Home Vacation Rentals By Owner In Key West, FL

Showing 1120 Of 2059 Vacation Rentals
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Exceptional(1)

$364.18

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Private Vacation Home

**TRUMAN’S TROVE @ THE ANNEX** Private Home & Pool + LAST KEY SERVICES…

Key West, Florida, United States

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival!brbrHunting for the perfect Key West vacation home can feel like a daunting task. However, once you discover TRUMAN’S TROVE, you’ll know that you’ve struck gold! This two-story private home has been beautifully furnished and designed to the highest standard. In addition, TRUMAN’S TROVE offers an ideal location within Truman Annex, Key West’s most exclusive Gated Community. TRUMAN’S TROVE combined with Last Key Realty's Five-Star Guest Services and Complimentary Concierge, is guaranteed to be a treasured Key West vacation experience.brbrTHE LIVING AREA & KITCHEN…brbrTRUMAN’S TROVE has an open and airy layout. The spacious living room features a large flat-screen TV and comfortable seating options. The plush sofa pulls out to a Queen sleeper to accommodate extra guests. The indoor dining area has a large dining table with seating for six and there is an additional three seats at the kitchen bar. The fully equipped kitchen has top-of-the-line stainless steel appliances and all the tools you'll need to prepare meals at home. There’s also a wine chiller next to the kitchen bar. A convenient powder room is located on the first floor.brbrTHE BACKYARD…brbrSwing open the double French doors and step outside to the tropical backyard. The covered outdoor lounge area is perfect for relaxing in the shade. Feeling competitive Challenge your group to a cornhole tournament. Once you’ve worked up an appetite, treat everyone to a BBQ of today’s fresh catch using the propane grill and outdoor dining table that seats six. The backyard is fully fenced and landscaped for ultimate privacy. Tiki torches and landscape lighting allow the backyard to be enjoyed both day and night. The back walking gate opens to Eaton Street, for easy access to all the downtown action from your vacation home.brbrTHE GATED COMMUNITY…brbrTruman Annex is the most exclusive private residence community in Old Town Key West. Located just off the main drag of Duval Street, Truman Annex is an oasis of calm, quiet streets lined with palm trees and beautiful Floridian homes. Within Truman Annex, Admirals Lane is even further tucked away down a small cul-de-sac with ultimate privacy. The entrance to Truman Annex is secured by a 24-hour staffed guard gate and you can use the residential entry gate keys to come and go on foot at night.brbrTHE COMMUNITY POOL & FORT ZACHARY TAYLOR STATE PARK…brbrThe landscaped community pool is located at the end of the lane, with chaises and a cabana with restrooms. Or you can walk to Fort Zachary Taylor State Park, with the prettiest beach in Key West, just a half mile away from your front door.brbrCompliance with Truman Annex Community Rules & Regulations is expected of all Last Key guests. This includes “Quiet Time” in all outdoor areas, public and private, after 10PM.brbrTHE ACCOMMODATIONS…brbr** Master Suite: Located on the Second Floor with a King bed, two closets, a flat-screen TV, a private balcony, and an en-suite bathroom with double sinks and a walk-in shower.brbr** Second Bedroom: Two Twins OR One King bed, a full closet, a flat-screen TV, and access to the hall bathroom with a shower and tub combo.brbrALL LAST KEY VACATION HOMES INCLUDE: brbr** Washer and Dryer br** Central Heat and A/C br** Ceiling Fans Throughoutbr** Flat Screen Cable TVs in Living Room & Bedrooms br** Fully Equipped Kitchenbr** Basic stock of spicesbr** Starter supply of paper productsbr** Starter set of cleaning productsbr** Linens and Towels provided br** Wireless high-speed Internet access and full cable is included br** Full Time Concierge Service brbrIn addition, this fully stocked home also includes, but is not limited to the amenities on this list: brbr** Fully Fenced & Landscaped Private Yard br** Community Pool Accessbr** Propane BBQ Grillbr** Sleeper Sofa br** Assigned Off-Street Parking for One Vehiclebr** Cornhole SetbrbrOther notes: brbr** Interim housekeeping provided upon request br** This property will accommodate up to 6 adultsbr** No Pets Allowedbr** Last Key Realty vacation homes are rented to family groups and responsible adult groups only. Groups who expect they may cause after hours noise will not be a good fit for this home and should be aware they may incur additional penalties when in residence for violations. There will be a $500 charge for after-hours dispatch of our staff in response to calls resulting from verified noise complaints for violations by our guests in residence.
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Bath 2

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Sleep 6

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Exceptional(3)

$213.72

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Private Vacation Home

CASA DE CANAL ~ Beautiful Renovated 3 BR, 2 Bath Canal Front Home w/Dockage!

Key West, Florida, United States

KEY WEST BOATER'S BONANZA...brThis waterfront gem is a dream for boating and fishing enthusiasts. Indulge in all your nautical fantasies at this 1600 sq. ft. 3 bedroom 2 bath home that boasts 65 feet of canal waterfront with a step down sea wall and deck overlooking the waterway. Rev up your engine and strap in your island soul for seafaring nirvana!br***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGEbrbrDETAILS AND SLEEPING ARRANGEMENTS...brThis island retreat has been remodeled and offers all the creature comforts you'll need when you return at the end of the day with your fresh catch. Enter the front door to a large open concept living and kitchen area. Cool off and relax with your favorite beverage on the couch and cushioned seating. Escape and binge on your favorite shows on the large wall-mounted TV. The large, modern kitchen has a huge island with seating for four and ample space for preparing your favorite dishes. Stainless appliances and a variety of cooking tools will delight your culinary pursuits. Dine with friends and family at the indoor dining table which resides between the living and kitchen areas. A full shower bathroom and washer/dryer closet complete the open space. There is a primary king bedroom with TV and ensuite bathroom with a shower/tub combination. One guest room offers two full beds and the other has a queen bed. This home is equipped with Youtube TV.brbrOUTSIDE LIVING...brA sizable enclosed patio a perfect storage area for all your boating gear and leads out to the back yard on the end of a peaceful canal with incredible boating access. Prep your catch at the filet table and dine al fresco at the outdoor dining table. Snooze in the hammock under the covered patio and exhale under sultry stars! Located only 0.25 miles from a Rivera Canal Public Boat Ramp with incredible boating access to the Gulf and Atlantic Ocean! br***Please refer to your tide charts for boating and dockage depths.br***NO BOAT LIFT BUT THERE IS SHORE POWER (POWER ON THE DOCK) brbrPARKING...brThis home has ample parking to include a boat trailer.brbrPETS...brPets are considered at this home 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 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). brbrPERFECT NAUTICAL GETAWAY ...
Bed 3

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Bath 2

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Sleep 8

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Exceptional(2)

$415.17

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Private Vacation Home

**ISLAND INSPIRATION @ OLD TOWN** Elegant Home & Pool + LAST KEY SERVICES…

Key West, Florida, United States

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival!brbrIn the same way that the island of Key West has captured the hearts of so many, this charming monthly vacation home will capture yours. ISLAND INSPIRATION combines the appearance and charm of a historic Keys home, with all of the modern conveniences you have come to appreciate. This special home is situated on Margaret Street at the edge of where Old Town meets the highly desirable Casa Marina neighborhood. Located just a few blocks from both Duval Street and Higgs Beach, you couldn’t ask for a more ‘inspiring’ location. Best of all, ISLAND INSPIRATION includes Last Key Realty’s renowned Five-Star Guest Services, known for providing memorable Key West vacations. So leave your worries behind and let Key West’s island vibes be the inspiration you’ve been searching for.brbrTHE LOCATION…brbrImagine your vacation home being just steps in either direction from all of the shops, restaurants, and sites of Duval Street and the beach. Take a short stroll or bike ride down to the best of Key West, to hit local favorites like La Te Da, Louie’s Backyard, La Grignote, and El Siboney (which is only a few doors down the block). Just a few blocks towards the coast you'll find yourself at Higgs Beach and the White Street Pier. ISLAND INSPIRATION is a dream for beach-lovers who prefer to pack their coolers and towels and walk down to the sand and water. Watch the sunset from the White Street Pier just around the corner from Higgs Beach or grab a beach-side meal at Salute! On The Beach. Although you won’t need a vehicle to get around the island from this prime location, there is covered parking for two standard sized vehicles (larger vehicles will not fit) in the rear of the property.brbrTHE LIVING AREA...brbrFrom the moment you enter ISLAND INSPIRATION, you'll immediately notice the open and airy layout of the first floor. The living room has a large flat screen TV and plenty of comfortable seating options for everyone. The dining room table seats six and is located between the living room and the fully equipped kitchen. The kitchen has every tool and appliance you’ll need to prepare meals from home. There is also a convenient powder room located just off the living room.brbrTHE BACKYARD & POOL...brbrSlide open the large glass doors to step out and into your very own private backyard oasis. The private backyard is fully fenced and features mature island trees and lush tropical landscaping that provide maximum privacy. Between seating under the covered patio and chaise lounges on the pool deck, there’s plenty of room for everyone to spread out and relax in both the sun and shade. Taking a dip in the heated pool is the perfect way to relax after a long day of exploring Old Town. Treat your group to a poolside BBQ using the propane grill and outdoor dining table with seating for six.brbrTHE ACCOMMODATIONS...brbr** First Master Suite - Located on the Second Floor with a King bed, a flat screen TV, a closet, access to the front balcony, and an en-suite bathroom with a walk-in shower.brbr** Second Master Suite - Located on the Second Floor with a King bed, a flat screen TV, double closets, and an en-suite bathroom with a walk-in shower.brbr** Loft-Style Third Bedroom - Located on the Third Floor with 2 sets of Two Twin beds OR we can convert either/both sets into a King bed. This floor also has a separate sitting area with a sofa and a flat screen TV, and an en-suite bathroom with a shower and tub combo.brbrALL LAST KEY VACATION HOMES INCLUDE:brbr** Washer & Dryerbr** Central Heat and A/Cbr** Ceiling Fansbr** Flat Screen Cable TVs in Living Room & All Bedroomsbr** Fully-Equipped Kitchenbr** Basic stock of spicesbr** Starter supply of paper productsbr** Starter set of cleaning productsbr** Linens and Towels providedbr** Wireless high-speed Internet access and full cable is includedbr** Full Time Concierge ServicebrbrIn addition, this fully stocked home also includes, but is not limited to the amenities on this list:brbr** Fully Fenced & Landscaped Private Yardbr** Sleeper Sofabr** Private Heated Poolbr** Propane BBQ Grillbr** Covered Off-street Parking (with vehicle size restrictions)brbrOther notes:brbr** All monthly rentals include a mandatory interim clean. Multi-month stays require 1 interim clean per month.br** Additional interim cleanings availablebr** This property will accommodate up to 10 adultsbr** No Pets Allowed
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Exceptional(80)

$1101.4

/ Nightly
Private Vacation Home

Old Town Retreat near Upper Duval St

Key West, Florida, United States

Casa Caribe! When you think of the Caribbean, you think of tranquil blue green waters and a fun vibe. That's the feel when you walk into Casa Caribe, both inside and out. This wonderful four bedroom, four bath home is perfect for couples traveling together or a quiet family getaway. This is a new property to our rental program and was previously called Sea Biscuit Cottage.brbrThe Conch main house:brEnter the home into the great room and kitchen. Cathedral, pine wood ceilings and high windows across the room bring lots of light into the room. Sliding glass doors open to the outdoor lounge and pool area. The living area has an aqua colored sofa with four comfy chairs to relax in and catch something on one of the five televisions on the property. You probably didn't come to Key West to cook while on vacation, but if you want to there is a perfectly appointed kitchen with wood tone cabinets and granite counters.brbrStep down the hall and you will find two bedrooms and two baths, each with step-in shower. Both bedrooms feature Cuban tile floors that speak to the history of the home. The front main bedroom, has access to the original front porch that is perfect for people watching.brbrOut back, you will find the covered outdoor sitting are with sectional sofa and the awning covered dining table to enjoy being outside all times of the year. A gas barbeque is provided for your grilling pleasure. The pool is heated during the cooler season for your enjoyment.brbrThe Cottage:brDirectly off the pool is the cottage and its first-floor guest suite. French doors open to the bedroom suite with king bed, kitchenette and ensuite bathroom. Stairs from just outside the gates provide access to the second floor bedroom suite. A king bed, separate sitting area with television and full bath provide the perfect getaway. brbrDine outside or lounge on the patio under the palm trees to enjoy this tropical getaway. The home is steps from the quieter, upper Duval neighborhood and the Southernmost Point. Easy walking distance to lower Duval Street, while still having wonderful restaurants and conveniences close by.brbrThe laundry area is located under the stairs on the outside of the cottage and accessible to the conch house and the cottage.brbrBedding: 3 kings, 1 queenbrMax occupancy (including children) is 8brThere is one, smaller off-street parking space.brbrAmenities:brPrivate poolbrGas BarbequebrRangebrMicrowavebrDishwasherbrRegular coffee makerbrKeurig coffee makerbrHigh speed internetbrInternet TV servicebrAll linens are provided
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Bath 4

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Exceptional(5)

$202.36

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Condo

**DRIFTWOOD DREAMS @ 1800 ATLANTIC** Beachside Condo & Pool + LAST KEY SERVICES.

Key West, Florida, United States

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival!brbrThis freshly renovated condo is located at 1800 Atlantic Blvd on the beach, just steps from the Atlantic Ocean and sand in your toes. Enjoy quiet afternoons with those balmy Key West breezes wafting through the floor-to-ceiling sliding glass doors, or while sitting on your private balcony surrounded by the palm tree tops. DRIFTWOOD DREAMS is located in an upscale private community within walking or biking distance to all of your favorite Key West spots, including beaches, restaurants, shopping, and the beautiful waters surrounding the island. DRIFTWOOD DREAMS combined with Last Key Realty's Five-Star Guest Services will make your month in Key West a memorable one.brbrTHE LIVING AREA and KITCHEN...brbrThe living room has beautiful driftwood floors and tasteful furnishings, with plenty of light streaming in from the floor-to-ceiling glass doors. There's a very large flat screen TV, and plenty of comfortable seating for your whole group to gather before heading out to enjoy Key West. The sofa pulls out to a sleeper for two additional guests. The open kitchen is fully equipped with all of the tools and appliances you’ll need to prepare a meal at home, should you tear yourself away from the fantastic restaurants nearby. The dining table will seat six comfortably and there are two additional seats at the kitchen bar. You can also enjoy a meal on the balcony using the dining set in the treetops.brbrTHE POOL, THE BEACH, THE FITNESS CENTER and TENNIS...brbr1800 Atlantic offers Resort-style amenities, including an extra large Community Pool right downstairs. There are chaise lounges surrounding the pool for your comfort, and a cabana with restrooms for your convenience. Please note this is a shared pool with set rules, such as no music and no coolers. We ask that our guests be mindful of their neighbors and respect the rules.brbrFrom the pool, there's a walking path that leads to the on-site beach. The on-site beach offers a relaxing setting, with chaise lounges and soft sand. There is no direct water access from this beach, but Smathers Beach, Key West's largest public beach, is located within walking distance right next door. There is also an oversized Jacuzzi and a picnic area with BBQs available for guest use. You'll also have access to the newly built fitness center and Key West's only clay tennis courts, both located on-site.brbrTHE ACCOMMODATIONS...brbr** Master bedroom: a King bed, a large flat screen TV, direct access to the balcony, and an oversized shower.brbr** Second bedroom: Two Twin beds OR One King bed, a flat screen TV, direct access to the balcony, and access to the full second bathroom.brbrALL LAST KEY VACATION HOMES INCLUDE:brbr** Washer and Dryerbr** Central Heat and A/Cbr** Ceiling Fansbr** Flat Screen TVs in Living Room & All Bedroomsbr** Fully Equipped Kitchenbr** Basic stock of spicesbr** Starter supply of paper productsbr** Starter set of cleaning productsbr** Linens and Towels providedbr** Wireless high-speed Internet access & full cable includedbrbrIn addition, this fully stocked home also includes, but is not limited to the amenities on this list:brbr** Community Pool Accessbr** Community Jacuzzi Accessbr** Assigned off-street carport for 1 car (Parking Garage has a low clearance of 6'2)br** Key West's only clay tennis courtsbr** Handball courtsbr** Fitness Centerbr** Dry Saunasbr** Picnic areas with BBQsbr** Recreation rooms available for private partiesbrbrOther notes:brbr** All monthly rentals include a mandatory interim clean. Multi-month stays require 1 interim clean per month.br** Additional interim cleanings availablebr** This property will accommodate up to 6 adultsbr** This complex has both visitors and locals living here, we expect our guests to be mindful & respectful of the posted rulesbr** Last Key Realty vacation homes are rented to family groups and responsible adult groups only. Groups who expect they may cause after hours noise will not be a good fit for this home and should be aware they may incur additional penalties when in residence for violations. There will be a $500 charge for after-hours dispatch of our staff in response to calls resulting from verified noise complaints for violations by our guests in residence.
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Sleep 6

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Exceptional(21)

$399.88

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Apartment

Shared Heated Pool, Near Duval - Poolside Retreat

Key West, Florida, United States

Summary:brPoolside Retreat is the PERFECT vacation home for a couple or small group of friends looking for a fun-filled getaway in the heart of Key West. The tropically themed home shares a heated pool and sun deck with Poolside Suite which is located directly next door, ideal for individuals looking to make new friends! Not to be left out, this property has a designated off street parking spot - a luxury in Key West!brbrThe Space:brSleeping up to four guests there is a queen size bed in the bedroom and queen pullout couch in the living room. This updated home is complete with a shared pool with waterfall, and lush, outdoor seating area. As an added bonus, this home comes with private, off-street parking for one vehicle - a real luxury in the Keys! brbrKick back and relax in your cozy home away from home with free WiFi, watch your favorite shows on two cable TVs, or cool off out back in the semi-private swimming pool. With the fully updated, modern kitchen and the gas grill outside, everything you need to have a cookout is right at your fingertips.brbrGuest Access:brOur contactless check-in procedure makes check-in easy. Guests will receive a personalized access code prior to arrival.brbrShared features: Pool, patio, driveway and laundry facilities.brbrThe Neighborhood:brPoolside Suite is located in the heart of Old Town Key West and is just half a block from world famous Duval St. You are well within walking distance to some of the most popular spots in Key West such as the Earnest Hemingway Museum, the Southernmost Point, Key West Lighthouse, The Butterfly Conservatory and much more. There is a CVS about a block away in case you need to stock up on drinks and snacks. There are also amazing restaurants nearby such as Blue Heaven, Seven Fish, Santiago's Bodega, and the Better Than Sex Dessert Restaurant.brbrGetting Around:brThere is one off street designated parking spot for Poolside Retreat and it is located at 517 Olivia St. Park your vehicle in the designated parking spot labeled Poolside Retreat. Please make sure not to park in the spot labeled Poolside Suite as that belongs to the unit next door.brbrThere are a variety of great ways to explore Key West including by bicycle, pedi-cab, moke, scooter, golf cart, Uber, Taxi, or by feet. As this unit is located in downtown Key West, many attractions are within walking distance. Feel free to ask us for recommendations!brbrOther Things to Note:br- New Mattress March 2023!br- Shared washer/dryer located in the back of the home.br- This unit is pet friendly. Our requirements are as follows: br•40lb maximum per petbr•$25/per nightbr•2 pet maximumbrPlease let us know if you plan on bringing your pet.br- This unit is apart of a small compound Poolside Paradise - combined with this unit and Poolside Suite next door, allowing for larger groups of up to 10 guests!
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Sleep 4

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Exceptional(23)

$876.38

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Private Vacation Home

Heated Pool, Steps to Duval St - Poolside Paradise

Key West, Florida, United States

Summary:brThis 3 bed 2 bath home with an amazing HEATED pool is located right off the quieter end of Duval St. The home consists of 2 separate units Poolside Suite and Poolside Retreat which are side-by-side and have their own living rooms and kitchens. This property is perfect for larger groups looking for a memorable time in Key West and is walking distance to popular restaurants, attractions, shops and bars!brbrThe Space:brBring the whole family together for a reunion or holiday celebration at this spacious, Key West home located just a block from the non-stop fun of Duval Street. This rental, with space for up to 10 guests, features an enclosed yard, a private pool, a furnished patio, two full kitchens, and off-street parking for two vehicles (a real rarity in Key West). And dogs up to 40 pounds are welcome for a small nightly fee.brbrPoolside Retreat Bed Layout: brBedroom 1: Queen brLiving Room: Queen pullout couchbrPoolside Suite Bed Layout:brBedroom 1: KingbrBedroom 2: QueenbrLiving Room: Queen pullout couchbrbrIdeal for an extended family or a few couples traveling together, this home offers free WiFi, four cable TVs, two full kitchens, and a gas grill for a family cookout on the furnished patio.brbrGuest Access:brOur contactless check-in procedure makes check-in easy. Guests will receive a personalized access code prior to arrival.brbrThe Neighborhood:brThis home is located one block from Duval Street, the most popular street in all of Key West, where you'll find fantastic restaurants, unique local shops, and year-round special events and festivals. Play on the sand and people-watch at Southernmost Beach, just a half-mile away. Visit the many historic sites including the Ernest Hemingway Home & Museum and the Key West Lighthouse, both only a couple blocks from your front door, as well as the Truman Little White House and the Mel Fisher Maritime Museum, just under a mile away over on Front Street.brbrGetting Around:brParking Information: There are 2 private off street parking spots on the Olivia St side of the property. They are labeled Poolside Retreat & Poolside Suite.brbrThere are a variety of great ways to explore Key West including by bicycle, pedi-cab, moke, scooter, golf cart, Uber, Taxi, or by feet. As this unit is located in downtown Key West, many attractions are within walking distance. Feel free to ask us for recommendations!brbrOther Things to Note:br- Private washer/dryer located outside.br- This unit is pet friendly. Our requirements are as follows: br•40lb maximum per petbr•$25/per nightbr•2 pet maximumbrPlease let us know if you plan on bringing your pet.br- Are you within 90 days of your check in date a & have a smaller group Rent just Poolside Retreat or Poolside Suite!
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$425.62

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Apartment

Raphael Suite: 2/2 Studio Rooms - Pool, Patio w/grill, 2 blocks from Duval!

Key West, Florida, United States

The Galleria was once a haven for traveling artists who frequented Key West. With a tranquil pool area and spacious patio. The Galleria has now been transformed into an oasis for all travelers looking for relaxation and inspiration during their time in Key West.brbrThe Space: brThis micro-efficiency near downtown Key West is a ground floor unit with two studio rooms (two separate rooms with bathrooms), sleeps 4 guests. Each room has a queen size bed and a small European style bathroom. Amenities include a swimming pool and patio. brbrRelax while you enjoy the cable TV and free Wifi for your personal streaming device after a long day at the beach. Prepare yourself a quick breakfast in the kitchenette before walking around town for the day. Inside each room kitchenette you will find a microwave, mini fridge, basic kitchen utensils/dish ware and a Keurig coffee maker.brbrGuests will have access to the pool, onsite laundry facility, bike rack, sundeck, and gas grill.brbrGuest Access:brOur contactless check-in procedure makes check-in easy. Guest will receive a keyless entry access codes upon check-in. brbrbrEach unit is supplied with, shampoo, conditioner, shower gel ,body lotion, bar soap, bathroom tissue, paper towels, dish detergent, snack basket, two chilled bottles of water, laundry pods,dryer sheets,sink sponge, trash can liners, Keurig pods,creamer, sugar. This unit is perfect for those that want to spend all their time enjoying all the festivities that world renowned Key West has to offer but then desire a location that is quiet and comfortable to rest up for the next days’ adventures. The Galleria Condominiums has plentiful decking surrounding the property and is perfect for relaxing and enjoying the tropics. For those that wish to experience living like a true Conch in Key West, this unit will suit your needs.brbrThe Neighborhood:brBahama Village is a historic, mostly residential neighborhood just a few short blocks from the main strip of Duval Street. Visitors (and locals) love this area because its beautiful, Bahamian-inspired atmosphere, as well as its close proximity to famous attractions and amazing food options. Walk, bike, or scooter down to the Southernmost Point, Key West Lighthouse, Butterfly Conservatory, Truman Waterfront Park, and the Earnest Hemingway Museum. Enjoy some of Key West's most popular restaurants such as Blue Heaven, Santiago's, Firefly, and Rams Head Southernmost.brbrParking Information:brThere is no on-site parking provided. Free limited street parking is available on a first-come first-service basis and located directly in front and on side of the Galleria complex. There is no guaranteed availability or proximity to the unit. Should you find a parking spot, please note you can not park in one marked Residential and some spots may be pay-to-park on neighboring streets.brbrGetting Around:brThere are a variety of great ways to explore Key West including by bicycle, pedi-cab, scooter, golf cart, Uber, Taxi, or by foot. As this unit is located in downtown Key West, many attractions are within walking distance. Feel free to ask us for recommendations!br
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Exceptional(5)

$227.61

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Condo

**THE COZY STARFISH @ THE ANNEX** Condo Near Duval & Beach + LAST KEY SERVICES…

Key West, Florida, United States

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival!brbrTHE COZY STARFISH is a newly furnished and decorated first floor condo located in the Truman Annex, a private gated community situated in the heart of the island. Despite being only steps away from all that Old Town Key West has to offer, THE COZY STARFISH is a peaceful retreat within a private gated community that offers access to a large, shared pool and a designated off-street parking space. Combined with Last Key Realty’s renowned Five-Star Guest Services, THE COZY STARFISH is the perfect home base for your stay in paradise.brbrTHE LOCATION...brbrTruman Annex is a private, gated community right in Old Town, Key West. You'll be just a few blocks from Mallory Square, Duval Street and all the restaurants, shopping, and attractions of Old Town, yet you'll benefit from the peace and quiet that Truman Annex is known for. Although you won't need a car to get around from this excellent location, there is a reserved off-street parking space.brbrTHE LIVING AREA & BACK PATIO...brbrThe living room features a large flat screen TV and comfortable seating options to enjoy when you’re not out exploring Old Town. Swing open the French doors of the living room to let in the tropical breezes. Relax in the sun on the back patio or under the covered porch. The fully equipped kitchen provides every appliance and tool you’ll need to prepare meals at home. Dine indoors at the kitchen bar or enjoy an outdoor meal using the dining table and propane grill on the back patio.brbrTHE COMMUNITY POOL & FORT ZACHARY TAYLOR STATE PARK...brbrThe community pool is located just around the corner, with chaises and a cabana with restrooms. Or you can walk to Fort Zachary Taylor State Park, with the prettiest beach in Key West, just a half mile from your front door. The entrance to Truman Annex is secured by a 24-hour staffed guard gate and you can use the residential entry gate keys to come and go on foot at night.brbrCompliance with Truman Annex Community Rules & Regulations is expected of all Last Key guests. This includes “Quiet Time” in all outdoor areas, public and private, after 10PM.brbrTHE ACCOMMODATIONS...brbr** Bedroom #1: King bed, flat screen TV, closet, and access to the hall bathroom with a walk-in shower.brbr** Bedroom #2: Two Twin beds OR One King bed, flat screen TV, closet, and access to the hall bathroom with a walk-in shower.brbrALL LAST KEY VACATION HOMES INCLUDE:brbr** Washer & Dryerbr** Central Heat and A/Cbr** Ceiling Fansbr** Flat Screen TVs in Living Room & All Bedroomsbr** Fully Equipped Kitchenbr** Basic stock of spicesbr** Starter supply of paper productsbr** Starter set of cleaning productsbr** Linens and Towels providedbr** Wireless high-speed Internet access & full cable includedbrbrIn addition, this fully stocked home also includes, but is not limited to the amenities on this list:brbr** Community Pool Accessbr** Assigned Off-street Parking for 1 Car (with vehicle restrictions - no vehicle over 18’ long or 80’’ wide)brbrOther notes:brbr** Interim housekeeping provided upon requestbr** This property will accommodate up to 4 adultsbr** No Pets Allowed
Bed 2

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Bath 1

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Sleep 4

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Exceptional(33)

$622.91

/ Nightly
Condo

**THE PIRATE’S PENTHOUSE @ BAHAMA VILLAGE** Condo + LAST KEY SERVICES…

Key West, Florida, United States

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival!brbrLocated across the street from Blue Heaven, above the delicious La Creperie French Cafe, sits THE PIRATE’S PENTHOUSE. This hidden gem is ideally located in the heart of Bahama Village and within walking distance to everything Duval has to offer. THE PIRATE’S PENTHOUSE has touches of maritime decor sprinkled throughout this spacious condo, complete with a statue of the Captain himself on the wraparound porch, keeping a watchful eye on Petronia Street. Paired with Last Key Realty’s Five Star Guest Services, your stay at THE PIRATE’S PENTHOUSE is certain to be ‘argh’mazing.brbrTHE LOCATION...brbrTHE PIRATE’S PENTHOUSE sits at the legendary corner of Petronia & Thomas, right across the street from the beloved Blue Heaven restaurant and atop the incredible La Creperie French Cafe making it a foodies dream come true! From THE PIRATE’S PENTHOUSE you’re only a short walk to the heart of Old Town Key West, and an easy walk or bike ride to the best beaches and sunset views at Fort Zachary Taylor State Park and the newly constructed Truman Waterfront Park. brbrNo visit to Key West would be complete without a selfie at the iconic Southernmost Point Buoy, which is located just a few blocks away. You’ll also be within walking distance to a number of Key West's best and most unique restaurants, including Santiago's Bodega, Moondog Cafe and 915. While you won't need a car to get around, this home does have off-street parking available in the driveway, able to fit up to a mid-size SUV, should you bring a vehicle or rent a golf cart.brbrTHE LIVING AREA...brbrUpon entering the PIRATE’S PENTHOUSE you’ll immediately notice the vaulted ceilings and surprising amount of space for a 2 bedroom condo. The living area features a love seat, a sleeper sofa that pulls out to a queen-sized bed, and a large flat-screen TV for those moments between meals. One of two entrances to the incredible, private wrap-around porch sits off the living area, giving you access to one of the best places in Key West to people-watch and enjoy a morning cup of coffee or an evening cocktail.brbrTHE KITCHEN...brbrThe fully-outfitted country-style kitchen sits off the living area with luxury appliances and tools, equipped with everything you'll need to prepare a meal at home in between enjoying the fantastic array of Old Town restaurant options located just steps away.brbrTHE ACCOMMODATIONS...brbr** Master Bedroom aka the Flamingo Room - Located on the first floor of the unit (second floor of the building) features a King bed, flat-screen TV, full closet, balcony access and the bathroom across the hall.brbr** Guest Bedroom - Located on the second floor of the unit (third floor of the building) features a Queen bed, flat-screen TV, full closet, and access to the bathroom across the hall.brbr** The Living Area Sofa pulls out to a Queen-size bedbrbrALL LAST KEY VACATION HOMES INCLUDE:brbr** Washer and Dryerbr** Central Heat and A/Cbr** Ceiling Fansbr** Flat Screen TV in Living Roombr** Fully Equipped Kitchenbr** Basic stock of spicesbr** Starter supply of paper productsbr** Starter set of cleaning productsbr** Linens and Towels providedbr** Wireless high-speed Internet access & Hulu Live TV includedbr** Full Time Concierge ServicebrbrIn addition, this fully stocked condo also includes, but is not limited to the amenities on this list:brbr** Parking for a mid-size SUV in the drivewaybr** Private wraparound porch overlooking Thomas & PetroniabrbrOther notes:brbr** Interim housekeeping provided upon requestbr** This property will accommodate up to 6 adultsbr** Pets Not Allowedbr** No Smoking Allowed - not even on the porchbr** Last Key Realty vacation homes are rented to family groups and responsible adult groups only. Groups who expect they may cause after hours noise will not be a good fit for this home and should be aware they may incur additional penalties when in residence for violations. There will be a $500 charge for after-hours dispatch of our staff in response to calls resulting from verified noise complaints for violations by our guests in residence.
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Exceptional(13)

$821.26

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Private Vacation Home

Hemingway Caribbean Townhome/Private Pool by Beach,Key West charm,free parking

Key West, Florida, United States

Enjoy a luxurious tropical stay at this first floor 2-bedroom 2 bath 1,100 sqft townhome in Key West Florida. It features a king and two queen beds, ensuring a serene night's sleep for all guests. With amenities like AC, heating, and full ensuite bathrooms, your comfort is our top priority. The living room offers additional space with a cozy sofa bed for additional guests. The private outdoor grilling area and complete gourmet kitchen with a full size refrigerator with ice maker, electric oven and many gourmet appliances allows for full meal preparations for everyday and special occasions. Our heated private pool, outdoor shower and sundeck along with a smaller cocktail pool are one of a kind. You can even connect additional rooms and suites to sleep up to 12 guests. We also offer room service, bike rental, grocery and beverage shopping and full concierge services. We are just a 3 minute stroll from the public beach at Higgs, city park, children's playgrounds, tennis, pickleball, professional bocee courts, great restaurants, beach volleyball, a dog park, a dog beach and a fishing pier, all located in the peaceful high-end Casa Marina residential neighborhood, perfect for leisurely walks with someone special. The Key West Garden Club's landscaping display and orchid showings are also located on the beach. Art galleries, museums, live music venues, theaters and the world famous Duval Street are all within walking distance. You are sure to make many treasured memories with a stay at our townhome in paradise. We are located in the heart of historic Old Town. For your security and peaceful enjoyment, this property is surrounded by a bamboo privacy fence. This desirable property is highly recommended and reasonably priced. No resort or parking fees.brbrLocationbrYour Hemingway Caribbean Townhome is situated in a prime island location on the southern side of Key West in the prestigious residential Casa Marina neighborhood surrounded by majestic and luxurious homes with beautiful tropical gardens, perfect for pleasant walks any time of day. We are only a 3 minute stroll to Higgs Beach, Salute's Restaurant and West Martelo Tower, a Civil War Fort which is now home to the Key West Garden Club and walkable tropical gardens. We are a 13 minute walk to the Southernmost Point and a 12 minute walk to the Butterfly House. We are also close to several excellent restaurants and only a 9 minute drive from the airport.brbrOther Nearby Restaurants and AttractionsbrNearby access to the free Duval Loop Bus, provides access to the Historic Seaport, aquarium, Sloppy Joes, Truman Waterfront Park, Southernmost Point, Butterfly House and Nature Conservatory, Mel Fisher and Sails to Rails museums, art galleries and other attractions. Walking minutes to several nearby restaurants include: Durato's (2min), Ana's Cafe and Southernmost Grocery Store (8min), El Siboney Cuban (8min), Oasis Mediterranean (7min), White Street Pizza (7min) and famous Sandy's Cafe for authentic Cuban coffee and sandwiches (5min).brbrBeach, Pool and Outdoor LivingbrJust steps from the beach, your townhome is surrounded by lush gardens and palm trees. You can lounge on your private sundeck, next to your private heated lagoon-style pool, amidst lush palm trees in your private garden setting. There is also a private grilling area next to your pool. The common area is complete with hammock swings and a dining table under our mango tree and a putting green. Higgs Beach, which is just down the street, is also ideal for romantic evening walks for stargazers.brbrFurnishingsbrOur decor reflects a true Key West vibe. The gourmet kitchen is complete with an electric range, full size refrigerator with ice and water in the door, microwave, double sink, a george/forman, Keurig and a drip coffee maker, toaster, silverware, pots/pans, cookie sheets, roasting pans, grilling tools, a large and a mini blender to make your tropical drinks, an electric griddle, a dishwasher and many other speciality appliances. Your livingroom includes a lounging and sleeping area in front of a smart TV as well as a seating area with a reading library and a coffee table suitable for playing board games (which are also provided). brbrSleeping ArrangementsbrYour townhome sleeps up to six guests and includes a king and a queen bedroom. Each bedroom has an ensuite bathroom. Bodywash, shampoo, conditioner, extra toilet paper, large bath sheet towels and a hair dryer are provided. The king bedroom also has a large double sink vanity with drawers and shelves for your toiletries. Our bedrooms are equipped with cozy Tommy Bahama comforters. Each bedroom has a television complete with cable channels and free WiFi for your entertainment and convenience. Your livingroom includes a queen sofa bed and a separate couch suitable for a restful night's sleep, perfectly arranged for families or couples with friends. brbrDetails and AmenitiesbrYour first-floor Carribbean Townhome is 1,100sqft. Your private lagoon style pool is heated and sunrounded by a raised sundeck. For your convenience bike rentals, an iron and ironing board and washer/dryer service are all available on our property. We are family and pet friendly. Wrapped breakfast bars, nuts, fruit snacks, gourmet meatsticks, cheese and crackers, mini muffins, coffee/teas are provided in the condo along with fresh Florida oranges and grapefruits in our common area. Higgs Beach city park is nearby, complete with tennis, pickleball, sand volleyball, professional bocce courts, two playgrounds for children, White St. fishing and observation piers, an oceanside restaurant and a dog park. The White Street Pier is a quarter mile over the ocean with spectacular views of sunrise and sunset and excellent fishing.brbrConcierge ServicesbrEnjoy our concierge service to assist you before or during your stay with planning activities with the very best of Key West. From bike/scooter/golf cart rentals to any excursion you can think of including snorkeling and sunset sails, sandbar excursions, scuba diving, jet ski rentals, parasailing, kayaking, fishing, paddle boarding and much more. We can also arrange licensed massage therapy for you and your party, in our gardens or in your suite and have your condo stocked with groceries, adult beverages and all the necessities in advance of your arrival.brbrParkingbrFree off-street parking in front of and around the townhome compound.brbrYou Need To KnowbrOur property is equipped with fire extinguishers and smoke detectors.brOnsite parties, weddings and other events can be scheduled with prior approval by property owner.brGovernment issued photo ID and a credit or debit card or cash deposit may be required at check-in for incidential chargesbrExtra person charges may apply per the property's policies.brReport any damages prior to check out.brKey West Quiet Time may apply after 10pm on weekdays and 11pm on weekends through 8am in the morning. Thank you for supporting our efforts to be a good neighbor. Please note that your condo is located in a noise sensitive area. When you return from the parties, celebrations and live music on Duval street you will have a quiet, tranquil and restful sleep.brbrMake special memories that will last for a lifetime while relaxing at our paradise townhouse.
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$1949.37

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Private Vacation Home

Family Reunion Compound - Great for Groups! Large pool.

Key West, Florida, United States

Thinking about getting your extended family or friends together for a Key West family reunion vacation This one-of-kind gated Key West vacation rental compound, with large shared swimming pool in spacious landscaped tropical garden setting, could be the perfect place.brbrFamily Reunion Key West vacation rental includes: The Flower Power House, a 2-story house with attached cottage suite, plus a 3-story town home - Coco`s Poolside Retreat . Gated together in an authentic Old Town Key West compound, this layout lends itself ideally to being combined and rented together. The compound is shared with one additional townhouse within the gates.brbrA special feature of this `mini-compound` property is the large 40’ x 16’ swimming pool that is edged with irregular flag-stone rocks which gracefully `grow` into the landscaped garden. The garden has ample lounging areas. Just a few short blocks from the beach, this unique private complex is located in Old Town Key West conveniently close to shopping, art galleries and restaurants. There is one covered parking space, some off-street parking, and street parking is not metered.brbrBedding Summary:brbr1st Floor 1 King size bed, 1 Queen size bed, 2 Twin size bedsbr2nd Floor - 1 King size bed, 4 Twin size beds.brAttached Cottage Suite - Floor Planbrbr 2nd Floor – 1 King size bedbr1st Floor – Built in Twin bed with trundle bed (2 twin beds)brCoco`s Poolside RetreatbrbrSecond Floor - 1 Queen size bed, 1 Queen size sleeper sofabrThird Floor - 1 king, 2 twin beds (can be make into a King size bed)brbrAmenities: Spacious tropical garden. Large 40` X 16` feet swimming pool (heated, shared), smart TV`s, a/c, stereo, telephone, washer dryer, linens and towels provided, fenced yard, large porches, kitchens.brbrActivities: Close to Higgs Beach (a short walk), and 2 parks. Ride your bike to Duval Street and the southernmost point of the U.S. in fewer than five minutes. Walk to Duval Street in 20 minutes.brbrArea: This property is ideally located in the White Street Gallery District of Old Town Key West in a historic neighborhood just a few streets from White Street and Higgs Beach. From this location you can quickly walk to Fausto`s Fine Food Palace (fine wine, cheeses, and gourmet foods), Sandy`s Cafe of Cuban coffee, numerous art galleries (White Street Gallery area), and yoga and exercise studios. Duval Street shops, attractions, and the Historic Seaport District is about twenty minute walk.brbrRestrictions: Smoking permitted only outside please. No pets. We do not accept guests less than 25 years of age unless accompanied by a family group or guardian.brbrPAYMENT: Payment for the rental will be processed outside of VRBO according to the terms of your rental agreement (sent for review upon reservation). Payments by credit card are subject to an additional 2.95% merchant processing fee.
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$161.65

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Private Vacation Home

Tropical Tee-Time: 2BR Townhome in Key West Golf Club with Two Shared Pools, Fitness Center, Dogs OK

Key West, Florida, United States

County zoning requires a minimum rental period of 28 nights, and no exceptions can be made. Please review additional policies below. brbr brbrWelcome to Tropical Tee-Time – your serene island escape nestled in the lush, gated Key West Golf Club community on Stock Island! brbr brbrThis charming 2-bedroom, 1.5-bath townhome offers a peaceful retreat just minutes from the excitement of downtown Key West. Step inside to find a bright, open-concept living space with tropical décor and all the comforts of home. The fully equipped kitchen makes it easy to whip up meals, while the private back deck is perfect for morning coffee or evening cocktails surrounded by swaying palms. As a guest at Tropical Tee-Time, you’ll have access to two resort-style community pools, including a beautiful lagoon-style pool, as well as a well-equipped fitness center for staying active during your stay. This home is also dog-friendly, so your furry companion can enjoy the island vibes right alongside you. Ideally located just five miles from the energy and excitement of Duval Street, you’ll be close to world-class dining, shopping, and nightlife. Smathers Beach is only four miles away for sun-soaked days by the sea, and Marathon is just an hour’s drive, making this the perfect home base for exploring the Lower Keys. Whether you're hitting the greens, lounging poolside, or discovering the charm of Key West, Tropical Tee-Time offers the perfect blend of comfort, convenience, and island adventure. brbr brbrSLEEPS MAXIMUM OF 4 GUESTS: brbr brbrBedroom 1 (2nd Floor): Queen Bed, Smart TV (no cable/satellite available) brbr brbrBedroom 2 (2nd Floor): Queen Bed, Smart TV (no cable/satellite available) brbr brbrLiving Room: Sofa w/ Two Recliners, Chair, Smart TV (no cable/satellite available) brbr brbrKitchen: Nicely equipped (everything needed to prepare and serve meals) brbr brbrAMENITIES: brbr brbr- Two Shared Pools (chlorine & not heated) brbr brbr- Private Patio brbr brbr- Propane BBQ Grill brbr brbr- Single Serve & Drip Coffee Maker, Toaster, Blender brbr brbr- Parking for up to 2 Vehicles brbr brbr- Linens and towels provided brbr brbr- 3.6 miles to Smathers Beach brbr brbr- 4.6 miles to Duval Street brbr brbr- 4.7 miles to Southernmost Point brbr brbr- 4.7 miles to Key West Historic Seaport brbr brbr- 5.2 miles to Mallory Square Sunset Pier brbr brbr- 5.3 miles to Forty Zachary Taylor State Park Beach brbr brbrIMPORTANT POLICIES FOR YOUR STAY: brbr brbrAge & Occupancy: The booking tenant must be 25 years or older and must occupy the property for the entire duration of the stay. This property is exclusively available as a vacation rental and not for worker housing. brbr brbrPeak Season Monthly Bookings: All bookings from December through March must be for the entire month, starting at the beginning and ending at the end of the month. Consecutive months may be booked if they follow this requirement. Bookings that do not adhere to this policy are subject to cancellation. If you are interested in alternative dates, please contact us for approval before booking. brbr brbrPet Policy: Up to one friendly and well-behaved dog 25 LBS or less will be considered with a $10/night pet fee. To help maintain a safe and welcoming environment for all, we require every guest to submit pet or assistance animal information through BetterPet Passport. Guests will simply submit household pet information, request an accommodation for an assistance animal, or confirm they are not bringing a pet/animal. It's free, and only requires creating an account if you're bringing a pet or animal. After booking, you'll receive a link to complete the process. brbr brbrSmoking Policy: Smoking is strictly prohibited to maintain a smoke-free environment. brbr brbrMid-Stay Cleaning: For stays of 28 nights or more, we reserve the right to require a mid-stay cleaning to maintain the quality of the property. For longer stays, a mid-stay cleaning will be required every 28 nights thereafter. The cost will be collected separately, and the number of cleanings depends on the length of your stay. brbr brbrLocal Wildlife & Pest Control: The Florida Keys are home to various insects (mosquitoes, no-see-ums, termites), reptiles, chickens, Key deer, and other wildlife. While routine pest control is in place, complete elimination is not possible. Guests should take precautions, such as using insect repellent and keeping doors closed, to minimize exposure. brbr brbrConstruction & Renovation Notice: Due to ongoing growth in the Florida Keys, renovations, construction, and road repairs may occur without prior notice. While we strive to provide a peaceful stay, iTrip Key West is not liable for any inconveniences caused by nearby construction. brbr brbrPhoto Disclaimer: All images are for illustrative purposes only. Individual features such as bed sizes, bedding, décor, appliances, colors, and amenities may vary, as these are privately owned homes and updates occur regularly. Lighting conditions and screen settings may also affect how colors appear. Please refer to the written description and reach out with any specific questions or concerns. All furnishings and décor are subject to change at any time. brbr brbrSecurity Cameras: For the safety and security of our guests and property, two exterior security cameras monitor the front and back porches. These cameras are for security purposes only and do not monitor any private interior or outdoor living spaces.
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