Vacation Home Rentals By Owner In Key West, FL

Welcome! This beautiful cottage (sleeps 6) is located in the Coconut Mallory Resort & Marina on the eastern end of Key West. This secluded, waterfront oasis includes outdoor pools, hot tub, on-site marina and boat dock. There's also a new bar & grill, Gumbo's, in the resort. When you want to get out and explore KW, you're only minutes from beaches, the Seaport and world famous Duval Street! Bikes, kayaks, paddle boards and golf carts can be rented locally. Remember to bring your shades, flip flops, sunblock and bug repellant! brbrI'm an experienced super host with a handful of rentals and I expect you'll be delighted with the cleanliness and amenities provided at this Poolside Cottage. brbrThe cottage sleeps 6 peoplebrbrSleeping Arrangement:brbrBedroom #1:br- King Size Bed (sleeps 2)br- Two Nightstands with Reading Lampsbr- Dresserbr- 25 Flat Screen TVbrbrLiving Room:br- Sofa with Pull-Out Queen Size Bed (sleeps 2)br- Murphy Bed (sleeps 2)br- Chairbr- Desk and Chairbr- 46 Flat Screen TVbrbrDining Room:br- Dining Table with Seating for 4brbrKitchen:br- Fully Equipped (all things necessary to prepare and serve a meal)br- Coffee Makerbr- Toasterbr- Blenderbrbr--------------------------------------------brbrAMENITIES:br- 2 Outdoor Community Pools and a Hot Tubbr- Picnic Area with BBQ Grillsbr- Boat Slips (limited availability & additional fee. Please see additional information below)br- Trailer Parking (limited availability. Please see additional information below)br- Bikes, Kayaks, Paddle Boards and Golf Carts can be rented locallybr- Full-Size Laundry designated for #411 & #412br- Linen's and Towels ProvidedbrbrThere is one dedicated parking space for #411brbrBoat slip or trailer parking is not included, but guests can reserve a boat slip and trailer parking through Coconut Mallory Resort in advance and for a fee. They are both generally available, though we highly recommend booking as soon as you book the cottage.brbrRegarding reservations: all guests have an option of paying a $59 fee that is non-refundable (it covers us in case of damage) OR you can pay a $1500 deposit that IS 100% refundable, assuming there's no damage.brbrBy reserving the Poolside Cottage, you acknowledge and agree to our Rental Agreement & Release of Liability, which can be found under the Rental Agreement section of this listing. We’ve included this just to keep everything clear and safe, so you can focus on relaxing and enjoying your tropical getaway.

Poolside Cottage #411

Key West, Florida, United States

Bed

1

Bath

6

Sleeps

$317.95

Summary:brbr3 bedroom house in downtown Key WestbrbrbrbrThe Space:brbrSet in the heart of Key West's vibrant Meadows district, this delightful 3-bedroom vacation rental on iconic White Street is a gateway to unforgettable memories. Perfectly positioned for convenience, a mere stroll unveils sun-kissed beaches, eclectic dining venues, and vibrant entertainment spots. Exuding a vibrant and quirky charm, the spacious house is tailor-made for families seeking a fun-filled escape. Boasting 3 well-appointed bedrooms and 2 bathrooms, complete with a captivating clawfoot tub and walk-in glass shower, the property exudes character at every turn. A fully equipped kitchen, welcoming living area, and a charming outdoor space provide the perfect backdrop for relaxation and togetherness. Embrace the essence of Key West living in this whimsical haven, promising a memorable vacation filled with laughter, comfort, and exploration at every corner.

GypsyGinny's Hideaway

Key West, Florida, United States

Bed

Bath

Sleeps

$584.86

Summary:brbrWaterfront 5 bedroom residence with pool and 35 dockbrbrbrbrThe Space:brbrEscape to a luxurious waterfront oasis located at Key Haven, just a stone's throw from Key West. Bring your boat up to 35 FT. This expansive 3000 square foot mansion boasts 5 bedrooms and a sprawling open floor plan encompassing the living and dining areas. Revel in the mesmerizing water vistas from your personal paradise. Each bedroom features an en suite bathroom, with 2 master bedrooms on separate floors for added privacy and comfort. Entertainment is effortless with a charming Wet Bar area perfect for family movie nights or game evenings. The 2-car garage ensures convenience, while the generous pool and observation deck invite relaxation and stargazing. Dockage for a boat up to 35 FT adds to the allure of this exquisite property, providing easy access to aquatic adventures. Security is paramount with a gated perimeter, offering peace of mind throughout your stay. Nestled on a double lot, the lush landscaping enhances the serene ambiance, creating a tranquil haven for your Key Haven getaway.

Tideview Haven- 5 bedroom with pool& dock

Key West, Florida, United States

Bed

Bath

Sleeps

$2551.71

Perfect for large families or groups of friends, this property offers great amenities including a private pool, open floor plan, 2 kitchens, and a large laundry room, right downtown Key West.brbrYou hear all the time about grand homes tucked away in little private corners of Key West. Well, this is one of them. Located on a dead-end street just one block from Duval Street. There is parking for 2 vehicles -- a bonus in Old Town where parking is worth its weight in gold.brbrCasa Grande was built for hosting large gatherings for family and friends. A private home with plenty of space for everyone to relax in privacy or gather for food and fun. A wide-open floor plan encompasses the spacious living room and gourmet kitchen which opens to the magnificent pool, one of the largest private pools on the island.brbrLounge, dine or BBQ, you'll spend most of your time in this fully private backyard complete with a half bath and outdoor shower.brbrThere are two bedrooms on the first floor. The first bedroom has a king-sized bed and en-suite bathroom. Further down the hall is a suite with a kitchenette, a living area with a queen sleeper sofa, a second bedroom with a queen-sized bed, and an en-suite bathroom.brbrThe laundry room on the first floor is equipped with 2 sets of washers/dryers to ensure a clean supply of shorts, T-shirts, and swimsuits during your stay.brUp the stairs to the second floor are 3 additional bedrooms (1 king and 2 queens), 2 with bath en-suite bathrooms and all with flat-screen TVs and DVD players. One of the queen bedrooms has a trundle bed as additional sleeping accommodation for late night sleepovers.brbrCasa Grande offers one of the best locations in Key West. Less than one block off Duval Street you will be able to walk or bike to all the best activities that the island has to offer, including live entertainment, dining, and shopping. A short walk and you are at South Beach and the Southernmost Point. You can't help but enjoy the history of the island from this ideal location.brbrEntry Levelbr- Fully Equipped Kitchen with lots of counter spacebr- Seating for 12 around the high-top dining table and countertopbr- Additional Eat-in-Kitchen nook seats 6 to 8br- Glass cooktop stove and large 3-door refrigerator with Ice Makerbr- Living Room with 4 leather sofas and 1 is a Queen pull out Sleeper Sofabr- 50 flat-screen TV, games, and poker chipsbr- A king bedroom with attached bathroom with vanity and showerbr- Laundry Room with 2 Washers and 2 Dryersbr- Suite with an additional kitchen, living room, and queen bedroom with en-suite bathroombrbrUpper Levelbr- A king bedroom with en-suite full bathroombr- Queen bedroom with en-suite full bathroombr- Queen bedroom with additional Day Bedbr- Half bathroom in hallwaybrbrOutsidebr- Large swimming pool, 14 feet by 29 feetbr- 8 Lounge chairs, dining table, and chairsbr- Gas Bar-B-Que Grillbr- Large patio with bathroom and outdoor showerbr- Parking for two vehicles directly in front of the housebrbrKey West is the place to visit the lively nightlife and relax in the historic charm, flamboyance, and conch-style architecture that early Bahamian settlers made famous. It embodies a clash of the past and the present, and every building (including this rental) in Key West reflects this eclectic ambiance!brbrAvantStay provides a personalized hospitality experience to elevate your stay. With our Concierge Service, guests have access to our tech-enabled services like fridge stocking, private chefs, massages, transportation, special occasion celebrations, baby gear rentals, ski gear, beach gear, and more. For anything you need, we’re at your fingertips!brbr*Home Truths:*br- This home also features a sleeper sofa for additional sleeping.br- Pool heat is not available between 4/1 and 10/31.br- Pool heat is available for an additional fee but must be requested at least 48 hours before your stay.br- We allow service animals at this home. If undisclosed pets are brought into the home without AvantStay's approval there is a fine of $500 per pet.br- Any reservations 28 days or longer will require additional clean/cleans to be scheduled. Additional payment will be collected and the amount of cleans will depend on the length of your stay.br- All bookings 28 days or longer require a security deposit to be charged after booking.br- This home is on a monthly pest control schedule. The area of Key West is home to many insects such as termites, no-see-ums, and mosquitos. Pest control can not eliminate these insects during the swarming season. You may also encounter geckos, lizards, iguanas, frogs, and chickens during your stay in the area.br- Key West is a resort island where renovation of existing historic properties, new construction, and road repair sometimes occur without forewarning. AvantStay is not liable for any guest inconveniences caused due to construction in the area.br- Please note that max occupancy includes infants.br- Please be advised that documentation may be necessary for ESA/service animals to gain entry.brbrParking Details:brParking for two vehicles.brbr---brbrThe room configuration is as follows:brbrPrimary Bedroom / King bed w/ ensuitebrBedroom 2 / King bed w/ensuitebrBedroom 3 / Queen bed w/ additional kitchen and ensuitebrBedroom 4 / Queen bed w/ ensuitebrBedroom 5 / Queen bed & day bedbrbr---brbrThis is a smoke-free property. Violation of the no-smoking policy will result in forfeiture of the security deposit, a $300 smoking fee, and liability for any fire or property damage costs.brbrAs part of our commitment to being good neighbors, occupancy limits and quiet hours (9pm-8am) are strictly enforced. No speakers or sound systems will be provided for use in our properties. Violation of any noise ordinances will be subject to fines that can reach up to $10,000 per violation. brbrEvents or parties are not allowed without prior written approval and an additional fee. Any unauthorized parties or events will be shut down and a fine will be assessed. Please inquire for more information about our event policies and fees. brbrThere is nothing more important to us at AvantStay than the health, safety, and experience of our guests & staff. We've enhanced our cleaning and sanitation protocols and are taking extra care to disinfect all surfaces between reservations with hospital-grade disinfecting solutions.brbrAs a reminder, we do work with 3rd party vendors to maintain the property, and although we adhere to the strictest CDC guidelines and advise all contractors to wear PPE equipment, we can not always enforce. We strongly advise guests to please deny access if any vendors fail to meet and adhere to these standards.brbrIDs will be requested for verification after booking. brbrWe report and prosecute all Credit Card Fraud.

Casa Grande by AvantStay | Dt Key West | Near South Beach w/ Pool

Key West, Florida, United States

Bed

Bath

Sleeps

$211.53

*Please note that this home is available for 28+ night stays only.*brbrLocated in one of Key West’s historic and most cultural neighborhoods this lovely condominium will give you a cause to celebrate the island's way of life.brbrA fabulous location that will allow you to walk or bike to all the island highlights. In the heart of Old Town, Duval Street is an easy stroll to the live music, entertaining shops, and galleries along with Mallory Square where hundreds gather nightly to celebrate the setting sun and watch the local street performers. Fabulous food everywhere but the local's favorite and a Key West must, Santiago’s Bodega is just steps away and Blue Heaven where visitors flock for key lime pie and roosters run about your feet.brbrLocated in a private building with only four condominiums, this ground-level unit has been recently updated with appliances, granite countertops, and beautiful wood cabinets. The trendy urban feel to Emma’s Secret comes complete with flat-screen TVs, WIFI, and all you need in your home away from home. Cozy living spaces for the days you need a time out or place to hang your bag in between island adventures.brbrRelax by the breathtaking free-form pool and enjoy the hot tub as it spills over creating a soothing tropical retreat. A perfect place for collecting sunshine or just lazing the day away. Beautiful tropical foliage will surround you in this island oasis.brbrThis property will sleep 4 guests, with 2 bedrooms and 1 bath. Emma’s Secret features a queen bed along with a set of bunks for a dreamy night's rest and a fabulous full kitchen to whip up our favorite island fare or just a margarita.brbrThese properties are available on a monthly basis only but that’s OK, pack your bags, and bring a little extra because you might just not want to leave.brbrKey West is the place to visit the lively nightlife and relax in the historic charm, flamboyance, and conch-style architecture that early Bahamian settlers made famous. It embodies a clash of the past and the present, and every building (including this rental) in Key West reflects this eclectic ambiance!brbrAvantStay provides a personalized hospitality experience to elevate your stay. With our Concierge Service, guests have access to our tech-enabled services like fridge stocking, private chefs, massages, transportation, special occasion celebrations, baby gear rentals, ski gear, beach gear, and more. For anything you need, we’re at your fingertips!brbr*Home Truths:*br- Please note that all bookings 28 days or longer will require a security deposit of $2000 which will be collected after the booking has been made. Multiple months reservations might be subject to a higher security deposit fee.br- Any reservations 28 days or longer will require additional clean/cleans to be scheduled. Additional payment will be collected and the amount of cleans will depend on the length of your stay.br-This home has access to a community pool and hot tub. It is a combined pool & spa where water can flow.br- This home features a sleeper sofa for additional sleeping options.br- We allow service animals at this home. If undisclosed pets are brought into the home without AvantStay's approval there is a fine of $500 per pet.br- This home is on a monthly pest control schedule. The area of Key West is home to many insects such as termites, no-see-ums, and mosquitos. Pest control can not eliminate these insects during the swarming season. You may also encounter geckos, lizards, iguanas, frogs, and chickens during your stay in the area.br- Key West is a resort island where renovation of existing historic properties, new construction, and road repair sometimes occur without forewarning. AvantStay is not liable for any guest inconveniences caused due to construction in the area.br- Please note that max occupancy includes infants.br- Please be advised that documentation may be necessary for ESA/service animals to gain entry.brbrParking Details:brStreet parking only,brNo assigned parking space, the parking next to the property is owner's parking ONLY.brbr---brbrThe room configuration is as follows:brbrPrimary Bedroom / Queen bed brBedroom 2 / Queen bedbrbr---brbrThis is a smoke-free property. Violation of the no-smoking policy will result in forfeiture of the security deposit, a $300 smoking fee, and liability for any fire or property damage costs.brbrAs part of our commitment to being good neighbors, occupancy limits and quiet hours (9pm-8am) are strictly enforced. No speakers or sound systems will be provided for use in our properties. Violation of any noise ordinances will be subject to fines that can reach up to $10,000 per violation. brbrEvents or parties are not allowed without prior written approval and an additional fee. Any unauthorized parties or events will be shut down and a fine will be assessed. Please inquire for more information about our event policies and fees. brbrThere is nothing more important to us at AvantStay than the health, safety, and experience of our guests & staff. We've enhanced our cleaning and sanitation protocols and are taking extra care to disinfect all surfaces between reservations with hospital-grade disinfecting solutions.brbrAs a reminder, we do work with 3rd party vendors to maintain the property, and although we adhere to the strictest CDC guidelines and advise all contractors to wear PPE equipment, we can not always enforce. We strongly advise guests to please deny access if any vendors fail to meet and adhere to these standards.brbrIDs will be requested for verification after booking. brbrWe report and prosecute all Credit Card Fraud.

Emma's Secret by AvantStay | Heart of Old Town | Month Long Stays Only

Key West, Florida, United States

Bed

1

Bath

4

Sleeps

$408.04

Savor the Key West Lifestyle at Margarita on Margaret - Private All Oasis. Escape to your own private slice of paradise in the heart of Old Town Key West. This beautifully restored historic conch-style home with a charming guest cottage offers the perfect blend of classic island character and modern comfort. With three bedrooms and two and a half bathrooms, it’s an ideal retreat for families and friends looking to relax, recharge, and enjoy the best of Key West living.brbrStep through the white picket gate and into a lush, fully fenced property surrounded by vibrant tropical landscaping. A welcoming front porch with cozy seating sets the tone for the warm, inviting atmosphere you’ll find inside.brbrThe main house features an open-concept living room and kitchen with soaring tongue-and-groove wood ceilings, white beams, and plenty of natural light. A wall of accordion glass doors opens fully to the spacious deck and sparkling pool, creating seamless indoor-outdoor living. The kitchen is well-appointed with stainless steel appliances, a large granite island with seating, and everything you need to prepare meals at home.brbrBoth bedrooms in the main house are spacious retreats with en suite bathrooms, vaulted ceilings, TVs, and charming island details, including a Dade County Pine accent wall in the primary suite. The separate cottage overlooks the pool and features a cozy cabinet bed, high ceilings, sliding glass doors, and a half bath en suite — a private hideaway for guests.brbrOutdoors, you’ll find everything you need for the ultimate tropical escape: a large pool with sun loungers, an outdoor shower, a grill, and a dining area for six. Whether you’re swimming, sunbathing, or enjoying cocktails poolside, the private backyard is the perfect spot to unwind.brbrLocated in a desirable Old Town neighborhood, the home offers the best of both worlds: a quiet residential feel just steps away from all the action. You’ll be within walking distance of Duval Street’s restaurants, shops, and nightlife, as well as Higgs Beach, the White Street Pier, and the famous El Siboney Cuban Restaurant.brbrVacation like a local and make unforgettable memories in this one-of-a-kind Key West retreat.

Savor Margarita on Margaret w/ PRIVATE Pool

Key West, Florida, United States

Bed

Bath

Sleeps

$321.01

The best of living on the water, just 10 miles from Key West on a canal with 35 ft. water frontage and direct access to the Atlantic. Excellent paddle boarding, kayaking, and boating! Beautiful, clean, and lovingly updated 3 bedroom, 2 bath home for your pleasure. Enjoy the wonderful local ambiance of Geiger Key Marina just a short walk or paddle from the house. Take in a waterfront happy hour and delicious fresh local seafood, or take a short 10 mile drive (or Uber) for the culture, nightlife, and dining experiences of down town Key West!brbrOur family home comes complete with 3 speed cruiser bikes for a casual ride down to Boca Chica beach, and we have beach chairs, BBQ, hammock, etc. to create your perfect vacation experience.brbrThe kitchen is stocked with utensils, pots and pans, dishware, glassware, toaster oven, coffee makers(Keurig and drip), blender, and microwave in addition to oven and fridge. Across from the kitchen is the 3rd bedroom, that functions as an office, exercise, playroom, and comes with a twin bed. You can also use a double bed blow up mattress provided (as pictured). As you proceed down the hallway, on the left side is the hall bathroom, and at the end of the hallway is the second bedroom complete with queen adjustable bed. On the right side is the master bedroom and bathroom with a queen adjustable bed, TV, and bathroom with shower and a Toto washlet.brbrDisclaimer: There are occasional naval jets that fly overhead. When flying overhead they are loud, although cool to see, especially when flying in formation. These instances are random and days can go by without hearing them at all. They never fly at night. That said, we want our guests to know that these fly-bys can occur.

The Local's favorite spot.

Key West, Florida, United States

Bed

Bath

Sleeps

$3027.32

Short walk to Duval Street. Central location. Restaurants nearby. Surrounded by charm of Key West. 7 to 8 rooms with ensuite bathrooms for the family. Explore the city then come back home to hang out with family & friends or by the plunge pool. There is an outdoor shower and propane gas BBQ available for use. 2 onsite parking spots included for regular & compact vehicles. Large/oversized SUVs may find it difficult to fit 2 vehicles side by side but there is a parking garage located just 1.5 blocks away.brbrWe offer a portable crib please request in advance. Subject to availability. brbrMain House:brRoom 1 - located downstairs w/ensuite bathroombrRoom 2, 3, 4, & 5 - located upstairs with ensuite bathroombrLiving room has TV and gamesbrKitchen, laundry room, & small dining areabrbrGuest House:brRoom 6: King bed, downstairs, ensuite bathroombrRoom 7: (couch/queen Murphey bed cabinet/kitchenette as seen in photo) flex space w/bathroombrRoom 8: King bed, downstairs, ensuite bathroom

Quaint Key West Getaway: Historic Knowles House w/Private Pool & Rooftop Deck

Key West, Florida, United States

7

Bed

8

Bath

16

Sleeps

Prime Key West LocationbrbrEscape to laid-back island living in this inviting Key West retreat, where tropical beauty and everyday comfort come together seamlessly. Tucked away in a quiet, greenery-filled neighborhood, this single-story home offers a peaceful setting while keeping you close to everything that makes Key West unforgettable.brbrStep outside to your private backyard oasis, complete with a sparkling pool, tranquil garden views, and a charming avocado tree that adds to the authentic island vibe. Grill up your fresh catch on the gas grill and dine alfresco under the stars, or cool off indoors with central air conditioning after a day in the sun.brbrPerfect for couples, families, and remote workers, this well-equipped home features fast WiFi, a dedicated workspace, and a private washer and dryer for added convenience. At night, unwind in comfortable bedrooms designed for restful sleep, so you're refreshed and ready for the next day's adventure.brbrNearby Attractions:brLocated just one mile from Old Town Key West, you're moments from world-famous Duval Street, the Ernest Hemingway Home & Museum, and the Key West Butterfly & Nature Conservatory. Spend your days soaking up the sun at Higgs Beach or Smathers Beach, or enjoy a scenic walk to White Street Pier and the historic Martello Tower for breathtaking coastal views.brbrWhether you're exploring the island's rich history, chasing beach days, or simply relaxing poolside with a good book, this home provides the ideal backdrop for an extended stay in paradise.brbrThings to knowbr• Minimum stay of 28 nights requiredbr• Optional pool heat available for $7.50 per nightbr• Pool heat must be requested at least 48 hours prior to arrival and applies to the full staybr• Fully equipped kitchen with dishwasherbr• Flat path to the front doorbr• Located on a bike path and bus routebr• Beach towels providedbr• Futon in the living room offers additional sleeping spacebr• Snowbird-friendly—contact us for detailsbr• Please note: an active security camera is located in the garage and faces the carportbrbrThis property is managed by Vacasa Florida LLC.

Sumptuous Home w/ Private heated pool, Central AC, WiFi & Private Washer/Dryer

Key West, Florida, United States

Bed

Bath

Sleeps

$430.78

UNMATCHED ISLAND RETREAT…brTucked away within one of the island’s most impressive lanes in the Casa Marina district, this retreat is sure to offer optimal serenity from your everyday reality. An expansive estate revealing a classy blend of luxurious details and everyday comforts, your Key West escape is sure to be spent to the fullest. br***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGEbrbrDETAILS AND AMENITIES…brPull up to a convenient off-street parking space and step into this generous, open layout with wood flooring throughout. Mesmerizing at a glance, exceptional décor and precise finishes reveal pure perfection. A bright gourmet kitchen offers top of the line stainless steel appliances with gorgeous custom cabinetry and a build in bar for happy hour. Come together among cozy living room furnishings and a flat screen smart TV with a powder room nearby. Cheery natural light pours in through multiple French doors creating an inviting indoor outdoor space. A desk lies in the upstairs hallway for those working remotely. Enjoy cable TV in the flex room off the living room and smart TVs throughout the rest of the house! This property is equipped with a Ring Doorbell located next to the front door of the home. brbrSLEEPING ARRANGEMENTS…brTotaling 3 bedrooms and 3.5 bathrooms, this home allows ample space and privacy for all your guests. Follow the stairs to the second level to find two guest rooms outfitted with king beds connected by a jack and jill bathroom with a shower. Down the hall is the primary suite with a king bed, flat screen TV and a private en suite full bathroom with a tub/shower combo. All upstairs rooms have access to an oversized balcony overlooking the lush outdoor oasis below. A convenient laundry room resides on the second level hallway. Off the downstairs Great Room is another living space with a sleeper sofa, TV and an en suite bathroom with a glass shower. brbrOUTDOOR LIVING…brStep out to a covered back porch with vibrant garden views surrounding a heated, lagoon shaped pool, dining table for 8, flat screen TV and outdoor shower. Unwind as your sip on your crafted cocktail and turn up the music on the Sonos system before you hop in to town for a taste of all the action! brbrPARKING...brThere is off street parking for your convenience. brbrPETS...brNo pets please.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 much 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(s).brbrFIND YOUR LATITUDE ADJUSTMENT…

LATITUDE ADJUSTMENT ~ Prestigious 3 Bedroom, 3.5 Bathroom Home with Pool!

Key West, Florida, United States

Bed

Bath

Sleeps

This beautifully home with quaint charm has a one month minimum stay requirement because of local zoning regulation. Colorful and breezy with covered front and back porches. Sliding back doors open onto lush landscaping and one of a kind lazy river heated pool. brbrEquipped with full kitchen, washer/dryer, local art that includes an original Shel Silverstein mural. (Shel was a beloved Key West artist and author.) brbrSteps from Blue Heaven Restaurant, Hemingway.House and Duval Street but you can retreat to a quiet home in one of the last authentic Key West neighborhoods. Two bicycles come with the property. One parking space is included with this property, however, you don't need a car! Everything is a short walk or bicycle ride away!brThe heated pool is shared within a five home community. Responsive and helpful and friendly owners live just across from the pool. brbrTwo bedrooms each have a queen size bed. Two bathrooms each have walk in showers. HDTV cable and high speed WIFI are all included.brbrThis is a one month minimum rental! Come join us and live like a Conch in the Conch Republic for a month or longer! If you can work from your laptop, you have two full desks and wifi so you can work in paradise and play in paradise when you are finished telecommuting.

Lazy River Pool, Enchanting Garden, Old Town Key West, Free WiFi, Bikes & Parkin

Key West, Florida, United States

Bed

Bath

Sleeps

$290.08

Summary:brbrReynolds Paradise- 2BDR/2BA house with Jacuzzi close to Duval StreetbrbrbrbrThe Space:brbrCome stay in this perfect Key West cottage located just a few short blocks from Higgs Beach in the historic Casa Marina neighborhood. This piece of paradise is within walking distance of the famous Duval Street and all its fabulous restaurants and nightlife. From the moment you enter the property, you will be captured by your private garden oasis. Enjoy morning coffee from the covered porch with an outdoor fan and cafe lights. Grill on the outdoor BBQ or lounge in the sparkling jacuzzi. Kick back and relax in this beautiful hideaway after a busy day exploring the fabulous Florida Keys.brbrbrbrA newly decorated living room with comfortable furnishings opens to a bonus sunroom which, with its wall of glass, provides several peaceful retreats to relax or work. A well-appointed Chef's kitchen makes for an enjoyable gathering place to cook with friends and family. A casual dining room nook overlooks the garden. The Master bedroom suite features a king-size bed with a new Perfect Sleeper mattress and an ensuite bathroom with a stand-up glass shower. The spacious guest bedroom has a queen-size bed and ensuite bathroom with another large glass shower. Both bedrooms are conveniently located on the main floor but apart to allow for privacy. The living room has a Bassett pullout sofa with a comfortable mattress that sleeps two.brbrbrbrReynolds Paradise Features:brbrbrbrNew kitchen appliances including a Nespresso machinebrbrMaster bedroom with King bed, Guest Bedroom with Queen bed, sleeper sofa in living roombrbrTwo full bathrooms with stand up showersbrbrBonus sunroom/officebrbrAmple street parkingbrbrbrbrWasher/DryerbrbrCentral A/CbrbrCeiling FansbrbrSmart televisions in the living room and both bedroomsbrbrFully equipped kitchenbrbrStarter supply of paper productsbrbrStarter set of cleaning productsbrbrLinens and towels providedbrbrWireless high-speed Internet accessbrbrInterim housekeeping provided upon requestbrbrGrill and jacuzzibrbrbrbrThis property will accommodate up to six adultsbrbrGuests must be 25 years of age or older unless accompanied by an adultbrbrPet-friendly, non-refundable pet fee of $250brbrThis is a non-smoking home and propertybrbrbrbrA RENTAL AGREEMENT IS REQUIRED TO BE SIGNED

Reynolds Paradise

Key West, Florida, United States

1

Bed

Bath

6

Sleeps

Now more than ever it is important it is important to choose a home that is thoroughly cleaned and well maintained. We inspect our homes multiple times each month and follow the AHLA Stay Safe Guidelines to ensure your stay is safe and comfortable. You will also find an initial supply of cleaning and paper products along with handsoap and toiletries. The home has a private entrance and contactless Check-In/Out.brbrNeed to stay connected during your trip We offer high speed cable internet.brbrLocated in the gated community of Truman Annex: a popular and beautifully landscaped community in Old Town Key West. Enjoy the peaceful tropical landscape and pool while only 2 blocks from the excitement of Duval St. We are just outside the entrance to Ft Zachary Taylor State Park and Beach and so close to many of Key West’s popular attractions. After a full day of taking in many of the island's wonderful experiences, come back to all the comforts of home. This open airy home offers a fully furnished kitchen, eating area, living room and 2 bedrooms and 2 1/2 baths. Two sets of French doors open to a large deck and beautiful private backyard where you can enjoy a meal or relax and sip umbrella drinks on the chaise lounges in your own private tropical paradise. Gated parking lot with one reserved space.brbrAmenitiesbrbr- Televisions in bedrooms and living areabrbr- 2 Bicycles for Guests to use during their staybrbr- Bed Linens, Bath & Beach Towels brbr- Hairdryerbrbr- Beach Chairs & Coolerbrbr- Access to Southard Court Poolbrbr- Balconies off each bedroom and private enclosed backyard with deckbrbr- Reserved parking place in front of homebrbr- Secure high speed wireless internetbrbr- Only a few short blocks from Duval Street and Mallory Squarebrbr- Short walk to the Fort Zachary Taylor State Park Beachbrbr- Fully equipped Kitchen with Silestone counter and eat in bar- Silverware, Dishes, Cooking Utensils Provided, Stove/Oven, Refrigerator, Microwave, Dishwasher, Coffee Maker & Blender

Location, Beauty & Comfort @ Truman Annex

Key West, Florida, United States

Bed

Bath

Sleeps

$784.13

Key West is waiting for you at this clean & spacious 2-bedroom guest house. Good for up to 6 people. This cozy retreat offers an office table for those who need to squeeze in a little work time as well. The shared backyard offers a plunge pool, lounge chairs, propane BBQ, & roof deck. Our place will help you feel at home while you're traveling in Key West. Guests love being able to walk to so many landmarks and restaurants in the area. Access to guest house is through Elgin Ln alley way.brbr1 onsite parking spot in front of the house is included for regular & compact vehicles. There's a parking garage located just 1.5 blocks away.brbrGuest House:brRoom 6: King bed, downstairs, ensuite bathroombrRoom 7: (living room/couch/queen Murphey bed cabinet/kitchenette as seen in photo) flex space w/bathroombrRoom 8: King bed, downstairs, ensuite bathroombrbrWe offer a portable crib please request in advance. Subject to availability. brNo laundry room or kitchen sink available.

Charming 2 room guest house, access to Pool, A/C, & WiFi, Key West, near Duval

Key West, Florida, United States

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$1662.75

Short walk to Duval Street. Central location. Restaurants nearby. Surrounded by charm of Key West. Explore the city then come back home to hang out with family & friends or by the plunge pool. There is an outdoor shower and propane gas BBQ available for use. 1 onsite parking spots included for regular or compact vehicle. Large/oversized SUV may find it difficult to park side by side. There is a parking garage located just 1.5 blocks away for additional vehicles.brbrMain House:brRoom 1 - located downstairs w/ensuite bathroombrRoom 2, 3, 4, & 5 - located upstairs with ensuite bathroombrLiving room has TV and gamesbrKitchen, laundry room, & small dining areabrbrWe offer a portable crib, please request in advance. Subject to availability. brOutdoor areas are shared with any guests that book the guest house. Please don't ask if guest house is booked or not. The occupancy status can change daily. If you would like to have the entire place to yourself, please book entire home.

Spacious 5-bdrm 5 bathroom house in charming Key West with AC, WiFi, Plunge Pool

Key West, Florida, United States

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Bath

Sleeps

$412.62

MODERN CUSTOM ELEGANCE…brSurrender your cares in this tropical state-of-the-art luxury sanctuary! If nothing but the latest and greatest will suffice, this modern beauty merges clean lines with the ultimate flow in design and cradles you in crisp yet cozy spaces. Nestled in the exclusive Casa Marina neighborhood, this residence features 2 bedrooms and 2 bathrooms - a perfect retreat for 2 couples seeking island serenity with a nod to cutting-edge visual aesthetics. Bonus item is a mere 3 minute walk to the beach!br***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGE. THIS HOME IS NOT SUITABLE FOR CHILDREN.brbrDETAILS AND AMENITIES...brIndulge in the utmost privacy as you enter the exquisite design interior. The chef's kitchen boasts Miele appliances with a center Carrera marble island that opens to the living/dining areas, showcasing a dramatic collapsing wall of sliding doors that invite the backyard oasis indoors in classic Key West fashion. Plush couches and a large wall-mounted TV in the living space encourage lazy conversations amidst peaceful outside water sounds or an evening of movie watching with a cool aperitif on the coffee table. For your convenience, a washer/dryer closet is located outside, just off the primary bedroom. brbrSLEEPING ARRANGEMENTS...brThe primary bedroom whispers privacy and intimacy, featuring a king size bed, dual sink, large shower bathroom, walk-in closet, wall-mounted tv, and a wall of windows that open to a private patio that houses a delightful outdoor shower. On the other side of the kitchen you'll find the guest bedroom with two twin beds that can be converted to a king bed upon request and its own gorgeous ensuite large shower bathroom, desk area, 2 closets, and a wall-mounted tv. brbrOUTDOOR LIVING...brThe glamorous enclosed backyard garden and pool area was designed by Craig Reynolds and has been featured in Dwell Magazine. There are defined gathering spaces for sunbathing, outdoor dining and a fire pit with seating for 4 for the occasional cool evening. The saltwater pool can be heated with a waterfall feature. Wash the day off under the outdoor shower then toss steaks or your fresh catch onto the stainless Weber propane grill. brbrPARKING...brThere is off-street parking available.brbrPETS...brDogs are considered at 35 lbs or under and a pet fee is required. Please include the size and breed in the comments when inquiring. 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 offered only 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).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 much more. They can also have your fridge stocked with all the necessities in advance of your arrival!brbrRESTORE AND REHABILITATE IN STYLE…

GOLDEN HOUR ~ Upscale 2 BR/2Ba Home w/ Pool!

Key West, Florida, United States

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Welcome to your home away from home! Casa Amelia is a charming Conch house in the historic Gato Cigar Village. Wake up in the morning and sip coffee in comfort on the covered front porch. In the afternoon, enjoy a private backyard, swimming pool and tiki bar, or venture out to famous Duval Street, only steps away for a day of shopping and bar-hopping. This is the perfect vacation getaway in the heart of Old Town Key West. Just a half-block off Duval Street with off-street parking, a big plus! Location, location, location! Our home is just around the corner from Key West Light House, the Hemingway house, Southernmost point and many restaurants, bars and galleries. Simply park and walk. Casa Amelia is also on the free Duval Loop Route. Take the free bus to the Historic Seaport. We are stop number 9.brbrAccommodationsbrOur home is a 3 bedroom and 2 bath home. The first bedroom has 2 twin beds and is right off the living room. The second bedroom has a queen-size bed and TV and is off the dining room and connects to the main bathroom. The third bedroom has a queen-size bed, TV and bathroom located at the back of the house off the kitchen.brbrAmenitiesbrCasa Amelia includes a washer and dryer, central A/C and heat, TVs in 2 bedrooms and living room, fully equipped kitchen, starter supply of paper products, starter set of cleaning products,iron and ironing board, linens, bath and pool towels, Wifi, Direct TV, private heated pool, Tiki bar, off-street parking, propane BBQ grill, cleaning service bi-weekly.

*Casa-Amelia-Key-West* 1/2 block off Duval Street

Key West, Florida, United States

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Bath

Sleeps

$220.04

OLD TOWN GEM...brThis 2 bedroom, 2 bathroom cutie resides down a charming lane surrounded by historic residences and is a stone's throw from world -class dining, shopping, galleries, and the Historic Seaport. Ease on down to this idyllic sanctuary and watch your cares melt away in Paradise!br***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGEbrbrDETAILS & AMENITIES…brBegin your Key West story in this delightful abode that offers all the creature comforts and promises hours of serenity and bliss. Plan your day's adventures over a hot cup of coffee on the quaint front porch with seating. Enter your retreat from reality and enjoy your delightful living area that invites you to indulge in your favorite TV shows or escape into your latest vacation novel. The spacious and modern kitchen comes fully equipped with all the culinary tools you'll need to create fresh fare and craft icy cocktails. Enjoy seating at the breakfast bar while you feast with loved ones. A stacked washer/dryer closet is just off the kitchen for your convenience.brbrSLEEPING ARRANGEMENTS…brSink into slumber in one of the 2 queen bedrooms. The primary bedroom is located upstairs with an en suite shower bathroom and a desk for those working remotely. The downstairs bedroom resides next to a full bathroom with a shower/tub combination. A sleeper sofa with a very cozy mattress resides in the living room for additional sleeping arrangements. brbrOUTDOOR LIVING…brFrench doors in the kitchen lead to your covered sanctuary. Fire up the grill on your enclosed and private deck area. This cheerful space invites hours of happy conversations or opportunities for quiet solitude. brbrPARKING... brThis home has on street parking only.brbrBOOKING DATES...brThis home is offered only 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.brbrPETS...brThis NOT a pet-friendly home.brbrMULTI MONTH RESERVATIONS... brFor monthly reservations, the following fees will be added PER MONTH: brMid-stay cleanbrPool/hot tub heating fee (if applicable)brPet fee (if applicable)brbrCONCIERGE SERVICES...brEnjoy 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 much 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% refundbrbrCancellations 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).brbrGET ON ISLAND TIME…

WASTIN' A WAYLAND ~ Renovated 2 BR/2 Ba Home in Old Town!

Key West, Florida, United States

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6

Sleeps

$811.75