Vacation Rentals By Owner In Key West, FL

$771.71

Dream Getaway at the Beach House Resort+Amenities. 2BR

Key West, Florida, United States

Welcome to Experience Key West Paradise at the Beach House Resort Retreat! ️brbrAdditional $500-$1000 SAVINGS available with on certain 7-Night stays, short stays or custom dates. brbrReservations at this property require owners to rent our units out in 7-Night increments from Sunday-Sunday ONLY. Stays that exceed the 7-Night deed may require a unit move.brbrPlease know, ★ provides stays shorter than 7-Nights but *may incur a higher nightly rate.brbrWelcome to your dream getaway at the Hyatt Vacation Club Beach House in stunning Key West! Unveil the magic of this premier residence club that boasts an irresistible combination of luxury, leisure, and beachside bliss.brbr ️ Private Beach & Dock Oasis brbrIndulge in the ultimate coastal escape with your very own private beach and dock area! Whether you're in the mood for soaking up the sun, taking a refreshing dip, or even embarking on a nautical adventure, the possibilities are endless.brbr Lagoon-Shaped Pool Paradise ‍♂️brbrDive into relaxation at our lagoon-shaped pool, where the fun is endless and entry is a breeze with the zero-entry design. No matter the time of year, the pool's wheelchair accessibility and year-round operation make it a watery wonderland for everyone to enjoy!brbr Sip, Savor, and Socialize ️brbrTantalize your taste buds with culinary delights at the bay-view grill restaurant, where the ocean's beauty meets delectable flavors. Unwind with a drink in hand at the lively bar, sharing laughs and stories that will create cherished memories.brbr Hot Tub Heaven brbrLet the bubbling waters of our hot tub melt your worries away as you gaze at the starlit skies above. It's the perfect place to find tranquility amidst the vibrant energy of Key West.brbr Luxurious Accommodations brbrUnwind in style in our lavish two-bedroom, two-bath units that can host up to six lucky guests. Whether you're traveling with family or friends, our spacious units provide unparalleled comfort and breathtaking views that will leave you in awe.brbr Convenience at Your Fingertips ️brbrOur front desk is at your service from 7:00 AM to 11:00 PM, ensuring your check-in experience is as smooth as the ocean breeze. Need to check in later No worries – simply reach out to us and we'll make arrangements just for you.brbr Easy Parking & Shuttle Services brbrPark your worries aside with our complimentary parking, and if you're flying in, take advantage of our airport shuttle (additional charge). Your journey to paradise is hassle-free from start to finish!brbr Stay Connected, Even in Paradise brbrFor those who can't completely escape work, our business center offers you the convenience of staying connected while surrounded by palm trees and ocean waves.brbr Explore Key West's Gems ️brbrNestled on the northeastern tip of Key West, our lush and landscaped retreat is your gateway to Mallory Square's legendary sunsets and the bustling streets of Duval. From shopping to dining and electrifying nightlife, the adventures await just minutes from your doorstep!brbrDon't just dream of a tropical getaway – live the dream at Hyatt Vacation Club Beach House. Your unforgettable Key West adventure starts here, where every moment is a memory waiting to be made. Book now and make waves in paradise! brbr Capture the MagicbrbrMake sure to snap photos of your amazing adventure and share them with us on social media using # . We can't wait to see the fun and excitement you experience at our resort haven!brbr Note: Images serve as representative depictions of potential resort units and amenities. Actual offerings may vary or have evolved since these snapshots were taken. Views, Features, furnishings, and amenities may differ from images. The floor plans are intended to provide a tantalizing glimpse of possibilities, not an exhaustive catalog. Your slice of paradise may vary, please inquire with your host!

2

Bed

2

Bath

6

Sleeps

$690.29

/ Nightly

Condo

Panoramic Ocean: Beach from every window

Key West, Florida, United States

Key West Paradise Found is perched on the top floor with breathtaking Ocean Views, Reconfigured Master Bedroom and Remodeled Kitchen. If you have a larger party we also own the 2 units right next door so they can all be rented together. Enjoy your luxury condo with breathtaking view of the deep blue Ocean and sparkling salt water pool within our tropical garden.....There is nothing like it...anywhere.... at any price. Paradise Found is a TOP FLOOR spacious, clean and comfortable Key West condo experience. Enjoy your PRIVATE BALCONY for lounging sunbathing and dining.. This is a two bedroom two bath spacious condo. Newly renovated for 2020 and enhanced with Comfortable Beds. The Master has a KING. The second bedroom offers a QUEEN with an additional TWIN for sleeping flexibility. There is also a Queen sleeper sofa in the living room. brThis is Key West's most coveted location. Nestles between two of Key West's best beaches, Smathers Beach is just a 20 yard walk on the side walk. We are within 2 miles of most locations on the island. Enjoy the nightlife and excitement of Duval Street (restaurants, bars, live entertainment). Scuba Diving, Jet Skiing, Kayak Rentals, Deep-Sea Fishing, Cruises. Close to 18-Hole Golf Course, Moped/ Bicycle Rentals, Airplane/Seaplane Tours. We hope that you will enjoy staying on the ocean with all the comfort of home . After your first visit we hope you will agree.... Paradise has been found!brOur other VRBO Listings #4091146 & #4091149brbrCONSTRUCTION NOTICE - There will be concrete restoration project happening at 1800 Atlantic Starting in May 2025 through the Spring of 2026. The building our units are in has been complete and we have new balconies. The work will be in the West building until Spring of 2026.

Bed

Bath

Sleeps

$212.63

/ Nightly

Condo

Quaint Island Escape Condo w/Spacious Balcony Deck in Beautiful Truman Annex

Key West, Florida, United States

This lovely Island Escape Condo is a upper level condo located in the prestigious Truman Annex. Not just another rental property! Location is everything.!!! Close to Duval.brStarting Jan 2026 , this beautiful condo will become monthly! Stays will have to be 28- 30 days. 10% discount for monthly rentals. Make plans to stay longer, relax or work remotely from paradise for a full month in 2026. br-Large private corner balconybr- Free High Speed Internetbr- Secure Parkingbr- Fully equipped kitchen with microwavebr- Washer and Dryerbr- Towels, Linens, Beach Chairsbr- Large community swimming pool for Shipyard residentsbr- Water park across the streetbr- Entertainment and cuisine in easy walking distancebr- Close to Fort Zachary park and Beach (Key West's most beautiful Beach)br- Just a few blocks to Mallory SquarebrbrbrOur favorite room is the spacious covered deck that opens up from living room with ceiling fans, tropical foliage, dining/sitting for 4.brThe Island Escape is a corner condo which allows for more privacy. The condo's parking stall is right at your front door and bike racks beside condo. Shipyard community pool is close and heated. Windows across the front of the condo let in lots of light and tropical breezes. No need for a car you can walk 2 blocks to Duval Street where you will find restaurants, shopping, night clubs and museums. Fort Zachary Beach is also close. You can rent kayak, canoe, or paddle board and launch on the beach. You can also picnic or grill in the park. Mallory Square where sunset is celebrated every night has local vendors and entertainment. Breakfast at Blue Heaven, visit Hemingway's House then have a drink and enjoy music at the infamous Green Parrot Bar. Visit the Historic Seaport District where you can watch boats, find great dining or catch a sunset cruise.brCheck out the Waterfront/Splash Park just behind the complex. Playground for kids, walk the pier at night to watch sunsets, entrance to Fort Zachary Beach and much more. You are close to everything!!! brThis condo is also our vacation home. We take pride in our condos and want our guests to relax and feel as if they are in their home away from home. br To see our other VRBO Key West listings:brTruman Annex Shipyard (2 bed, 1 bath) Conch Retreatvrbo.com/261681habrTruman Annex Shipyard (3 bed, 2 bath) Sea Breeze Cottage vrbo.com/987489ha

Bed

Bath

Sleeps

$469.2

/ Nightly

Private Vacation Home

Hemingway Hideaway in the Truman Annex

Key West, Florida, United States

Hemingway Hideaway – Charming Townhouse in Truman Annex at Historic Foundry BuildingbrbrDiscover your perfect Key West retreat in this beautifully positioned 3-story townhouse within the coveted Truman Annex community. Just steps away from the vibrant heart of Key West, Hemingway Hideaway offers the ideal blend of comfort, convenience, and classic island charm.brbrProperty Highlights:brbrGated Entry & Private Courtyard: Enjoy privacy and tranquility as you enter your own peaceful oasis.brbrOpen Floor Plan: The spacious first floor seamlessly connects the living room, dining area, and fully equipped kitchen — perfect for relaxing or entertaining.brbrHalf Bath/Powder Room: Conveniently located off the kitchen.brbrMaster Suite on Second Floor: King-size bed, ensuite bathroom, two linen closets, in-unit washer/dryer, and a private balcony for morning coffee or evening relaxation.brbrThird Floor Bedroom: Queen-size bed occupies the entire level with its own ensuite bathroom.brbrDesignated Parking: One assigned parking space located at the rear of the unit.brbrPrivate Pool: Enjoy access to the Foundry building’s exclusive pool — a refreshing escape after a day exploring.brbrComplimentary Bicycles: Two bikes included to effortlessly explore Key West like a local.brbrPrime Location:brJust steps from the Truman Amphitheater & Splash Park, Fort Zachary Taylor, the Historic Seaport & Mallory Square, Truman’s Little White House, and popular spots like the Green Parrot. Within a 4-block radius of the lively 200 block of Duval Street — where all the action happens!brbrBooking Notes:brbrHemingway Hideaway – Charming Townhouse in Truman Annex at Historic Foundry BuildingbrbrDiscover your perfect Key West retreat in this beautifully positioned 3-story townhouse within the coveted Truman Annex community. Just steps away from the vibrant heart of Key West, Hemingway Hideaway offers the ideal blend of comfort, convenience, and classic island charm.brbrProperty Highlights:brbrGated Entry & Private Courtyard: Enjoy privacy and tranquility as you enter your own peaceful oasis.brbrOpen Floor Plan: The spacious first floor seamlessly connects the living room, dining area, and fully equipped kitchen — perfect for relaxing or entertaining.brbrHalf Bath/Powder Room: Conveniently located off the kitchen.brbrMaster Suite on Second Floor: King-size bed, ensuite bathroom, two linen closets, in-unit washer/dryer, and a private balcony for morning coffee or evening relaxation.brbrThird Floor Bedroom: Queen-size bed occupies the entire level with its own ensuite bathroom.brbrDesignated Parking: One assigned parking space located at the rear of the unit.brbrPrivate Pool: Enjoy access to the Foundry building’s exclusive pool — a refreshing escape after a day exploring.brbrComplimentary Bicycles: Two bikes included to effortlessly explore Key West like a local.brbrPrime Location:brJust steps from the Truman Amphitheater & Splash Park, Fort Zachary Taylor, the Historic Seaport & Mallory Square, Truman’s Little White House, and popular spots like the Green Parrot. Within a 4-block radius of the lively 200 block of Duval Street — where all the action happens!brbrBooking Notes:brbrMinimum 7-night stay required between January 1 – April 30, 2020, with Saturday-to-Saturday check-in/check-out.brbrOutside this period, flexible arrival and departure days.brbrDiscounts available for stays of 28 nights or longer.brbrIf this property is booked, we can recommend other great homes in the area.brbrPack your suitcase and get ready for an unforgettable Key West getaway in your home away from home!brbrOutside this period, flexible arrival and departure days.brbrDiscounts available for multiple months staysbrbrIf this property is booked, we can recommend other great homes in the area.brbrPack your suitcase and get ready for an unforgettable Key West getaway in your home away from home!

2

Bed

2

Bath

6

Sleeps

$392.56

/ Nightly

House Boat

Serene 3-bedroom house boat with AC in Key West

Key West, Florida, United States

Discover the charm of “Old Key West” aboard Vita Felice and embark on the journey of a lifetime by staying on a Luxurious Vintage Yacht and a piece of American History. This stay is paired with a smaller boat for cruising and exploring the waters. The location near downtown Key West is perfect for exploring the island on land but also provides a great opportunity to enjoy activities normally provided by boat charters. This unique opportunity gives you a secluded stay with a beautiful open water view unmatched by any other Key West lodging but also gives you freedom of water activities that would normally require a charter. Fishing, lobstering, and snorkeling are among many of the activities, including exploring on a small boat that can be used for island hopping and sandbars.brbrThis yacht was “The first Hatteras” certified for charter and is anchored offshore Key West Island and it’s accessible by boat. This elegant vessel offers a timeless escape into the Grandeur of the Past in True Old Key West Style. Experience authentic boating living in the ocean at anchor with a secluded tropical paradise on the water, without neighbors in close proximity! Anchored just a short boat ride from land.brbrExperience the Enchantment of Key West and unwind while Snorkeling, Swimming, or Fishing, and Capture a Breathtaking Iconic Sunset at Sea!brbr#Provided Equipment (No extra charge):brSnorkeling GearbrLobstering Kits brbrThis yacht offers everything you could desire! Perfect for Catch, Clean & Cook videos to share with friends and family.brbr#Amenities On Deck! brSpacious Bow & Aft DeckbrBow Cushions for Lounging and SunbathingbrAft Deck Chairs & Couch for Entertaining br]Outdoor Sink & Tables for Cooking & Cleaning your Catch , Inside full kitchen for cooking.brColor-changing led lightsbr brInside, Features Beautifully Preserved Original Mahogany Woodwork and Down Helm for Authentic Boating Experience and Pictures to Document and Share of Your Vacation.brbr#The Main Salon Includes:brBose sound bar system brSmart TV brWi-FibrColor-changing led lightsbrElectric CoolerbrDedicated A/C brTwo Convertible Couches Option into Two Twin Beds or a California King Bedbrbr#This Yacht comes Equipped with a Full Kitchen with Modern Home-Sized Appliances: brFull Sized Refrigerator brFull Sized 4 Burner Flat Range with OvenbrLarge Microwave brComplete Cookware and DishesbrToaster brTea KettlebrPantrybrbr#The Captain's Quarters Accommodations: brQueen Walk-Around Bed Nautical-Themed Bedding with Memory Foam ToppersbrTwo End Tables with Lampsbr32” Smart TVbrDedicated A/CbrAmple LightingbrFull ClosetbrEn Suite Full Private Bathroom Stocked with Fluffy Towels, Hair Dryers and Complimentary Toiletriesbrbr#The Guest Cabin: brTwo Single Beds with Nautical-Themed Bedding with Memory Foam ToppersbrFull ClosetbrDedicated A/CbrFull Guest Bathroom Stocked with Fluffy Towels, Hair Dryers and Complimentary Toiletriesbrbr#The V Berth includes: brBunk Beds with Nautical-Themed Bedding with Memory Foam ToppersbrDedicated A/CbrWasher/Dryer Combobr Linen Closet brExtended Shower Room with Vanity Stocked with Fluffy Towels, Hair Dryers and Complimentary ToiletriesbrbrVita Felice is Perfect for your next Special Occasion or Fun Getaway! brComplete with its Extensive Accommodations and Amenities! brbr#Spacious Timeless Classic Yacht for Events:brCelebration of Life/Memorial CeremonybrBachelor/Bachelorette PartiesbrProposalsbrHoneymoonbrBirthday Party'sbrbrThe dinghy rental for this boat is required and is the deposit for your nightly stay. Deposit is paid within 3 Days after you book your nightly stay. Pricing for the dinghy is $215 per day and is a bareboat rental that can be self drive or you can hire a captain to drive you and a list of captains can be provided. In addition to the dinghy rental there is a water taxi that can be used. We recommend the self drive dinghy as it allows for an extra guest, cheaper and is fairly easy to operate.brbrWe give a low nightly rate along with the second boat rental as a 2-in-1 deal to give you a good price for your vacation and ultimate freedom on the water for up to 8 guests. This is like being on charter during your entire vacation to allow for water activities you cannot experience in a marina. With Vita Felice in a fixed, stationary state at anchor the costs are tremendously reduced. ON A TYPICAL LARGE BOAT CHARTER the majority of your costs are crew and when the boat is moving to anchor from the dock and from anchor back to the dock and once the boat is anchored out on the water is the only time you can enjoy different water activities. With this option you stay at anchor during your ENTIRE STAY, in a location where a charter would usually take place; a regular paid charter is only a few hours. THIS IS NOT A REGULAR EXPENSIVE CHARTER FOR ONLY A FEW HOURS, the boat for your stay is moored in the water away from land like what you would do at the peak of a regular paid charter, to enjoy activities! With your stay at anchor you can then use the small self drive boat to further your exploration making for a very exiting yet cost effective stay with the ability to get the absolute most from your vacation! If you are wanting to spend thousands on a private captained charter this is not for you. This option provides much more time and freedom on the water enjoying the activities that most seek in Key West! Enjoy having the time to experience all the different water activities like Snorkeling, Lobstering, Fishing, Sandbars, Island hoping and much more! We provide Snokeling Gear and Lobster Kits free for our guests!brbrBoth boats require a liability release contract as boating and associated activities are inherently dangerous. All guests need to be physically capable because this is a large boat that sits high in the water and requires climbing a ladder to board. This is an authentic yacht boating experience and is at anchor. All rules and regulations of the water apply to your stay including driving a boat under the influence, which is not permitted and boaters safety course is required to rent(30 minute online course). Safety is of number one concern and safety liability is the renters responsibility, so BE SAFE!brbrPlease conserve fresh water and electric as water for the boat is from the onboard fresh water tank and electric is produced from a generator, excessive use will result in excess charges. One 30 Gallon Tank of propane for electric is included in the price and 75 gallons of fresh water. Please conserve during showers and any other use of water. Salt water is unlimited use!

3

Bed

2

Bath

8

Sleeps

$247.54

/ Nightly

Private Vacation Home

Angel Fish Cove | Updated Townhome Retreat Near Duval

Key West, Florida, United States

Angel Fish Cove | Tropical Townhome Retreat Near Duval StreetbrbrWelcome to Angel Fish Cove, a charming tropical townhouse tucked away in the serene Presidents Walk & Southard Court community of the highly sought-after Truman Annex in Old Town Key West. This beautifully renovated two-bedroom, two-and-a-half-bath monthly vacation rental offers the perfect blend of island tranquility and unbeatable walkability. Just two short blocks from Duval Street and less than half a mile from one of Key West's best beaches, Angel Fish Cove places you close to everything—while still giving you a peaceful place to unwind and recharge.brbrWhether you're here to explore historic Old Town, soak up the sun, or enjoy world-class dining and nightlife, Angel Fish Cove is your private slice of paradise in the heart of Key West.brbrThe Ambiance:brStep inside Angel Fish Cove and immediately feel the relaxed island vibe. Tropical décor, thoughtful updates, and inviting indoor-outdoor spaces make this townhouse ideal for an extended Key West stay. Designed for comfort and ease, the home includes:brbr- Two comfortable bedrooms offering privacy and space for rest and relaxationbr- Two full bathrooms plus a convenient half bath for guestsbr- An updated kitchen with modern appliances, perfect for cooking at homebr- Three TVs throughout the home, including flat screens upstairsbr- Complimentary high-speed Wi-Fi to stay connectedbr- Covered parking for one vehiclebrbrThis home's layout and atmosphere make it easy to settle in, slow down, and truly enjoy the Key West lifestyle.brbrGuest Access:brGuests enjoy full access to the entire townhouse, including private outdoor spaces and a designated covered parking spot. Located within the secure Truman Annex community, Angel Fish Cove offers a quiet residential feel while remaining close to all the action of Old Town.brbrLocation Highlights:brAngel Fish Cove is perfectly positioned in the heart of Old Town Key West within the desirable Truman Annex community, offering the ideal mix of convenience and tranquility. Just two blocks from lively Duval Street, you'll have effortless access to the island's best restaurants, bars, boutiques, and nightlife. Historic landmarks, cultural attractions, and scenic прогул spots are all within easy walking distance, while one of Key West's most beautiful beaches is less than half a mile away. From sunset strolls and water adventures to dining and entertainment, everything that makes Key West unforgettable is just moments from your door—yet the home remains peacefully tucked away for true relaxation.brbrTransportation Tips:brWith a dedicated covered parking space, exploring the island by car is easy. Many guests choose to walk or bike everywhere, thanks to the home's central location. Scooters, bikes, golf carts, taxis, and rideshares are all readily available for getting around Old Town and beyond.brbrOther Things to Note:br- Covered parking includedbr- High-speed Wi-Fi and multiple TVs throughout the homebr- A minimum stay of 30 days is required, in accordance with local regulationsbr- Guests must be 25 years of age or older to reservebrbrCheck-in: 3:00 PMbrCheck-out: 11:00 AMbrbrAt Colocada Vacation Rentals, we take pride in offering thoughtfully curated homes that let you experience Key West like a local. If you have questions or would like recommendations for dining, activities, or hidden gems, we're always happy to help make your stay at Angel Fish Cove unforgettable.

2

Bed

2

Bath

6

Sleeps

$234.0

/ Nightly

Cottage

Sea Breeze Cottage 2 Large Decks, pool, free parking/wifi in Truman Annex

Key West, Florida, United States

Sea Breeze Cottage Cottage is a private, tropical, stand alone cottage located in the prestigious Truman Annex. brStarting Jan 2026 , this beautiful cottage will become monthly! Stays will have to be 28- 30 days. Discount of 10% for monthly stays. Make plans to stay longer, relax or work remotely from paradise for a full month in 2026. LOCATION is what it's all about. No need for a car, everything is close. Upper deck looks out over the Waterfront Park. br- King bed and Queen bed upstairsbr- Twin beds downstairs can be converted to a king by request. br- Bathroom upstairs has double sinks and separate room with toilet and walk-in shower. br- Bathroom downstairs with walk-in shower, vanity w/sink and toilet. br- Fully equipped kitchen has everything you need for your stay.br- Washer & Dryer, towels & linens, including beach towels and beach chairsbr- Central air & ceiling fans.br- Sea Breeze living area has 2 sets of double doors that opens to large covered deck with outdoor furniture seating for 6.br- Large deck upstairs off of queen bedroom with outdoor br furniture seating for 6.br- TV's in all bedrooms and living room with cable and Air Playbr- Free Hi speed internetbr- Assigned parking for 1 vehicle. br- Large heated pool for Shipyard guests only.brbrYou are close to everything! Explore the Waterfront Park behind the complex. Take a stroll to the Waterfront Pier, watch sunsets and sailboats. Fort Zachary Park and Beach is a short walk or bicycle ride. Mallory Square where you can watch nightly Sunset Celebrations, local vendors and entertainment. brJust 2 blks to Duval Street, for dining, shopping, night clubs and museums. You are steps away to the Truman Annex heated pool. brOur Luxury Caribbean Cottage is Spacious & Quiet!! brThere is much to do and see in this Southernmost City.brbrTo see our other VRBO Key West listings:brTruman Annex Shipyard (1 bed, 1 bath) Island Escape vrbo.com/934388habrTruman Annex Shipyard (2 bed, 1 bath) Conch Retreat vrbo.com/261681ha

3

Bed

2

Bath

6

Sleeps

$2227.46

/ Nightly

Hotel

3BR Villas for Your Beach Getaway with Shuttle Service, Onsite Parking, Pools!

Key West, Florida, United States

This listing is for 2 separate rooms within a hotel. The price shown in the listing covers all 2 rooms.brbr✦ Each room is 1525 sq. ft, equipped with complimentary toiletries, TV.brbr✦ Rooms are not adjoining and possibly not next to each other. Spaces are assigned upon arrival based on availability.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✦ Fitness center is available.brbr✦ Pool is available.brbr✦ Paid valet parking – 1 space(s), available for $32.25 per day.brbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A mandatory resort fee of $51.00 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.

6

Bed

2

Bath

16

Sleeps

$1074.35

/ Nightly

Hotel

Family Fun at a Beachfront Location with Onsite Pools, Parking, Shuttle Service!

Key West, Florida, United States

This listing is for a room within a hotel.brbr✦ Your room is 1525 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✦ Fitness center is available.brbr✦ Pool is available.brbr✦ Paid valet parking – 1 space(s), available for $32.25 per day.brbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A mandatory resort fee of $51.00 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.

Bed

Bath

Sleeps

$1418.63

/ Nightly

Hotel

Tropics Escape in Key West with Onsite Pools!

Key West, Florida, United States

This listing is for 2 separate rooms within a hotel. The price shown in the listing covers all 2 rooms.brbr✦ Each room is 925 sq. ft, equipped with complimentary toiletries, TV.brbr✦ Rooms are not adjoining and possibly not next to each other. Spaces are assigned upon arrival based on availability.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✦ Fitness center is available.brbr✦ Pool is available.brbr✦ Paid valet parking – 1 space(s), available for $32.25 per day.brbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A mandatory resort fee of $51.00 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.

Bed

Bath

Sleeps

$709.81

/ Nightly

Hotel

Relaxing Beach Getaway, 2BR Villa, with Onsite Pools, Onsite Parking, Shuttle!

Key West, Florida, United States

Step into a world of white sands and glimmering pools, where boat drinks and watersports are just steps from your front door. Explore vibrant Duval Street's shops and nightlife. Lounge at Smathers Beach via our complimentary shuttle. Immerse in historic Old Town Key West's charm. Adventure with kayaking and water sports, then unwind at our four pools. Your ideal Key West getaway awaits!brbrThis listing is for a room within a hotel.brbr✦ Your room is 925 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✦ Fitness center is available.brbr✦ Pool is available.brbr✦ Paid valet parking – 1 space(s), available for $32.25 per day.brbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A mandatory resort fee of $51.00 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.

2

Bed

2

Bath

4

Sleeps

$2036.3

/ Nightly

Hotel

Two 3BR Paradise Suites in Key West, Shuttle Service, Onsite Parking, Pools!

Key West, Florida, United States

This listing is for 2 separate rooms within a hotel. The price shown in the listing covers all 2 rooms.brbr✦ Each room is 1525 sq. ft, equipped with complimentary toiletries, TV.brbr✦ Rooms are not adjoining and possibly not next to each other. Spaces are assigned upon arrival based on availability.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✦ Fitness center is available.brbr✦ Pool is available.brbr✦ Paid valet parking – 1 space(s), available for $32.25 per day.brbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A mandatory resort fee of $51.00 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.

Bed

Bath

Sleeps

$1009.07

/ Nightly

Hotel

3BR Family-Friendly Unit in Key West, Onsite Parking, Poolside Bar!

Key West, Florida, United States

This listing is for a room within a hotel.brbr✦ Your room is 1525 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✦ Fitness center is available.brbr✦ Pool is available.brbr✦ Paid valet parking – 1 space(s), available for $32.25 per day.brbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A mandatory resort fee of $51.00 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.

3

Bed

3

Bath

8

Sleeps

$340.83

/ Nightly

Private Vacation Home

Hemmingway's Paradise! Walk or bike to all that Old town Key West has to offer

Key West, Florida, United States

Welcome to Hemmingway's Paradise! brLocated on an almost hidden enchanting lane in Old Town Key West, this cottage is the perfect hideout for guests. Knowles lane is a very small 1 block single lane street with only a few historic homes built on it. Remodeled to historic requirements in 2023, this home has been meticulously maintained and outfitted for guest pleasure and comfort. brThis 3 bedroom and 2.5 bath home is sure to wow guests with its top-of-the-line finishes and decor. brWith two historic original front porches, you'll most likely find yourself front porch sitting enjoying your morning coffee or enjoying a glass of wine on the wooden porch swing as neighbors walk by and say hello, no traffic on this lane! Even though the home has 2 off street parking spaces, one for a car and one for a golf cart or small compact car, most cars won't drive the small lane.brThe home features a teak wrap-around deck with a new hot or cool spa and ladder stairs leading up to the rooftop tanning deck with loungers, a patio mister and tropical foliage where you can soak up the sun during the day and stargaze at night. All deck and garden areas are equipped with timed soaker hoses or drip lines and you can pick your fresh limes and lemons from the potted citrus trees and relax amid the lush tropical foliage and optimal privacy. brThe front suite with its large ensuite bathroom has your private front door entry and porch and an additional bathroom door leading to the outside deck. brFront Suite amenities include a Keurig coffee station, mini fridge and microwave to allow you to rise and shine or end your evening at your own pace. The main living area features full corner glass double doors leading to the outdoor deck living area and the weekly maintained new jetted Spa, outdoor patio lighting, outdoor shower, and the ladder to the rooftop tanning deck. brThe kitchen offers everything you'll need to create a gourmet meal in home or to chill out and blend up that perfect pitcher of Pina coladas. New stainless appliances including an in fridge craft ice maker to mold up the ultimate large round ice spheres, cubed or crushed ice, a wine fridge, a full pot or K-cup coffee maker and a Nespresso machine for your morning espresso. brTake a short leisurely walk or bike ride to Higgs beach, Duval Street, The Hemmingway House, the Key West waterfront, restaurants, world famous bars and shopping and all that Old Town has to offer. Bicycles with locks, beach chairs and beach towels are also included.

Bed

Bath

Sleeps

$655

/ Nightly

Private Vacation Home

Admiral's Paradise at the Truman Annex in Key West

Key West, Florida, United States

Newly renovated town home located on a charming lane in the Truman Annex. The generous open floor plan features 10 foot ceilings both on the first and second levels with hardwood floors and crown molding. Enjoy the theater style kitchen with new quartz counter tops and stainless-steel appliances with a gas cook top. The large living and dining area feature custom built-ins and ample storage. The beautiful rear tiled patio enjoys plenty of room for outdoor living and entertaining and includes an additional storage space. The second floor has two generous sized bedrooms with private baths. One assigned covered parking space. With access to a refreshing community pool right out side your front door.brbrPlease note: This property is monthly rental - This property has a 28 night minimum stay

2

Bed

2

Bath

4

Sleeps

Select Dates for Price

Coastal Living Charm with Pool and Backyard Oasis

Key West, Florida, United States

Welcome to your getaway in The Meadows, one of Key West’s most desirable and peaceful neighborhoods. This newly constructed beautifully designed 3-bedroom, 3-bath Coastal Living–inspired home offers a perfect blend of luxury, comfort, and effortless vacation living. Ideal for couples, families, or two families traveling together, this retreat is designed for pure relaxation—where style, serenity, and connection come naturally. brbrAs soon as you step inside, you’re greeted by gorgeous fir wood floors that lead you into a spacious living room that seamlessly flows into a fully equipped kitchen, features include stainless steel appliances, quartz countertops and large island. Full sliding doors lead out to a private deck, creating the perfect indoor–outdoor retreat with outside dining and grill plus heated pool, surrounded by palm trees and tropical landscaping for added privacy. brbrThis property is just seven blocks from the Famous Duval Street, making it the perfect location for those who want to be close to the action while enjoying a peaceful retreat. On-street parking is available for your convenience. Free WiFi is included, so you can stay connected while you relax.brbrThe estimated square footage of this home is 1500 sf providing plenty of space for you and your guests to spread out and make yourselves at home. brbrPlease note that this is available only for monthly rentals, with a minimum stay of 28 days. Don't miss out on the opportunity to experience the tranquility and serenity of this beautiful vacation rental. Book your stay today and start planning your dream vacation!

Bed

Bath

Sleeps

$601.25

/ Nightly

House Boat

Charming 1-Bedroom, Sailboat in wonderful Key West

Key West, Florida, United States

A Unique Key West Getaway!brWelcome aboard Sparhawk! This beautiful 30-foot Baba double-ender sailboat offers a cozy and unforgettable stay for up to 2 adults. Crafted with warm teak interiors and timeless nautical charm, Sparhawk is perfect for couples, small family or adventurous souls looking for something off the beaten path.brbrWhat makes Sparhawk special:brbr- Authentic teak interior with vintage maritime charmbr- Docked at the upscale Perry Hotel & Marinabr- Access to 2 pools, 3 restaurants, and daily happy hourbr- Complimentary shuttle to downtown Key Westbr- Optional sailing trips for additional cost with an experienced Captain—just ask!brbrWhether you’re sipping coffee on deck as the sun rises or hopping on the shuttle to Duval Street for nightlife and island vibes, Sparhawk offers the perfect mix of adventure and relaxation.brbrWant to set sail Let us know and we’ll arrange a private trip with one of our Captain!brbrGuest have full access to the entire boat and all of the amenities of the marina and resort free of charge - parking, pools, clubhouse, poolside bar, fitness center, etc...

1

Bed

2

Sleeps

Exceptional(9)

$565.75

/ Nightly

Private Vacation Home

Shared Pool & Parking - The Cottage at James House

Key West, Florida, United States

Summary:brbrEscape to this cozy 1-bedroom, 1-bath cottage at the historic Curry Mansion Inn in downtown Key West. This fully equipped retreat features a kitchen, comfortable living area, and private parking. Just steps from Duval Street, enjoy easy access to top dining, nightlife, and attractions. Blending historic charm with modern amenities, it’s the perfect island getaway. brbrNote: Pool closed April 20–27.brbrbrbrThe Space:brbrThis comfortable 1 bedroom,1 bathroom offers everything you need for a Key West getaway. With its full kitchen and private entrance you will feel right at home!brbrAs part of your stay, you’ll have access to the beautiful shared outdoor spaces at Curry Mansion. Relax on the porch, or take a dip in the communal pool to cool off after a day in the Florida sun. brbrbrbrBed Layout:brbrBedroom: Queen BedbrbrLiving room: Full Sized Sleeper SofabrbrFull Kitchen: Stove/Oven, Refrigerator, MicrowavebrbrbrbrGuest Access:brbrOur contactless check-in makes the process seamless. Guests will receive a personalized access code before arrival as well as code to the front door code to the James House & Curry Mansion amenities. Guests will also have direct contact to a local guest experience manager for any questions, needs or recommendations during their stay.brbrbrbrThe Neighborhood:brbrEnjoy live music every Saturday from 6-8pm at George's Bar!brbrbrbrPlaced perfectly between downtown Key West and the Historic Seaport, enjoy walkable attractions like Fury Water Adventures for a day at sea, the Mel Fisher Maritime Museum for some Key West history and the famous Mallory Square for a Sunset Celebration. brbrbrbrSteps from Duval Street, the Curry Mansion is steps away from Key West's most famous bars and kitchens. Food is at your fingertips with locals favorite restaurants, such as First Flight, Bagatelle and Two Friends Patio, less than a 5-minute walk from your front door. Got a sweet tooth Keep an eye out for Kermit’s Key Lime Pie Shoppe 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 will also find Fausto’s Food Market with locally sourced groceries.brbrbrbrGetting Around:brbrThere are a variety of great ways to explore Key West whether it be by bicycle, pedi-cab, Moke, scooter, golf cart, Uber, taxi or foot. Being in the heart of downtown Key West, many attractions are within walking distance. Please note we can not guarantee parking, but feel free to ask us for recommendations!brbrbrbrOther Things to Note:brbr- Laundry facilities are shared - to get you started we supply detergent and dryer sheets.brbr- Pet friendlybrbr•40lb maximum per petbrbr•$25/per nightbrbr•2 pet maximumbrbr- Private Parking Spot

Bed

Bath

Sleeps

$412.62

/ Nightly

Private Vacation Home

SOUL OF THE SEA ~ Charming 3 BR, 3 Ba Home w/ Pool and Parking!

Key West, Florida, United States

HISTORIC ISLAND CHARM...brLocated in the Casa Marina Area of Old Town which is known for lovely and sophisticated homes, this unmatched retreat is no exception. Modern architectural elegance emanates from every corner, inviting you to bask in serenity and escape reality. Winner of the Ceramic Star from the Historic Florida Keys Foundation, your idyllic abode is filled with expansive entertaining space both inside and out. Enter through your white picket gated fence onto the delightful covered porch where your day begins with a morning coffee and an island song in your heart.br***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGEbrbrDETAILS AND AMENITIES..brThoughtfully designed and well appointed, the open-concept living-room, kitchen and dining area offers endless possibilities and dramatic ceiling heights. The kitchen includes every modern convenience with a gorgeous island with seating for 4, hood, gas stove top and sparkling stainless appliances. Dine on your fresh catch at the rectangular dining table that seats 8, then revel in your favorite tv shows from the inviting modern couch or plush seating on your large tv. Oversized windows invite Key West natural light in, coaxing you to your backyard oasis, just beyond the large sliding glass doors.brbrSLEEPING ARRANGEMENTS...brThe first bedroom resides just off the entrance hallway, a delightful space with two twin beds that can be converted to a king, TV, dressers, hanging closet and bathroom with quartz sink vanity and tiled shower, which can be entered from the hallway also. The second bedroom is also located on the entrance hallway and includes a plush king bed, TV, dressers and hanging closets, and a private bathroom with large tiled shower. Travel up the steps to the vaulted bonus room and primary suite. A perfect entertaining space, this intimate living area hosts a sitting area with TV and a workspace. Travel down the hallway that offers closets, storage drawers and a washer/dryer space. The bedroom is outfitted with a king bed, TV, storage cabinet and a luxurious bathroom with a shower and jet soaking tub.brbrPOOL AND OUTDOOR LIVING...brSink into outdoor seating and table for 4 on your patio under the stars or stretch out in one of the lounge chairs and gaze into your private sparkling pool (heated in winter months). Lush landscaping and balmy breezes surround you, captivating your island soul. Fire up the gas grill for your outdoor feast with a crafted cocktail in hand. This home is walking distance to the Key West Artisan Market and Higgs Beach so you can enjoy ocean views and pickle ball courts at your leisure. brbrPARKING...brOne larger off street parking is provided.brbrPETS...brThis is NOT a pet friendly home, and the owners do not make exceptions.brbrMULTI MONTH RESERVATIONS... brFor monthly reservations, the following fees will be added PER MONTH: brMid-stay cleanbrPool/hot tub heating fee (if applicable)brPet fee (if applicable)brbrBOOKING DATES...brThis home is only available as a monthly rental (28 night minimum). We prefer to book by the calendar month (first day of the month to the last). We may consider alternate dates if the calendar allows or if the owner will make an exception.brbrCONCIERGE SERVICES...brEnjoy our concierge service to assist you with planning activities for your trip, from bike/scooter/golf cart rentals to any excursion you can think of including snorkeling and sunset cruises, jet ski rentals, parasailing, kayaking, fishing, paddle boarding and more. They can also have your fridge stocked with all the necessities in advance of your arrival!brbrCANCELLATION...brBookings canceled at least 90 days before the start of stay will receive a 100% refund. brbrCancellations inside of 90 days may receive a refund if we are able to re-rent any or all of the dates of the stay. The refund amount is dependent upon the rate of the new reservation. For multi-month reservations for January through March, a refund will only be offered in the event we are able to re-rent. The refund amount is dependent upon the rate of the new reservation.

Bed

Bath

Sleeps

$1409.57

/ Nightly

Private Vacation Home

MERMAID COVE - A collection of four units on Duval

Key West, Florida, United States

Mermaid Cove features four separate units (two cottages and two apartments), each with a private entrance and all decorated and furnished in charming tropical fashion. The units surround a central courtyard with outdoor patio furniture and a large gas BBQ grill. Mermaid Cove allows you to gather as a group, but also enjoy privacy. With accommodations for up to 10 people, it is perfect for extended families, a bunch of friends, bachelor/bachelorette parties, or wedding parties.brbrMermaid Unit 1 is an upstairs unit with a king bed, full kitchen, full bathroom, and living room with full sofa and a mini-split air conditioner. The living room has a flat-screen Smart TV and French doors that open onto a deck with table and chairs. It sleeps two people.brbrFunky Unit 2 is downstairs with a queen bed, full bathroom, mini kitchen with under-the-counter fridge, microwave, toaster oven, coffee maker, blender, a smart TV, and a mini-split air conditioner. It sleeps two people.brbrOcean Cottage 3 is free standing and has a king bed with French doors that open onto the central courtyard. The bathroom includes a shower. The kitchen has a mini-fridge, microwave, toaster oven, coffee maker, blender, smart TV, and a mini-split air conditioner. It sleeps two people.brbrNautical Cottage 4 is at the rear of the courtyard and features natural cedar walls. At the entrance is a beautiful mosaic-tiled 20-foot wall with a one-of-a-kind mural of a Key West beach scene with a Mermaid! This unit features 2 queen beds, a bath with shower, kitchen with a mini-fridge, microwave, toaster oven, coffee maker, blender, a flat screen smart TV, a small sitting area/dining table, and a mini-split air conditioner. It sleeps four people.brbrThe courtyard has a large Weber Genesis grill and large outside stainless steel sink that can be used to clean your catch of the day from your fishing excursions. The lights on the patio at night can be casual with the blue rope or blue lamps, or you have the ability to turn on a powerful LED light to light up the entire patio. The courtyard also has a Mermaid bottle opener and a weathered bell to get everyone's attention for a special toast or occasion. brbrNote: Parking in Key West is very limited. This property has no assigned parking and is street parking only. You are responsible for finding parking for your vehicle.brbrPlease note that this property does not have a pool. brbrThe individual making the reservation must be 25 years or older with proper identification and be an occupant of the property. The maximum number of people allowed in this property is 10. If there are more than 10 people are in your party upon arrival, your party will be asked to leave without compensation. Violation of ANY house rules will result in your party being asked to leave without compensation.

4

Bed

4

Bath

10

Sleeps

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