Vacation Rentals By Owner In Key West, FL

QUAINT AND PRIVATE HIDEAWAY...brThis Key West classic checks all the boxes for your blissful getaway to our tiny island paradise. Immerse yourself in our rich history from the doorstep of this light infused contemporary cottage that merges modern comfort with preservation of its timeless historical charm. After a day enjoying our calming azure waters, you are but a 3 block stroll to all the fanfare of Duval Street, where an array of fine dining, theatre, live music, museums and galleries await your arrival.br***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGEbrbrDETAILS AND AMENITIES…brCome inside and cast your cares aside as you enter this elegant and cozy retreat. Tropical sunshine floods the open living, dining and kitchen areas, warming you up for your next southernmost adventure. Fashion your favorite dishes in the sleek and functional kitchen that is well-supplied for your fresh cuisine. The soothing and plush living area invites calm relaxation and respite after a fun-filled day in the sun. The home boasts Dade County Pine, cathedral ceilings, a washer/dryer and a wall of French doors that open to your outdoor oasis for the perfect Key West ambiance. brbrSLEEPING ARRANGEMENTS…brYou will relish your night time slumber in one of the 2 lovely bedrooms. There is a 4 poster queen bedroom with an en suite bathroom with a shower and storage closet. The king primary bedroom has a double entry bathroom with a shower/tub combination and storage closet. Both bedrooms offer a TV for your enjoyment. A Queen Murphy bed resides in the living room for additional sleeping arrangements. brbrOUTDOOR LIVING…brUnwind with a mug of coffee on the charming front porch or sip chilled cocktails on the rear patio deck with comfy furnishings. A refreshing dip pool is perfect for your sultry summer afternoon (comes heated in the cooler months and you may also request it to be chilled during the warmer months for an additional fee). brbrPARKING...brThis home offers 1 off street parking space for your car.brbrPETS...brThis home welcomes up to 2 dogs with a 50 lb. weight limit and a pet fee is required.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. 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).brbrARE YOU READY FOR PERFECTION...

CASA DEL SUR ~ Renovated 2 BR/2Ba Home with Heated Dip Pool!

Key West, Florida, United States

Bed

Bath

Sleeps

$154.88

City of Key West zoning requires a minimum rental period of 30 days, and no exceptions can be made. Please review additional policies below. brbr brbrEscape to the serene oasis of Lotus Blossom, your ultimate vacation rental in the heart of Key West! brbr brbrNestled in a tropical paradise, this private retreat offers a perfect balance between peaceful tranquility and proximity to the vibrant pulse of Duval Street. With three spacious bedrooms, Lotus Blossom can comfortably accommodate your entire group. The vibrant island decor and inviting interiors create a warm and welcoming atmosphere, making you feel right at home. The highlight of this property is the tropically landscaped courtyard. As you step outside, you'll be greeted by lush greenery, swaying palms, and the soothing sound of a nearby fountain. Picture yourself sipping your morning coffee or afternoon cocktail in the shade of the courtyard, surrounded by colorful flora and abundant seating options. But the true gem of the Lotus Blossom courtyard is the private hot tub. Whether you're unwinding after a day of exploring Key West's attractions or simply indulging in a bit of relaxation, the hot tub is your personal slice of paradise. With a prime location, you're just a stone's throw away from all that Key West has to offer. Explore the historic sites, lively bars, and world-class restaurants of Old Town Key West, and then retreat to the peace and privacy of Lotus Blossom. Whether you're seeking adventure, romance, or simply a tranquil escape, Lotus Blossom is the perfect vacation rental for your Key West getaway. Book your stay today and experience the best of both worlds: a private tropical haven and easy access to the action of Duval Street. brbr brbrSLEEPS MAXIMUM OF 6 GUESTS: brbr brbrBedroom 1 (1st Floor): Queen Bed, Flat Screen TV brbr brbrBedroom 2 (2nd Floor): Queen Bed, Flat Screen TV brbr brbrBedroom 3 (2nd Floor): King Bed, Flat Screen TV brbr brbrLiving Room: Sofa, Loveseat, Flat Screen TV brbr brbrKitchen: Nicely equipped (all things necessary to prepare and serve a meal, there is no dishwasher) brbr brbrAMENITIES: brbr brbr- Private Hot Tub brbr brbr- Outdoor Seating brbr brbr- Propane BBQ Grill brbr brbr- High Speed WiFi (1.2 TB of data per month, guest will pay for any overages) brbr brbr- Linen's and towels provided brbr brbr- Street parking, no off-street parking available brbr brbr- 2.1 miles to Smathers Beach brbr brbr- 2.5 miles to Duval Street brbr brbr- 2.5 miles to Southernmost Point brbr brbr- 2.8 miles to Historic Seaport brbr brbr- 3.3 miles to Mallory Square Sunset Pier brbr brbr- 3.5 miles to Fort Zachary Taylor State Park Beach brbr brbrIMPORTANT POLICIES FOR YOUR STAY: brbr brbrAge & Occupancy: The booking tenant must be 25 years or older and must occupy the property for the entire duration of the stay. This property is exclusively available as a vacation rental and not for worker housing. brbr brbrPeak Season Monthly Bookings: All bookings from December through March must be for the entire month, starting at the beginning and ending at the end of the month. Consecutive months may be booked if they follow this requirement. Bookings that do not adhere to this policy are subject to cancellation. If you are interested in alternative dates, please contact us for approval before booking. brbr brbrNo Pets: Pets are strictly prohibited. To help maintain a pet-free environment for all, we require every guest to confirm they are not bringing a pet/animal. It's free, and does not require creating an account. After booking, you'll receive a link to complete the process. brbr brbrSmoking Policy: Smoking is strictly prohibited to maintain a smoke-free environment. brbr brbrMid-Stay Cleaning: For stays of 28 nights or more, we reserve the right to require a mid-stay cleaning to maintain the quality of the property. For longer stays, a mid-stay cleaning will be required every 28 nights thereafter. The cost will be collected separately, and the number of cleanings depends on the length of your stay. brbr brbrLocal Wildlife & Pest Control: The Florida Keys are home to various insects (mosquitoes, no-see-ums, termites), reptiles, chickens, Key deer, and other wildlife. While routine pest control is in place, complete elimination is not possible. Guests should take precautions, such as using insect repellent and keeping doors closed, to minimize exposure. brbr brbrConstruction & Renovation Notice: Due to ongoing growth in the Florida Keys, renovations, construction, and road repairs may occur without prior notice. While we strive to provide a peaceful stay, iTrip Key West is not liable for any inconveniences caused by nearby construction. brbr brbrPhoto Disclaimer: All images are for illustrative purposes only. Individual features such as bed sizes, bedding, décor, appliances, colors, and amenities may vary, as these are privately owned homes and updates occur regularly. Lighting conditions and screen settings may also affect how colors appear. Please refer to the written description and reach out with any specific questions or concerns. All furnishings and décor are subject to change at any time. brbr brbrSecurity Cameras: For the safety and security of our guests and property, exterior security cameras monitor the front entryway and courtyard. These cameras are for security purposes only and do not monitor any private interior or outdoor living spaces.

Lotus Blossom: Discover Paradise, 3BR Home W/ Tropical Courtyard, Hot Tub & Minutes from Old Town!

Key West, Florida, United States

Bed

Bath

Sleeps

$381.43

Discover the heart of Old Town Key West! This hotel is located steps from Duval Street and Hemingway's home. Stroll to Sunset Pier, explore local beaches, and unravel history at Key West Shipwreck Treasure Museum.brbrThis listing is for a room within a hotel.brbr✦ Your room is 180 sq. ft, equipped with complimentary toiletries, TV.brbr✦ Cleaning services included in the nightly price.brbrThere are a few additional details to know before you book:brbr✦ The minimum age required for check-in is 21 years old.brbr✦ Please ensure you have a valid ID for check-in, as it is mandatory for entry.brbr———————————————brbrGuest Access:brDuring your stay, you will have access to the property and amenities according to the following schedule:brbr✦ Check-in is available from 04:00 pm.brbr✦ Pool is available.brbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A credit/debit card is required at check-in for a $50 per night refundable deposit, returned after check-out if no damages occur.brbr✦ A mandatory resort fee of $45.00 per night will be collected upon check-in, not included in the daily rate.brbr✦ Pets are welcome. Pets allowed: $50/night, no restrictionsbrbr✦ We use multi-unit listings, so rooms are similar but may have small differences.brbr✦ The required refundable security deposit is charged per night on a valid credit card.

Tropical Island Retreat Near Florida Beaches with Pool & Views, Free Breakfast

Key West, Florida, United States

Bed

Bath

Sleeps

$384.73

This listing is for a room within a hotel.brbr✦ Your room is 420 sq. ft, equipped with complimentary toiletries, standard quality TV, available with Standard 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 18 years old.brbr✦ Please ensure you have a valid ID for check-in, as it is mandatory for entry.brbr———————————————brbrGuest Access:brDuring your stay, you will have access to the property and amenities according to the following schedule:brbr✦ Check-in is available from 04:00 pm.brbr✦ Outdoor shared pool is available, opened from 7:00AM to 10:00PM.brbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A credit/debit card is required at check-in for a $100 per night refundable deposit, returned after check-out if no damages occur.brbr✦ A mandatory resort fee of $45.00 per night will be collected upon check-in, not included in the daily rate.brbr✦ Pets are welcome.brbr✦ We use multi-unit listings, so rooms are similar but may have small differences.brbr✦ Pets are welcome with an additional charge of USD 50.00 per night, with no restrictions on size or breed.

Tropical Island Retreat Near Florida Beaches with Pool & Views!

Key West, Florida, United States

Bed

Bath

4

Sleeps

$485.96

This listing is for a room within a hotel.brbr✦ Your room is 360 sq. ft, equipped with complimentary toiletries, TV.brbr✦ Cleaning services included in the nightly price.brbrThere are a few additional details to know before you book:brbr✦ The minimum age required for check-in is 21 years old.brbr✦ Please ensure you have a valid ID for check-in, as it is mandatory for entry.brbr———————————————brbrGuest Access:brDuring your stay, you will have access to the property and amenities according to the following schedule:brbr✦ Check-in is available from 04:00 pm.brbr✦ Pool is available.brbr✦ Street parking – 1 space(s).brbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A credit/debit card is required at check-in for a $50 per night refundable deposit, returned after check-out if no damages occur.brbr✦ A mandatory resort fee of $45.00 per night will be collected upon check-in, not included in the daily rate.brbr✦ Pets are welcome. extra charge of $50 per nightbrbr✦ We use multi-unit listings, so rooms are similar but may have small differences.

Sunny Florida Escape with Pool, Beach Access & Stunning Views

Key West, Florida, United States

Bed

Bath

4

Sleeps

$562.52

Enjoy vibrant Key West: steps to Duval Street's nightlife, historic sites, and serene beaches. Perfect for culture and sea lovers.brbrThis listing is for a room within a hotel.brbr✦ Your room is 250 sq. ft, equipped with complimentary toiletries, TV.brbr✦ Cleaning services included in the nightly price.brbrThere are a few additional details to know before you book:brbr✦ The minimum age required for check-in is 21 years old.brbr✦ Please ensure you have a valid ID for check-in, as it is mandatory for entry.brbr———————————————brbrGuest Access:brDuring your stay, you will have access to the property and amenities according to the following schedule:brbr✦ Check-in is available from 04:00 pm.brbr✦ Outdoor shared pool available all year, opened from 7:00AM to 10:00PM.brbr✦ Street parking.brbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A credit/debit card is required at check-in for a $50 per night refundable deposit, returned after check-out if no damages occur.brbr✦ A mandatory resort fee of $45.00 per night will be collected upon check-in, not included in the daily rate.brbr✦ Pets are welcome. $50 per pet, per night plus taxbrbr✦ We use multi-unit listings, so rooms are similar but may have small differences.brbr✦ The required refundable security deposit is charged per unit, per night, on a valid credit card.brbr✦This is an adult-only property. Only guests aged 21+ are permitted.

Charming Hideaway with Pool Access – Walk to Duval St! Free Breakfast!

Key West, Florida, United States

Bed

Bath

Sleeps

$385.88

This listing is for a room within a hotel.brbr✦ Your room is 240 sq. ft, equipped with complimentary toiletries, high definition 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.brbr✦ Outdoor shared pool available all year, opened from 7:00AM to 10:00PM.brAdditional features:br • Heated poolbrbr✦ Paid parking lot, available for $30 per day.brbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A credit/debit card is required at check-in for a $50 per night refundable deposit, returned after check-out if no damages occur.brbr✦ A mandatory resort fee of $45.00 per night will be collected upon check-in, not included in the daily rate.brbr✦ Pets are welcome. $50 per pet per night. No breed or size limitsbrbr✦ We use multi-unit listings, so rooms are similar but may have small differences.brbr✦ The required refundable security deposit is charged per unit, per night, on a valid credit card.

Cozy Key West Escape – Near Shops, Bars & Famous Duval Street! Free Breakfast

Key West, Florida, United States

Bed

Bath

Sleeps

$535.5

This listing is for a room within a hotel.brbr✦ Your room is 300 sq. ft, equipped with complimentary toiletries, TV.brbr✦ Cleaning services included in the nightly price.brbrThere are a few additional details to know before you book:brbr✦ The minimum age required for check-in is 21 years old.brbr✦ Please ensure you have a valid ID for check-in, as it is mandatory for entry.brbr———————————————brbrGuest Access:brDuring your stay, you will have access to the property and amenities according to the following schedule:brbr✦ Check-in is available from 04:00 pm.brbr✦ Pool is available.brbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A credit/debit card is required at check-in for a $50 per night refundable deposit, returned after check-out if no damages occur.brbr✦ A mandatory resort fee of $45.00 per night will be collected upon check-in, not included in the daily rate.brbr✦ Pets are welcome. Pets allowed: $50/night, no restrictionsbrbr✦ We use multi-unit listings, so rooms are similar but may have small differences.brbr✦ The required refundable security deposit is charged per night on a valid credit card.

Romantic Key West Getaway with Heated Pool, Patio & Breakfast | Near Sunset Pier

Key West, Florida, United States

Bed

Bath

Sleeps

$837.16

'SOUTHARD LOVE' is located on Southard Street on the corner of LOVE LanebrbrThis home is a perfect example of WHY people come to Key West to stay for a month or more! Live the island lifestyle outside enjoying the front porch, the second floor balcony, and the side lounge area with cocktail pool.brbrThe weather in Key West is absolutely amazing and this home maximizes the indoor outdoor living experience Key West has to offer.brbrDid we mention the home is walking distance to everything Key West has to offer brbrThe perfect blend of Historic architecture and the casual beachy cottage feel will make you, your family, and your friends feel comfortable and pampered.brbrThe extra large square footage assures everyone their own private space while the living room and open concept living area allow everyone to come together.brbrSimply tell your friends and family to meet you at the corner of Southard Street and Love Lane, one of Key West’s premier Old Town addresses. This spectacular, three-story, historic and award-winning home has been fully renovated to meet the most discerning tastes. Dappled sunlight plays across the Dade County pine in the cool, comfortable, inviting interior spaces and brightens the touches of warm tropical colors in the high-end furnishings and finishes.brbrSouthard Love is a home made for family gatherings or a lazy season away with friends. Its first floor primary suite opens through French doors to the large front porch that suggests a cup of coffee and a good book while people watching along Southard. The first floor includes a gourmet kitchen, the primary bedroom and bath, a guest room and bath and expansive living areas for playing games, gathering with friends or simply curling up and enjoying a peaceful evening. brbrWalk through the French doors from the living area and the kitchen to a private deck and classic Key West cocktail pool, surrounded with lush landscaping and tall, artistic privacy fences. The deck and its pool are made for entertaining and star-gazing.brbrUpstairs on the second floor is the private alternate primary suite with soaring ceilings, beautiful windows and elegant primary bath with a walk-in shower. But, it’s the master suite hammock porch that will capture your imagination. Fitted with deep, comfortable hammocks, leave the set of 3 French doors opens to the perfect island breeze. Enjoy the privacy of the porch, in the perfect blend of indoor and outdoor living. This primary suite with its beautiful, unique and private indoor-outdoor spaces will convince you to return year after year.brbrThere is more to explore on the third floor. The large, light-filled room under the eaves could become a child’s hideaway or an adult’s getaway space. You have the option of two twin beds or join them together as a king bed, providing flexibility for your family or your guests.brbrSouthard Love with its four bedrooms, three bathrooms and multiple indoor-outdoor areas is a gracious family home that welcomes its guests from the moment they turn the key in the vibrant sunny, yellow front door. It is a home to be enjoyed, to be shared and to be loved. brbrSouthard Love is located perfectly for a long stay in Key West. Simply park your car and unlock your bike or scooter. It’s two blocks (.2 miles) to all that Duval Street has to offer and 4 blocks (.4 miles) the Historic Seaport. There’s the added advantage of the designated bike lane, which runs the length of Southard, making it a straight shot across Southard to the beaches at Fort Zachary Taylor State Park. Fausto’s grocery is close enough to walk and there are wonderful neighborhood restaurants just blocks away.brbrOur prices include all fees. No hidden fees.

Southard Love: 2.5 Blocks to Duval, beach & historic seaport. 4 Beds, 3 Baths

Key West, Florida, United States

4

Bed

Bath

7

Sleeps

$360.72

Summary:brbrOcean View Penthouse in Downtown Key WestbrbrbrbrThe Space:brbrOceanfront Penthouse at Historic Mills Place – Truman AnnexbrbrWelcome to Oceanfront Truman Annex Penthouse, an exceptional vacation retreat perched in the heart of Mills Place, the most desirable section of Key West’s prestigious Truman Annex. This rare and spacious penthouse condo offers one of the most spectacular views in all of Key West, overlooking the turquoise waters of the Gulf and the bustling harbor where cruise ships gracefully arrive and depart right outside your window.brbrbrbr Unmatched Ocean Views & Spectacular SunsetsbrbrWith four exposures and three private balconies, this home is designed to capture the island’s natural beauty from every angle. Watch breathtaking sunsets over the ocean each evening as you unwind in the expansive living room or enjoy dinner on the main west-facing balcony. Floor-to-ceiling windows flood the living area with light and provide panoramic views of the water, creating an unforgettable backdrop for your stay.brbrbrbr Spacious Interior with Soaring CeilingsbrbrThe penthouse features a grand open living space with 18-foot cathedral ceilings and oversized windows on three sides, making the interior feel light, airy, and endlessly inviting. The fully equipped chef’s kitchen, elegant dining area, and large living room provide the perfect setting for cooking, entertaining, or simply relaxing with loved ones.brbrbrbr Luxurious Bedrooms & Private RetreatsbrbrThe primary suite offers a serene escape with its own private balcony, spa-like en suite bathroom complete with a separate shower and jacuzzi bathtub, and ocean-facing windows. A sleeper sofa in the primary suite adds flexibility for additional guests. The second bedroom is furnished with a plush queen size bed, ensuring everyone enjoys a restful night’s sleep.brbrbrbr☀️ Resort-Style Amenities & Prime LocationbrbrGuests have access to a large, fully equipped pool just steps from the condo, perfect for cooling off after a day in the sun. The home’s prime location means you’re just two blocks from iconic Duval Street, with its world-class restaurants, galleries, and nightlife, and only a short walk or bike ride to Fort Zachary Taylor State Park, home to one of Key West’s most beautiful beaches.

Azure Vista Penthouse

Key West, Florida, United States

Bed

Bath

Sleeps

$321.56

Experience what is like to live in Old Town at the desirable Historic Seaport. This beautiful home is filled with amazing furniture, artwork and amenities that give you the tropical, old town feel you seek when visiting Key West. The smallest details have not been missed, high thread count sheets, luxury bedding, fluffy towels, gourmet kitchen, flat screen tv’s, lovely front porch with comfy cushioned rocking chairs to drink your morning coffee and gorgeous property. The backyard is tranquil and secluded with mature plants including a Meyers Lemon Tree, Palm Trees and a gorgeous dining and resting area to relax, read a book or take a nap.brbrTwo lovely appointed bedrooms that take full advantage of the outside views. Master bedroom upstairs has a bonus room that is great for reading and meditating and is equipped with a handcrafted swing and couch for a quiet hideaway.brbrThe living room is beautifully decorated and spacious for entertaining. It has a brand new comfortable Queen Sleeper sofa for visiting friends or family. Large flat screen smart TV and plenty of seating.brbrBrand new gourmet kitchen with breakfast bar, stainless steel appliances, quartz counters and every amenity needed to enjoy a meal on your country farm table. French doors open to a lovely backyard oasis so you can feel the breeze while drinking your morning coffee. brbrThe Dade County Pine floors have been refurbished and are stunning throughout the home giving it a fresh old town feel.brbrLocation has a high walkability score of close to 100, a car is not needed. A block from the Historic Seaport and all the finest restaurants. A few blocks from Duval Street and a minute away from the best Cuban coffee and fresh baked bread. This beautiful original Conch home will immerse you in the Key West lifestyle where you will relax and enjoy your time in Paradise Found.br

Ohana Paradise At The Historic Seaport , Old Town. Private Home.

Key West, Florida, United States

Bed

Bath

Sleeps

$361.63

Summary:brbrLocated in downtown Key West, the 'Rose Petal Petite Suite' offers a cozy and charming accommodation experience. This one-bedroom, one-bathroom unit is perfect for up to 2 guests. Unwind in comfort with its cozy furnishings and convenient amenities. The central location provides easy access to local attractions, while the shared pool offers a relaxing retreat after exploring Key West's vibrant atmosphere and historic sites. Ideal for a weekend getaway or extended stay, this suite promises tranquility amidst excitement.brbrbrbrThe Space:brbrRose Petal Petite Suite' is a charming one-bedroom, one-bathroom unit accommodating up to 2 guests. brbrbrbrThe space features an open floor plan with a bedroom with a king-size bed and includes a fully-equipped kitchen with a stove, refrigerator, coffee maker, and essentials, plus a full bathroom with a shower and extra towels. brbrbrbrGuests have ample closet space, a washer and dryer, air conditioning, and fans for comfort. Amenities include reserved parking, a front balcony for morning coffee, a flat-screen TV with cable, and a private back deck with dining seating. In the shared backyard you will find a pool, outdoor shower, and lush tropical greenery.brbrbrbrGuest Access:brbrOur self check-in makes the process seamless. brbrbrbrGuests will receive a personalized access code prior to arrival and direct contact to a local guest experience manager for any questions, needs or recommendations during their stay.brbrbrbrThe Neighborhood:brbrRosé Retreat is located in the heart of Key West's action, with plenty of dining and entertainment within walking distance, including historic Duval Street. Stroll a few blocks north to the docks, where snorkeling, boating, and other aquatic adventures await you.brbrbrbrHalf a block from Duval Street, this spacious studio is just steps away from Key West's most famous bars and dining spots. Locals' favorite restaurants, such as First Flight, Bagatelle and Two Friend’s patio are less than a 5 minute walk from your front door. Got a sweet tooth Keep an eye out for Kermit’s Key Lime Pie Shop in the Historic Seaport known for the best Key Lime Pie in Key West, or grab some homemade fudge and candy from River Street Sweets.brbrbrbrForgot something, or need a quick fix Shorty’s Market has your last minute necessities for your weekend getaway. Just 2 blocks away you can also find Fausto’s food market for locally sourced groceries.brbrbrbrGetting Around:brbrParking Information: This unit comes with a designated parking spot.brbrbrbrThere are a variety of great ways to explore Key West including by bicycle, scooter, golf cart, Uber, Taxi, or by feet. As this unit is located in downtown Key West, many attractions are within walking distance.brbrbrbrOther Things to Note:brbrThis unit is pet friendly! Our 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.

Apartment

Rose Petal Petite Suite - Near Duval Street

Key West, Florida, United States

Bath

Sleeps

Exceptional(4)

$761.38

Summary:brbrEscape to paradise with this luxurious Key West retreat, perfect for families and groups looking to unwind in style. Nestled in a serene neighborhood, this home boasts two bedrooms, a loft bedroom, and not one, but two fully-equipped kitchens, ensuring plenty of room for everyone to relax and enjoy. Just steps from Duval enjoy downtown Key West or hang back and relax by the private pool.brbrExperience a slice of paradise at this charming historic retreat in Key West, ideal for families and groups seeking a stylish getaway. Nestled in a serene neighborhood, the home features two bedrooms, a loft bedroom, and two fully equipped kitchens, providing space for everyone to unwind. Enjoy the convenience of being just steps away from Duval Street and downtown Key West, or opt for a relaxing day by the private pool.brbrbrbrThe Space:brbrThe Rosé Retreat is made up of two individual units that can be rented separately or as a compound. The compound features two bedrooms with comfortable king-size beds and a loft with a double bed, accommodating up to six guests. With multiple outdoor lounge areas and plenty of space for family dining, the spacious backyard features a pool, an outdoor shower, and lush tropical greenery.brbrbrbrThe fully equipped kitchen on the first floor has a stove, refrigerator, dishwasher, coffee maker, and all essentials are perfect for preparing delicious meals. Each floor has a full bathroom with showers and is stocked with extra towels, sheets, and other necessities. brbrWith an in-unit washer and dryer, air conditioning, and fans for your comfort the Rose Retreat is ready for your next vacation.brbrbrbrGuest Access:brbrOur self check-in makes the process seamless. brbrbrbrGuests will receive a personalized access code prior to arrival and direct contact to a local guest experience manager for any questions, needs or recommendations during their stay.brbrbrbrThe Neighborhood:brbrRosé Retreat is located in the heart of Key West's action, with plenty of dining and entertainment within walking distance, including historic Duval Street. Stroll a few blocks north to the docks, where snorkeling, boating, and other aquatic adventures await you.brbrbrbrHalf a block from Duval Street, this spacious studio is just steps away from Key West's most famous bars and dining spots. Locals' favorite restaurants, such as First Flight, Bagatelle and Two Friend’s patio are less than a 5 minute walk from your front door. Got a sweet tooth Keep an eye out for Kermit’s Key Lime Pie Shop in the Historic Seaport known for the best Key Lime Pie in Key West, or grab some homemade fudge and candy from River Street Sweets.brbrbrbrForgot something, or need a quick fix Shorty’s Market has your last minute necessities for your weekend getaway. Just 2 blocks away you can also find Fausto’s food market for locally sourced groceries.brbrbrbrGetting Around:brbrParking Information: This unit comes with two designated parking spots.brbrbrbrThere are a variety of great ways to explore Key West including by bicycle, scooter, golf cart, Uber, Taxi, or by feet. As this unit is located in downtown Key West, many attractions are within walking distance.brbrbrbrOther Things to Note:brbrThis unit is pet friendly! Our 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.

Rose Key Cottage - Private Pool & Near Duval

Key West, Florida, United States

Bed

Bath

Sleeps

$338.22

The newly remodeled home is located in the middle of Old Town down a private lane just a block from Duval Street. One off-street parking space is provided, not that you really need a car. You are a few blocks from the Old Town attractions. When you enter the front gate you walk onto the front deck where you can grill out and enjoy dinner under the stars and palm leaves or just relax in the hot tub. There is also a rear deck off of the home with couple of chaise lounges chairs great for sunbathing. Along the side of the home is an outside shower that is great to use when you return from the beach or really anytime. When you walk into the home via the large sliding patio door you enter the living room and dining area. In the living room there is a large couch (queen size sleeper sofa) with chaise lounge and 55 Smart TV. Dining area features a 4 person table and bar top with seating for 3. The kitchen features Cafe appliances, smooth top range, microwave, dishwasher, refrigerator, quartz countertops and Kohler coffee maker. The main bathroom has 36 floating vanity with a lighted Kohler medicine cabinet mirror and tile shower with shower head, couple of body jets, and handheld shower wand. The bedroom has a king size bed with nightstands on each side, a 44 Smart TV mounted on shiplap wall and a patio door that leads to rear deck. The half bath off of the bedroom also includes the LG laundry center and built in closet storage center. Enjoy all that Old Town Key West has to offer just steps from your home or don't go anywhere and just enjoy relaxing at home.

Cottage

Old Town cottage

Key West, Florida, United States

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Bath

Sleeps

$354.32

This Harbour Place condominium is in Key West's most prestigious community of Truman Annex offering breath taking water and sunset views from the large and luxurious pool area. This beautifully decorated stately Condo has wonderful views of the Truman's Little White House Museum grounds where United States Presidents and many other world wide heads of state have come throughout history to speak or even stay. There are often weddings and other important ceremonies under the huge presidential shade trees. The balcony has some limited water views along the length of the historic administration building. This community is located 2 blocks from Duval Street and all of the Old Town Key West attractions. The properties are also located mile from one of the best beaches on the island. This unique property is outfitted with washer/dryer, pots and pans, towels, linens, central air conditioning, covered off street parking and a gorgeous waterfront pool.brbrPlease note: The minimum rental period is 29 nights/30 days, except for February, which is 28 nights.

Forever Young at The Truman Annex in Key West

Key West, Florida, United States

Bed

Bath

Sleeps

$329.49

The Presidents Walk and Southard Court community is located in the Truman Annex Complex which is located 2 blocks from Duval Street and all of the Old Town Key West attractions. The properties are also located less than a half mile from one of the best beaches on the island, Fort Zachary Taylor State Park and Beach. The Presidents Walk properties are two level townhouses which have private courtyards on the first level and balconies on the second level. All properties are outfitted with washer/dryer, fully equipped kitchen, towels and linens, have central air conditioning, off street parking and pool access. brbrPlease note: This property is monthly rental - This property has a 28 night minimum stay

Sailor's Story at The Truman Annex in Key West

Key West, Florida, United States

Bed

Bath

Sleeps

$158.76

Alhambra is a charming one bedroom, one bath first floor unit with a huge outdoor deck!brShipyard Condominiums are located in the award winning gated community of the Truman Annex Complex.brLocated 2 blocks from Duval Street and all of the Old Town Key West attractions this beauty is outfitted with washer/dryer, pots, pans, towels, linens, king sized bed, central air conditioning, off street parking and pool access. brPlease note: This property has a 28 night minimum stay

Alhambra at The Truman Annex in Key West

Key West, Florida, United States

Bed

Bath

Sleeps

$509.33

Enjoy a beautiful private home located in the Historic Truman Gated Community in Old Town Key West. This beauty if only steps away from Duval Street and all the activities and restaurants of Key West. Swim in the private heated pool with spa jets, large outdoor patio and back deck with grill. Relax on the upstairs wrap around porch. Master Bedroom suite is furnished with a King bed, ensuite bathroom plus an enclosed attached Den with seating area and a queen pull out sofa bed. 2 charming Guest Bedrooms each have queen beds and share a full bathroom and open to a wrap around porch. Downstairs features open floor plan with a spacious kitchen dining area and living room, half bath and French doors open to the private back yard and pool area. brWasher/Dryer, full kitchen setup, towels, bedding, central air, ceiling fans, WiFi, cable and a private carport for one car.brbrPlease note: This property is monthly rental -This property has a 28 night minimum stay

A Sunset Breeze at the Truman Annex in Key West

Key West, Florida, United States

Bed

Bath

Sleeps

$324.96

Summary:brbrEscape to Old Town Key West - 3 Bedroom 2.5 Bathroom Townhome with a Private PoolbrbrbrbrThe Space:brbrEscape to Old Town Key West and indulge in a monthly retreat at our charming 3-bedroom, 2.5-bathroom townhome. Nestled in the heart of the historic district, this hidden gem offers not only a tranquil oasis but also easy access to Key West's vibrant attractions.brbrbrbrStep into your temporary abode and discover a spacious layout designed for comfort and relaxation. With three bedrooms, there's ample space for your family or group of friends to unwind. The master bedroom features a plush king-size bed and an en-suite bathroom, while the other bedrooms offer cozy accommodations and convenient access to a shared bathroom. Enjoy the streaming tv's in every bedroom.brbrbrbrAfter a day of exploring, take a refreshing dip in your private sparkling pool. Lounge on the poolside deck with a cold drink in hand, soaking up the warm Florida sun. This beautiful outdoor area has a fire table in the backyardbrbrbrbrConvenience is key, and our townhome boasts off-street parking, ensuring hassle-free arrival and departure. Plus, with a fully equipped kitchen, you have the option to whip up your favorite meals or dine out at some of Key West's best restaurants, all within walking distance.brbrbrbrSpeaking of walking distance, you'll find yourself just moments away from a myriad of attractions, including beaches, eclectic shops, and lively entertainment venues. Whether you're seeking outdoor adventures or cultural experiences, you'll find it all right at your fingertips.brbrbrbrDon't miss out on the opportunity to experience the magic of Key West from the comfort of our inviting townhome. Book your monthly stay now and start counting down the days to your unforgettable getaway.

Helluva Happy Place

Key West, Florida, United States

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Bath