Key West

Key West Homestays

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Popular Homestays in Key West

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Galleon Resort beach hotel luxury in Old Town Key West
Galleon Resort beach hotel luxury in Old Town Key WestGalleon Resort beach hotel luxury in Old Town Key West
Hotel near Key West 88.9% of visitors choose this area
This is a large (1245 SF) 1BR/1BA condo on the 6th floor of the Galleon Resort & Marina.....and is a one of a kind. It features a fantastic, fully equipped kitchen with new cabinetry and granite countertops, dining room, living room and a very spacious master bedroom & bath. This suite will sleep 5, with a king bed and a twin pullout in the master bedroom and a queen pullout in the living room. Also, one of a kind, is the huge deck with an outside table & chairs, private hot tub and a spiral staircase to a private rooftop deck for fantastic views of all of Key West. For added convenience, this suite offers 2 TVs with cable, DVD players, washer/dryer, iron & ironing board, free wireless internet and a safe..About pets:No pets allowed.About checkOut:Check out before 10:00 AM.About children:Children allowed: ages 0-17.About checkIn:Check in after 4:00 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 21.About events:No events allowed.
Amazing
53 reviews
9.6/10
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Fully renovated Condo with Private Balcony, Shared Pool, Hot Tub and Parking
Fully renovated Condo with Private Balcony, Shared Pool, Hot Tub and ParkingFully renovated Condo with Private Balcony, Shared Pool, Hot Tub and Parking
Hotel near Key West
*Brand New Listing* Welcome to Captains Choice The NICEST Unit at Sunrise Suites Resort in Key West- Unit 302.Tropical winds, excellent weather, and Key West charm await when you book your stay in this gorgeous completely renovated two bedroom, two bathroom condo "Captains Choice". This condo is equipped with BRAND NEW everything from top to bottom with nothing but the finest appliances, fixtures, and furnishings. Enjoy the game or your favorite movie on our new Samsung smart TV's in each bedroom including a 60 inch in the living room. Sit back and enjoy your private balcony, and catch the sunset over the salt ponds while sipping your beverage of choice. Other in-unit amenities include a brand new Keurig machine with pods and full size washer and dryer. Take advantage of some of the amenities located at the resort: Heated community pool, hot tub, gym, and tennis court.Sleeping Arrangements -1 King in Master Bedroom1 Queen in Spare Bedroom1 High End full size sleeper sofa in living room*All bedding is of high qualityNearby:Key West International Airport (2-3 minutes away)Smathers Beach (along with walking, running, and bike path)Bodhi Spa and WellnessSeaside Grocery (convenience store)Great restaurants and bars including La Trattoria, Benihana, and Coconut Mallory's Bar. Key West Golf Club (2 miles)Comfort and relaxation await you in this luxurious condo. Our reservation calendar is up to date. Book your reservation today!This condo is an end unit, located on the 3rd floor (with elevator access)Parking: Your booking comes with FREE parking. We have parking Spaces on both sides of the building. We only ask that you do not park under any of the covered parking, as these are reserved spaces. Everything else is first come first served. Thank you & enjoy your stay at Captains Choice!About pets:No pets allowed.About checkOut:Check out before 11:00 AM.About children:Children allowed: ages 0-17.About checkIn:Check in after 4:00 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 25.About events:No events allowed.
Outstanding
42 reviews
9.8/10
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Welcome To Poseidon Too - A Newly, Completely Renovated Condo @ Sunrise Suites!
Welcome To Poseidon Too - A Newly, Completely Renovated Condo @ Sunrise Suites!Welcome To Poseidon Too - A Newly, Completely Renovated Condo @ Sunrise Suites!
Hotel near Key West
Welcome to Poseidon Too! A completely, newly renovated two bedroom two bath condo located at Sunrise Suites. Poseidon Too is located on the south side of Key West, and only about 1 mile away from Smathers Beach, and 5 miles away from downtown Duval St. Our condo is for guests that enjoy the finer things in life. The condo has just gone through a full renovation from top to bottom with only the best in mind. You will find high end furniture, a brand new kitchen/appliances, and amazing spa like bathrooms.Sleeping Arrangements:Master Bedroom - One king size bed with ensuite bath.Second Bedroom - One queen size bed with easy access to second bathroomLiving Room - One queen size sleeper sofa**All of our beds have excellent quality mattresses and come with high end bedding to give you a great nights sleep**The Space:Poseidon Too is equipped with smart TV's in each room, high speed internet, central AC, new fully equipped kitchen with beautiful quartz countertops, new, in unit washer/dryer, and private balcony with amazing sunset views. Things To Note:- Guests will have full access to shared pool, hot tub, fitness room, tennis court.- Sunrise Suites has elevator or stair access- Parking - There are parking spaces on both sides of the building. all spaces are first come first serve. Please do not park under the building as these are reserved spots.- Guests Access - will be contactless and you will be provided a code upon arrival.- We can accommodate up to 6 guests- Our condo is equipped with both a Keurig (with pods), and a drip pot.About pets:No pets allowed.About checkOut:Check out before 11:00 AM.About children:Children allowed: ages 0-17.About checkIn:Check in after 4:00 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 25.About events:No events allowed.
Outstanding
13 reviews
9.8/10
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Key West
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Castaway Cove: 2/2 Condo near the beach with shared pool and hot tub
Castaway Cove: 2/2 Condo near the beach with shared pool and hot tubCastaway Cove: 2/2 Condo near the beach with shared pool and hot tub
Hotel near Key West
Welcome to the tranquil, tucked away community of Sunrise Suites in beautiful Key West, Florida. When you choose to spend your vacation with us at the pet-friendly Castaway Cove Condo, you will be just 1 mile from Smather's Beach and a quick 10 minute drive to the fun and excitement of downtown Duval Street with tons of restaurants, bars, art galleries, museums, live music and people watching. Castaway Cove offers all of the creature comforts you are used to at home including a full kitchen with cooking/dining essentials, Keurig & drip coffee machines and dishwasher. Meals can be enjoyed indoors on the peninsula countertop (up to 4) or outside on the private patio (up to 4). A Master Suite with ensuite bathroom, queen bedroom with bathroom attached (also accessible from living room) and a pull-out sofa in the living room can accommodate up to 6 guests for a restful night of sleep after a day of island exploration. Our guests also enjoy central AC, Free Wi-Fi, multiple smart TV's with cable and streaming capabilities, and in-unit washer and dryer. The Sunrise Suites community offers our guests access to the following shared amenities:-Heated Pool & Hot Tub-Sunbathing decks & loungers -Fitness Center -Tennis Courts -Free parking on a first come, first serve basis (not assigned, not covered, proximity to unit not guaranteed)-Walking Paths/Biking Trails -Corner Store a quick 5 minute walk awayAbout pets:Pets allowed: dogs less than 50 lbs per pet (limit one pet total).About checkOut:Check out before 11:00 AM.About children:Children allowed: ages 0-17.About checkIn:Check in after 4:00 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 25.About events:No events allowed.
Outstanding
13 reviews
10.0/10
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June - October 2025 Low Rates!!! Atlantic Hideaway- Key West
June - October 2025 Low Rates!!! Atlantic Hideaway- Key WestJune - October 2025 Low Rates!!! Atlantic Hideaway- Key West
Hotel near Key West
Welcome to Atlantic Hideaway a stunning fully remodeled 2 bedrooms, 2-bathroom condo checks all the boxes for your vacation needs and sleeps up to 6 people! Located in the 1800 Atlantic condo complex with two large communal swimming pools, spa, tennis courts, fitness facilities, private beach, walking paths, BBQ area and recreation room/ library. The opportunities for entertainment are endless in this private condo resort and the location is perfect. Just 1 mile from the Key West International Airport and 2 miles to Duval Street you are in the perfect spot for easy access all over the island. The unit is a spacious 2-bedroom, 2-bathroom 3rd floor unit with water and garden views. Inside the unit you will find a well-appointed kitchen with stainless appliances, shaker style cabinets, quartz countertops and breakfast bar and seating. The formal dining area for 6 guests, wet bar and beverage center is great for entertaining family and guests. The living room has sofa sleeper, love seat and accent chair and has large wall to wall glass sliding doors that lead out to a spacious outdoor lanai with outdoor dining and conversation seating. The primary bedroom offers a king size bed, chest of drawers, full length mirrors and large sliding doors leading out to the unit's shared lanai. The suite is complete with a private bathroom with custom tile shower, dual vanities and large closets. The guest bedroom has a queen size bed, chest of drawers, large closet and sliding doors to the unit's shared lanai. A second shared bathroom is located in the hallway of the unit and has a shower/bathtub combo and custom vanity. Also located in the unit is a full-size washer & dryer, beach chairs & beach towels. The unit comes with 1 assigned covered parking space in secured garage and there is overflow unassigned parking for 1 additional vehicle or golf cart as available. We look forward to hosting you at Atlantic Hideaway.About pets:No pets allowed.About checkOut:Check out before 10:00 AM.About children:Children allowed: ages 0-17.About checkIn:Check in after 4:00 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 28.About events:No events allowed.
Amazing
49 reviews
9.6/10
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Two-bedroom, two-bath condo close to the Ocean. Full kitchen, living r & balcony
Two-bedroom, two-bath condo close to the Ocean. Full kitchen, living r & balconyTwo-bedroom, two-bath condo close to the Ocean. Full kitchen, living r & balcony
Hotel near Key West
This condo is located approximately three miles from Duval and one mile from Smathers beach. Walking distance to the Ocean. Grocery stores, marina, and water sports nearby. Outdoor spa, Gym, Private balcony, Tennessee court.About pets:No pets allowed.About checkOut:Check out before 11:00 AM.About children:Children allowed: ages 0-17.About customRules:NO-SMOKING property! $200 fee will be added for disregarding our NO-SMOKING rule. Please turn off all lights, fans, and AC before check-out..About checkIn:Check in after 4:00 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 28.About events:No events allowed.
Very Good
20 reviews
8.8/10
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Beautiful Stock Island Rental ~10 Min from Downtown Key West
Beautiful Stock Island Rental ~10 Min from Downtown Key WestBeautiful Stock Island Rental ~10 Min from Downtown Key West
Hotel near Key West
Enjoy the tropics without leaving the states! Relax, and catch your breath while enjoying ocean views from the large private balcony, master bedroom, or living room!This spacious 3 bed 2 bath condo on Stock Island offers a quiet & peaceful atmosphere with a short 15 min ride to downtown Key West. Truly offering the best of both worlds. Enjoy the community pool and hot tub right outside the front door. This space offers top of the line appliances in a kitchen built for entertaining. The fluid style and aesthetic will leave you relaxed, wanting more time in paradise.Arriving by boat? Oceans Edge Marina offers gated access right on-site. Don't forget to try Yellowfin Bar and Restaurant conveniently located just a short walk away.About pets:No pets allowed.About checkOut:Check out before 11:00 AM.About children:Children allowed: ages 0-17.About checkIn:Check in after 4:00 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 25.About events:No events allowed.
Amazing
39 reviews
9.6/10
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Key West Condo close to the Ocean. 1 mile to Smathers & 3 miles to Duval St.
Key West Condo close to the Ocean. 1 mile to Smathers & 3 miles to Duval St.Key West Condo close to the Ocean. 1 mile to Smathers & 3 miles to Duval St.
Hotel near Key West
This 2 bedroom (one King and one Queen, plus Queen size pull out couch in the living room), 2 bathroom unit offers all the convenience and comfort of your own home. It is spacious and fully equipped. Located one mile from Smathers Beach, two miles from Higgs Beach and just minutes away from the Key West Lighthouse Museum. Many species of birds inhabit the salt ponds preserve that borders this property. About pets:No pets allowed.About checkOut:Check out before 10:00 AM.About children:Children allowed: ages 0-17.About customRules:NO-SMOKING property! $200 fee will be added for disregarding our NO-SMOKING rule. Please turn off all lights, fans, and AC before check-out..About checkIn:Check in after 4:00 PM.About smoking:Smoking is not permitted.IF DISREGARDED - $200 FEE WILL BE ADDED..About minBookingAge:Minimum age to rent: 28.About events:No events allowed.
Great
33 reviews
9.2/10
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BOOKING SMOKING HOT 2025 DEALS NOW!
BOOKING SMOKING HOT 2025 DEALS NOW!BOOKING SMOKING HOT 2025 DEALS NOW!
Hotel near Key West 88.9% of visitors choose this area
City of Key West Business License # 28224We hope you will enjoy this home where Ernest Hemingway and Jimmy Buffet memorabilia welcome you into the abode our first guest affectionately called “The Writer's Retreat'.This two bedroom, one bath condo with bleached grey hardwood flooring throughout is highlighted by a massive 65 inch Plasma TV loaded with thousands of movies at your fingertips. Relax on the designer furniture while enjoying the full collection of Hemingway's books or lose yourself in The Master Bedroom retreat which has been luxuriously decorated with 1000 thread count bedding on the Romantic Canopy Bed with French doors leading out to a spacious rear patio overlooking the pool.The guest bedroom has two twin upgraded pillow top beds that can be converted to a King bed to accommodate a family or two couples. The King is stocked with a very thick down padding and luscious linens for maximum comfort. Enjoy the sounds of the keys or music of Buffet as the guest bedroom is decorated in tribute to crooner and the island lifestyle detailed in framed sheet music.If staying in for the evening or fixing breakfast or lunch have fun in the 1950’s themed state of the art kitchen equipped with an imported European SMEG Fridge and Stainless Appliances. Likewise, the bathroom has been decorated in an art deco style typical of an earlier time in the Keys. The front Family room area has features a queen sleeper sofa bed with a down pad and bedding for extra sleeping space. All pillows and bedding are down and of high quality in order to provide maximum comfort on your stay. Quite simply, we designed this home to fit in with the Keys lifestyle. It is bright, open and lends itself to a vibe which we hope catapults you to a great stay in our beloved Keys.Please enjoy the slide show of our new wonderful home in Key West and we hope to accommodate your vacation needs.TO VIEW OUR OTHER PROPERTIES VISITVRBO Listing #412277 & #497962 for Catalina Island VRBO Listing #316356 PGA WEST La QuintaVRBO Listing #592709 for San Clemente BeachVRBO Listing #633858 for Park City UtahVRBO listing #724909 for Garden District New OrleansVRBO listing ID 815366 For Kiawah Island, Charleston South CarolinaVRBO Listing ID 901935 for Newport BeachPlease see contract for additional details.About pets:No pets allowed.About checkOut:Check out before 10:00 AM.About children:Children allowed: ages 0-17.Two twin beds or can be converted to King.About customRules:RENTAL AGREEMENT - A valid Driver's License and signed Short-Term Rental Agreement are due after booking confirmation..About checkIn:Check in after 3:00 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 25.About events:No events allowed.
Great
57 reviews
9.2/10
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Frequently Asked Questions

What are the popular Homestays in Key West?

Whether you're travelling for business or tourism to Key West, Heron House Court - Adult Only , Heron House - Adult Only and Nyah - Adult Exclusive are preferred.

What's the average rate for Homestays in Key West?

For Homestays in Key West, the average price on weekdays is AU$ 1,202, while the average price on weekends (Friday–Saturday) is AU$ 1,590.

Which Homestays in Key West have swimming pools?

There are many Homestays in Key West with swimming pools. Nyah - Adult Exclusive , Authors Key West Guesthouse and La Pensione Inn - Adult Exclusive are very popular.

Which Homestays in Key West have fitness facilities?

Which Homestays in Key West have bars?

What Homestays in Key West offer breakfast?

Which Homestays in Key West have parking available?

Which Homestays in Key West provide a luxury experience?

Looking for a luxury experience? The Artist House is very popular.

What deals are there for Homestays in Key West?

Trip.com has a range of promotions and discounts for Homestays. You can head over to the promotions page to check out the current deals on Trip.com.

Homestays Information in Key West

Total Properties10
Number of Reviews3,094
Highest PriceAU$ 6,376
Lowest PriceAU$ 159
Average Price (Weekends)AU$ 1,590
Average Price (Weekdays)AU$ 1,202