pool in the KW Golf Club Sanctuary!

Key West, Florida, United States

Bed

Bath

Sleeps

$276.42

Hello, I am Francine -- new owner who recently listed the condo on VRBO. This is why I do not have yet any rating and if you are anything like me -- you are looking for best rating. However, if you trust me and are looking for a relaxing and attractive place while still being in the middle of the action, this place does exist at the Shipyard Condominiums. brbrIt's located in the prestigious gated community of Truman Annex in Key West’s old town area which is 2 blocks from Duval Street, close to the beach and all the Old Town Key West attractions and great restaurants. You can walk to the grocery store (Fausto's), have drinks at the Green Parrot (2 blocks away) and enjoy Fort Zachary Taylor State Park which is around the corner. brbrI just renovated this 2 bedrooms /1 bath condo which is outfitted with washer/dryer, all new appliances in the kitchen, pots/pans, towels, linens, have central air conditioning, pool access and assigned parking inside the gated community. brbrThis end unit condo is on the ground floor and has big, beautiful French doors in the living room and master bedroom. They open onto the private back deck with has outdoor patio furniture. You also have a fully equipped modern kitchen, renovated bathroom, and flat screen TV’s in the living room and wireless internet access. The master bedroom has a king size bed and the guest bedroom has a queen size bed and each bedroom has flat screen TVs. brbrAfter a full day of taking in the island’s many wonderful experiences, come back to the comfort of this home. The manicured landscaping, verdant palms, and white picket fences give the Shipyard and Truman Annex a lovely park atmosphere. All this tranquility makes it hard to imagine that Duval Street, Key West’s central artery of entertainment is only two blocks away. brbrI am looking forward to welcoming you to this lovely sunny condo.brPlease reach out if you have any questions - +1 914 648 8943. Best, Francine

Great Location- Remodeled Condo- Old Town-Truman Annex Close to all attractions

Key West, Florida, United States

Bed

Bath

Sleeps

$293.36

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival!brbrAs soon as you enter, you'll feel like you stepped into a dream. Welcome to DEEP BLUE DREAMS, a modern coastal retreat in the heart of Truman Annex, Key West’s most exclusive neighborhood. This freshly updated 2 bedroom, 2.5 bathroom condo brings a new level of style to island living — sleek and modern, yet relaxed and inviting, with subtle touches of deep ocean blue that inspire its name. brbrJust steps from the waterfront, you’ll enjoy the best of both worlds: the quiet elegance of a gated community and the excitement of Old Town only moments away. Walk to Fort Zachary Taylor State Park and its iconic beach, or head to Duval Street, where world-class dining and entertainment await. Paired with Last Key Realty’s 5-star Guest Services and complimentary Concierge, a stay at DEEP BLUE DREAMS will be so memorable you'll be dreaming about it for years to come.brbrTHE LIVING AREA…brbrDEEP BLUE DREAMS features high ceilings, contemporary furnishings, and a cool color palette accented by deep sapphire walls — a nod to the ocean just beyond. The living room offers ample space to unwind, with a plush leather sofa and matching chairs that you’ll just sink into. A large Smart TV provides entertainment for evenings in, while the glass doors open to a private balcony perfect for morning coffee or a sunset cocktail.brbrThe fully equipped kitchen has everything a home chef could want — stainless appliances, quartz countertops, and all the cookware you’ll need when you’re not dining out at one of Key West’s top restaurants. Gather your group for a home cooked meal at the dining table that seats 4. A convenient powder room is located just off the living area.brbrTHE POOL & THE BEACH…brbrThe Community Pool is waiting outside; large, heated, and lined with comfortable chaises for relaxation. The pool deck overlooks the Gulf of Mexico, offering front-row seats to Key West’s world-famous sunsets. For those who prefer the beach, Fort Zachary Taylor State Park is just a short stroll away, offering swimming, snorkeling, and shaded picnic areas beneath the pines.brbrTHE ACCOMMODATIONS…brbrPrimary Bedroom – King bed, Smart TV, large closet, and an en-suite bath with a glass-enclosed shower and modern finishes.brbrGuest Bedroom – Two Twins or One King (your choice), Smart TV, large closet, balcony access, and easy access to the hall bath with a tub/shower combo.brbrALL LAST KEY VACATION HOMES INCLUDE:brbr** Washer and Dryerbr** Central Heat and A/Cbr** Ceiling Fansbr** Smart TVs in Living Room & 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 & Full CablebrbrIn addition, this fully stocked home also includes, but is not limited to the amenities on this list:brbr** Large Heated Community Poolbr** Covered Off-Street Parking for 1 Car (vehicle restrictions apply — no vehicle over 18’ long or 80’’ wide)br** Two Twin Rollaway BedsbrbrOther notes:brbr** Interim housekeeping available upon requestbr** Accommodates up to 6 guestsbr** No Pets Allowedbr** Suitable for families and responsible adult groups only. Groups expecting to host late-night gatherings or make excessive noise should seek alternative accommodations.

**DEEP BLUE DREAMS @ THE ANNEX** Oceanside Condo & Pool + LAST KEY SERVICES…

Key West, Florida, United States

Bed

Bath

Sleeps

$322.93

Welcome to your Key West retreat. This well-appointed 2-bedroom, 2-bath residence offers a comfortable, elevated stay for up to four guests, with ocean views and an ideal location near the island’s best spots.brbrThe open living area is bright and inviting, with comfortable seating and direct access to a private 4th-floor balcony. From here, you’ll enjoy a beautiful ocean view—perfect for a quiet morning coffee or relaxing at the end of the day.brbrThe layout is both comfortable and flexible. The primary bedroom features a king bed and en-suite bathroom. The second bedroom offers two twin beds that can be combined into a second king, making the space well-suited for couples traveling together, friends, or families.brbrBoth bathrooms include showers, with one also offering a tub.brbrThe kitchen has been fully updated with brand new appliances and is equipped for anything from light meals to full dinners at home. A dedicated dining area provides a comfortable space to gather.brbrThe location is one of the property’s standout features. You’re within walking distance to Smathers Beach and just a short bike ride to Duval Street, putting dining, nightlife, and activities all within easy reach.brbrThis is an ideal option for guests looking for a clean, well-located property with a great view and a bit more space to relax.

Vitamin Sea at LaBrisa - Oceanfront View!

Key West, Florida, United States

Bed

Bath

Sleeps

$181.74

Summary:brbrEclectic Duval Street studio with shared poolbrbrbrbrThe Space:brbrExperience the heart of Key West in this eclectic studio available for monthly rental only and located right on iconic Duval Street. Perfectly positioned behind The Grand Cafe at 314 Duval St., this charming retreat places you steps from the island’s best dining, nightlife, shopping and attractions — all while offering a peaceful escape right off the complex's shared courtyard pool.brbrbrbrThis cozy studio blends Key West’s signature character with modern comfort. The Murphy bed lets you switch from a comfortable couch during the day to a bed at night. A compact kitchenette is equipped with essentials for light meals or morning coffee before you explore the island. Step just outside your door to relax by the shared pool, surrounded by lush tropical foliage — an inviting oasis in the middle of Old Town.brbrbrbrUnbeatable LocationbrbrYou can’t get more central than Duval Street. Stroll to Mallory Square for sunset celebrations, visit The Ernest Hemingway Home and Museum, or enjoy nearby hotspots like Sloppy Joe’s, Fogarty’s and The Bull. Whether you’re here for live music, art galleries or quiet afternoons by the pool, everything you love about Key West is within easy walking distance.brbrbrbrGood to KnowbrbrGated entrybrbrShared courtyard poolbrbrShared coin laundrybrbrMonthly rental only (29-day minimum per local ordinance)brbrNo parking available – walking or biking is the best way to explore Old TownbrbrNo pets and no smoking allowedbrbrProper county and state taxes collected regardless of booking platformbrbrbrbrThis unique Duval Street studio is ideal for guests seeking a true Old Town Key West experience — steps from the action, yet tucked into a charming tropical retreat.

Apartment

Cabana on Duval | Monthly studio w/ shared pool

Key West, Florida, United States

Bath

Sleeps

Exceptional(1)

$159.77

Charming Studio Retreat with Pool Access in Old Town Key West. Escape to island living at this delightful studio located in the heart of Key West’s Old Town. Tucked away on Grinnell Street, this cozy hideaway offers everything you need for a relaxing stay. Step inside to find a bright and inviting space, complete with a fun, well-equipped kitchen perfect for whipping up tropical cocktails or a light meal after a day of exploring.brEnjoy access to a shared swimming pool, where you can lounge in the sun or cool off under the palms. The studio’s thoughtful design makes the most of its space, giving you comfort and convenience just steps from Duval Street, local dining, galleries, and nightlife. Whether you’re here for a quick getaway or an extended island escape, this Grinnell Street gem offers the perfect blend of comfort and Key West charm. Classic Old Town neighborhood atmosphere.br✨ Features:brStudio layout with queen bedbrFun, colorful kitchen with essentialsbrShared swimming pool & sun deckbrClose to Duval Street, shopping & restaurantsbrbrAGE 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 EXCEPTIONSbrbrDiscover the charm of Old Town Key West in this inviting 1-bedroom, 1-bathroom studio apartment. Just 10 minutes from lively Duval Street, this cozy retreat offers the perfect balance of comfort and convenience. Enjoy a full kitchen for at-home meals, a private washer and dryer, and access to a refreshing shared pool for sunny afternoons. Whether you’re here to explore the island’s history, nightlife, or beaches, this studio is the ideal home base for your Key West getaway.brbrTHINGS 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.

Old Town Studio Cottage with Full Kitchen, In-Unit Laundry & Shared Pool

Key West, Florida, United States

Bed

Bath

Sleeps

$312.41

First impressions are everything. And it`s love at first sight with the charming 2BR 2BA Casa Bella Petite le Bleu. This classic Key West cigar-maker`s cottage was originally built in 1889, on a lazy little narrow lane. It was so lovingly restored and renovated in 2011, that it received the coveted Historic Florida Keys Foundation Preservation Award.brbrOver a century later, Casa Bella Petite le Bleuis a luxurious charming pool-garden home. Situated on the quiet upper end of famous Elizabeth Street, this house is dripping with authentic charm. From its stunning transformation to its enviable location, this Key West house is a great place to stay for a month or more.brbrLAYOUTbrbrFrom the front curb this cottage is a picture of perfection. Nestled amongst a remarkable collection of authentic structures, its historic characteristics are captivating. On the left side you`ll notice tin sawtooth roof. Designed for function in the 1800`s, the steep roof was designed to shield the cottage from the heat of the tropical sun. You`ll also see its notable modern feature - the off-street brick paved parking area. Parking is an enviable perk in Old Town Key West. Plus, it has Tesla charging station mounted on the fence.brbrAs your eyes pan away from the driveway to the right, take-in the crisp white clapboard cottage accented by bright blue storm shutters and a traditional metal roof. The ample covered porch invites you to linger for a moment in its shade to savor the fragrant island breeze wafting by. This porch features comfortable outdoor furnishings and roll down sunscreen shades for privacy and protection from the afternoon sun.brbrThis is the perfect cottage for two to four people. If friends and family become enchanted and decide they want to come. No Problem! Right across the street is the extraordinary 5BR 5.5 BA Bella Grand Premier EstatebrbrThe Great RoombrbrAs you step through the front door into the great room, you`ll be taken by the skillful blending of clean modern lines within this historic Key West cottage. The original Key West heartpine wood warms and personalizes the environment. The tall wood-paneled ceiling with bright white open beams creates a sense of openness and makes the room feel larger. The pine flooring adds warmth to the entire main level except for the kitchen and bath areas, which are finished in beautiful ceramic tile. The sense of openness is amplified by the plentiful outdoor views afforded by the many windows and glass doors which wrap around the room. Tasteful, clean contemporary furnishings include a queen sleeper sofa. The two large double French doors on the wall to your left seamlessly merge the room with the swimming pool garden. The garden is a room, in and of itself, and is made to feel private with lush tropical foliage.brbrMain Level BedroombrbrThe interior wall directly opposite the poolside French doors, is the only Great Room wall without windows. Immediately to the right of the home`s front door is the entrance to the 1st floor bedroom. This downstairs bedroom offers a queen sized bed, large flat screen TV and spacious double closet.brbrUpstairs Bedroom SuitebrbrNext as we pass by the interior wall, we come to an artistically simple open stairway. The stairway leads up to the second floor Master Suite. As you reach the top of the stairs, you find enter the 2nd floor suite. This room runs the entire width of the house. The low ceiling is tucked up to the roof-lline. Turn to your right, and you`ll be led to the bedroom area with its king bed and 40` flat screen TV. On the other end, just past the stairs, is the open bath area. The bathroom features a spacious glass-enclosed shower with rainfall shower head and hand held spray. A 12-light sash window in the shower looks out over the treetops outside.brbrKitchenbrbrHeading back down the stairs, we find ourselves approaching the kitchen, separated from the living by a four-stool breakfast bar. The kitchen space has a vaulted ceiling, which adds a nice sense of volume to the space.brbrThe upscale Viking appliances make the kitchen a pleasure to cook in. It has a large capacity dishwasher, a two over one refrigerator/freezer, and a smooth-top stove featuring a state-of-the-art downdraft venting system. A large double stainless sink with high end fixtures plus disposal and under-counter lighting finish out the beauttiful and efficient work space. Two large windows and a French door bring in lots of natural light and never let you forget for a moment that you`re in a tropical paradise.brbrMaster Bath/Rear DeckbrbrOn the opposite wall from the kitchen is the entrance to the master bath. Under its vaulted ceiling, you`ll find the bathtub complete with rain shower head, and ample closet space. In its own closet, you`ll find a Frigidaire washer/dryer stack. Step through the frosted glass French door, and you`re under a shady little lanai which opens onto the back deck. Here you`ll spot a table and chairs for luxurious dining under the stars, and also an open shower stall, handy for rinsing off after a swim.brbrTropical Pool GardenbrbrAround the corner from the rear deck to the side of the house, we find the swimming pool garden. French doors connected the pool-garden deck with the great room. The roomy heated swimming pool features a sparkling sheet waterfall, The soothing sound of the splasing waterfall contributes to the peaceful ambiance. The pool is surrounded by a deck wwith chaises for sunbathing or retreating to a shady corner for a refreshing afternoon beverage. We suspect that throughout your stay at Casa Bella Petite le Bleu, this beautiful pool area will be your prime go-to spot for relaxing, swimming or reading a good book.Settle back and relax ... you`ve arrived!brbrBedding Summary (Sleeps Six):brbrbrUpstairs Bedroom Suite - King size bedbrbrFirst Floor Bedroom - 1 Queen size bedbrbrLiving Room - Queen sleeper sofa.brbrbIMPORTANT: How payments work/bbrVRBO collects only their service fee. Reservation payments are paid directly to VHKW in two installments in accordance with the terms of your rental agreement (sent for review upon reservation). Payments to VHKW by credit card are subject to an additional 2.95% merchant processing fee.brbrAmenities: This is an upscale complete renovation with many extras. Comfortably decorated and furnished. Fully equipped user-friendly Viking kitchen. 55- inch flat screen TV in the 1st floor bedroom, 40-inch flat screen TV in the 2nd floor suite. Central A/C. Linens and Towels are provided. There is a laundry closet in the 1st floor bath with stacked Frigidaire washer/dryer. Heated swimming pool, lush tropical landscaping, large private sun deck, outdoor shower, kettle style charcoal smoker/BBQ grill. There is a full outdoor dining set complete with high-end umbrella.brbrActivities:Casa Bella Petite is conveniently located in a classic Key West residential neighborhood. It is an easy 5-10 minute walk straight ahead to Duval St., around the midpoint between the Atlantic and the Gulf. Along this bustling strip, you`ll find a wide selection of shops and galleries as well as restaurants of every style and price point. And of course you`ll want to check out the many bars and nightspots for which Duval is famous. Walk 10-15 minutes to your right and you`ll find yourself at the colorful Key West Historic Seaport with its myriad of attractions, restaurants, bars and shops on the land side, and boats and ships of every description docked along the waterfront.brbrArea:Although not really much of a hill by the usual standards, Solaris Hill is actually the highest point of land on our little island. This neighborhood was developed in the late 1800`s, and is comprised mainly of smaller homes built for Key West`s early working folks. A few larger homes are dotted throughout, though, as is not unusual in Old Town. From this home, a half a block from the dead center of this `hill`, you are only two blocks from the fascinating Key West Cemetery (circa 1847), host to over 100,000 former Conchs and many entertaining gravestones. From such a central location, you will have easy access to beaches, attractions, shopping and galleries all over the historic end of the island. This is a terrific spot for guests who opt to rent bicycles rather than a motor vehicle.brbrParking: This home has a private designated off-street parking area paved with bricks for one car or a couple of golf carts or scooters. A Tesla charging station is provided. A convenient gate in the parking area fence allows easy access to the side pool deck where you can securely stash your rental bicycles.brbrRestrictions: Month minimum rental. Smoke free house.No pets please. Not suitable for staging loud parties. Maximum of 8 guests allowed. We do not accept guests less than 25 years of age unless accompanied by a family or group.

Casa Bella Petite le Bleu - Luxury Key West Cottage w Pool - 2 Blocks Off Duval

Key West, Florida, United States

Bed

Bath

Sleeps

$363.22

A Historic Cigar-Makers Conch Home, privately owned by a native hospitable family in the heart of Downtown, a few minutes walk from Duval St. Accommodates 1-2 couples. Your car will be safe in this parking spot, nowhere near the street. The Cottage is set back from the sidewalk so you are not subjected to traffic noises. brbrbrNote two things:br1. The price listed is for 2 guests only. There is an additional charge of $75/night for an additional guest. brbr2. The cottage is set back from the street but nearby at Hank's there is live music...luckilybr as of around 10.18.23 - their music is now set further back from us! The music ends at midnight.brbrbrKitchen with Dishwasher (not fully equipped)brFull Size Refrigerator and Stovebr1 King Bed, 1 Queen BedbrCentral Air ConditioningbrTVs with Premiere CablebrFull Size private Washer & Dryer on premises. For use by tenant and this tenant only.brFree InternetbrParking: Off-Street, 1 parking space, only to be used for those staying at the cottage.br Adults only. No Pets. No Smoking. No raw fish in the refrigerator or freezer.

Cottage

Heart of Downtown Key West Cottage With Off-Street Parking

Key West, Florida, United States

Bed

Bath

Sleeps

$291.43

A Change In Latitudes is a non-smoking, 1st floor end unit in the serene section of Shipyard, Truman Annex. All the amenities of home and just a few steps away from the climate controlled pool and a brief stroll to Fort Zachary State Park where you'll find the most beautiful beach and picnic area in Key West. brbr1 block away from the famous Green Parrot and 2 blocks to Duval Street. Walking distance to Mallory Square, steps to Truman Waterfront, and all that Key West has to offer. Full size refrigerator, stove, wine glasses, blender, spices, TV with Wi-Fi and high speed internet, and DVD player. brbrPlease send a request to book prior to entering your credit card or sending a payment. Occasionally, a guest misses some of the rules, has pets, or is trying to book years in advance. Once we accept the booking, we plan on your staying with us so up front communication prior to booking is helpful for both you the traveler and me, the host. We book 12 months in advance.brbr***PRICES REFLECTED ON THIS SITE ARE FOR 29 night STAYS or longer. Guests staying with us get first priority to stay on future bookings for the same month.

A CHANGE in LATITUDES; Shipyard 165 NOW AVAILABLE SEPT - OCT - NOV - DEC 2026

Key West, Florida, United States

Bed

Bath

Sleeps

$799.88

This listing is for a room within a hotel.brbr✦ Your room is 500 sq. ft, equipped with TV.brbr✦ Cleaning services included in the nightly price.brbrThere are a few additional details to know before you book:brbr✦ The minimum age required for check-in is 21 years old.brbr✦ Please ensure you have a valid ID for check-in, as it is mandatory for entry.brbr———————————————brbrGuest Access:brDuring your stay, you will have access to the property and amenities according to the following schedule:brbr✦ Check-in is available from 04:00 pm.brbr✦ Pool is available.brbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A credit/debit card is required at check-in for a $50 per night refundable deposit, returned after check-out if no damages occur.brbr✦ A mandatory resort fee of $45.00 per night will be collected upon check-in, not included in the daily rate.brbr✦ Pets are welcome. Pets allowed: $50/night, no restrictionsbrbr✦ We use multi-unit listings, so rooms are similar but may have small differences.brbr✦ The required refundable security deposit is charged per night on a valid credit card.

Hotel

Charming 2BR Stay, Ella’s | Garden Retreat w/ Pool Access and Free Breakfast!

Key West, Florida, United States

Bed

Bath

Sleeps

$627.82

This lovely single-family, two-story luxury home is in the prestigious Truman Annex gated community on a very private cul-de-sac. At the end of a brick drive is a beautiful french door gate house entrance to the property. Once inside this gem you will find a fabulous, heated pool and lush tropical foliage, wrap around porches, large balconies' and lots of doors and windows in which bring the outdoors in for the perfect island setting. This large and very comfortable 4-bedroom home is complete with designer interior finishes, crown molding, high ceilings, gourmet kitchen & plenty of space to entertain or just simply hang out. brbrPlease note: This property is monthly rental (28 night minimum stay)

A Palm Tree Haven at the Truman Annex in Key West

Key West, Florida, United States

Bed

Bath

Sleeps

$525.74

Your Home Away from Home in Beautiful Key WestbrbrWelcome to Southernmost Swim & Social Club — where you and your loved ones can enjoy your own slice of paradise in mid-town Key West.brbrPrime Location:brNestled conveniently between uptown shopping and the vibrant Old Town, you’re just minutes away from iconic Duval Street, Hemingway House, Southernmost Point, and many more must-see sites.brbrThe Home:brThis modern 3-bedroom, 2-bath retreat comfortably sleeps up to 8 guests, offering:brbrMaster Suite: King-size bed, walk-in closet, and private en-suite bathroom with shower.brbrBedroom 2: Queen-size bed sharing a hall bathroom.brbrBedroom 3: Queen-size bed sharing the same hall bathroom.brbrLiving Room: Queen sleeper sofa.brbrChef’s Kitchen:brFully stocked with stainless steel appliances, a wine fridge, and a breakfast bar — perfect for creating meals and memories.brbrOutdoor Oasis:brDive into one of Key West’s largest private saltwater pools, surrounded by a 6-foot privacy wall, mature palms, and lush foliage. Lounge under the tiki hut’s cool shade, soak up the sun, or fire up the gas grill for a BBQ feast. Pool heating is available seasonally (Nov 15 - May 1) for an additional fee.brbrExtras:brExplore Key West with 4 complimentary bicycles and a 6-passenger gas golf cart included with your stay.brbrPet Policy:brBring your furry friend! Pre-approval required for one dog (max 50 lbs). A $20/day pet fee applies, and the maximum occupancy is reduced by one guest.brbrReady to relax, explore, and soak in the Key West lifestyle Book your stay at Southernmost Swim & Social Club today!

SOUTHERNMOST SWIM AND SOCIAL CLUB

Key West, Florida, United States

Bed

Bath

Sleeps

$806.64

Slack Tide: Location, location, location! Balcony overlooking Duval Street, just 2 blocks from the beach and Southernmost Point, with lively Duval Street nightlife down the street and the Hemingway House nearby. brbrEnjoy a beautifully newly decorated interior and a central Key West stay with free parking for 1 car plus washer and dryer—everything you need for life at Slack Tide On Duval, that calm, perfect moment between the tides.

Apartment

Slack Tide On Duval Street

Key West, Florida, United States

Bed

Bath

Sleeps

$748.14

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

Villa

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

Key West, Florida, United States

Bed

Bath

Sleeps

$401.73

Great top floor 2 bedroom Condo on the Atlantic ocean with views of the ocean and courtyard. The property has a full size fully equipped kitchen with a washer/dryer.brBoth bedrooms and the living room have impact doors open to your private balcony.brThere is a King bed in the master bedroom and a queen in the guest bedroom and queen pull out sofa. brFlat screen TV's in each room. The master bath has a tub and a custom walk in shower. Free WI FI for guests and an assigned parking space in the garage.brThe renovation is incredible with no attention to detail spared. Pictures coming soon. New stainless appliances and top of the line fixtures. Every detail is incredible.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.

Blue Moonshine upgrades throughout modern finishes, close to Smathers Beach

Key West, Florida, United States

Bed

Bath

6

Sleeps

$637.83

Inspired by romantic turn-of-the-century architecture, Bella Grand Premier Estate is a unique Old Town Key West estate with a new twist on history. Custom built on a 7,520 square foot lot, it was designed to reflect the historic neighborhood, while reinventing the Key West luxury lifestyle.brbrThe property is comprised of a grand 2,900 sq ft 2 - Story Main House situated toward the rear of the property, plus an equally stunning 1,400 sq ft 2 - story Guest House at the front, providing all the spaciousness and upscale amenities expected in a contemporary luxury island home.brbrIn the middle of the estate property, both houses border a spectacular Zen-garden swimming pool, trickling tiled waterfalls and a spa. Wide stone bridges built over the pool sleekly connect the houses together. Walking over the water bridges, past trickling waterfalls gives a sense of being faraway in an exotic resort.brbrA traditional Key West front sitting porch, complete with colorful Adirondack chairs, spans the width of the Guest House. A tree garden and quintessential white picket fence provide an idyllic spot to sit and enjoy the ambiance of the neighborhood.brbrYou enter the Guest House through the main entrance, accessed from the street side front sitting porch. Inside the front door, the visual transformation from the traditional Key West porch to the expansive modern great room is stunning and provides a taste of what’s ahead.brbrAt the back of the great room, a fully equipped chef’s kitchen, with double stainless sink, stainless steel appliances, is beautifully built-out with cream colored French Country cabinetry and spectacular green-tone Brazilian granite. For extra food prep, a butcher-block island with pendant lighting, is set in the center of the kitchen. The lighting also makes a beautiful serving table. A standing height breakfast counter with stools is the perfect place for snacking, cocktails, and chatting while cooking.brbrImmediately to the left of the breakfast counter, a hallway leads past the bottom of the staircase to a half-bathroom with a sink and commode. In our slideshow, you can see the open door to the bathroom at the end of the hall. This bathroom also serves as the ‘pool-bath,’ with an exterior door that leads to the pool deck. Along the hallway, a laundry center with folding table, is conveniently hidden away behind doors.brbrMoving upstairs. The top of the staircase intersects with the bedroom hall. This hallway parallels the right side of the house, from the back to the front. Bedroom one is situated closest to the landing, at the back of the house. This bedroom suite provides a king size bed, a walk-in closet, and is handsomely furnished.brbrLocated at the opposite end of the hall from the first bedroom suite, it is at the front of the house. Eclectically furnished with a notable queen size mahogany antique bed, a matching drop leaf desk, and Parisian style chair, give the room a classic touch. The coastal style side tables, floor lamp, and beach knick knacks bring in the island vibe. There is no need for a bureau, as this bedroom also has a spacious walk-in closet.brbrBack downstairs, and immediately outside the Guest House kitchen, a deep covered porch spans the width of the house. It is comfortably furnished with chaise lounges and a table and chairs for outside dining. This porch seamlessly joins the pool deck with textured stone tile that spans around the pool and forms the bridges leading to the Main House.brbrThere are two stone swimming pool bridges that span the width of the pool. They are wide, aesthetically impressive, and easy to cross. Along the way, you may be enticed to pause and dangle your feet in the water or come right back for a relaxing dip. But the pool bridges are much more than mere aesthetics and water entertainment, they also fulfill the important function of leading you to the grand Main House at the back of the estate.brbrApproaching the Main House as you cross the pool, you may understandably think this is a renovated historic Key West home dating to the late 1800’s. Some people guess it is the original house that was built back off the street with a deep front yard. Set in this historic Old Town Key West neighborhood, among a variety of heritage houses and cottages, the masterful design looks convincingly authentic. Built with wood, covered porches with tall ceilings, capital topped posts, turned balustrades, and traditional wooden shutters all contribute to the look. But when you step inside, it’s different story.brbrDesigned as a grand great room, the open concept space spans all the way from the front porch doors that lead to the living room area, to the gourmet kitchen at back of the house. The entire space is painted in a soft cream and trimmed in white. Same as the Guest house, mahogany floors span the entire space and high ceilings with recessed lighting, and multiple sash windows, give the room an uplifting feel.brbrThe living room is set with a long-curved cotton-duck sectional sofa and a cream-colored Berber style rug. The sofa is large enough for the entire family to sit together and view the wall mounted flat screen TV. One of grandest features of this space is the wooden switch-back staircase, which sits prominently in the center of the room. The staircase adds an elegant historic feature to the room, with its curved railing, dark wood steps and white painted risers. It also creates a natural divider between the living room area and kitchen / dining room located at the back of the house.brbrArchitecturally designed to look like a historic Key West front porch, the grill porch tastefully blends in with the home. You can access it through side doors connected with the great room or from steps that lead to the pool deck. Built with everything a grill-master could want, it has a large stainless-steel Viking grill, beverage-sized fridge and stainless-steel prep sink. Granite counter tops, and Cherrywood cabinets make the space beautiful, and a porch swing invites you to hang out while the griller makes the magic.brbrStepping back inside the great room, our tour takes us past the banister staircase where we pause for a moment, to admire the beautiful black Steinway Piano and Acoustic Martin Guitar. With a heart-felt intent to spread the magic of music with this home, the owners invite guests to enjoy these top-quality instruments.brbrSituated at the back of the great room, the main gourmet kitchen has all the upscale attributes a professional chef would expect, including stainless prep sink, double kitchen sink, and top-of-the-line stainless-steel appliances. The gas Viking stove has double ovens and grill top, and the large capacity refrigerator offers plenty of space.brbrCream tone French Country style cabinets built to the ceiling and contrasting beige and gold granite countertops. The design is beautiful and well thought out with perfect lighting, and plenty of room to cook together and store your goods. A dual height island in the center of the kitchen, holds the prep sink on the bottom level, and above is the breakfast countertop.brbrDecorated with a pretty mix of white farmhouse and coastal furniture, the downstairs bedroom provides a wooden queen size bed with matching dresser and mirror. To the left of the door is an ample size walk in closet / dressing room. To the right of the door, there is matching desk set against the wall. The desk is large enough for a laptop and printer.brbrReturning to the downstairs hallway, the office / den is directly across the hall from the bedroom. Painted a grey-green and trimmed in white, it sets an unobtrusive tone to allow for focus without distraction. This room is on the front side if the house. It is filled with natural light with four large sash windows that look out into the grill porch described above.brbrThe office/den is minimally furnished with a tailored beige sofa at one end of the room, and a flat screen TV on the opposite wall. A 6-foot wooden table makes a great space to work, study, play a game of chess, draw, or put together an ongoing puzzle the entire family can work on.brbrThe entrance for the master suite is the first door on your left in the foyer upstairs foyer. The layout is ideal with a dedicated space for everything you look for in a luxury master suite. Four different rooms seamlessly flow together through double pocket doors, spanning the entire width of the house.brbrThe master bedroom is furnished with top quality mid-century modern wooden furniture, including a king size platform bed, a splayed legged 6 drawer bureau, bedside tables, plus a classic curved arm leather easy chair. The dark wood tone is a handsome contrast to the khaki-colored bedroom walls.brbrLast, but not least, is the separate commode room - and … it has a view! A real wow factor for sure - a sash window with a private view of a mature tree garden outside, creating the illusion of being in a remote forest.brbrThe fifth bedroom suite is located at the front of the Main House, directly across the foyer from the master suite. The design, layout, and décor resemble the downstairs bedroom suite. White farmhouse and lime green coastal furniture are combined to create a pretty bedroom the offers a wooden queen size bed, dresser, and generous size desk. In contrast, walls are painted in an upbeat tropical green with bright white trim. To the left of the desk, is a large walk-in closet with lots of hanging rods and shelves. The enviable feature of this bedroom is the private entrance the French doors give to the 2nd floor covered porch on the front of the house.brbrParking: Off-street parking is available for two vehicles on a gated bricked driveway and a covered carport. If you bring cars, once you’re settled in, enjoy walking or biking everywhere. You won’t really need a car in most instances, and you’ll avoid the expense and hassle of parking around the tiny island.

Bella Grand Premier Estate Key West - 2 Blocks off Duval w Private Pool

Key West, Florida, United States

Bed

Bath

Sleeps

$383.94

Experience the beauty of Key West's famous sunsets from the comfort of your own vacation home at The Green Goddess. This secluded and peaceful property is located just off Whitehead Street, less than a block from the Southernmost Point and only a short bike ride or stroll from all of the island's top attractions.brbrFeaturing 4 bedrooms and 3 full bathrooms, this home is perfect for large groups or families. The first floor features a guest bedroom with a full shower bathroom that can be accessed from both the bedroom and the hallway, serving as the primary bathroom for the first floor. The second floor has a master bedroom with a beautiful bathroom featuring lots of mirrors and storage. The second floor also has two guest bedrooms which share a full bathroom between them. brbrThe interior of the Green Goddess is designed with mid-century modern furniture. The open-concept living area features a fully equipped kitchen with all new appliances. The living room also features a home theater with an 85-inch 4K Smart TV with cable, Apple TV, and Blue Ray/DVD player with surround sound speakers. Just outside the living room is a fun back deck and private pool.brbrBut the real highlight of this home is the romantic rooftop deck, offering a complete and unobstructed view of the sunset. Spend your evenings up there, star gazing and taking in the stunning views. Or bring a meal to the roof deck and eat on top of the world. Book your stay at the Green Goddess and experience the best Key West has to offer, including breathtaking sunset views from the romantic rooftop deck and the opportunity to view the beautiful artwork of the home's owner. Don't miss out on this unique opportunity!brbrImportant Notice: Some booking platforms may not correctly display our security deposit requirements. This contract is based on a $125 non-refundable damage protection plan in place of a $5000.00 refundable security deposit; if you prefer to pay the $5000.00 deposit instead, please let us know. brbrGuests are subject to a 2% credit card processing fee. In order to avoid that fee, we encourage you to pay by check. brbrOther items to note:brThere is cable TV entertainment, and the bedrooms on the second floor each have their own TV.brThere is WiFi throughout the house with boosters to ensure strong signals.brAll linens are provided for your convenience.brMonthly rentals onlybrUnfortunately, no pets are allowed. brThere are no bed conversions available.

Green Goddess - Sunsets Included - 4BD/3Bath - 360° Rooftop - Private Pool

Key West, Florida, United States

Bed

Bath

Sleeps

$1764.91

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival!brbrAll year long you dream of a getaway to capture that feeling of Key West's endless summer - carefree days spent tooling around Old Town on bicycles or wandering the island streets in flip flops with the sun warming your shoulders. No plans, nowhere to be, no deadlines - only a to-do list of making memories with your family and friends and possibly the pressure of deciding where to splurge on a special night out. For those ready for this kind of a stay, ENDLESS SUMMER was designed to accommodate your group in a location just half a block from the famous Duval Street, yet tucked away on a quite lane you'll only find when looking for it. Five separate bedrooms with plenty of bathrooms, a private saltwater pool area, fully equipped kitchen, indoor and outdoor dining spaces, and off street designated parking make this home ideal for your memory-making vacation with your crew. Your only worry will be whether to head home or truly make that summer feeling endless...brbrTHE LIVING AREA...brbrENDLESS SUMMER provides a home base for a group excited to experience all that Old Town Key West has to offer just outside your door, while offering the privacy of separate bedrooms with mostly en-suite bathrooms. The living area is ideal for relaxing after a day full of adventure on island or out on the water, or for game planning the day's festivities over breakfast as a group. Around a large flat screen TV you'll find comfortable seating for the group, including a sofa that pulls out to a Queen bed with a tempurpedic mattress for extra guests. The kitchen sits off the living area with luxury appliances and tools, equipped with everything you'll need to prepare a meal at home in between enjoying the fantastic array of Old Town restaurant options, all just a few blocks walk away.brbrYOUR PRIVATE SALTWATER POOL...brbrThe living room and one of the first floor bedrooms open up to the private pool area, fully fenced for privacy and featuring chaise lounges and an outdoor dining set to bring the group together in your own space for breakfast, happy hour, or an end-of-the-night dip. The saltwater pool can be heated upon request to your desired temperature. Lush tropical greenery decorates the fence and the BBQ grill is perfect for a poolside cookout.brbrTHE ACCOMMODATIONS....brbrFirst Floorbrbr• Bedroom #1: Two Twins OR One King bed, a flat screen TV, direct access to the Pool Area, and access to the full bathroom in the hall.brbr• Bedroom #2: Two Twins OR One King bed, a flat screen TV, and an en-suite bathroom with a glass shower.brbrSecond Floorbrbr• Master Suite - Bedroom #3: King bed, a flat screen TV, a closet, a private balcony overlooking the Pool, and an en-suite with a shower.brbr• Bedroom #4: Queen bed, a flat screen TV, and an en-suite bathroom with a shower.brbr• Bedroom #5: Two Twins OR One King bed, a flat screen TV, a private balcony, and an en-suite bathroom with a shower and tub combination. brbrFor rooms with Twin beds that convert to a King, just give us a heads up of how you'd like these beds prepared for your particular group and we'll have them ready for your arrival.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 and full cable includedbrbrIn addition, this fully stocked home also includes, but is not limited to the amenities on this list:brbr• Fully Fenced and Lushly Landscaped Private Yard br• Private Saltwater Pool with available Pool Heatbr• Assigned Off-street Parking Space (with vehicle restrictions)br• Propane BBQ GrillbrbrOther notes:brbr• Interim housekeeping provided upon requestbr• This property will accommodate up to 12 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.

**ENDLESS SUMMER @ OLD TOWN** New Villa & Pool + LAST KEY SERVICES...

Key West, Florida, United States

Bed

Bath

Sleeps

$700.51

Summary:brbrWelcome to Sky Suite On Duval Street - a newly remodeled masterpiece that overlooks world famous Duval Street. The front house of Sky Suite is a rare find on the 700 block of Duval Street. History meets luxury here in this 1935 home that has been updated with modern designs and finishes. The location provides a great home base for all of your activities on the island and a place to kick off your night on the town.brbrbrbrThe Space:brbrThe downstairs master suite features a King-sized bed and a chic, newly remodeled master bathroom with brushed-nickel light fixtures and a large walk-in shower with a rainfall showerhead. brbrbrbrInside the upstairs bedroom you will find another King-sized bed, large windows for letting the morning sunlight in and a gorgeous en-suite bathroom with glass shower doors and pebbled floors. brbrbrbrAlong with the spacious king suites, you can find a queen-size murphy-bed easily accessible in the living room for an additional two guests joining in on your trip.brbrbrbrThe spacious, colorful common area offers a plush, 3-seat tanned leather sofa, a unique dining table for six and french doors leading to the private balcony overlooking Duval Street. On your way up to the second bedroom, there is a powder room equipped with a stackable washer/dryer. The custom-built, gourmet kitchen features stainless-steel appliances including a dishwasher and Keurig coffee makerbrbrbrbrGuest Access:brbrOur contactless check-in procedure makes check-in easy. Guests will receive a personalized access code prior to check-in to enter the unit.brbrbrbrHow to access: This is a second-story home with stair access only.brbrbrbrThe Neighborhood:brbrOn the 700 block of Duval, The Sky Suites on Duval is centralized to everything Key West. Feel the energy of Duval Street from your own private balcony that overlooks downtown and has plenty of room to enjoy a quiet morning or a late night hangout.brbrbrbrIn the heart of Duval street you can find many of locals favorite's such as: Martins, 915, 801 Bourbon Street Pub, Moondog Cafe & The Hemingway House.brbrbrbrLooking for a night out Find Willy T's, Fogarty's and Fat Tuesday’s at the other end of Duval, but don’t worry there are pedicabs everywhere for easy transportation up and down Duval Street. Being in the heart of everything does come with noise of Duval street, but nonetheless an easy and convenient location to experience all Key West has to offer!brbrbrbrGetting Around:brbrParking Information: Worried about parking Don't! Sky Suite offers one private off-street parking spot located behind the building - quite the luxury in Key West! Please note the spot is tight and meant for smaller vehicles.brbrbrbrThere are a variety of great ways to explore Key West including by bicycle, 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- There is a private stackable washer/dryer. brbr- The freezer includes an ice-maker.brbr- This unit is not pet friendly.brbr- This home is apart of the Sky Suites Retreat including 2 condo's above Duval Street. Reserve both for a discounted price, sleeping up to 12 guests. (Contact us for more information!)

Apartment

Sky Suite with Balcony Overlooking Duval Street

Key West, Florida, United States

Bed