Vacation Villa Rentals By Owner In Key West, FL

Elegance and modern sophistication are apparent as you enter any one of these six conveniently located townhomes in a quiet Old Town Key West neighborhood just three blocks from Duval Street.brbrWindsor Townhomes #5 boast over 1700 sq ft. on two levels for your vacation destination, with it’s own private garden with heated pool. The open living/dining area features comfortable sofas and chairs, and a dining table to seat six. Just off the living room is your complete and fully-equipped modern kitchen with top-of-the-line appliances and a center island/bar. The half-bath is situated in the hall between the foyer and kitchen. Sliding doors open from the living area to a deck and the pool edged by variety of tropical plants. An inviting deck surrounding the pool provides atmosphere for peaceful conversation and relaxation after a day of sightseeing. One bedroom is on the first level with a queen bed and en-suite bath with shower only. The second level of the house offers two bedroom suites with en-suite bathrooms. The bedrooms are expertly decorated to offer luxury without being overbearing. Spacious and plush, the main suite has an elegant king bed and a grand tiled bath with his-and-hers sink and large shower. The second bedroom has two twin beds with luxurious linens and an en-suite bathroom with tub.brbrThe villas are equipped with central air-conditioning system, flat-screen TVs, security system, and fully-equipped kitchen. These elegant villas are a destination for those expecting a special and exclusive holiday with the warm atmosphere of your own home! Located across the street from the Basilica of St. Mary Star of the Sea, it is the perfect spot for destination wedding parties.brbrBedding: 1 king, 1 queen, 2 twinsbrParking: One off-street parking space

Relax in Style at Windsor Townhomes #4

Key West, Florida, United States

Bed

Bath

Sleeps

$562.53

Relax with the whole family at this peaceful, pet friendly, waterfront oasis Remodeled in 2021 with kayaks, pool table, bbq with large outside dining areas, only a 15 minute drive to key west. his beautiful home is family owed. We manage the property ourselves and work very hard to ensure you receive the best quality of service from cleanings, stocking the property with everything needed and always available to answer any questions. Enjoy the blue waters surrounding the property perfect to explore in kayaks. Fully equipped kitchen includes coffee, creamer, teas, spices paper towels, cleaning supplies with enough stock for long term rentals laundry includes detergent, tv on every bedroom , as well as sleeper sofa and air mattresses for extra guests brbrbrYou will feel at home in this beautiful quiet neighborhood surrounded by nature and a crystal-clear canal, a chef's kitchen fully stocked for your entire stay with essentials like coffee, spices, cleaning supplies, paper towels, tp and more. Brand new beds and luxurious mattresses for a restful sleep, luxury hotel grade linens for extreme comfort . A Beautiful under-home patio with a pool table ample lounge area and BBQ , two outdoor dining tables , a hammock, a small fridge for your convenience and an ice machine, under-house covered parking for two vehicles, a private yard with plenty of space surrounding the property , and cohesive decor throughout . Guests have access to 3 kayaks, two two-person kayaks and one single person kayak, extra large float and single floats available also beach chairs and umbrellas brbrThe waters surrounding the Saddlebunch Keys and most of the Lower Keys coastal waters are very shallow – 1 to 3 feet deep, boats must not draft more than 18- 20 inches. Geiger Key Marina is located 10-minutes from our home and offers boat ramp access, there are several public boat ramps for open water access on both Shark and Sugarloaf KeysbrbrbrExplore nearby places like Baby coffee, located 2 minutes away, also key west sky dive located 10 minutes from the propertybr

Home in Blue water Key

Key West, Florida, United States

3

Bed

2

Bath

6

Sleeps

$450.0

The Galleon is on the boardwalk, close to most of the waterfront restaurants and a few blocks walk to Duval Street and Mallory square.brbrThis is one of the few properties in key West with a private beach. The expansive dock and a rooftop observation deck overlooking the Gulf and Key West Marina provides a choice for a spectacular view of sunset brbrThere is a large pool and hot tub, a Tiki bar with live music daily on the dock, a restaurant and a gym.brbr1BRbrbrThis is one bedroom unit that sleeps 4. There is a king size bed and a fold out couch in the living room. A large balcony overlooks the Gulf and Marina. The unit has a full kitchen equipped with stainless steel appliances including a dishwasher. There is a stacked washer and dryer in the unit.

Hotel Resort

Galleon Resort 1BR Key West waterfront. 1Br, Liv room, kitchen, patio.

Key West, Florida, United States

Bed

Bath

4

Sleeps

$675.0

brbrLocation! Location! Location! You are in the middle of all the charm and high energy of Key West during your stay at Sunset Harbor. You are about two blocks from World Famous Duval Street including Sloppy Joe's and many of the great bars and restaurants Key West is known for. Relax in your condo with stunning sunset views and immerse yourself in the historic Hemingway Days festivities . This vacation rental offers a unique blend of luxury and relaxation, making it the perfect choice for your next trip to Key West.brAMENITIES: Pool and whirlpool spa • On-site washer and dryer • Central Old Town location • Access to the nearby Hyatt Centric Key West Resort & Spa • Complimentary Wi-Fi• Grills•No pets allowed with the exception of certified human assistance animals • Parasailing • Diving • Snorkeling • Fishing • Sailing • Sunset cruises • Bicycle and scooter rentals • Jala Spa at Hyatt Centric Key West Resort & Spa • SHOR American Seafood Grill and Blue Mojito Bar and Grill at the Hyatt Centric Hotel - 20% off food and drinks with your Hyatt key card! •On site ConciergebrCheck-in/Check-out : Sunday, July 19, 2026 4pm-Sunday, July 26, 2026-11 am. This much sought-after resort will be completely sold out on these dates! Housekeeping fee maybe due on checkout.brProperty address: 200 Sunset Lane, Key West, Florida-directly on the Gulf where cruise ships dock and spectacular sunsets are abundant! br-The premier unit is a 2-story luxurious townhome . The layout features the master bedroom, bath & private balcony with lounge chairs upstairs. The first floor features living room/dining room, kitchen, guest bedroom, bath and patio with table and chairs. A sofa-bed provides additional comfortable sleeping for guests. All units have ceiling fans and three TV's. brbrLimited parking is available for a small fee. Photos are general Sunset Harbor 2 BR photos and may vary slightly from unit.brbrMessage host for final confirmation of date availability.brbrView resort online: https://www.hyattresidenceclub.com/resorts/hyatt-sunset-harborbrbrYou must be at least 25 years old to check-in. A valid credit card and ID are required at check-in. Your credit card is put on file in case you want to charge items and incidentals to your room. They will also hold a $100 deposit which will be automatically released upon check out.

Hotel Resort

Sunset Harbor Resort+Key West-Hemingway Days 2 BR townhome-July 19-26, 2026

Key West, Florida, United States

3

Bed

3

Bath

6

Sleeps

$523.75

Waterfront Serenity – 2 Bedroom, 2 Bath Condominium.brbrWelcome to your slice of paradise! This beautiful two-bedroom, two-bath waterfront condo offers a peaceful escape in one of the most serene locations on the island. Surrounded by gentle breezes and calming water views, this home is the perfect retreat for those seeking quiet comfort and relaxation. Located in the Coconut Mallory Resort & Marina, this charming condo is just steps from the marina! Step inside beautiful home and enjoy the open-concept living area, thoughtfully designed for both comfort and connection. The spacious living room features plush seating and a large flat-screen TV, perfect for unwinding after a day of island adventures. For additional guests, a queen-sized Murphy bed conveniently folds down from the cabinet, allowing the space to easily transform for sleeping up to six people in total. The fully equipped kitchen has everything you need to prepare a home-cooked meal — from modern appliances to cookware, dishes, and utensils. Gather around the indoor dining table for six, or enjoy a quick bite at the kitchen bar with two additional seats. One of the highlights of this home is the large wrap-around balcony, offering a tranquil outdoor setting with seating for four. Whether you’re sipping your morning coffee as the sun rises over or enjoying an alfresco dinner under the stars, this peaceful outdoor space provides the perfect backdrop for every moment. Both bedrooms are comfortably appointed and include large flat-screen TVs, ample storage, and relaxing décor that captures the essence of coastal living. The two full bathrooms are clean and modern, offering convenience and privacy for families or couples traveling together. From the soft sound of the waves to the gentle rhythm of island life, this condo invites you to slow down and savor the view. Whether you’re here for a romantic getaway, a family vacation, or simply to recharge in a beautiful, quiet setting, you’ll find everything you need to make your stay unforgettable.brbr THE ACCOMMODATIONS...brbrPrimary Bedroom: King bed, flat screen TV, walk in closet, balcony access, and en suite bathroom with double sinks, a jacuzzi tub, and a walk-in shower. brbrGuest Bedroom: Two Twin beds that can be converted into one King bed, flat screen TV, large closet, balcony access, and bathroom adjacent full bathroom with a walk in shower.brbr THE COMMUNITY POOL & GROUNDS...Coconut Mallory is a waterfront community about 3 miles from Duval Street that provides resort-style amenities, including two large pools, oversized Jacuzzi, BBQ grills, picnic tables, and much more. There is a large old bar area there at Coconut Mallory that is no longer open, but a lovely covered area, great to hang out in with family and friends. brbrSmathers Beach, Key West's largest public beach just 2 miles away. brbrHOME INCLUDES:** In-home Washer and Dryer** Central Heat and A/C** Ceiling Fans** Flat Screen Smart TVs in Living Room & All Bedrooms** Fully Equipped Kitchen** Salt & Pepper** Starter supply of paper products & trash bags** Linens, blankets, extra pillows and Towels provided** Pool towels** Cooler to keep beverages cold** Wireless high-speed Internet access & full cable included.brbr PARKING** Off-street Covered Parking for 2 cars (height restriction of 6'6)BOAT SLIPS** Are available to rent for no more than a 35 ft boat. To inquire you will reach out to Dave the Coconut Mallory dock master personally. (320) 362-7877. brbrOther notes:** Interim housekeeping provided upon request at guest's expense** brbrThis property will accommodate up to 6 adults** No Pets Allowed** No Smoking** Sunset Vacation and Management homes are rented to family groups and responsible adult groups only.brbr**Cooler Rentals Available, For your convenience, we are happy to offer cooler rentals for the duration of your stay for a flat fee of $50. Available options include large insulated coolers in approximately 70-quart capacity (40” x 18”) and 60-quart capacity (24” x 17”), as well as a rolling insulated cooler for easy transport. We also have a round YETI-style bucket cooler with an approximate 45-quart capacity. Complimentary drop-off and pick-up service is included, ensuring a seamless and hassle-free experience during your stay. brbrGuest Access - Our contactless check-in procedure makes check-in easy. Guests will receive an access code prior to arrival.

Apartment

Coastline Comfort at Coconut Mallory

Key West, Florida, United States

Bed

Bath

Sleeps

$538.37

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival!brbrWant to be in the heart of the action but have privacy and seclusion when it’s time to relax That’s what’s in store for your stay in the CALUSA SUITE at the Seaport Inn! You’ll be miles from reality, but just steps away from the Seaport Inn’s pool and everything else Old Town has to offer. Upon arrival and a walk past the pool, you’ll find your front door and private patio for this ground level suite. Open the door to find your studio suite equipped with a kitchenette. Included with your rental is Last Key Realty’s Five-Star Guest Services and Complimentary Concierge, known for providing memorable vacations that'll keep Key West on your mind long after your departure.brbrTHE SEAPORT INN...brbrWelcome to the Seaport Inn, where timeless island charm meets modern comfort in the heart of Old Town Key West. Seaport Inn was originally constructed in 1892 and features six suites, each boasting an en-suite bathroom and kitchen facilities. Situated just one block from the iconic Historic Seaport and a mere three blocks from the vibrant energy of Duval Street, you couldn't ask for a more convenient location to experience Key West. Steeped in history and architectural beauty, the Seaport Inn exudes historic Key West character and offers guests authentic Old Town accommodations.brbrTHE ACCOMMODATIONS...brbrCALUSA SUITE is a first floor suite that is equipped with a kitchenette, chest of drawers, and a closet. There's also a King bed, a flat-screen TV, and a full bathroom with a walk-in shower.brbrTHE COMMUNITY POOL & TIKI BAR...brbrThe oversized outdoor common space of the Seaport Inn boasts ample space for relaxation and entertainment. Take a refreshing dip in the large pool, sip cocktails at the inviting tiki bar, or bask in the serenity of lush tropical landscaping.brbrALL SEAPORT INN SUITES INCLUDE:brbr** Central Heat and A/Cbr** Ceiling Fanbr** Flat Screen TVbr** Basic stock of spicesbr** Starter supply of paper productsbr** Starter set of cleaning productsbr** Linens and Towels providedbr** Wireless high-speed Internet access & full cable includedbr** Full Time Concierge Servicebr** Community Pool exclusively for Seaport Inn Guestsbr** Community Propane BBQ Grillbr** Community Outdoor showerbrbrOther notes:brbr** Interim housekeeping provided upon requestbr** This property will accommodate up to 2 adultsbr** No Pets Allowedbr** 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.

**CALUSA SUITE @ SEAPORT INN ** Historic w/ Community Pool + LAST KEY SERVICES..

Key West, Florida, United States

Bed

Bath

Sleeps

$429.51

****Welcome to the Parothdhideaway in Key West****brThis unique property offers an excellent place for groups or families looking to experience the vibrant island life. This central air-conditioned 3-bedroom home with two bathrooms—one equipped with a shower and the other with a relaxing claw-foot bathtub, both with a bidet, offering luxury and comfort. When you arrive at the house, you will have your own off-street parking spot and a handicap-accessible ramp leading to a large wraparound deck and an intimate pool. The washer, dryer, and ironing board ensure convenience and comfort. It's easy to see why you'll be able to unwind during the day and look great at night. brbrA secure bike rack is provided, and we also offer discounts on bike rentals. This is our way of ensuring that you can explore the island at your own pace and convenience.brbrThe house is located within minutes of the bustling Duval Street, the heart of Key West's entertainment district, where shopping, restaurants, and famous bars are just a quick bike ride or walk away. The property is also conveniently located near other popular attractions, making it an ideal base for your Key West adventure.brbrThe Layout of the house br- First Floor - br*Main bedroom with Queen Bed and Private entrance.br*Main bathroom with walk-in shower br*Living roombr*Kitchenbr*Dining roombrbr- Second Floor - br*2nd Bedroom with Queen bed, sitting area, and (rollaway bed available upon request)br*3rd Bedroom with 2 Double Bedsbr*2nd Bathroom with claw-foot bathtubbrbrAdditional features: brThe washer/Dryer is located in the shed outside.brCentral A/CbrCeiling fansbrFlat-Screen Smart TVs in the Living Room and all BedroomsbrFully equipped KitchenbrBasic stock of spicesbrStarter supply of paper productsbrAll beds come with linens and additional setsbrTowels providedbrHigh-Speed Wireless Internet accessbrFamily Games and Puzzles for those rainy daysbrbrUpon Request: br- housekeeping provided during your stay, additional costs (inquire by message for more information)br- Pets are considered - max of 2 allowed, and a fee of $200 per pet/stay will applybrbrWe kindly ask that you respect our neighbors and the residential area by keeping noise levels down past 11 PM. If we are notified of a violation of this, an additional charge of $200 may be imposed, and the rental may be terminated without refund. We appreciate you understanding and the cooperation in this matter.

Parothdhideaway - 3 bed w/pool and parking. Walking distance from Duval Street.

Key West, Florida, United States

Bed

Bath

Sleeps

$497.63

Summary:brbrWelcome to Sunrise Suites, a peaceful community on Key West's southeast side. Just 1 mile from the beach and 10 minutes from Duval Street's attractions, this two-bedroom condo complex features uniquely designed units. Enjoy access to a shared hot tub, heated pool, walking paths, biking trails, a tennis court, and on-site laundry facilities—everything you need for a relaxing stay!brbrbrbrThe Space:brbrThe Trinidad Suite offers a spacious layout, featuring a master bedroom with a king-size bed and a private en-suite bathroom. The second bedroom includes a queen-size bed with direct access to the hallway bathroom. For additional sleeping arrangements, the plush blue sofa unfolds into a queen-size bed, comfortably accommodating up to 6 guests. Relax on the private balcony with seating for four, or unwind on the couch while enjoying cable TV.brbrbrbrThis condo is part of the upscale Sunrise Suites community, conveniently located just minutes from Key West International Airport, ensuring a seamless journey home. For those driving in, the condo includes one designated parking space for added convenience.brbrbrbrGuest Access:brbrOur contactless check-in procedure makes check-in easy. Guests will receive a personalized access code prior to arrival.brbrbrbrThe Neighborhood:brbrTrinidad Suite is located inside of the Sunrise Suites Resort Community located just minutes away from the World Famous Duval Street and its vibrant restaurants, art galleries and nightlife. Inside the community you can find a corner store, spa, walking and biking trails. It is also located just a short drive away from the nightly Sunset Celebration and entertainment at Mallory Square.brbrbrbrGetting Around:brbrOne of the best parts of staying in Key West is how close everything is on this charming 2x4-mile island! There are plenty of ways to get around. If walking isn’t your style, rent a bike from Fury or Island Bicycles and enjoy a morning ride to breakfast or a sunset ride along the water. Both providers offer convenient pick-up and drop-off services. For a more unique island experience, explore Key West by scooter or golf cart from Minty’s Rentals, where “island time” becomes your mantra.brbrbrbrIf you prefer traditional transportation, Uber, Lyft, and taxis are readily available. Pink Taxi is a reliable, affordable option, perfect for rides from the airport to your rental.brbrbrbrEach apartment includes one parking space, but spots are unmarked and available on a first-come, first-served basis, so proximity to your unit isn’t guaranteed. If additional spaces are available, feel free to park a second vehicle free of charge, depending on the lot’s vacancy.brbrbrbrOther Things to Note:brbrPrivate washer/dryerbrbrThere are shared washer and dryers available on the first floorbrbrUnit has both elevator and stair access.brbrPets are welcome!brbrOur requirements are as follows: brbr•40lb maximum per petbrbr•$25/per nightbrbr•2 pet maximumbrbrPlease let us know if you plan on bringing your pet.

The Trinidad at Sunrise Suites - Shared Pool

Key West, Florida, United States

Bed

Bath

Sleeps

$770.59

You will be back year after year! Unit features full kitchen with Master King Bedroom, Guest Bedroom with Twin Beds, and Pull out Sleeper Sofa in Living Room. 2 Bdrm, 2 Bath, Pull out sofa. Sleeps 6. Jacuzzi Tub in Master. Property features Pool, Sauna, Private Beach, Tiki Bar, Rooftop viewing deck, Grills and daily activities. Premium location for easy walks to Duval Street, Mallory Square, Key West Aquarium, Shipwreckers Museum, Mel Fisher Museum and much, much more.

Sunset views at the Galleon

Key West, Florida, United States

Bed

Bath

Sleeps

$1105.86

This mid-town Key West home is recently refreshed with light colors and beautiful British Colonial furnishings. It features three bedrooms and three baths. The open living/kitchen area is decorated with light colored walls with striking tropical tones in the accent furnishings and tile, and soft fabrics. The dining room is outside in the attached pavilion. brbrEach of the bedrooms opens to a different part of the yard, extending the private space for each bedroom outside as well. The master bedroom opens to the pool area with two walls of French doors and windows. The master bath features a large tiled walk-in shower. The second bedroom is freshly painted with cool green tones and Key West art set to inspire. The third bedroom has two twin beds that can be also be made as a king. Villa Paradiso is in a very quiet residential neighborhood in close proximity to the beaches on the south side of the island. It is an easy bike ride to Duval Street and even closer to the Casa Marina area. A retreat vacation spot. Bedding: 2 kings, 2 twin beds

Villa Paradiso: A unique mid-town paradise

Key West, Florida, United States

Bed

Bath

Sleeps

$283.06

Keys living!!! Come enjoy a relaxing vacation on a 34’ catamaran sailboat, enjoying local sandbars upon charter request(different rates apply) during the day and star gazing at night! This unique sailboat only drafts 1.5 ft of water allowing you to explore back country and relax with the locals if your up for it! If not spend a quiet night at the dock enjoying great views and paddle boarding! Blue Dream Charters has several boats in its fleet including a 28’ whitewater used for short beach days, fishing, and snorkeling and also a 39’ sport fish available for full day offshore fishing for a trophy fish of a lifetime. Born and raised in key west so if you need help with anything I can lead you in the right direction. If you want to get out on the water let me know as soon as you book and discounts can be applied to charter. What are you waiting for Let’s get out on the water in Key West with a local!

House Boat

34’ Catamaran Sailboat

Key West, Florida, United States

Bed

Bath

Sleeps

$159.33

There's no better way to experience island time - that slow shifting of hours that makes Key West such an ideal vacation spot-than staying at Royal Palm. Located in the prestigious Foundry building within the exclusive Truman Annex gated community, this two-bedroom, three-story brick townhouse offers privacy and includes access to a gorgeous residents-only heated pool. Yet you are only several blocks from the main artery for entertainment-world-famous Duval Street-and in close proximity to Ft. Zach Beach, where you can claim your spot in the sand with a rented umbrella and chaise lounge or just stretch out your colorful beach towel and plop down.brbrOnce you've left your car in the designated off-street parking, enter through a six-foot white picket fence that opens into the front garden of the Royal Palm private residence. Up a few stairs puts you on a deck with a seating area. The entry door is an architecturally impressive facade of wood and glass panels covering one entire wall of the residence and flooding the first floor with ambient light. Inside a paddle fan adds charm, functionality, and accentuates the expansiveness of the twelve-foot ceiling. Below white travertine flooring stretches throughout an open floor plan. brbrTo the right is a conversation area delineated by a colorful oriental area rug. Classic wicker chairs, a deep-seated couch, wicker coffee table, and wicker end tables make this a perfect setting for reading or playing games like Cranium or Balderdash with family or friends. Directly across is a glass-top desk complete with wireless high-speed internet, phone/fax machine, and printer awaiting your computer hookup. Or if you've left the electronics behind on purpose, maybe use the space for handwriting wish you were here postcards to friends back home. Next to the desk is a flat-screen TV perfectly situated for comfortable viewing from the conversation area. Interesting art work and a charming bird clock (complete with different bird calls for each hour) add color and interest to the cloud white walls. It goes without saying that cable, stereo, and DVD player are available when you need them.brbrThe dining area consists of a glass-top table, four high-backed chairs, and a downlight chandelier/paddle fan whirring above. Steps away is the breakfast bar that also serves as a convenient pass-through from the kitchen to the dining area should you be motivated to make dinner salads or a three-course meal. The kitchen itself has a contemporary vibe with a double sink and all the modern amenities you'd expect right at your fingertips. Plenty of cabinet space above and below make it easy to keep countertops clear. A utility closet and half-bath complete this level of the residence.brbrHardwood stairs lead to the second-story master bedroom with en suite full bath. Up another flight to the third level is the guest bedroom, also with en suite full bath and twin beds that can be converted to a king if that's your preference. The master has a comfy king bed dressed in vibrant stonewashed cotton linens that beckon at naptime and/or bedtime. Bedside tables with lamps, a flat-screen TV, a six-drawer wicker dresser with large mirror, and a wicker armchair tucked in one corner complete the scene. But the best part is the large glass double doors flanked by large glass panels and the private balcony beyond. Sit here in your jammies (or even less) for your morning coffee or nighttime cocktail. No one besides gently swaying palm fronds or maybe a flock of water birds passing overhead can glimpse you in this space. A linen closet, a generous clothes closet for your hanging items, a full bath, and washer/dryer closet round out this floor. brbrIn the third-floor bedroom, panel after panel of windows flood this room with Florida's incomparable daylight and myriad stars at night, while another ceiling fan silently marks the 24-hour progression. Use this bedroom for children or guests while you maintain your own privacy on the floor below.brbrRoyal Palm is just minutes from the fun and frivolity you came to Key West to check out. Steps from your door enjoy the manicured landscaping, verdant palms, and interconnecting pathways that give your Truman Annex neighborhood its park-like atmosphere. Stroll out wrought iron privacy gates to find yourself immersed in the sights and sounds of Duval's tourist attractions. Check out the tours, museums, water sports, shopping, bars, and over two hundred restaurants, many with open-air seating, some right on the water. Don't miss the Butterfly & Nature Conservatory, boutiques, and especially the nightly sunset celebration at Mallory Square, where visitors and locals alike gather to applaud as the sun slips below the horizon. Then hang around afterwards for the spontaneous party. Unless you're been to the island before, pick up a guidebook to ensure you don't miss the vibrant art and culture scene that includes live music, lectures, plays, movies, art galleries, and artists' talks.brbrIf this is your first trip to the Conch Republic, a guidebook from Books & Books on Eaton Street or a stop at the Chamber of Commerce Information Center on Greene Street will help make sure you don’t miss anything. Other info on the current music scene, movies, plays, gallery openings, and charitable events can be found at milezerokeywest.com (calendar section). Historic Hideaways' informative Area Guide/Events page located on our website also has a Calendar of Events. We DO NOT guarantee that the information VRBO (and affiliated sites) scrapes from our site to display on theirs is 100% accurate, particularly the amenities. If you come to us through them, be sure to look at all the information on our site related to your rental once you book to be sure you have accurate and up to date information.

Royal Palm

Key West, Florida, United States

Bed

Bath

Sleeps

$458.54

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival!brbrYou can skip Key Largo and Montego and go straight to Kokomo! The KOKOMO SUITE at the Seaport Inn that is. Just as suggested by the song's lyrics, you can get there fast since it is close to all of the action Duval Street, Old Town, and the Historic Seaport have to offer. You can also take it take it slow, which many residents and visitors of the island do. After experiencing the KOKOMO SUITE at the Seaport Inn’s Old Key West vibes coupled with Last Key Realty's Five-Star Guest Services & Complimentary Concierge, you’ll be saying, “that’s where we want to go!”brbrTHE SEAPORT INN...brbrWelcome to the Seaport Inn, where timeless island charm meets modern comfort in the heart of Old Town Key West. Seaport Inn was originally constructed in 1892 and features six suites, each boasting an en-suite bathroom and kitchen facilities. Situated just one block from the iconic Historic Seaport and a mere three blocks from the vibrant energy of Duval Street, you couldn't ask for a more convenient location to experience Key West. Steeped in history and architectural beauty, the Seaport Inn exudes historic Key West character and offers guests authentic Old Town accommodations.brbrTHE ACCOMMODATIONS...brbrKOKOMO SUITE is a first floor suite that is equipped with a kitchenette, a two-seat high-top dining table, chest of drawers, and an armoire for hanging clothes. There's also a King bed, a flat-screen TV, and a full bathroom with a walk-in shower.brbrTHE COMMUNITY POOL & TIKI BAR...brbrThe oversized outdoor common space of the Seaport Inn boasts ample space for relaxation and entertainment. Take a refreshing dip in the large pool, sip cocktails at the inviting tiki bar, or bask in the serenity of lush tropical landscaping.brbrALL SEAPORT INN SUITES INCLUDE:brbr** Central Heat and A/Cbr** Ceiling Fanbr** Flat Screen TVbr** Basic stock of spicesbr** Starter supply of paper productsbr** Starter set of cleaning productsbr** Linens and Towels providedbr** Wireless high-speed Internet access & full cable includedbr** Full Time Concierge Servicebr** Community Pool exclusively for Seaport Inn Guestsbr** Community Propane BBQ Grillbr** Community Outdoor showerbrbrOther notes:brbr** Interim housekeeping provided upon requestbr** This property will accommodate up to 2 adultsbr** No Pets Allowedbr** 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.

**KOKOMO SUITE @ SEAPORT INN** Historic Charm & Community Pool + LAST KEY SERVIC

Key West, Florida, United States

Bed

Bath

Sleeps

$1287.01

These beautiful villas boast over 1700 sq ft. on two levels for your vacation destination, with it’s own private garden with heated pool. The open living/dining area features comfortable sofas and chairs, and a dining table to seat six. Just off the living room is your complete and fully-equipped modern kitchen with top-of-the-line appliances and a center island/bar. The half-bath is situated in the hall between the foyer and kitchen. Sliding doors open from the living area to a deck and the pool edged by variety of tropical plants. An inviting deck surrounding the pool provides atmosphere for peaceful conversation and relaxation after a day of sightseeing. One bedroom is on the first level with a queen bed and en-suite bath with shower only. The second level of the house offers two bedroom suites with en-suite bathrooms. The bedrooms are expertly decorated to offer luxury without being overbearing. Spacious and plush, the main suite has an elegant king bed and a grand tiled bath with his-and-hers sink and large shower. The second bedroom has two twin beds with luxurious linens and an en-suite bathroom with tub.brbrThe villas are equipped with central air-conditioning system, flat-screen TVs, security system, and fully-equipped kitchen. These elegant villas are a destination for those expecting a special and exclusive holiday with the warm atmosphere of your own home! Located across the street from the Basilica of St. Mary Star of the Sea, it is the perfect spot for destination wedding parties.brbrBedding: 1 king, 1 queen, 2 twinsbrParking: One off-street parking space

Modern Elegance at Windsor Townhomes #5

Key West, Florida, United States

Bed

Bath

Sleeps

$328.81

CLASSIC OLD KEY WEST HOME...brThis home is boasting a rare combination of location and character. A mix of historic details and modern charm are evident throughout. Perfect for couples traveling together or those who have visitors during their stay in Paradise.br***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGEbrbrDETAILS AND AMENITIES.... brWalk in the door and be surrounded by Dade County pine and wood flooring. The main floor offers a large living room that is convenient for work and play and indoor dining for 6. You will find a full bathroom off the living room with a beautiful claw foot tub, pedestal sink and original mosaic tile. There is a fully stocked kitchen which over looks the private yard. Fabulous natural light through an abundance of wood windows finished in bright white moldings to compliment the home. The second floor is where the bedrooms lie in wait. There is abundant storage upstairs as well as the second full bathroom. brbrSLEEPING ARRANGEMENTS....brThe two bedrooms are located up the original wood staircase on the second floor. The master bedroom has a comfortable queen size bed, sitting area and a French door that opens to the rear deck. This room comes with a flat screen, smart TV so you can catch all your favorite shows on Netflix! There is an ensuite full bathroom with a shower stall and pedestal sink. The guest bedroom has two twin beds that can be converted to a king upon request. The hallway has a trundle bed with two twin beds. The downstairs living room has a sleeper sofa. br brOUTDOOR LIVING...brStep onto the front porch where there is seating to people watch while you take your morning coffee. If privacy is what your searching for then you can enjoy the refreshing dip pool with a beautiful backdrop of manicured tropical landscaping. Gather together under the pergola with cozy outdoor furnishings or enjoy dining together at the bench style table with plenty of seating available. brbrLOCATION...brThe location of this home is perfect for strolling through Old Town looking at the historic homes. Just a few blocks away you will run into Simonton & Duval street's where shops, galleries and restaurants line the area. There is always plenty to do or see like watching the sun set at Mallory Square or catching the Conch Train to hear the history of the island and how it became the coveted retreat it is today for visitors from all over the world!brbrPARKING...brOn street parking is available in the surrounding area for this home. Please park in unmarked spaces as residential permit spaces are only for Key West residents.brbrPETS...brPets are considered at this property and a pet fee is required. Please include the size and breed in the comments.brbrMULTI MONTH RESERVATIONS... brFor monthly reservations, the following fees will be added PER MONTH: brMid-stay cleanbrPool/hot tub heating fee (if applicable)brPet fee (if applicable)brbrBOOKING DATES...brThis home is only available as a monthly rental (28 night minimum). We prefer to book by the calendar month (first day of the month to the last). We may consider alternate dates if the calendar allows or if the owner will make an exception. brbrCONCIERGE SERVICES...brEnjoy our concierge service to assist you with planning activities for your trip, from bike/scooter/golf cart rentals to any excursion you can think of including snorkeling and sunset cruises, jet ski rentals, parasailing, kayaking, fishing, paddle boarding and much more. They can also have your fridge stocked with all the necessities in advance of your arrival!brbrCANCELLATION...brBookings canceled at least 90 days before the start of stay will receive a 100% refund. brbrCancellations inside of 90 days may receive a refund if we are able to re-rent any or all of the dates of the stay. The refund amount is dependent upon the rate of the new reservation. For multi-month reservations for January through March, a refund will only be offered in the event we are able to re-rent. The refund amount is dependent upon the rate of the new reservation(s).brbrLOCATION IN PARADISE!

ORCHID ESCAPE~ 2 bedroom 2 bath set in Old Town with private dip pool!

Key West, Florida, United States

Bed

Bath

Sleeps

$371.98

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival!brbrIf you’d like to spend your month in a neighborhood engulfed in as much history as the Matecumbe Keys, look no further! Located on William Street in Old Town atop the Seaport Inn, MATECUMBE SUITE offers simple island comfort matched with easy access to all the action and historical landmarks. When you add on Last Key Realty’s Five-Star Guest Services and Complimentary Concierge, you'll see that living the island dream is not a thing of the past!brbrTHE SEAPORT INN...brbrWelcome to the Seaport Inn, where timeless island charm meets modern comfort in the heart of Old Town Key West. Seaport Inn was originally constructed in 1892 and features six suites, each boasting an en-suite bathroom and kitchen facilities. Situated just one block from the iconic Historic Seaport and a mere three blocks from the vibrant energy of Duval Street, you couldn't ask for a more convenient location to experience Key West. Steeped in history and architectural beauty, the Seaport Inn exudes historic Key West character and offers guests authentic Old Town accommodations.brbrTHE COMMUNITY POOL & TIKI BAR...brbrThe oversized outdoor common space of the Seaport Inn boasts ample space for relaxation and entertainment. Take a refreshing dip in the large pool, sip cocktails at the inviting tiki bar, or bask in the serenity of lush tropical landscaping.brbrTHE ACCOMMODATIONS...brbrMATECUMBE SUITE, also known as unit 5, perched at the top of the Seaport Inn, taking up the entire 3rd floor. You’ll enter into a secluded foyer on the 2nd floor and head straight up to the living area. Once upstairs you’ll see the queen sized sleeper sofa and the flat screen TV. This suite features a kitchenette, so great for anyone who likes to dine out at Key West’s world class restaurants. The bedroom features a queen bed and flat screen TV. There is a private bath just off the living area with a walk-in shower.brbrALL SEAPORT INN SUITES INCLUDE:brbr** Central Heat and A/Cbr** Ceiling Fansbr** Flat Screen TVs in Living Room & All Bedroomsbr** Basic stock of spicesbr** Starter supply of paper productsbr** Starter set of cleaning productsbr** Linens and Towels providedbr** Wireless high-speed Internet access & full cable includedbr** Full Time Concierge Servicebr** Fully Fenced and Lushly Landscaped Private Yardbr** Community Pool exclusively for Seaport Inn Guestsbr** Community Propane BBQ Grillbr** Community Outdoor showerbrbrOther notes:brbr** All monthly rentals include a mandatory interim clean. Multi-month stays require 1 interim clean per month.br** Additional interim cleanings availablebr** This property will accommodate up to 4 adultsbr** No Pets Allowedbr** 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.

**MATECUMBE SUITE @ SEAPORT INN** Guest Suite w/ Pool Access + LAST KEY SERVICES

Key West, Florida, United States

Bed

Bath

Sleeps

$436.36

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival!brbrLooking for a month-long stay where you’ll have easy access to the heart of Key West coupled with genuine Old Town charm Quaint island decor, a cozy space, and a convenient location can all be found in the BARBUDA SUITE at the Seaport Inn. You're just a short walk to the most popular attractions in Old Town and have a comfortable space to duck out of the action when it’s time to relax. Of course, a month at BARBUDA SUITE at the Seaport Inn comes with Last Key Realty’s Five-Star Guest Services and Complimentary Concierge, which makes island life a breeze!brbrTHE SEAPORT INN...brbrWelcome to the Seaport Inn, where timeless island charm meets modern comfort in the heart of Old Town Key West. Seaport Inn was originally constructed in 1892 and features six suites, each boasting an en-suite bathroom and kitchen facilities. Situated just one block from the iconic Historic Seaport and a mere three blocks from the vibrant energy of Duval Street, you couldn't ask for a more convenient location to experience Key West. Steeped in history and architectural beauty, the Seaport Inn exudes historic Key West character and offers guests authentic Old Town accommodations.brbrTHE COMMUNITY POOL & TIKI BAR...brbrThe oversized outdoor common space of the Seaport Inn boasts ample space for relaxation and entertainment. Take a refreshing dip in the large pool, sip cocktails at the inviting tiki bar, or bask in the serenity of lush tropical landscaping.brbrTHE ACCOMMODATIONS...brbrBARBUDA SUITE is located on the 2nd floor of the Seaport Inn and is also known as unit 4. Upon entering you’ll walk into the living area, featuring a queen sized sleeper sofa and a flat screen TV. Further into the unit you’ll see the fully equipped kitchen, including two seats at the kitchen bar to dine at. Beyond the kitchen sits the bedroom, featuring a queen sized bed and an en-suite bathroom with a walk-in shower.brbrALL SEAPORT INN SUITES INCLUDE:brbr** Central Heat and A/Cbr** Ceiling Fansbr** Flat Screen TVs in Living Room & All Bedroomsbr** Basic stock of spicesbr** Starter supply of paper productsbr** Starter set of cleaning productsbr** Linens and Towels providedbr** Wireless high-speed Internet access & full cable includedbr** Full Time Concierge Servicebr** Fully Fenced and Lushly Landscaped Private Yardbr** Community Pool exclusively for Seaport Inn Guestsbr** Community Propane BBQ Grillbr** Community Outdoor showerbrbrOther notes:brbr** All monthly rentals include a mandatory interim clean. Multi-month stays require 1 interim clean per month.br** Additional interim cleanings availablebr** This property will accommodate up to 4 adultsbr** No Pets Allowedbr** 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.

**BARBUDA SUITE @ SEAPORT INN** Guest Suite w/ Pool Access + LAST KEY SERVICES..

Key West, Florida, United States

Bed

Bath

Sleeps

$436.36

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival!brbrIf the allure of the Caribbean is calling you but you don’t want to pull out your passport, a month at the ANTIGUA SUITE at the Seaport Inn does just the trick! This suite is perched on the second floor of the Seaport Inn and just a short walk to all Old Town has to offer. Paired with Last Key Realty’s Five-Star Guest Services and Complimentary Concierge, your month in the ANTIGUA SUITE at the Seaport Inn will have you ready to forget your passport and keep coming back to Key West!brbrTHE SEAPORT INN...brbrWelcome to the Seaport Inn, where timeless island charm meets modern comfort in the heart of Old Town Key West. Seaport Inn was originally constructed in 1892 and features six suites, each boasting an en-suite bathroom and kitchen facilities. Situated just one block from the iconic Historic Seaport and a mere three blocks from the vibrant energy of Duval Street, you couldn't ask for a more convenient location to experience Key West. Steeped in history and architectural beauty, the Seaport Inn exudes historic Key West character and offers guests authentic Old Town accommodations.brbrTHE COMMUNITY POOL & TIKI BAR...brbrThe oversized outdoor common space of the Seaport Inn boasts ample space for relaxation and entertainment. Take a refreshing dip in the large pool, sip cocktails at the inviting tiki bar, or bask in the serenity of lush tropical landscaping.brbrTHE ACCOMMODATIONS...brbrThe ANTIGUA SUITE is located on the 2nd floor of the Seaport Inn and is also known as unit 3. When you walk in, you’ll notice the charming living area, which features a queen sized sleeper sofa, flat screen TV and the kitchen area. The kitchen features everything you’ll need to prepare a meal at home. From there you head into the back bedroom which features a king bed and the en suite bathroom with a walk-in shower.brbrALL SEAPORT INN SUITES INCLUDE:brbr** Central Heat and A/Cbr** Ceiling Fansbr** Flat Screen TVs in Living Room & All Bedroomsbr** Basic stock of spicesbr** Starter supply of paper productsbr** Starter set of cleaning productsbr** Linens and Towels providedbr** Wireless high-speed Internet access & full cable includedbr** Full Time Concierge Servicebr** Fully Fenced and Lushly Landscaped Private Yardbr** Community Pool exclusively for Seaport Inn Guestsbr** Community Propane BBQ Grillbr** Community Outdoor showerbrbrOther notes:brbr** All monthly rentals include a mandatory interim clean. Multi-month stays require 1 interim clean per month.br** Additional interim cleanings availablebr** This property will accommodate up to 4 adultsbr** No Pets Allowedbr** 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.

**ANTIGUA SUITE @ SEAPORT INN** Guest Suite w/ Pool Access + LAST KEY SERVICES..

Key West, Florida, United States

Bed