Vacation Rentals By Owner In Key West, FL

$571.46

Oceanfront Property - 2BR/2BA - Near Smather's Beach - Poolside Bar and Grill

Key West, Florida, United States

★Excellent Key West Location - Oceanside Resort - Two Bedroom - Two Bath - Sleeps 6br★Very Clean - Very Nice Property.brbrThis Oceanside two-bedroom condo features a primary bedroom with a king size bed, and adjoining bathroom with a walk-in shower and a relaxing jetted tub. The guest bedroom features a queen size bed and access to full guest bathroom. There is a living room with a sleeper sofa, TV and wi-fi access. The unit can accommodate up to six people. It features a full kitchen with granite countertops and appliances, including a full size refrigerator, stove-top burners, a microwave, a sink, a coffee maker, and a toaster. The condo also features a washer and dryer, for convenience.brbrCome and enjoy the outdoor accommodations, from sparkling infinity edge pool and jacuzzi, a shuffleboard court, pool, ping pong, foosball tables, a beach volleyball court, a restaurant, and concierge services right on site.brbrEnjoy the white sands of the world-famous Smathers Beach. Only 3 miles away is the famous Southernmost Point, old town Key West, and all the fun of Duval street. Just minutes away guests will find the Fort East Martello Museum, the Key West Aquarium, Mallory Square, world class fishing, and excellent restaurants.brbrROOM AMENITIES INCLUDE:br- Entertainment with complimentary Wi-Fi, phone, and premium TV channels, alarm clockbr- Kitchen with refrigerator, microwave, stove-top, oven, coffee/tea maker, toaster, sink, cookware, dishware, and utensilsbr- Shower; Jetted tubbr- In room climate control (air conditioning)br- Hair dryerbr- Iron/ironing boardbr- Separate sitting areabr- In room safebr- Sleeper sofabr- Portable cribs/pack 'n plays (available upon request)brbrPROPERTY AMENITIES INCLUDE:br- Luggage storagebr- Elevatorbr- ATMbr- Front deskbr- Pool and pool chairsbr- Laundry facilities in unitbr- Complimentary Wi-Fibr- Outdoor infinity-edge poolbr- Outdoor jacuzzibrbrProperty offers complimentary self parking.brNo recreational vehicle parking is permitted.brbrUnits are assigned at check-in. The unit's location, decor and view may vary. Room views need to be discussed ahead of booking. Room moves may be required with multiple week stays.brbr- Resort fee of $22.50/per day will be charged at check-in, along with a refundable $100 security deposit for incidentals (subject to change).brbrA split week fee of approximately $125 may apply for reservations shorter than one week. (Subject to Change).brbrThe resort will be undergoing an enhancement project from May 2026 to August 2026. During this time, guests may experience limited-view obstructions if located in building under renovation. Additionally, anticipate minor construction noise between the hours of 9AM to 5PM.brbrPlease note, there is no cash available at this resort and credit cards are the only acceptable form of payment.brbrWe do not accept liability for any inconveniences beyond our control including but not limited to temporary defects or outage of utilities, closures of resort amenities, or limitation of any other service. We will not provide refunds, reimbursements, or compensation for inconvenience or interruption of utilities, resort amenities, or any other service.

2

Bed

2

Bath

6

Sleeps

$312.2

/ Nightly

Private Vacation Home

Historic Key West charm @ San Souci - A Monthly Rental

Key West, Florida, United States

Sans Souci is a gorgeous Key West vacation home with a pool and lush tropical foliage. Relax by your own private pool or go out on the town! Key West Seaport is only two blocks away!brbrIn a peaceful alley just a 10 minute walk from Duval Street, your private paradise awaits. Sans Souci is a completely restored Key West home that promises rest for the weary and access to the best entertainment the island has to offer. The 2 bed/2 bath main house is a relaxing gathering place with a guest cottage nestled in a tropical garden just behind. Throw open the French doors into your private deck retreat with heated pool and spa to suit all guests.brbrEntertain friends and family in Sans Souci's spacious interior with a wall of glass that invites the sun and colors of Key West's gorgeous flora into your living room. The fully equipped kitchen with brand new stainless steel appliances and granite counter tops finishes the completely modern layout. Each bedroom has a TV and full length mirror. There is a sleeper sofa in the primary bedroom.brbrYou'll feel right at home in your upstairs primary suite with full bath and copious closet space. A downstairs guest room with twin beds is perfect for 2 more with an additional full bath. The guest cottage in the rear lives in its own little world with queen bed, half bath and outdoor shower. Sans Souci is a home the entire family will adore.brbrTHIS IS A MONTHLY RENTAL IT RENTS THE FIRST OF THE MONTH TO THE END OF THE MONTH ONLY. WE DO NOT SPLIT MONTHS.

Bed

Bath

Sleeps

$390.68

/ Nightly

Condo

Peaceful 2 BR Condo with All Amenities

Key West, Florida, United States

Enjoy the comforts of home in the midst of paradise. brbrComfortable, reasonably priced 2-bedroom condominium in Sunrise Suites Resort. The Resort offers concierge service, heated swimming pool, outdoor spa, gym facilities, tennis court and Internet service. The unit is on the 3rd floor, accessible by elevator. Has completely equipped kitchen, 2 fully furnished bedrooms and 2 baths. Living room has sofa bed that opens to a queen-sized bed. Has private balcony overlooking the adjacent Salt Ponds Preserve. Sufficient parking space close to the unit. brbrWithin walking distance from the airport, Smathers Beach, seaside hiking or running. Minutes away from Duval Street. brbrKeywords: Condominium

Bed

Bath

Sleeps

$268.4

/ Nightly

Condo

PAINTED SKY~2 BR/2 BA Waterfront Condo at Sunset Marina w/ Pool & Boat Slip!

Key West, Florida, United States

ISLAND MASTERPIECE...brIn the private gated community of Sunset Marina, this exquisite waterfront condo's view is awash in an artist's loving brush strokes of light, shadow and panoramic beauty resembling a watercolor work of art. The perfect palette for a memorable stay, you are merely a brief drive from the excitement of Old Town yet tucked away in a secluded community with a spacious balcony that boasts a spectacular view of the Florida Bay and the Gulf of Mexico.br***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGE. We do not accommodate bachelor/bachelorette parties, student workers or construction workers. brbrDETAILS AND AMENITIES…brThis renovated first floor gem has been meticulously designed and furnished to delight you as soon as you walk through the door. The open living area and large main balcony give you plenty of room to relax and spread out. Plush seating options include a queen sleeper sofa for hours of serenity and pleasure in your very own paradise. Enjoy the large flat screen TV, wet bar and a fully stocked kitchen that begs for culinary creations. The kitchen bar seats 4 and is perfect for casual dining and conversation. Dine in the comfortable indoors or at the balcony dining table. There is a ring doorbell located on the front door of the home.brbrSLEEPING ARRANGEMENTS…brThe primary suite offers a king bed, flat screen TV, direct access to the main balcony, a large walk-in closet, and an en-suite bathroom with double vanity, oversized shower and a separate oversized tub.brThe second bedroom suite features two twin beds that can be converted to a king, flat screen TV, ample closet space, and an en-suite bathroom with a walk-in shower.brbrOUTDOOR LIVING…brUnwind at the community pool area, a serene setting in which to spend the day. Set right on the waterfront, bask in dreamy views of the marina and the Florida Bay beyond. A beautiful boat slip is available that will hold up to a 40ft vessel. Swim in the pool or unwind in oversized Jacuzzi. There are plenty of chaise lounges, sitting areas, and a cabana for your convenience. brbrPARKING...brSunset Marina offers plenty of off-street parking, with one covered space in the ground-level garage and a visitor space. There is an elevator that takes you from the parking area to the condo. brbrPETS...brThis is not a pet friendly home.brbrMULTI MONTH RESERVATIONS... brFor monthly reservations, the following fees will be added PER MONTH: brMid-stay cleanbrPool/hot tub heating fee (if applicable)brPet fee (if applicable)brbrCONCIERGE SERVICES...brEnjoy this 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, kayaking, fishing, paddle boarding and much more. They can also have your fridge stocked with all the necessities in advance of your arrival!brbrBOOKING DATES...brThis home is only available as a monthly rental (28 night min.). 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.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).brbrTHE PERFECT CANVAS TO PAINT YOUR DREAM OF PARADISE...

Bed

Bath

Sleeps

$1190.43

/ Nightly

Private Vacation Home

Palm Trees Ocean Breeze Key West FL

Key West, Florida, United States

Three bedroom, four bathroom private home with heated pool . Breathtaking sunsets can be seen from third floor deck overlooking the Ocean. High definition TV and surround stereo throughout the home. High Speed internet and faxing available as well.brbrHigh security inside: guarded and gated Truman Annex. Only three blocks to Jimmy Buffets, Sloppy Joes and Duval Street entertainment. One of the nicest homes in the best area of Key West. Watch sailboats and sunsets from the decks during the day and feel refreshing ocean breezes throughout home at night. brbrOne week minimum stay is required.br

3

Bed

4

Bath

8

Sleeps

$902.1

/ Nightly

Private Vacation Home

**THE PLAYFUL PELICAN @ OLD TOWN** Home & Pool Near Duval + LAST KEY SERVICES...

Key West, Florida, United States

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival!brbrThinking of flying south to Key West for your next vacation Consider a vacation home that blends comfort, style, and offers enough space to spread your wings. THE PLAYFUL PELICAN lives up to its name with plenty of room, both inside and out, for fun and relaxation. Inside, open living areas provide the perfect place for gathering and creating memories, while private bedroom suites allow guests to settle in comfortably after a day of exploring the island. Outside, a refreshing private pool and welcoming lounge area invite you to soak up the sunshine, and convenient off-street parking makes it easy to be ready for your next island outing. THE PLAYFUL PELICAN is just a short stroll or bike ride to Duval Street and the Historic Seaport, making it the perfect perch for groups ready to dive into the best of Key West. Coupled with Last Key Realty’s unrivaled Guest Services & In-house Concierge, a stay at this modern island home will surely be one you treasure forever!brbrTHE LOCATION...brbrImagine your vacation home being just steps in either direction from all of the shops, restaurants, and sites of Duval Street and the Historic Seaport. Take a stroll or ride your bike down to the best of Key West, three blocks down Olivia Street to hit local favorites like Moondog Cafe, Martin's, and Nine-One-Five. Just a few blocks down Windsor Lane and you'll be at BO's Fish Wagon or Schooner Wharf.brbrTHE LIVING AREA & KITCHEN...brbrTHE PLAYFUL PELICAN offers an upscale retreat defined by soaring ceilings and chic, contemporary design. Sunlight pours into the main living space, creating a fresh, open feel from morning to evening. The inviting living room features plush seating arranged around a large Smart HDTV, with a seamless connection to the impressive, fully updated kitchen. From mixing drinks at the wet bar to cooking with top-tier appliances, everything is in place for relaxed gatherings and entertaining. Enjoy meals together at the dining table for six, or opt for a casual bite at the three-seat breakfast bar. A conveniently located powder room can be found just off the hallway.brbrTHE PRIVATE POOL...brbrBeyond the doors, you’ll find the standout feature of the home: a secluded tropical haven all your own. Fully enclosed by a privacy fence and surrounded by vibrant, exotic landscaping, this inviting outdoor space is perfect for gathering and unwinding. Relax on the comfortable chaise lounges that can easily be adjusted to chase the sunshine or settle into the shade beside the private pool, with the option to add heat for extra comfort. In the evening, take advantage of the propane grill for a laid-back poolside cookout, then enjoy dining under the open sky at the refined table set for six.brbrTHE ACCOMMODATIONS...brbr** First Floor Bedroom: Queen bed and an en-suite bathroom with a walk-in shower.brbr** Second Floor Master Bedroom: King bed, private balcony, and an en-suite bathroom with dual sinks and a walk-in shower. brbr** Second Floor Guest Bedroom: Two Twins OR One King bed, private balcony, and an en-suite bathroom with a shower and tub combination. brbrALL LAST KEY VACATION HOMES INCLUDE:brbr** Washer and Dryerbr** Central Heat & A/Cbr** Ceiling Fansbr** Flat Screen Cable TVs in Living Room & All Bedroomsbr** Fully-Equipped Kitchenbr** Basic stock of spicesbr** Starter supply of paper productsbr** Starter set of cleaning productsbr** Linens and Towels providedbr** Wireless high-speed Internet access and full cable is includedbr** Full-Time Concierge ServicebrbrIn addition, this fully stocked home also includes, but is not limited to, the amenities on this list:brbr** Fully Fenced & Landscaped Backyardbr** Private Saltwater Pool with Available Pool Heatbr** Propane BBQ grillbr** Off-Street ParkingbrbrOther notes:brbr** Interim housekeeping provided upon requestbr** This property will accommodate up to 6 adultsbr** Pets Consideredbr** 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.brbrNEED MORE SPACE...brbrLast Key Realty manages several neighboring townhomes in this intimate complex. Inquire for details!

3

Bed

4

Bath

6

Sleeps

$537.74

/ Nightly

Private Vacation Home

**SOUTHERNMOST BLISS @ OLD TOWN** Newly Renovated Home & Pool + LAST KEY SERVICE

Key West, Florida, United States

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival!brbrSOUTHERNMOST BLISS is a historic Key West eyebrow home that recently underwent a complete renovation, and the result is nothing short of pure bliss. This home was designed to combine the best of classic Key West with luxurious modern comfort. SOUTHERNMOST BLISS features 3 bedrooms in the main house and a 4th bedroom in the Guest House, each with its own private bathroom. The common areas of the living room, kitchen, and backyard all provide plenty of space for your group to spread out. brbrIn addition to the fresh renovation and fabulous design of this home, the location could not be better. SOUTHERNMOST BLISS is located at 518 Frances Street, a quiet street considered by many to be the 'Park Avenue' of Key West. You can stroll a few short blocks to the Key West Seaport or enjoy the nearly 20 restaurants within short walking distance of this amazing home.brbrTHE LIVING AREA & KITCHEN…brbrYou will undoubtedly fall in love with this home from the moment you enter. The porcelain tile floors and elegant light fixtures combined with the pine walls provide the perfect blend of modern and historic. The open living area offers plenty of comfortable seating options, including a plush sofa and love seat situated in front of a large flat-screen TV hanging on the wall. Next to the TV area is a versatile space that can be utilized as a separate sitting area or home office. brbrThe fresh and fully equipped kitchen is tucked away off the living room and features top-of-the-line stainless steel appliances. There is even a pass-thru window to the backyard for those cold drink refills and afternoon snacks. The indoor dining table offers seating for six. A convenient powder room is located just off the living area and features a laundry closet with the washer & dryer. brbrTHE BACKYARD & POOL…brbrA truly unique feature of this home is the back wall of the living area, with Euro doors that fold open to create an epic indoor/outdoor living space. The entire backyard is fenced and surrounded by mature tropical landscaping for maximum privacy. You’ll have plenty of room on the spacious pool deck for everyone to lay out in the chaise lounges or relax on the outdoor furniture. brbrTake a refreshing dip in the pool to cool off on those warm South Florida days or crank up the pool heat to your liking in the cooler months. Enjoy a poolside BBQ using the propane grill and outdoor dining tables. There’s a convenient passthrough window from the kitchen to the outdoor dining area.brbrThe front of the house features a delightful shaded porch with plush cushioned seating. It’s the perfect spot for a morning coffee, private phone call, or a chance to greet folks as they walk by.brbrTHE ACCOMMODATIONS…brbr** Master Bedroom: Located on the First Floor with a King bed, a flat-screen TV, a separate dressing room with double closets and a twin-sized sleeper sofa, a gorgeous en-suite bathroom with double sinks and a custom walk-in shower.brbr** Second Bedroom: Located on the Second Floor with a Queen bed, a flat-screen TV, double closets, and an en-suite bathroom with a walk-in shower.brbr** Third Bedroom: Located on the Second Floor with Two Twin beds OR One King bed, a flat-screen TV, double closets, and an en-suite bathroom with a shower and tub combo.brbr** Guest House: Located just off the pool area with a Queen Murphy bed, a flat-screen TV, a closet, and an en-suite bathroom with a private outdoor shower.brbrALL LAST KEY VACATION HOMES INCLUDE:brbr** Washer & Dryerbr** Central Heat and A/Cbr** Ceiling Fansbr** Flat Screen Cable TVs in Living Room & All Bedroomsbr** Fully-Equipped Kitchenbr** Basic stock of spicesbr** Starter supply of paper productsbr** Starter set of cleaning productsbr** Linens and Towels providedbr** Wireless high-speed Internet access and full cable is includedbr** Full Time Concierge ServicebrbrIn addition, this fully stocked home also includes, but is not limited to the amenities on this list:brbr** Fully Fenced & Landscaped Private Yardbr** Private Heated Poolbr** Propane BBQ Grillbr** Off-street Parking in Drivewaybr** Twin Sleeper SofabrbrOther notes:brbrbr** In person welcomebr** 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 9 adultsbr** Small Dogs Allowed - Max of 2 dogs allowed and an additional fee of $200 per pet will apply

Bed

Bath

Sleeps

$172.7

/ Nightly

Apartment

ESCAPE ON FLEMING - A charming 2 bedroom home

Key West, Florida, United States

28 DAY MINIMUM RENTAL ... This property is not allowed to accept pets.brbrBreak away from it all at Escape on Fleming. This comfortable and fresh two bedroom one bathroom apartment is located in Historic Old Town. Conveniently located near charming Old Town restaurants such as Azur and Cafe Sole, yet off the beaten path, it is the perfect location for a relaxing escape. With wood floors and ceiling fans throughout, this apartment has the perfect feel for a Key West vacation. brbrUpon entering the front door the beautiful island colors of the living room invite you in. The sectional sofa provides ample room to enjoy the flat screen TV. A bright and cheery reading nook sits directly off the living room. The kitchen features stainless steel appliances and a beautiful glass tile backsplash. Just across from the kitchen is a small dining table with seating for four. The bathroom includes a pedestal sink, mirrored bathroom cabinet with storage space and tub with shower. The downstairs bedroom has a double bed and is decorated in traditional charm with calming blues and neutral browns. brbrThe master bedroom space is accessed by a staircase near the front of the house. This room is spacious, open and offers plenty of closet space as well as a dresser with a flat screen TV. The queen bed is decorated in calming blues and greens and provides a nice contrast to the dark wood furniture throughout the room. If you need to get some work done, or inspiration strikes you, there is a desk offering you the space to do so. The master room also has private access to a balcony that overlooks Fleming Street. Here you can people watch with a cocktail at the end of the day or start it right with a Cuban coffee from the famous 5 Brothers just three blocks away!brbrIn the shared backyard space there is a small pool for a quick dip and a relaxing rock waterfall. br brSleeps: 4, Bedding: 1 double, 1 queen

Bed

Bath

Sleeps

Select Dates for Price

Condo

Galleon Resort and Marina, Paradise Found in Old Town, Private Beach and Fishing

Key West, Florida, United States

Fantastic Old Town destination right on water and boardwalk. Five Star Gold Crown resort with private fishing pier. Recently upgraded bathrooms,kitchens,electronics exercise room. Walk to Duval Street and Mallory Square. Don't need car, walk to everything. brbrEaster/Conch Republic Celebration, Memorial Day , other wks availablebrbrPrivate beach, fishing pier, fantastic Old Town location on water, newly renovated kitchens, bedrooms, electronics, appliances. washer dryer, ice maker in full size refrigerator, fully stocked kitchenbrbrSome units have two twins or queen in guest suite, inquire if importantbrbrUpgraded furniture, wifi Dec 2025

2

Bed

2

Bath

6

Sleeps

$286.79

/ Nightly

Private Vacation Home

Conch Keys | Private Pool & Outdoor Bar Paradise!

Key West, Florida, United States

Conch Key | Private Pool & Outdoor Bar Paradise!brbrWelcome to Sunset Palms Retreat — a beautifully renovated 2-bedroom, 2-bath vacation home designed for indoor comfort and outdoor living. This monthly rental offers the perfect blend of convenience, style, and resort-style amenities, featuring a private pool and an expansive entertainment-ready patio complete with a covered bar area.brbrThe Ambiance:brThoughtfully designed with a fresh, coastal-modern aesthetic, this home comfortably sleeps up to 4 guests. The fully equipped kitchen features stainless steel appliances, stone countertops, and all the essentials you need to cook or entertain with ease. The bright, open living space flows seamlessly to the outdoor area, where a sparkling private pool, shaded lounge areas, and a covered bar and entertainment zone await — perfect for relaxing days or evening cocktails under the stars.brbrGuest Access:brGuests enjoy easy, contactless check-in with a personalized access code and full access to the home and all outdoor amenities.brbrThe Neighborhood:brCentrally located with quick access to the best of Key West — including Duval Street's lively dining and nightlife, historic landmarks, pristine beaches such as Fort Zachary Taylor, and even Fausto's, a local grocery store. Everything you need is just a short ride away.brbrTransportation Tips:brThe home includes off-street and covered parking, a valuable perk in Key West. Explore Key West effortlessly by bicycle, scooter, golf cart, or on foot, as many attractions are easily accessible from the cottage. Feel free to ask for local recommendations!brbrOther Things to Note:br- Central A/C throughout the home.br- Washer and dryer included.br- Pet-friendly upon request.br- Mid-stay cleanings available upon request.br- Guests must be 25 years of age or older to reserve this property.br- A minimum stay of 30 days is required, in accordance with local regulations.brbrCheck-in time is 3:00PMbrCheck-out time is 11:00AMbrbrTo enhance guest safety and security, this property is equipped with exterior security cameras for safety and monitoring purposes. Cameras are located around the perimeter, including entrances, driveway, walkways, pool, and common outdoor areas. No cameras are placed in private or interior spaces.brbrAt Colocada Vacation Rentals, we're dedicated to providing a relaxing and memorable Key West experience. If you have any questions or need recommendations, don't hesitate to reach out! We're here to help make your stay as special as possible.

2

Bed

2

Bath

4

Sleeps

$313.32

/ Nightly

Condo

SUGAR PALM STUDIO ~ Adult Only Studio w/ Community Pool & Close to Town!

Key West, Florida, United States

ENTER YOUR GARDEN PARADISE...brRelease your cares and bask in the beauty of this adults only, tropical inn of Travelers Palm with unique suites and studios, offering king beds, private baths and gorgeous garden views. You are only a relaxing three block stroll from all of the excitement of Duval Street, yet tucked away in a private setting that envelops you in its serene beauty. The SUGAR PALM STUDIO greets you with clean and cozy furnishings and just the right amount of creature comfort essentials for two people. Enjoy your island getaway in style with a private deck that overlooks tranquil and lush gardens and a pool with a waterfall feature. A contactless check in/out process with a virtual innkeeper allows for a seamless experience!br***All guests must be 18 years of age or older as this is an adult only property AND the primary renter must be 25 years of age or older.brbrDETAILS AND AMENITIES: brYour island getaway begins as you step foot into this casual compound with a delightful private porch and conch-style cottage that will captivate your island soul. Carry your crafted cocktail to the deck area and pool which comes heated in the winter months, cooled by the protective canopies, exquisite swaying palms and gentle breezes. Stretch out in a deck chair for a lazy nap or delve into your guilty reading pleasure. Toss some burgers on the shared outside grill for an al fresco treat. brbrSLEEPING AND KITCHEN ARRANGEMENTS...brStep into this charming studio with island-inspired decor and updated sleeping accommodations. The bedroom offers a newly-remodeled king bed with plush bedding, ceiling fan and wall-mounted HD TV. The kitchenette includes a quartz countertop and wet bar sink, microwave, refrigerator, and keurig station. Wash the day off in your private en suite bathroom with enclosed glass and marble tiled shower, quartz sink counter and large bathroom mirror. Slip outside to your private deck to view our botanical gardens that overlook the pool and stone waterfall.brbrPARKING...brParking is offered on a first come first serve basis, and there is plenty of free street parking available if a space is not available upon your arrival.brbrBEACHES...brHiggs Beach is 0.6 mi.brSmathers Beach is 1.9 mi.brFort Zachary Taylor Beach is 1.6 mi. brSouth Beach is 0.5 mi.brSimonton Beach is 1.2 mi.brbrCancellations requested at least 30 days prior to arrival receive a full refund.brCancellations requested at least 14 days prior to arrival receive a 50% refund.brbrYOUR HEAVENLY OASIS BECKONS YOU...

1

Bed

1

Bath

2

Sleeps

$396.01

/ Nightly

Condo

SUGAR PALM SUITE ~ Adult Only, Cozy 1 BR, 1 Ba w/ Kitchen and Community Pool!

Key West, Florida, United States

SULTRY GARDEN SANCTUARY...brSteal away from reality and find your way to the quintessential, tropical & adults only Travelers Palm Inn with secluded suites and studios that offer king beds, private baths and exquisite garden views. We are only three blocks from all of the culinary delights and diversions of Duval Street, yet tucked away in a private setting that offers peace and serenity. The SUGAR PALM SUITE is a vacation charmer with a private gated entrance (also has common area entrance), inviting you to make yourself at home in this contemporary abode with nine-foot ceilings, a dining room, living room, and a fully-equipped kitchen. You'll be living the island dream with a private deck that overlooks exquisite gardens and a pool with a waterfall feature. A contactless check in/out process with a virtual innkeeper allows for a seamless experience!brbrDETAILS AND AMENITIES: brYour serenity begins as you step foot into this casual compound with a delightful private porch and conch-style cottage that will captivate your island soul. Carry your crafted cocktail to the deck area and pool which comes heated in the winter months, cooled by the protective canopies, exquisite swaying palms and gentle breezes. Stretch out in a deck chair with your favorite mystery novel or toss some kabobs on the shared outside grill for an al fresco treat.br***All guests must be 18 years of age or older as this is an adult only property AND the primary renter must be 25 years of age or older.brbrDINING AND SLEEPING ARRANGEMENTS...brDelight in your meal creations as this modern kitchen comes with a dishwasher, stove and a full-sized refrigerator. It also includes all the necessary utensils, dishes and cookware that you will need to feed your loved ones. The bedroom features a newly-remodeled king size bed with luxurious bedding, ceiling fan and wall-mounted HD TV. The private updated bathroom has a glass and marble tile enclosed shower with 8 glass wall and door. Make room for others in the comfy living room that offers the convenience of a pull-out queen sofa bed, table seating for 4 and mounted HD TV. This all-encompassing suite has everything you need!brbrPARKING...brParking is offered on a first come first serve basis, and there is plenty of free street parking available if a space is not available upon your arrival.brbrBEACHES...brHiggs Beach is 0.6 mi.brSmathers Beach is 1.9 mi.brFort Zachary Taylor Beach is 1.6 mi. brSouth Beach is 0.5 mi.brSimonton Beach is 1.2 mi.brbrCancellations requested at least 30 days prior to arrival receive a full refund.brCancellations requested at least 14 days prior to arrival receive a 50% refund.brbrYOUR GARDEN RETREAT BECKONS YOU...

1

Bed

1

Bath

4

Sleeps

$313.32

/ Nightly

Condo

COCONUT PALM STUDIO ~ Adult Only Studio, Community Pool & Close to Town!

Key West, Florida, United States

A GLORIOUS GARDEN AWAITS YOU...brA mere three blocks from all of the food, fun and shenanigans of Duval Street, yet tucked away in a serene and private setting that will soothe your traveler's soul, the adult only COCONUT PALM STUDIO within the Travelers Palm Inn welcomes you to unwind with everything two people need to be comfortable in paradise. This newly-remodeled studio beckons you inside with its nine-foot ceilings, lovely contemporary decor and an abundance of Florida sunshine to brighten your day. A contactless check in/out process with a virtual innkeeper allows for a seamless experience!br***All guests must be 18 years of age or older as this is an adult only property AND the primary renter must be 25 years of age or older.brbrDETAILS AND AMENITIES: brYour happy getaway begins as you step foot into this casual compound with a delightful private porch and conch-style studio that will captivate your island soul. Carry your crafted cocktail to the deck area and pool which comes heated in the winter months, cooled by the protective canopies, exquisite swaying palms and gentle breezes. Stretch out in a deck chair for a decadent nap or reading escape. then satisfy your culinary cravings at the shared outside grill for an al fresco treat.brbrSLEEPING AND LIVING ARRANGEMENTS...brPamper yourself in your private bathroom with glass and marble tile, quartz countertop, large mirror, and roomy glass shower. The bedroom features a newly-remodeled king bed with luxurious bedding, ceiling fan and wall-mounted HD TV. Whip up your refreshing beverage and light meal in the kitchenette, which includes a quartz countertop and wet bar sink, microwave, mini-fridge, and keurig station. Slip outside to your private deck with views our botanical gardens that overlook the pool and stone waterfall.brbrPARKING...brParking is offered on a first come first serve basis, and there is plenty of free street parking available if a space is not available upon your arrival.brbrBEACHES...brHiggs Beach is 0.6 mi.brSmathers Beach is 1.9 mi.brFort Zachary Taylor Beach is 1.6 mi. brSouth Beach is 0.5 mi.brSimonton Beach is 1.2 mi.brbrCancellations requested at least 30 days prior to arrival receive a full refund.brCancellations requested at least 14 days prior to arrival receive a 50% refund.brbrIMMERSE YOURSELF IN PARADISE ...

1

Bed

1

Bath

2

Sleeps

$395.05

/ Nightly

Condo

COCONUT PALM SUITE ~ Adult Only, 1 BR, 1 Ba w/ Kitchen & Community Pool!

Key West, Florida, United States

BOTANICAL MAGIC AWAITS YOU...brOnly three blocks from all of the fine dining and entertainment of Duval Street, yet tucked away in a private setting that soothes your senses and pushes your worries aside, The adult only COCONUT PALM SUITE within the Travelers Palm Inn will delight your traveler's soul, complete with everything a party of 4 needs to unwind and enjoy your island getaway. Immerse yourself in our contemporary tropical furnishings and admire the gorgeous views from a rocking chair on one of the two garden-side porches. A contactless check in/out process with a virtual innkeeper allows for a seamless experience!br***All guests must be 18 years of age or older as this is an adult only property AND the primary renter must be 25 years of age or older.brbrDETAILS AND AMENITIES: brYour serenity begins as you step foot into this casual compound with a delightful private porch and conch-style suite that will captivate your island soul. Carry your crafted cocktail to the deck area and pool which comes heated in the winter months, cooled by the protective canopies, exquisite swaying palms and gentle breezes. Stretch out in a deck chair with your favorite mystery novel or toss some kabobs on the shared outside grill for an al fresco treat.brbrSLEEPING AND LIVING ARRANGEMENTS...brEnter the light and airy suite where you are greeted by beautiful tropical decor, separate living and dining areas, flat screen tv and a fully-equipped modern kitchen for all your culinary desires. The cozy sofa has a queen size pull out bed to accommodate extra loved ones during your stay. The bedroom boasts a newly-remodeled king bed with luxurious bedding, ceiling fan and wall-mounted HD TV. Wash the day off in your private bathroom with enclosed glass and marble tiled shower and quartz sink counter. Slip outside to your private deck to view our botanical gardens that overlook the pool and stone waterfall.brbrPARKING...brParking is offered on a first come first serve basis. If there is not a space available upon your arrival, there is plenty of non-residential (free) street parking.brbrBEACHES...brHiggs Beach is 0.6 mi.brSmathers Beach is 1.9 mi.brFort Zachary Taylor Beach is 1.6 mi. brSouth Beach is 0.5 mi.brSimonton Beach is 1.2 mi.brbrCancellations requested at least 30 days prior to arrival receive a full refund.brCancellations requested at least 14 days prior to arrival receive a 50% refund.brbrYOUR MAGICAL GARDEN AWAITS YOU...

1

Bed

1

Bath

4

Sleeps

$395.05

/ Nightly

Condo

ROYAL PALM SUITE ~ Adult Only, 1 BR, 1 Ba w/ Kitchen and Community Pool!

Key West, Florida, United States

ESCAPE TO A BOTANICAL HIDEAWAY...brImmerse yourself at the charming adults only Travelers Palm Inn with unique suites and studios that offer king beds, private baths and gorgeous garden views. We are only three blocks from all of the fine dining and entertainment of Duval Street, yet tucked away in a private setting that soothes your senses and pushes your worries aside. The ROYAL PALM SUITE is our premier suite, which beckons you inside with elevated ceilings, plush tropical furnishings and charming outdoor porches. Enjoy your island getaway in style with a private deck that overlooks tranquil and lush gardens and a pool with a waterfall feature. This unit offers separate living and dining areas and can sleep 4 people. A contactless check in/out process with a virtual innkeeper allows for a seamless experience!br***All guests must be 18 years of age or older as this is an adult only property AND the primary renter must be 25 years of age or older.brbrDETAILS AND AMENITIES: brYour serenity begins as you step foot into this casual compound with a delightful private porch and conch-style cottage that will captivate your island soul. Carry your crafted cocktail to the deck area and pool which comes heated in the winter months, cooled by the protective canopies, exquisite swaying palms and gentle breezes. Stretch out in a deck chair with your favorite mystery novel or toss some kabobs on the shared outside grill for an al fresco treat.brbrLIVING AND SLEEPING ARRANGEMENTS...brEnter the airy sun-kissed suite where you are greeted by island-inspired furnishings and tropical decor, separate living and dining areas, flat screen tv and a fully-equipped modern kitchen for all your culinary desires. The cozy sofa has a queen size pull out bed to accommodate a party of 4. The bedroom boasts a newly-remodeled king bed with luxurious bedding, ceiling fan and wall-mounted HDTV. Wash the day off in your private bathroom with enclosed glass and marble tiled shower and quartz sink counter. Slip outside to your private deck to view our botanical gardens that overlooks the pool and stone waterfall.brbrPARKING...brParking is offered on a first come first serve basis, and there is plenty of free street parking available if a space is not available upon your arrival.brbrBEACHES...brHiggs Beach is 0.6 mi.brSmathers Beach is 1.9 mi.brFort Zachary Taylor Beach is 1.6 mi. brSouth Beach is 0.5 mi.brSimonton Beach is 1.2 mi.brbrCancellations requested at least 30 days prior to arrival receive a full refund.brCancellations requested at least 14 days prior to arrival receive a 50% refund.brbrYOUR MAGICAL GARDEN AWAITS YOU...

Bed

Bath

Sleeps

$731.25

/ Nightly

Condo

Key West On THE BEACH New Years! Dec 27th - Jan 3rd 2026

Key West, Florida, United States

PLEASE READ CAREFULLY BEFORE YOU EMAIL OWNER brbrThis rental is for a 7 NIGHT HOLIDAY 1 week RENTAL ONLY!brbrThis is for 7 nights Saturday to Saturday rental ONLY !! No alterations to the listed dates are available. MINIMUM RENTAL AGE is 25 years old. Maximum occupancy is for 6 people.brbrCoconut Beach Resort; a private quaint tropical paradise right up on the Atlantic Ocean. Watch spectacular views of the sunset from your balcony. Unit has King, Queen, Queen sleeper sofa, kitchen & living room. Heated pool w/ hot tub. Walk to Duvall Street.brbrThis is a rental is for the exact dates posted. Please do not email me with requests for any other dates than listed. This is for 7 nights Saturday to Saturday Christmas week rental OR Saturday to Saturday New Years week rental. Check in 4:00PM and check out 10AM. The dates and price are not flexible as this is a timeshare that I occasionally rent.brbrNO SMOKING IS PERMITTED IN UNITS

Bed

Bath

Sleeps

Select Dates for Price

Private Vacation Home

NEW LISTING Old Town Private Pool in Garden Of Eden tropical spa-like Oasis

Key West, Florida, United States

( NEW LISTING SEE VRBO LISTING 1223004 for reviews on my other property ) Newly renovated, invitingly spacious, serenely quintessential two-bedroom , want-for-nothing original “conch home” conveniently located on one of Old Town's famously peaceful side streets . A secluded location with encapsulating foliage, immaculate amenities, and a clean aesthetic combine to create a Zen-like private getaway minutes from Duval Street. Float or lounge poolside in the newly-installed saltwater pool. The modern kitchen with touchpad Wolfe convection oven and Thermador induction cooktop, John Pawson Demeyere cookware, Georg Jensen flatware and Rosenthal china for a serious cook or to make a simple cocktail . Laundry closet with Electrolux 2020 washer/dryer; living room equipped with flat-screen 45-inch TV loaded with major streaming services nestled behind a recessed remote-controlled drop down piece of art -- all connected via high-speed wifi -- allow for modern amenities amidst unparalleled spa -like paradise. Outdoor relaxed lounge seating surrounding another television, a state-of-the-art propane-fueled Weber grill and large outdoor dining space with seating for 10 next to the pool provide world class spa-like accommodations. The overall beauty of this home provides an island oasis in close proximity to all that Key West has to offer, allowing guests a world of entertainment only a few minutes walk away.

2

Bed

4

Sleeps

Exceptional(48)

$303.75

/ Nightly

Condo

Tranquil 2-BR Condo in Truman Annex, Steps to Pool & 5-Min Walk to Duval St.

Key West, Florida, United States

Welcome to our lovely condo which is located in the famed Truman Annex Complex right in the heart of fabulous Key West. Our condo has 2 bedrooms and 1 bath.. Enjoy everything that Key West has to offer and more. Lounge on the newly refinished deck. Enjoy the beautiful landscaping and the picturesque scenery. Take a short walk to the heated pool, get some sun, read a book, take a dip. Paradise awaits you. If you want all the activities and excitement of downtown/old town Key West - it is only a 5 minute walk from the condo. Truly the best of both worlds of privacy/ relaxation and the restaurants, shops, pubs and tourist activities of Key West. brbrThe condo is conveniently located on the first floor. Reserved parking is provided and located directly at your front door.brbrThere are so many activities and attractions to see, breathtaking Mallory Square sunsets, Fort Zachary Beach and the famous Duval Street - just to name a few. So take a leisurely stroll or hop on your bike and find out for yourself why Key West is the best.brbrNo matter what your pleasure you're sure to find it here.brbrThanks for visiting our site, we hope to hear from you soon.brbrbrKeywords: Key, West, Condo

Bed

Bath

Sleeps

$196.73

/ Nightly

Private Vacation Home

Paradise found at the Key West Golf Club!

Key West, Florida, United States

We selected the best of everything to create paradise in Key West. Enjoy tropical breezes as you sip your morning coffee or celebrate another amazing sunset with an evening cocktail on one of four open air decks surrounding this beautifully appointed townhouse in the prestigious Key West Golf Club. Located directly off a gorgeous, heated pool complete with a waterfall, this is your home away from home to spend your days relaxing, playing a round of golf, fishing, snorkeling and enjoying all that Key West has to offer. Please note this is a monthly rental as stays with us require a minimum of 28 days. brbrKey West offers restaurant choices meeting all your needs from casual to fine dining, but we know sometimes you just want a home cooked meal. We offer a fully appointed kitchen with all the amenities as well as a Weber grill to cook up a fresh catch. Fully renovated in 2022, this modern and bright kitchen will meet all your needs. Seat six comfortably for in home dining if you would like to entertain guests. br brThere are plenty of places to relax whether inside in the beautifully appointed living room or outside with comfortable outdoor seating on the open-air porch located just off the living room. High speed internet and a 65-inch smart TV allows you to enjoy a movie, surf the internet and play your favorite music on a Bose sound system in the main living area. The living room also offers a comfortable queen-sized pull-out sofa to accommodate additional guests for short stays. br brWhen it's time to rest you can enjoy a wonderful night's sleep on 1,000 thread count sheets. The main bedroom on the second floor offers a king-sized bed with Tommy Bahama bedding, plenty of closet space and a 55-inch smart TV for your entertainment. The large open-air porch just off the main bedroom features a two-person hammock and a day bed perfect for naps. brbrThe guest room also located on the second floor features a full-sized sleigh bed and houses a full-sized washer and dryer (new in 2024) for your convenience. Enjoy a writer's desk in the guest room to send postcards home or work remotely with high-speed internet access. The guest room offers a 40-inch smart TV and additional closet space. The open-air porch off the guest room is the perfect spot to enjoy the morning sun or star gaze in the evening in reclining chairs. brbrA newly remodeled and modern full-sized bathroom is located on the second floor and an updated half bath can be found on the main floor. Rinse off from the beach or pool with an outdoor shower that provides plenty of privacy. All linens, towels and pool towels are provided for your convenience. Just pack a bag and come to paradise for a month or more. You will be so glad you did. brbrPET POLICY: As pet lovers ourselves, we understand that bringing your companion along to paradise is a priority. Dogs are welcome up to 35 lbs. for a one-time non-refundable $250 fee. Be sure to select this optional fee when booking if you are bringing a pet. Please contact the owner, Barbara, if you have any questions about the eligibility of your pet. brbrThe Key West Golf Club is a gated community offering the “Old Key West” charm, two heated pools, a fitness center, free parking for one vehicle, 24-hour security, and access to the only 18-hole golf course in the Florida Keys.brbrFor safety and liability purposes, the property is equipped with two exterior cameras, one above the front door and one on the roofline in the rear. The cameras in no way infringe upon the guests’ expectations of privacy in these public areas of the property.

Bed

Bath

Sleeps

$484.91

/ Nightly

Private Vacation Home

Spotless Fully Renovated Family Home. Free parking WiFi Pool.

Key West, Florida, United States

Welcome to our new fully renovated townhouse hosted by HomeAway Premier Partner Roy Svenningsen. This home is located in a lush, family oriented gated community across from the Key West Golf course.brThe home features all new stainless steel appliances, new furniture, all new flooring, marble counters, and top quality mattresses.brIn the center of the community is a beautiful pool and a clubhouse with a fitness area.brIncluded is parking for two cars, WiFi and high speed internet.brClose by there is Croissant de France a french bakery, a CVS drugstore and two family restaurants (Roostica and Chico’s).

3

Bed

3

Bath

8

Sleeps

Vacation Rentals By Owner In Key West, FL

$571.46

$312.2

$390.68

$268.4

$1190.43

$902.1

$537.74

$172.7

$286.79

$313.32

$396.01

$313.32

$395.05

$395.05

$731.25

$303.75

$196.73

$484.91

Rent a place that suits your needs

Most popular vacation rentals in Key West

$2168.85

$2433.36

$2377.08

$2193.75

$2179.76

$2078.34

$2059.55

$2072.19

$2489.04

$2144.26

Most Popular Cities in Florida