Vacation Home Rentals By Owner In Key West, FL

Summary:brbr1 bed, 1 bath condo w/shared pool at The Bayview HousebrbrbrbrThe Space:brbrDiscover your perfect island escape at The Caroline Suite, a recently refreshed 1 bedroom, 1 bathroom nightly vacation rental located in The Bayview House, a beautifully restored 1928 historic property in the heart of Old Town Key West. With tropical charm and modern comfort, this inviting ground-floor suite is ideal for couples, solo travelers or small families seeking a central home base for exploring paradise.brbrbrbrThis cozy suite comfortably sleeps up to 4 guests, featuring a queen bed in the bedroom and a queen sleeper sofa in the living room. The kitchen has a sink, refrigerator, two-burner cooktop, microwave, coffee maker and essentials for preparing light meals or snacks throughout your stay.brbrbrbrGuests of The Caroline Suite also enjoy access to premium amenities:brbrbrbr- Shared swimming poolbrbr- Shared on-site laundrybrbr- Air conditioning, Wi-Fi and flat-screen TVbrbr- First come, first serve off-street parking (2 spaces) + street parking availablebrbr- Prime location near Duval Street and top Key West attractionsbrbrbrbrBayview House places you within walking distance of Key West’s most popular attractions:brbrbrbr- Mallory Square – Celebrate the sunset with live entertainmentbrbr- Key West Historic Seaport – Waterside dining, shopping and boating excursionsbrbr- Ernest Hemingway Home & Museum – A must-see for literature loversbrbr- Fort Zachary Taylor State Park – Enjoy beach days, snorkeling and nature trailsbrbrbrbrWhether you’re here for a romantic getaway, a weekend adventure, or a relaxing escape, The Caroline Suite offers a stylish and comfortable place to unwind between your Key West adventures.brbrbrbrBook your stay at The Caroline Suite today and enjoy all the charm of a boutique inn with the privacy and convenience of a vacation rental, right in the heart of one of Florida’s most iconic destinations.

Apartment

The Caroline Suite | 1 bedroom condo w/shared pool

Key West, Florida, United States

1

Bed

1

Bath

4

Sleeps

$198.02

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 brbrWelcome to Castaway Cove! Nestled in the vibrant New Town area of Key West, Castaway Cove is your perfect home away from home! brbr brbrThis charming 2BR townhome offers a blend of comfort, convenience, and coastal charm, making it an ideal getaway for families, friends, or couples. Castaway Cove offers a spacious and tastefully decorated living area with comfortable seating and a flat-screen TV. Fully equipped kitchen with modern appliances, perfect for whipping up your favorite meals, as well as a cozy dining area for enjoying meals together. There are two well-appointed bedrooms with plush bedding and ample storage. Private patio with outdoor seating and a BBQ grill, ideal for al fresco dining and relaxing. Shared pool just steps away, perfect for cooling off and soaking up the Florida sun. Kayaks available for exploring the beautiful waters of Key West. Castaway Cove is situated in the heart of New Town, providing easy access to the island’s best beaches, an array of restaurants, cafes, and bars, local shops and popular attractions like the Key West Butterfly and Nature Conservatory, the Ernest Hemingway Home and Museum, and the vibrant nightlife of Duval Street. Whether you're seeking adventure on the water, relaxation by the pool, or exploring the local culture, Castaway Cove offers the perfect base for your Key West vacation. Book your stay today and experience the charm and beauty of this tropical paradise! brbr brbrSLEEPS MAXIMUM OF 4 GUESTS: brbr brbrBedroom 1: Queen Bed (adjustable), Smart TV (no cable/satellite available) brbr brbrBedroom 2: Queen Bed, Smart TV (no cable/satellite available) brbr brbrLiving Room: Sofa w/ Two Recliners, Chair, Smart TV (no cable/satellite available) brbr brbrKitchen: Nicely equipped (everything needed to prepare and serve meals) brbr brbrAMENITIES: brbr brbr- Shared Pool (heated and chilled) brbr brbr- Private Patio brbr brbr- Propane BBQ Grill brbr brbr- Keurig, Drip Coffee Maker, Toaster, Blender brbr brbr- Two Parking Spaces Included brbr brbr- Linens and towels provided brbr brbr- 2.2 miles to Smathers Beach brbr brbr- 2.2 miles to Duval Street brbr brbr- 2.3 miles to Historic Seaport brbr brbr- 2.4 miles to Southernmost Point brbr brbr- 2.8 miles to Mallory Square Sunset Pier brbr brbr- 3.0 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.

Castaway Cove: Charming 2BR Townhome in New Town, Key West with Shared Pool, Private Patio & Kayaks!

Key West, Florida, United States

2

Bed

1

Bath

4

Sleeps

$244.08

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

Newly Renovated Hotel w/ Outdoor Pool | Short Drive to Historic Old Town

Key West, Florida, United States

Bed

Bath

Sleeps

$244.08

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

Relaxing Double Queen, Fairfield Inn, Breakfast Included, Near Downtown Key West

Key West, Florida, United States

Bed

Bath

Sleeps

$184.9

Charming Pool Cottage in the Heart of Old Town Key WestbrbrPerfectly situated in historic Old Town Key West, this quaint and inviting pool cottage offers the ideal island escape for a couple, with room for occasional guests. Thoughtfully decorated and impeccably maintained, the home features a newly renovated kitchen and beautifully designed outdoor spaces to enjoy the island breeze.brbrProperty Highlights:br Comfortable Accommodations:br The primary bedroom includes a king bed, while the guest bedroom offers two single beds—perfect for visiting friends or family.brbrModern Conveniences:br A full-sized, fully equipped kitchen opens directly onto the stunning pool deck—ideal for entertaining. A stackable washer and dryer are included for added convenience.brbrOutdoor Living at Its Best:br Private Pool: Cool off or unwind by the pool, which can be heated for year-round enjoyment.br Front Porch: Sip your morning coffee and watch the world go by from the charming front porch.br Back Deck: Host a barbecue or relax after a day exploring Key West in this serene outdoor space.brbrParking:br Street parking is typically available within a block of the home.brbr This delightful cottage blends classic Key West charm with modern comforts—making it your perfect home away from home.brbrSTAYS FROM DECEMBER THROUGH APRIL NEED TO BEGIN ON THE 1ST OF THE CALENDAR MONTH - THANKS FOR UNDERSTANDING.

Old Town Elegance Island Breezes and Poolside Bliss

Key West, Florida, United States

Bed

Bath

Sleeps

$192.25

Prime Old Town location meets effortless island living in this 2‑bedroom, 1‑bath first‑floor Shipyard condo. Bright interiors, a private tropical patio, and a coveted ground‑floor layout make this home ideal for full‑time living or vacation use. Gated community, resort‑style pool, assigned parking, and just minutes to Duval Street and the beach. A rare opportunity in one of Key West’s most sought‑after neighborhoods.brbrPlease note: This property has a 28 night minimum stay

Another Day in Paradise at the Truman Annex in Key West

Key West, Florida, United States

Bed

Bath

Sleeps

$512.72

Duval Square Retreat is In the heart of Old Town. Duval Square is located at the artistic and quieter end of Duval Street. This recently upgraded unit is tastefully decorated with design elements from around the world. The first floor offers a well- equipped kitchen, and an open living and dining concept, French doors to a private balcony and a half bath powder room. brbrUpstairs, the main bedroom suite has a private balcony and ensuite bath. The second second bedroom also has an ensuite bath. brbrThere is central air conditioning and Wi-Fi internet. The complex's shared pool and sunning area overlooks world famous Duval Street. On the street level you will find a unique tree lined courtyard with restaurants and shops. While gated garage parking is provided here, all you really need is a bicycle for your main mode of transportation as you can walk or bike everywhere from Duval Square. brbrBedding: 2 QueenbrA shared, sun-drenched, rooftop pool and pavilion are just steps from your door.brbrThis is an unbeatable location offering easy pedestrian access to dozens of shops and restaurants, the Ernest Hemingway Home Museum and other notable local attractions, and of course the serene, turquoise ocean that the island is famous for. brbrGather your friends and family together and book a Key West vacation you will never forget at Duval Square Penthouse.brbrBeds: 3 Kings, 2 Twins, 1 Sleeper SofabrDuval Square is a charming community with shops and restaurants downstairs and secure, quiet, private residences, pool and pavilion upstairs. Although the condo includes one assigned parking space in the gated garage, you can stroll anywhere from this conveniently located condo. All of the shops, galleries, restaurants, and attractions on and around Duval Street and nearby beaches are just a leisurely stroll away. brbrWhen you enter the home you will find a fully equipped kitchen, dining area, spacious living room and a convenient half bath. French doors let in the natural sunshine and open to the private back deck with dining table and chairs perfect for outdoor entertaining. brbrOn the second floor, you will find 2 bedroom suites, each with their own private bathroom and an additional private balcony off the main suite.brbrBedding: 1 king, 1 queen, 1 queen sleeper sofa.brbrElevator access from ground level to the first floor of the condos. Stairs to the unit's second floor bedrooms.brbr1 Reserved Parking Space in the Gated Garage.brbr**Construction Disclaimer** From mid May through the month of June, 2026, the pool area will be under construction. This will create noise and dust that could impact your stay and may lead to pool closure as well.

Duval Square Retreat: A beautiful condo steps from the action

Key West, Florida, United States

Bed

Bath

Sleeps

$386.59

Part of a small collection of cottages known as The Colony, this quaint cottage sits to the back of the property and is located just two blocks from world famous Duval Street. Colony Calypso is surrounded by coconut palms and blooming bougainvillea. This charming one bedroom bungalow is a true island hideaway. brbrThe cottage features a one level open concept living and dining area with a full kitchen. The quaint cottage offers a spacious bedroom with a king size bed. The bathroom has a tiled shower bathtub combination. brbrThe cottage offers a nice private deck with a gas grill. The tropical common area grounds feature a large, beautiful swimming pool. Colony Calypso's convenient location and a quiet atmosphere make this a perfect place to relax in the comfort of your home away from home while still being in Old Town and close to Duval Street.brbrThis vacation rental property offers secure, coded keyless entry with contactless check in.brbrBedding: 1 king, 1 sleeper sofabrbrParking: There is a small parking lot for cottage guests and available on a first come first parked basis. If the lot is full, there is on-street parking right on Olivia Street and on surrounding side streets and lanes.

COLONY CALYPSO - A quaint 1 Bedroom Cottage just two blocks to Duval

Key West, Florida, United States

Bed

Bath

Sleeps

$492.64

28 DAY MINIMUM RENTALbrbrReynolds Retreat is quintessential Key West living. Located just a few blocks off Duval Street, Reynolds Retreat is a delightful cottage filled with historic charm and modern convenience.brbrThe wide stone patio surrounded by a white picket fence is the perfect spot for lounging with morning coffee or a cold afternoon drink. As you enter the home, buttery Dade County pine walls and floors flank an unobstructed view all the way into the backyard. To the right there is a bedroom with lovely transom windows and a dramatic, gray and green marble bathroom with a sunken tub. Just across the hall is a quaint sitting room.brbrThe living area is open-concept, with high ceilings and unobstructed views of the renovated kitchen, providing a perfect place to unwind and entertain. Walls of floor-to-ceiling sliding doors open to reveal a sparkling, cerulean, lagoon-style heat optional swimming pool. Another bedroom lies within the pool’s cabana, giving guests plenty of privacy and space.brbrThe exposed walls in the upstairs main suite are stained a soothing olive, and the bathroom is tiled in rustic, natural stone. Reynolds Retreat is a relaxing oasis just far enough from the bustle of Duval Street. It’s the perfect spot to make your home-away-from-home in paradise.brbrBedding: 3 QueenbrOn Street Parking

Reynolds Retreat - A Great Monthly Getaway

Key West, Florida, United States

Bed

Bath

Sleeps

$244.39

28 DAY MINIMUM RENTALbrbrThis bright and sunny cottage is situated on a quiet residential street. Guests can walk to the nearby beaches, White Street shops, and enjoy the sunny pool, hot tub and patio space.brbrA large open kitchen, skylights, light tile floors and french doors leading from the living room & both the bedrooms to the pool area create a real indoor/outdoor living experience. The living room is spacious & comfortable with bright tropical colors with a small lounging corner where you can relax in the overstuffed chaise, read a good book, take a nap, all while gazing out to the pool and patio. Several new upgrades have been added by the owners including a new ductless air conditioner to cool or heat the living area.brbrThe master bedroom sits to the rear of the property with french doors to a private patio space complete with the new 6-person hot tub. It's your own outdoor spa! The second bedroom is on the front of the house adjacent to the living room with French doors leading out to the pool. Bedding: 2 kings, 1 sleeper sofa.

South Street Cottage: Bright & Sunny with Pool, Patio & Hot Tub

Key West, Florida, United States

Bed

Bath

Sleeps

$766.94

In the heart of Old Town, convenient to everything, this condo is set above a brick and tree lined courtyard that includes shops and restaurants. This three bedroom two bath unit is in one of two standalone WALK-UP buildings in the Duval Square complex. You enter a large open living, dining, kitchen area with French doors & porch overlooking the courtyard below. The master bedroom with ensuite bath has a king bed and access to a second deck area overlooking the courtyard. There is a shared pool and sunning area that overlooks the world famous Duval Street. Central air conditioning/heat & 1 covered parking space. PLEASE NOTE THIS PROPERTY IS ACCESSED BY STAIRS ONLY. brbrBedding: 1 king, 1 queen, 2 twins, single rollaway & sleeper chair. brSleeps 6 & up to 8 with extra person charge.brbr**Construction Disclaimer** From mid May through the month of June, 2026, the pool area will be under construction. This will create noise and dust that could impact your stay and may lead to pool closure as well.

Duval Square Courtyard Condo is just steps from the action

Key West, Florida, United States

Bed

Bath

Sleeps

$1383.94

Enter the private courtyard of the home, to a lush tropical oasis. The large, free form pool with coral stone patio makes you ready to dive right in and relax poolside amongst the tropical foliage. A new expanded Ipe deck area is perfect for an outdoor dinner under the stars or lounge in the oversized sitting area tucked into the landscape. If you follow the path into the back corner of the property you will be rewarded with a beautiful rope loveseat to curl up into, perfect for an afternoon siesta or a good book.brbrStep inside the French doors into the rustic charm of this cottage with its Dade County Pine walls and cathedral ceilings in the living area. All new flooring throughout the common areas compliment the wood walls. The kitchen has new retro style appliances, quartz counters and mosaic backsplash that retain the character of the house. There is a laundry room just beyond the kitchen.brbrTo the front and back of common living areas are the two bedroom suites. You choose which one is your master suite! They both have the same character of the rest of the house with its rustic charm. Each bedroom, with queen bed, also has a bath attached with walk-in showers.brbrHavana Lane, the street itself, hearkens back to a time when cigar makers lived in the neighborhood, gathering on porch stoops to pass on the latest news. Near the notorious Key West Cemetery, the home is centrally located in an Old Town residential neighborhood, just a few blocks away from the White Street Art District. For shopping and nightlife, you can easily walk or bike to Duval Street, approx. 7 blocks, or the Historic Seaport. brbrA wonderful retreat for your vacation!brbrbrBedding: 1 King, 1 queenbrDuctless AC units, High speed Wifi, 1 TV in Living Room.brParking is on surrounding streets

Havana Lane: An updated classic conch cottage with still a rustic edge!

Key West, Florida, United States

Bed

Bath

Sleeps

$384.07

Poolside Breeze is a nicely decorated two bedroom 1st floor condominium with an excellent location very close to the pool. Poolside Breeze has an extra large floor plan with an extensive private balcony. brGorgeous new Kitchen renovated in 2018. Both bedrooms and the living room feature sliding glass doors that open on to the private balcony overlooking the lush tropical courtyard of 1800 Atlantic. There is a full size fully equipped eat in Kitchen and a dining room area that seats 6. Full size washer & dryer in the unit. The Master bedroom has a king size bed. The guest bedroom has a queen and for your convenience there is a queen size sleeper sofa in the Living room. The unit has wireless internet. There are Mexican tiled floors in the living room and hallways with carpet in the bedrooms. Enjoy the tranquility that this property has to offer.brbrMinimum length of stay requirement may be in place depending on high/low seasons. For stays shorter than 3 nights please contact the office or email your inquiry.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.

Poolside Breeze Retreat, Tropical flare, Key West spectacular getaway.

Key West, Florida, United States

Bed

Bath

Sleeps

$363.2

Escape to paradise in this spacious first-floor garden-view condo in beautiful Key West — the perfect setting for a relaxing island vacation.br“Nautical Adventures” comfortably accommodates families and groups with:brbrbrA king bed in the primary suitebrOne double bed and one twin bed in the guest bedroombrA queen sleeper sofa in the living roombrbrbrEnjoy seamless indoor-outdoor living with private balcony access from both bedrooms and the living room. Start your mornings with coffee overlooking lush tropical gardens and unwind in the peaceful island atmosphere.brThe condo features:brbrbrHigh-speed Wi-FibrFully equipped eat-in kitchenbrDining table seating for 6brSpacious living area perfect for gatheringbrFull-size washer and dryerbrOne assigned parking spacebrbrbrGuests are just a short stroll from the resort-style pool and Jacuzzi. Sports enthusiasts will love the three lighted tennis courts, including the island’s only clay court.brConveniently located just 1.5 miles from the Historic District, you’ll be close to the best dining, shopping, nightlife, and attractions Duval Street and Mallory Square have to offer while still enjoying a peaceful tropical retreat.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.

Our Nautical Home Key West prime location & amenities. Last minute specials.

Key West, Florida, United States

Bed

Bath

Sleeps

$1977.57

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival!brbrSOUTHERNMOST HOSPITALITY V is a luxurious private estate that occupies an entire corner of Old Town's famous Duval Street, just a block from the Southernmost Point. Don't let the address fool you... this upscale home has plenty of privacy in the spacious back yard with a tall fence surrounding the large private saltwater pool. Privacy also comes in the form of the all-suites accommodations: each bedroom is complete with an en-suite bathroom and flat screen TV. This fabulous home, combined with Last Key Realty's Five-Star Guest Services, will make your stay in Key West a memorable one.brbrTHE LOCATION...brbrIf you've heard of Key West, you undoubtedly know of the famous 'Duval Street' with its selection of fabulous restaurants, shops, galleries, and nightlife. With a prime Duval Street address, SOUTHERNMOST HOSPITALITY V is truly the choice location for a group that wants to be in the center of the action of Old Town Key West. Enjoy the views of Duval St passerby from your vast porches both on the first and second floors, or hide behind the tall fence blocking the views of your back yard from the street. Walk down your front steps to any of the handfuls of attractions within walking distance, including the Southernmost Point, Hemingway House, Southernmost Beach, and famous spots like Sloppy Joe's, The Green Parrot, and any number of delicious restaurants on and off Duval Street. Should you decide to venture off the island, you can park multiple cars in your large off-street private driveway. The driveway also has space for a number of your choice Key West transportation vehicles, be it bicycles, scooters, or electric cars.brbrTHE LIVING AREA and KITCHEN...brbrA large home deserves a grand living area. The spacious main foyer of this home opens to the spacious living room, with a large comfortable sofa and plenty of seating for a group. The sectional sofa, which also pulls out to a sleeper for extra guests, sits in front of a vast 60-inch flat screen Smart TV with DVD and BluRay player. There is also an iPod/iPhone docking station. Off the living area sits a stately dining area with space for 8 diners, plus additional seating at the kitchen bar. The kitchen is entirely upgraded with state of the art appliances and tools, including a Keurig coffee maker. Preparing a meal in this home will be a real treat for even a master chef.brbrTHE PRIVATE SALTWATER POOL and GROUNDS...brbrIt is hard to imagine a Duval Street address having privacy, but SOUTHERNMOST HOSPITALITY VII was built to provide the optimum group vacation experience and a private pool is a must. The tall privacy fence surrounding the back yard of this property provides the right amount of seclusion from the street and the surroundings. Enjoy a swim, or sit by the heat-optional private saltwater pool in any of the number of chaise lounges or plush outdoor furniture and dining sets. A poolside meal is a must at the full outdoor dining set using the deluxe BBQ grill. You'll have everything you need for a cookout with the whole gang.brbrTHE ACCOMMODATIONS...brbrSOUTHERNMOST HOSPITALITY V was designed to create the ideal amount of space and privacy for a large group.brbr• Master Suite: Located on the First Floor with a King bed, a flat screen TV, direct access to the back patio, and an en-suite bathroom with double sinks and a walk-in shower.brbr• Jimmy Buffet Suite: Located on the Second Floor with Two Twins OR One King, a flat screen TV, and an en-suite bathroom with a shower and tub combination.brbr• Chicken Coop Suite: Located on the Second Floor with Two Twin beds OR One King bed, a flat screen TV, and an en-suite bathroom with a walk-in shower.brbr• Robert the Doll Suite: Located on the Second Floor with a King bed, a flat screen TV, and an en-suite bathroom with a walk-in shower.brbr• Americana Suite: Located on the Second Floor with Two Twin beds OR One King bed, a flat screen TV, and an en-suite bathroom with a walk-in shower.brbrALL LAST KEY VACATION HOMES INCLUDE:brbr• Washer & Dryerbr• Central Heat and A/C br• Ceiling Fans br• Flat Screen TVs in Living Room & All Bedrooms br• Fully Equipped Kitchen br• Basic stock of spices br• Starter supply of paper products br• Starter set of cleaning products br• Linens and Towels provided br• 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• Fully Fenced & Lushly Landscaped Private Yard br• Private Saltwater Pool with available Pool Heat br• Off-Street Parking in Driveway br• Propane BBQ GrillbrbrOther notes:brbr• Interim housekeeping provided upon request br• This property will accommodate up to 16 adults br• Max of 2 Pets Allowed with Additional Fee of $200 per petbr• Last Key Realty vacation homes are rented to family groups and responsible adult groups only. Groups who expect they may cause after hours noise will not be a good fit for this home and should be aware they may incur additional penalties when in residence for violations. There will be a $500 charge for after-hours dispatch of our staff in response to calls resulting from verified noise complaints for violations by our guests in residence.

**SOUTHERNMOST HOSPITALITY V** 5BR/5BA & Pool + LAST KEY SERVICES...

Key West, Florida, United States

Bed

Bath

Sleeps

$335.78

Welcome to CasaBianca! Here you'll find the character & charm of Old Town blended perfectly with all the modern amenities of today. Conveniently located midblock on a quiet lane, quality restaurants, cafes, bike rentals and much more are only steps away. It's a five minute walk to Duvall Street & Mallory Square. This home is properly restored and updated, offering all the creature comforts you'd expect in a vacation home of this quality. You can choose the seclusion & calm of a private retreat inside, or the open and full connection to private deck with plunge pool. Off-street parking is a plus!

Quaint, Quiet & Convenient - CasaBianca is The Perfect Old Town Sanctuary

Key West, Florida, United States

Bed

Bath

Sleeps

$697.19

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 cottage 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. Rent this property as a four bedroom/ two bath or each Twin cottage may be rented separately as two bedroom / one bath. Bedding: 4 queens

Pete's Cottages: Twin Cypress cottages steps from Duval

Key West, Florida, United States

Bed

Bath

Sleeps

$431.57

La Brisa beach condominiums offer a Florida charm that is relaxing, easy and captivating. Named for the ocean breezes that flow around the pretty blue and white buildings, La Brisa is an ideal spot to enjoy your Keys vacation. Located on South Roosevelt Boulevard, this secure gated community is directly across from Smathers Beach. A residential complex, La Brisa offers a neighborly and relaxing atmosphere. Join in on community held activities at the club house, partake in a match on the tennis courts and enjoy the sizable kidney shaped pool, hot tub and a spacious common area for chatting, eating and relaxing in the sun.brbrUpon entering Ocean Vista, you are instantly struck by the magnificent view of the Atlantic Ocean and drawn out to your private balcony where you can relax and relish in your beachfront vacation. This appealing, two bedroom, two bathroom condo has been lovingly decorated. A large wall mirror is positioned to enhance the floral colors and rattan furniture and the open design of the living/dining area adds to the relaxing and airy atmosphere. The spacious kitchen is fully equipped, has ample cupboard space, double sink and a pretty dinette for two. After cooking delectable meals in your kitchen, enjoy good food and great conversation at your glass topped rattan dining table for four.brbrAdorned in charming floral prints and light wood, the Primary Bedroom, with a King Bed, offers peace and tranquility. There is an individual door to the private balcony, perfect to catch an early morning Sunrise, and the double windows facing out to ocean offer a breathtaking view. The Primary Bathroom has an individual vanity area with stocked linen closet. The second bedroom, delightful in its beachy motif, features two twin beds and a nice sized closet.brbrThis unit has WIFIbrbrLa Brisa captures a feel for island life, the way the locals live it, away from the clamor of downtown. Quiet moonlit walks on the beach, a morning café con leche from a local vendor and a beach sunrise make for an unforgettable vacation. And while you are away from the hubbub, you are not far away. There is a bike trail that leads you along the Atlantic Ocean, past many Key West sights, into the downtown area. The White Street shops are just a pleasant bike ride away, as are a myriad of fabulous Key West restaurants. While savoring the distinctive essence of La Brisa, take in the ocean, the Key West weather and when you see the bright red WWII Bi-Plane fly overhead on one of its daily excursions from our small airport, ask yourself, Why Not brbrThere is elevator access from the ground floor to the condos above. There is one reserved, covered parking space.brbr**ELEVATOR SHUT DOWN NOTICE: The East building elevator will be shut down starting April 27th, 2026 until April 25th, 2026 for a Elevator Modernization Project. The condo will ONLY be accessible via stairway.brbr**POOL CLOSURE** The pool and jacuzzi will be closed from July 6th to August 30th.brbrPlease note; the LaBrisa Condo Association requires additional registration in advance of your arrival. Details will be provided along with your RKWV rental agreement.brbr**Disclaimer**brbr*The peak sargassum season in Key West is typically from July thru September, with June may also see significant amounts which can impact your stay. While the naturally occurring seaweed itself is not dangerous, it can accumulate on beaches, producing a foul odor and potentially harboring organisms that cause skin irritation. We do not provide discounts for the situation.

Sunshine, beaches, and ocean breezes at Ocean Vista (La Brisa #403E)

Key West, Florida, United States

Bed

Bath

Sleeps

$470.54