Vacation Rentals By Owner In Key West, FL

Located on Stock Island this 3 bedroom home is 8 minutes from Duval street. Walking distance to several great restaurants. Gated community with a gym and large swimming pool. Queen bed on first floor. Upstairs 2 twin beds and king. Sofabed

Paradise found

Key West, Florida, United States

Bed

Bath

Sleeps

$381.14

Thank you for considering Isle Be Back for your escape to the tropical paradise of Key West. Here you will enjoy the lap of luxury with this two-bed & two-bath upstairs unit located in the highly desirable Shipyard section of the Truman Annex. Paradise awaits you just two blocks from the sights and sounds of Duval Street. A short walk or bike ride to Ft. Zachary State beach for sunbathing and snorkeling, Mallory Square to catch a spectacular sunset and the Ernest Hemingway House where the six-toed cats call home. Fine dining is an easy walk in any direction from this perfectly located condo where you get to live the laid-back tropical lifestyle of Key West. brPlease note: This property is monthly rental - the minimum rental period is 28 nights

Isle Be Back at The Truman Annex in Key West

Key West, Florida, United States

Bed

Bath

4

Sleeps

$731.25

The Galleon is on the Marina Walk in Old Town, close to dozens 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.brbr2BRbrThis is one bedroom unit that sleeps 6. There is a king size bed in the primary en suite bedroom 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 - Waterfront Key West

Key West, Florida, United States

Bed

Bath

8

Sleeps

$382.68

Experience the true spirit of Key West in this charming 3-bedroom, 2-bathroom oasis nestled in the tranquil mid-town neighborhood.brbrStep inside this beautifully renovated ranch-style home and instantly feel the stress of everyday life melt away. The open floor plan invites natural light to dance through oversized windows, highlighting the warm, airy spaces designed for comfort and connection.brbrHighlights:brbrSpacious 3 Bedrooms & 2 Bathrooms — sleeps up to 6 comfortablybrbrBedroom Highlights:brbrPrimary Bedroom: King-sized bed, chest of drawers, large closet, TV, and oversized windows filling the room with natural light — a perfect private sanctuary.brbrGuest Suite: Queen-sized bed, chest of drawers, closet, TV, and private en-suite bathroom for added comfort and privacy.brbrThird Bedroom: Queen-sized bed, chest of drawers, closet, TV — cozy and inviting for family or friends.brbrKids Pack and Play or Crib available upon request for families traveling with little ones.brbrBathroom Highlights:brbrBathroom 1: Shower, vanity, and toilet — shared by primary bedroom and third bedroom.brbrBathroom 2 (En-suite): Shower, vanity, and toilet — connected to the guest suite for private use.brbrImagine mornings spent gathered around the breakfast bar in the gourmet kitchen, the aroma of fresh coffee mingling with ocean breezes drifting in through the screened windows. This kitchen is a dream for anyone who loves to cook — with its commercial-grade refrigerator, sleek stainless steel appliances, and custom cabinetry, everything you need is at your fingertips.brbrFully Renovated Kitchen with commercial refrigeration, stainless steel appliances, and breakfast bar seatingbrbrLarge Pantry and Wine Refrigerator for storage and entertainingbrbrWhen it’s time to unwind, the living room beckons with plush sofas, a massive 65” flat-screen TV, and cozy sitting chairs perfect for conversations or movie nights. If work calls, there’s a dedicated office nook with a desk, monitor, and printer — making it easy to balance productivity with paradise.brbrOpen Living Room with 65” Flatscreen TV and comfy seatingbrbrBonus Office Space with desk, monitor, and printer — ideal for remote workbrbrOutside, the magic continues. Step into your own slice of tropical paradise with a sparkling 10 x 20 pool, complete with a splash pad that invites laughter and play under the warm Florida sun. Lounge on chaise chairs beneath an umbrella or gather around one of two outdoor dining areas — one nestled under a covered carport in front, and another in the lush, fully fenced backyard surrounded by mature trees and vibrant foliage.brbrPrivate 10x20 Heated/Chilled Pool with splash pad and chaise loungersbrbrTwo Outdoor Dining Areas — front covered carport and backyard oasisbrbrFully Fenced Yard with Mature Trees & Lush Landscaping for privacy and peacebrbrConvenience is key here: you’re just minutes from Key West International Airport, the bustling energy of Duval Street, and pristine spots like White Street Pier and Higgs Beach — yet tucked away in a peaceful neighborhood that feels like a world apart.brbrPrime Mid-town Location — quiet neighborhood but close to beaches, shopping, and nightlifebrbrParking for 1 Car in Driveway + 2 Street Spots, plus space for small trailer or boatbrbrPets may be considered on a case-by-case basis, so your furry friends can join the fun too.brbrPerfect for families, remote workers, or groups looking for an affordable, authentic Key West experience, this house is more than a place to stay — it’s your home away from home.brbrCome live like a local, create lasting memories, and enjoy the laid-back charm of Key West from the comfort of this inviting retreat. We can’t wait to welcome you!

ISLAND SANCTUARY KEY WEST - 3 Bedroom / 2 Bathroom with Pool and Parking!

Key West, Florida, United States

3

Bed

Bath

6

Sleeps

$380.98

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival!brbrGet ready to reel in your dream vacation! THE WICKED TUNA is a classic Key West home located in one of the most desirable areas of Old Town. This tastefully restored home features a historic appearance and charm, while offering all the modern conveniences one could desire. Located just down the street from the historic seaport, you’ll be within walking distance to the best restaurants, shopping, and attractions Key West has to offer. A month at THE WICKED TUNA also includes Last Key Realty’s unrivaled Guest Services and In-house Concierge, ensuring you’ll be ‘hooked’ on Key West for years to come.brbrTHE LOCATION…brbrTHE WICKED TUNA is located on the 300 block of William Street, just steps from the historic seaport and only a couple blocks from World-Famous Duval Street. Situated on one of the best blocks in Old Town, this private home is a short stroll from everything Old Town has to offer. Whether you’re looking to spend the day on Duval Street or watch the boats come and go at the seaport, you’ll be there in a few minutes. There is no dedicated parking space with this home, on-street parking only.brbrTHE KITCHEN & LIVING AREA…brbrThe living area and kitchen occupy the first floor of the home. French doors allow natural light to flow in, or open them up and head straight to the pool area. The living area features comfortable seating options for the whole group and a large flat screen TV to gather around for the big game or to binge watch your favorite show. There’s a full bathroom on the first floor with a walk-in shower.br brThere’s a wet bar tucked underneath the stairs, which is the perfect place to test your mixology skills. The fully equipped kitchen features modern appliances and every cooking tool needed to prepare meals at home. The indoor dining table comfortably seats six, and there’s additional seating at the kitchen bar.brbrTHE POOL AREA…brbrStep out the French doors from the living area and into your private backyard oasis. The entire backyard is fenced in and landscaped for maximum privacy. The refreshing private dip pool can be utilized year-round thanks to the convenient heater. Treat your group to a poolside BBQ of today’s fresh catch using the propane grill and outdoor dining set with seating for six. The outdoor shower is perfect for rinsing off after a day at the beach or out on the boat.brbrTHE ACCOMMODATIONS…brbr** Bedroom #1 - Located on the Second Floor with a King bed, a flat screen TV, a private balcony overlooking William Street, and access to the hall bathroom with two vanities and a walk-in shower.brbr** Bedroom #2 – Located on the Second Floor with a King bed, a flat screen TV, a private balcony overlooking the pool area, and access to the hall bathroom with two vanities and a walk-in shower.brbr** Bedroom #3 - Located in the Guest Cottage with a Twin over Twin bunk bed (250 lb max on the top bunk), a flat screen TV, and an en-suite half bathroom.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 & YouTube TV includedbrbrIn addition, this fully stocked home also includes, but is not limited to the amenities on this list:brbr** Fully Fenced & Lushly Landscaped Private Yardbr** Private Pool with Pool Heaterbr** Propane BBQ Grillbr** 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** There is no dedicated parking space with this home, on-street parking onlybr** Max of 2 Pets Allowed with Additional Fee of $200 per pet

**THE WICKED TUNA @ THE SEAPORT** Private Home & Pool + LAST KEY SERVICES…

Key West, Florida, United States

Bed

Bath

Sleeps

$816.8

Concierge Realty is proud to present luxury villas at Hyatt Beach House!brbr**Reservations are available in weekly (7 night) increments with arrivals and departures on Fridays, Saturdays, and Sundays only.brbr**All bookings are time sensitive and availability can change at any time. Send us a message to confirm exact availability prior to making a booking request. brbrGreat destinations in Key West should offer more than a good night's sleep, and Hyatt Beach House takes pride in offering you the best of everything -- a great location, luxurious rooms and super service. brbrHyatt Beach House Resort is surrounded by private marinas for easy access to boating and fishing. It’s also just a short distance from Old Town, the heart and soul of Key West. Key West is Florida’s capital of laid-back leisure. Enjoy the phenomenal dining, live music and bar scene.brbrMaster suite with king-size bed, adjoining bath, walk-in shower and spa tubbrGuest suite with king-size bed and full bathbrFully equipped kitchenbrDining areabrSofa bedbrPremium electronicsbrInternet brScreened-in balconybrbrThe resort has a breathtaking gulf coast setting. Paired with the gracious service, top-tier amenities and meticulous attention to detail, you are in for a wonderful vacation.brbrEnjoy the privacy 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. The beautiful plantation-style design creates an environment of relaxation, enjoy the outdoor lagoon pool and spa tub and complimentary Wi-Fi throughout.brbrResort amenities include:brComplimentary parkingbrconcierge servicesbrin-room washer and dryerbrchild care; cribs and high chairs upon requestbrbr**$41.00 housekeeping fee mandatory for all reservationsbrbrThe Vrbo calendar helps provide availability and estimated price quote. Always inquire with the agent and do not reserve airfare until your confirmation has been received.brbrAny issues with resort service, accommodations, physical plant, amenities, etc. are the direct responsibility of the developer and must be handled through the resort, not Concierge Realty. Photos are thought to be truly representative of the resort and accommodations. Any variation from the photo and actual property are unintentional, so guests are encouraged to do their own due diligence prior to reserving. Any variance or disruption including but not limited to renovation, unavailable amenity, change in decor, etc. during the stay, whether announced prior to reservation, occurring during the stay or announced after confirmation, is a matter strictly between the guest and resort, are not deceptive advertising, breach of contract or the responsibility of Concierge Realty.brbrNote that the images are representative of this villa and that a specific view type is not implied nor promised by virtue of the images. A specific view category must be addressed with rental agent. Concierge Realty reserved the right to reserve any view category unless one has been agreed upon in writing. The resort confirmation will show the view designation and the villa will be placed within that view category unless, in a rare instance the view will be noted as not guaranteed in which case the resort reserves the right to place the guest anywhere within the property. Issues regarding view within the guaranteed view category are to be addressed with the resort management as Concierge Realty is not responsible for villa placement.brbrPlease be advised that if a non-domestic credit card is used to reserve a vacation rental, additional fees may be incurred.brbrAll details are accurate to the best of our knowledge. Any questions with regard to view, amenities, bedding configuration, decor or other details should be addressed with Concierge Realty, Winter Garden, FL.brbrGuests are encouraged to do their own due diligence to assure that the resort and villa will meet their expectations.

Hyatt Beach House- 2 Bedroom Located On The Gulf With Private White Sand Beach!

Key West, Florida, United States

Bed

Bath

Sleeps

$617.63

We have the perfect accommodation for a family vacation or friends getaway in Old Town Key West, Florida. Our Two-Bedroom Poolside Villa has two bathrooms and features Dade County pine interior walls and floors with a gracious kitchen, dining area, and living room. This spacious vacation rental can accommodate up to six people, two in each of its two bedrooms and two additional people on a convertible sofa in the living room.brbr* 1 King, 1 Queen, 1 Queen Sleeper Sofabr* 2 Full Bathroomsbr* Sleeps up to 6 Peoplebr* Full Kitchen with Dining Areabr* Flat Screen TV with Cablebr* Shared Heated Poolbr* Continental Breakfast Includedbr* Parking by Reservation ($15/night plus tax)br* 200 Feet from Duval Street

Villa

Two Bedroom Two Bath Poolside Villa Steps from Duval!

Key West, Florida, United States

Bed

Bath

Sleeps

Select Dates for Price

Key West Paradise Found hes been renovated for 2020 and beyond. New Master Bathroom, Reconfigured Master Bedroom and Remodeled Kitchen. If you have a larger party we also own the 2 units right next door so they can all be rented together. Enjoy your luxury condo with breathtaking view of the deep blue Ocean and sparkling salt water pool within our tropical is nothing like .... at any price. Paradise Found is a TOP FLOOR spacious, clean and comfortable Key West condo experience. Enjoy your PRIVATE BALCONY for lounging sunbathing and dining.. This is a two bedroom two bath spacious condo. Newly renovated for 2020 and enhanced with Comfortable Beds. The Master has a KING. The second bedroom offers a QUEEN with an additional TWIN for sleeping flexibility. There is also a Queen sleeper sofa in the living room. brThis is Key West's most coveted location. Nestles between two of Key West's best beaches, Smathers Beach is just a 20 yard walk on the side walk. We are within 2 miles of most locations on the island. Enjoy the nightlife and excitement of Duval Street (restaurants, bars, live entertainment). Scuba Diving, Jet Skiing, Kayak Rentals, Deep-Sea Fishing, Cruises. Close to 18-Hole Golf Course, Moped/ Bicycle Rentals, Airplane/Seaplane Tours. We hope that you will enjoy staying on the ocean with all the comfort of home . After your first visit we hope you will agree....brPARADISE FOUND WELCOMES YOUR VISIT TO PARADISE.brbrbrElevator 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.

Key West Paradise Found - Amazing ocean views from every window

Key West, Florida, United States

Bed

Bath

Sleeps

$158.76

Find the best of Key West at your doorstep with this beautiful first floor one-bedroom condo, with a private patio, a shared swimming pool, and a wonderful location close to restaurants, beaches, and more!brbrPerfectly located between Truman Annex and Bahama Village, this comfortable condo sits only two blocks from the fantastic restaurants, nightlife, and shopping on Duval Street. Park your car in the off-street space, walk a quarter-mile to the Ernest Hemingway Home and Museum, and take afternoon bike rides to the soft sand at Fort Zachary Taylor Historic State Park three-quarters of a mile west.brbrThe living space has been meticulously decorated, offering central A/C, free WiFi, and French doors that open to the deck. When you're not dining at Blue Heaven nearby, you can sip cocktails outside among the palms and orchids, flip through the offerings on the HDTV, and splash around in the shared swimming pool. A full kitchen with granite countertops, a private off-street parking spot, and a private washer/dryer are also on hand.brbrPlease note: This property has a 28 night minimum stay

Another Siesta at The Truman Annex in Key West

Key West, Florida, United States

Bed

Bath

Sleeps

$358.94

Cool pastel, Caribbean inspired decor with original art throughout by Robin Hix. Blue tooth speaker, Alexa Echo, full kitchen w/dishwasher. 65” Smart TV ( bring your PW/UN for Netflix/Amazon or other programming you enjoy). Tumbled marble shower. Part of a gated compound with 3 other units. Beautifully landscaped, lots of orchids, native plants. Next door is the heated shared Family pool at 916 and the Adult heated pool is across the lane.brbrBuilt in 2010. Sleeps 2 with Luxury king bed (14` pillowtop memory foam mattress) accommodations with full kitchen (dishwasher), tumbled marble shower, 65” Smart TV (bring your Netflix, Amazon, etc. UN/PW to watch your favorite shows), Blue Tooth speaker, Alexa, private 2 person Solana jacuzzi, daily maid service. Shampoo, conditioner, body gel and lotion included.brbrTwo shared heated pools in tropical garden settings. One pool is the Family pool next door and the Adult’s Only pool is across the lane. You have the use of a Weber gas grill, bike rack and W/D for your use after 5pm on site. There is a second story deck which is perfect for coffee, lunch, dinner beneath a giant Sapodilla tree. Also an ice-maker there for your convenience.brbrI am usually around during the course of the day but have groundskeeper and maids there daily from 9-5.brbrQuiet, friendly, 2 block lane with restaurants, bike rentals, 24 hour CVS and Subway are within steps!brbrWalk, bike, mopeds, electric car. Rentals are at the corner of Center Street and they will return you to the airport upon departure when you rent from them. There is also a bus around Old-town and there is a map of all the stops in your scannable in-room information book. Stops are just around the corner from us!brbrPrivate, gated compound with 3 other units. You have use of the W/D, upstairs deck, grill, bike rack. Next door is the Family heated pool and across the lane is the Adult`s Only heated pool.br- Must be 25 or older to check-in during March/April (Spring Break). Please use quiet voices after 10 pm at the Family pool. Pets are WELCOME!

McCartney`s Manor - Deluxe K Suite W/Pvt. Spa!

Key West, Florida, United States

Bed

Bath

Sleeps

$216.05

Located just 1.8 miles from Key West International Airport, enjoy easy access to Duval Street’s vibrant nightlife and the iconic Hemingway House. Unwind on Smathers Beach or take in the lively sunset celebrations at Mallory Square. Perfect for families, couples, and adventurers, with nearby snorkeling, dining, and cultural spots for a memorable island escape.brbrThis listing is for a room within a hotel.brbr✦ Your room is 307 sq. ft, equipped with complimentary toiletries, standard quality 55-inch TV, available with Premium cable.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, and is flexible afterwards. If you expect to arrive later, please let us know as soon as possible to make the necessary arrangements.brbr✦ You may keep your luggage at the front desk if you arrive early.brbr✦ Public or shared fitness center open 24/7, available in the property.brbr✦ Outdoor shared pool available all year, opened from 6:00AM to 10:00PM.brAdditional features:br • Heated poolbrbr✦ Free parking lot – 1 space(s).brbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A mandatory resort fee of $25.00 per night will be collected upon check-in, not included in the daily rate.brbr✦ Pets are not allowed.brbr✦ We use multi-unit listings, so rooms are similar but may have small differences.brbr✦ The maximum number of days that you may book per reservation is only 28 days.brbr✦ Free buffet breakfast available 6:30 AM to 10:00 AM on weekdays and 7:00 AM to 11:00 AM on weekends.brbr✦ Free cribs are available upon request and subject to availability.brbr✦ Oversized vehicles, trailers, RVs, and boats incur a daily fee.

Hotel

Key West Stay Ideal For Couple Close to Mallory Square | Outdoor Swimming Pool

Key West, Florida, United States

Bed

Bath

Sleeps

$216.05

Located just 1.8 miles from Key West International Airport, enjoy easy access to Duval Street’s vibrant nightlife and the iconic Hemingway House. Unwind on Smathers Beach or take in the lively sunset celebrations at Mallory Square. Perfect for families, couples, and adventurers, with nearby snorkeling, dining, and cultural spots for a memorable island escape.brbrThis listing is for a room within a hotel.brbr✦ Your room is 307 sq. ft, equipped with complimentary toiletries, standard quality 55-inch TV, available with Premium cable.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, and is flexible afterwards. If you expect to arrive later, please let us know as soon as possible to make the necessary arrangements.brbr✦ You may keep your luggage at the front desk if you arrive early.brbr✦ Public or shared fitness center open 24/7, available in the property.brbr✦ Outdoor shared pool available all year, opened from 6:00AM to 10:00PM.brAdditional features:br • Heated poolbrbr✦ Free parking lot – 1 space(s).brbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A mandatory resort fee of $25.00 per night will be collected upon check-in, not included in the daily rate.brbr✦ Pets are not allowed.brbr✦ We use multi-unit listings, so rooms are similar but may have small differences.brbr✦ The maximum number of days that you may book per reservation is only 28 days.brbr✦ Free buffet breakfast available 6:30 AM to 10:00 AM on weekdays and 7:00 AM to 11:00 AM on weekends.brbr✦ Free cribs are available upon request and subject to availability.brbr✦ Oversized vehicles, trailers, RVs, and boats incur a daily fee.

Hotel

Key West King Escape, Fairfield Inn, Outdoor Swimming Pool | Near Mallory Square

Key West, Florida, United States

Bed

Bath

Sleeps

$521.99

Serenity by the Sea | 2BR/2BA Key West Condo at La BrisabrbrWelcome to your tropical retreat in paradise! This beautifully appointed 2-bedroom, 2-bathroom condo is located in the gated La Brisa Condominium complex—perfectly situated directly across the street from the iconic Smathers Beach in Key West. With palm trees swaying and turquoise waters just steps away, this is the island getaway you’ve been dreaming of.brbrStep inside to an open-concept space filled with natural light and coastal charm. The spacious living area features comfortable, beach-chic furnishings and sliding glass doors that lead to a private balcony overlooking peaceful salt ponds—where you can enjoy a morning coffee, spot native birds, or simply unwind in the ocean breeze.brbrThe fully equipped kitchen boasts stainless steel appliances, an induction stove, and a breakfast bar with seating for three. Just off the kitchen is a dining area with seating for four—ideal for a family meal or sunset dinner.brbrThe primary bedroom is a relaxing haven with a king-size bed, en suite bath, and direct balcony access. The second bedroom offers two twin beds that can be easily converted to a king, giving you flexibility whether you're traveling with friends or family. A washer and dryer are available in the unit for added convenience.brbrResort-Style Amenities at La Brisa Include:br*Large heated/chilled outdoor pool open 24 hoursbr*Hot tub and sauna-equipped poolside bathroomsbr*Lighted tennis court with pickleball linesbr*Outdoor grilling areabr*Electric charging station for vehicles, golf carts, and e-bikesbr*Designated washing and vacuuming station for your carbr*Covered reserved parking spot + guest parkingbr*Gated access for security and peace of mindbrbrAcross the Street: Smathers Beachbr*Just steps from your door, enjoy one of Key West’s most beautiful beaches with soft white sand, shallow turquoise waters, and plenty of space to relax, swim, paddleboard, or simply soak up the sun.brbrClose to the Actionbr*While the condo offers peace and serenity, you’re just a short bike ride or quick drive from the world-famous Duval Street—home to vibrant nightlife, delicious dining, local shops, and must-see attractions. It’s the perfect blend of quiet relaxation and island excitement.brbrWhether you're looking for adventure or relaxation, this condo has it all—from first-class amenities to an unbeatable location. Book your stay today and experience the laid-back island lifestyle that only Key West can offer!

Serenity by the Sea, 2BR/2BA Condo w/Pool at La Brisa across from Smathers Beach

Key West, Florida, United States

Bed

Bath

Sleeps

$470.76

This property has it all! The styling of the original shot gun homes of Key West restored with a beautiful natural cypress exterior combines with the clean lines of a contemporary home. Each Twin opens to it's own semi-private deck and lounge area with steps into a large kidney shaped pool with waterfall. Inside the comfortable living room there is a spiral staircase to the loft second bedroom with unique glass railing. Large windows in the kitchen bi-fold away to allow serving directly to the pool deck and capture the warm, tropical, Key West breezes. If cooking isn't for you on your vacation, stop by the Banana Cafe Restaurant or one of the many other delicious options steps away on Duval Street. The Twins allow for great flexibility in your vacation planning. Rent this property as a two bedroom/one bath or add the other unit to make it four bedrooms/ two bath. brBedding: 2 queens

Cottage

Pete's East Cottage: Cypress east cottage steps from Duval

Key West, Florida, United States

Bed

Bath

Sleeps

$1288.13

Great location, just half a block off Duval Street, walking distance to restaurants, the Atlantic beaches and the Southernmost Point. Casually decorated in soft pine and white, wicker furnishings and sofa sleeper in living room, this four bedroom, three and a half bath home provides a comfortable vacation hideaway. brbrAll bedrooms and two baths are located on the second floor. The dining area and kitchen are downstairs and French doors open to a deck with an ample pool. This home is an excellent choice for family reunions and larger groups. brbrBedding: 1 king, 1 queen, 1 double, 2 twins, 1 sleeping sofabrPet Friendly: Size and breed restrictions and additional fees applybrPARKING is in the driveway or on Louisa Street. The entire block of Louisa Street is free/ un-metered and not reserved for full-time residents. Please be sure not to block any driveways.

Louisa House: A comfortable four bedroom vacation hideaway

Key West, Florida, United States

Bed

Bath

Sleeps

$444.54

Coral Hammock – 3BR/3BA Home with Pool Views in Coral Hammockbrbr3 Bedrooms | 3 Full Bathrooms | Sleeps up to 8 | Backs to Community PoolbrbrWelcome to Coral Hammock, your home away from home in beautiful Key West! Built in 2004 and meticulously maintained, this spacious 3-bedroom, 3-bathroom home offers comfort, convenience, and unbeatable value—often for less than the price of a single hotel room.brbrLocated in the gated Coral Hammock community—home to just 55 properties—this detached home offers added privacy and direct access to the lushly landscaped community pool, right from your backyard.brInside You’ll Find:brbr A well-equipped kitchen with both Keurig and drip coffee makersbr TVs in the living room and each bedroombr High-speed internet to keep you connectedbr Comfortable accommodations for up to six guestsbr Queen air mattress brbrOutdoor Perks:brbr Two spacious decks—perfect for lounging, dining, or just enjoying the breezebr Complimentary beach chairs and umbrellabr Easy access to the community pool and clubhouse, including a small fitness centerbrbrThis is the perfect setting for families, couples, or friends looking to explore Key West while enjoying the peace of a residential-style stay.

Coral Hammock Poolside Home 3 bdrm 3 bath10 minute drive to Old Town Key West

Key West, Florida, United States

Bed

Bath

Sleeps

$581.33

Enjoy endless views just feet away from the tranquil waters of the Atlantic Ocean. “Beach Club #304” is a serene waterfront oasis located in an upscale gated community within walking or biking distance to the local’s finest spots, including restaurants, beaches, shopping, bars and the infamous Duval Street. This condo community prides itself for being one of the very few on the island that sits directly on the water.brbrThe Living room is brightly decorated exuding light from floor to ceiling. The breathtaking view can be seen as soon as you enter this spacious 2-bedroom coastal retreat, with comfortable seating for those spontaneous movie nights. The kitchen is fully equipped to make that perfect home cooked meal. Relax on the outdoor sofa or dine oceanside on your large, private balcony while soaking in the panoramic ocean views. The balcony is the perfect place to enjoy an evening cocktail or freshly brewed morning cup of coffee.brbrBedroomsbrMain Bedroom: King bed, flat screen TV, direct access to the balcony, oversized spa-like shower.brbrGuest room(Second room): 2 Twin beds OR One King Bed, flat screen TV, oversized spa-like showerbrbrUnit Features:brCentral A/C, Wi-Fi, washer/dryer, security entry, one reserved parking space in the garage and elevator accessbrbrCommunity Amenities: Resort amenities include two ocean side pools (heated), tennis court, outside cooking facilities, fitness center and sauna. Although there is no water access, Smathers Beach and Higgs Beach are conveniently located on either side of the complex. There are plenty of chaise lounges around the pool area as well as a cabana to enjoy during those sunny island afternoons.brbrAdditional things to know:brThe Key West Beach Club Condo Association requires additional registration, which includes providing copies of photo IDs for everyone over the age of 17, in advance of your arrival. Details will be provided along with your RKWV rental agreement.brbr*Disclaimer: Due to the property's oceanfront location, please be aware that Key West experiences seasonal occurrences of fermenting turtle grass along the south shore of the island brought on by our southern winds in the summer. This is a natural phenomenon that is outside of our control.brbrInterim housekeeping provided upon request brThis property will accommodate up to 4 adults brSorry, pets are not allowed.

OCEANFRONT ECSTASY - KW Beach Club #304

Key West, Florida, United States

Bed

Bath

4

Sleeps

$876

**About...** brHemingway Atlantic Retreat is a two-bedroom condo conveniently located near beaches and restaurants, just minutes away from Duval Street. Nestled in a gated oceanfront community, it offers a peaceful retreat with beautiful sunrise and ocean views from Smathers Beach on the private balcony. brbr**Furnishings...** brUnwind on the cozy couches while enjoying a movie, or gather around the dining table that seats six for a home-cooked dinner. brbr**Sleeping Arrangements...** brThe primary bedroom features a king-size bed, while the guest bedroom contains two twin-size beds that can be converted into a king upon request. Both bedrooms offer ample closet space and stunning sunrise and ocean views. Additionally, the living room includes a queen sleeper sofa, making it perfect for accommodating families, friends, or couples.brbr **Details and Amenities...** brHemingway Atlantic Retreat has been recently renovated and features two bedrooms and two full bathrooms. One bathroom includes a large tiled walk-in shower, while the guest bathroom has a tub. The well-equipped kitchen boasts beautiful countertops and amenities, including a drip coffee maker. Step out onto the private balcony to enjoy sunrise views and the refreshing ocean breeze, complete with comfortable seating for soaking up the morning sun while sipping a warm cup of coffee to start your day. brbr**Pool and Outdoor Living...** brCommunity amenities include a heated Olympic-sized pool and a bubbling 20-person hot tub, as well as three tennis courts, one of which boasts the only clay surface in Key West. There are bathrooms near the pool for convenience, whether you want to enjoy a sauna soak or a quick rinse before heading back to the condo. A small community library and fitness center are also available. Spend your evenings under one of the many pavilions while grilling your dinner and enjoying the refreshing breeze from the Atlantic Ocean. Plus, bask in the sun on the property’s private beach or take a short two-minute walk to Smathers Beach, the largest beach in Key West! brbr**Parking...** brEach unit comes with an assigned parking space in the garage, subject to height restrictions. Limited outside parking spaces are available on a first-come, first-serve basis. brbr**Concierge Services...** brTake advantage of our concierge services to help plan activities for your trip. We can assist with bikes, scooter, and golf cart rentals, as well as a variety of excursions, including snorkeling, sunset cruises, jet ski rentals, parasailing, kayaking, fishing, paddleboarding, and much more. We can even stock your fridge with all the necessities before your arrival. brBook Activities /keywestattractionsfishingdiving/brbrbr **Cancellation...**br Bookings canceled at least 30 days before the start of the stay will receive a refund, minus a $250 cancellation fee.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.

Hemingways Atlantic Retreat overlooks Smathers Beach upgrades galore Key West

Key West, Florida, United States

Bed

Bath

Sleeps

$495.31

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival!brbrThis freshly renovated condo is located at 1800 Atlantic Blvd on the beach, just steps from the ocean and sand in your toes. You'll be able to enjoy quiet afternoons at CONCH IN THE TREETOPS with those balmy Key West breezes wafting through the floor-to-ceiling glass doors, while sitting on your private balcony surrounded by the palm tree tops. CONCH IN THE TREETOPS is located in an upscale private community within walking or biking distance to all of your favorite Key West spots including beaches, restaurants, shopping, and the beautiful waters surrounding the island.brbrTHE LIVING AREA...brbrThe living room of CONCH IN THE TREETOPS is comfortably furnished, with plenty of light streaming in from the floor-to-ceiling glass doors and reflecting off the floor to ceiling mirrors. There's a very large flat screen TV, and plenty of seating for your whole group to gather before heading out to enjoy Key West. The living room sofa pulls out into a queen sized sleeper for extra guests in a pinch. The brand new kitchen with its new stainless steel appliances has everything a good chef would need to prepare any meal. The dining table will seat six comfortably. You can also take your meal out onto the balcony on your dining set in the treetops.brbrTHE POOL, THE BEACH & TENNIS...brbr1800 Atlantic offers Resort-style amenities, including an extra large Community Pool right downstairs. There are chaise lounges surrounding the pool for your comfort, and a cabana with restrooms for your convenience. Please note this is a shared pool with set rules, such as no music and no coolers. We ask that our guests be mindful of their neighbors and respect the rules.brbrFrom the pool, there's a walking path that leads to the on-site beach. The on-site beach offers a relaxing setting, with chaise lounges and soft sand. There is no direct water access from this beach, but Smathers Beach, Key West's largest public beach, is located within walking distance right next door. There is also an oversized Jacuzzi and a picnic area with BBQs available for guest use. You'll also have access to the newly built fitness center and Key West's only clay tennis courts, both located on-site.brbrTHE ACCOMMODATIONS...brbr** Master bedroom: a King bed, a large flat screen TV, direct access to the balcony, and an en suite with an oversized shower and tub combination.brbr** Second bedroom: Two Twin beds OR One King bed, a flat screen TV, direct access to the balcony, and access to full second bathroom.brbrALL LAST KEY VACATION HOMES INCLUDE:brbr** Washer and Dryerbr** Central Heat and A/Cbr** Ceiling Fansbr** Flat Screen TVs in Living Room & All Bedroomsbr** Fully Equipped Kitchenbr** Basic stock of spicesbr** Starter supply of paper productsbr** Starter set of cleaning productsbr** Linens and Towels providedbr** Wireless high-speed Internet access & full cable includedbrbrIn addition, this fully stocked home also includes, but is not limited to the amenities on this list:brbr** Community Pool Accessbr** Community Jacuzzi Accessbr** Assigned off-street carport for 1 car (Parking Garage has a low clearance of 6'2)br** Key West's only clay tennis courtsbr** Handball courtsbr** Fitness Centerbr** Dry Saunasbr** Picnic areas with BBQsbr** Recreation rooms available for private partiesbrbrOther notes:brbr** Interim housekeeping provided upon requestbr** This property will accommodate up to 6 adultsbr** This complex has both visitors and locals living here, we expect our guests to be mindful & respectful of the posted rulesbr** 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.

**CONCH IN THE TREETOPS @ 1800 ATLANTIC** Beach Condo / Pool + LAST KEY SERVICES

Key West, Florida, United States

Bed