33040, Florida, United States Vacation Rental Homes By Owner - Page 99

Duval Street, Smathers Beach, & Old Town charm await—Key West escape begins herebrbrThis listing is for a room within a hotel.brbr✦ Your room is 1525 sq. ft, equipped with complimentary toiletries, TV.brbr✦ Cleaning services included in the nightly price.brbrThere are a few additional details to know before you book:brbr✦ The minimum age required for check-in is 21 years old.brbr✦ Please ensure you have a valid ID for check-in, as it is mandatory for entry.brbr———————————————brbrGuest Access:brDuring your stay, you will have access to the property and amenities according to the following schedule:brbr✦ Check-in is available from 04:00 pm.brbr✦ Fitness center is available.brbr✦ Pool is available.brbr✦ Paid valet parking – 1 space(s), available for $32.25 per day.brbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A mandatory resort fee of $51.00 per night will be collected upon check-in, not included in the daily rate.brbr✦ Pets are not allowed.brbr✦ We use multi-unit listings, so rooms are similar but may have small differences.

Ideal Family Stay in Great Location! 4 Pools, Shuttle Service, Near Duval Street

Key West, Florida, United States

Bed

Bath

Sleeps

$778.51

Duval Street, Smathers Beach, & Old Town charm await—Key West escape begins herebrbrThis listing is for a room within a hotel.brbr✦ Your room is 925 sq. ft, equipped with complimentary toiletries, TV.brbr✦ Cleaning services included in the nightly price.brbrThere are a few additional details to know before you book:brbr✦ The minimum age required for check-in is 21 years old.brbr✦ Please ensure you have a valid ID for check-in, as it is mandatory for entry.brbr———————————————brbrGuest Access:brDuring your stay, you will have access to the property and amenities according to the following schedule:brbr✦ Check-in is available from 04:00 pm.brbr✦ Fitness center is available.brbr✦ Pool is available.brbr✦ Paid valet parking – 1 space(s), available for $32.25 per day.brbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A mandatory resort fee of $51.00 per night will be collected upon check-in, not included in the daily rate.brbr✦ Pets are not allowed.brbr✦ We use multi-unit listings, so rooms are similar but may have small differences.

Experience Key West! Suite with Private Terrace & Free Shuttle Service!

Key West, Florida, United States

Bed

Bath

Sleeps

$1020.39

Duval Street, Smathers Beach, & Old Town charm await—Key West escape begins herebrbrThis listing is for a room within a hotel.brbr✦ Your room is 622 sq. ft, equipped with complimentary toiletries, TV.brbr✦ Cleaning services included in the nightly price.brbrThere are a few additional details to know before you book:brbr✦ The minimum age required for check-in is 21 years old.brbr✦ Please ensure you have a valid ID for check-in, as it is mandatory for entry.brbr———————————————brbrGuest Access:brDuring your stay, you will have access to the property and amenities according to the following schedule:brbr✦ Check-in is available from 04:00 pm.brbr✦ Fitness center is available.brbr✦ Pool is available.brbr✦ Paid valet parking – 1 space(s), available for $32.25 per day.brbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A mandatory resort fee of $51.00 per night will be collected upon check-in, not included in the daily rate.brbr✦ Pets are not allowed.brbr✦ We use multi-unit listings, so rooms are similar but may have small differences.

Key West Vacation @ the Beach!Partial Waterview Suite Near Ernest Hemingway Home

Key West, Florida, United States

Bed

Bath

Sleeps

$630.03

Duval Street, Smathers Beach, & Old Town charm await—Key West escape begins herebrbrThis listing is for a room within a hotel.brbr✦ Your room is 622 sq. ft, equipped with complimentary toiletries, TV.brbr✦ Cleaning services included in the nightly price.brbrThere are a few additional details to know before you book:brbr✦ The minimum age required for check-in is 21 years old.brbr✦ Please ensure you have a valid ID for check-in, as it is mandatory for entry.brbr———————————————brbrGuest Access:brDuring your stay, you will have access to the property and amenities according to the following schedule:brbr✦ Check-in is available from 04:00 pm.brbr✦ Fitness center is available.brbr✦ Pool is available.brbr✦ Paid valet parking – 1 space(s), available for $32.25 per day.brbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A mandatory resort fee of $51.00 per night will be collected upon check-in, not included in the daily rate.brbr✦ Pets are not allowed.brbr✦ We use multi-unit listings, so rooms are similar but may have small differences.

Beachfront Accommodation w/ Shuttle Service & Pool! Minutes to Key West Airport!

Key West, Florida, United States

Bed

Bath

Sleeps

$878.63

Duval Street, Smathers Beach, & Old Town charm await—Key West escape begins herebrbrThis listing is for a room within a hotel.brbr✦ Your room is 925 sq. ft, equipped with complimentary toiletries, TV.brbr✦ Cleaning services included in the nightly price.brbrThere are a few additional details to know before you book:brbr✦ The minimum age required for check-in is 21 years old.brbr✦ Please ensure you have a valid ID for check-in, as it is mandatory for entry.brbr———————————————brbrGuest Access:brDuring your stay, you will have access to the property and amenities according to the following schedule:brbr✦ Check-in is available from 04:00 pm.brbr✦ Fitness center is available.brbr✦ Pool is available.brbr✦ Paid valet parking – 1 space(s), available for $32.25 per day.brbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A mandatory resort fee of $51.00 per night will be collected upon check-in, not included in the daily rate.brbr✦ Pets are not allowed.brbr✦ We use multi-unit listings, so rooms are similar but may have small differences.

Family Fun in Key West with 4 Pools & Free Shuttle! Close to Southernmost Point!

Key West, Florida, United States

Bed

Bath

Sleeps

$2433.36

Duval Street, Smathers Beach, & Old Town charm await—Key West escape begins herebrbrThis listing is for 2 separate rooms within a hotel. The price shown in the listing covers all 2 rooms.brbr✦ Each room is 1525 sq. ft, equipped with complimentary toiletries, TV.brbr✦ Rooms are not adjoining and possibly not next to each other. Spaces are assigned upon arrival based on availability.brbr✦ Cleaning services included in the nightly price.brbrThere are a few additional details to know before you book:brbr✦ The minimum age required for check-in is 21 years old.brbr✦ Please ensure you have a valid ID for check-in, as it is mandatory for entry.brbr———————————————brbrGuest Access:brDuring your stay, you will have access to the property and amenities according to the following schedule:brbr✦ Check-in is available from 04:00 pm.brbr✦ Fitness center is available.brbr✦ Pool is available.brbr✦ Paid valet parking – 1 space(s), available for $32.25 per day.brbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A mandatory resort fee of $51.00 per night will be collected upon check-in, not included in the daily rate.brbr✦ Pets are not allowed.brbr✦ We use multi-unit listings, so rooms are similar but may have small differences.

Family Fun in Key West with 4 Pools & Free Shuttle! 2 Waterfront Units!

Key West, Florida, United States

6

Bed

6

Bath

12

Sleeps

$472.55

Duval Street, Smathers Beach, & Old Town charm await—Key West escape begins herebrbrThis listing is for a room within a hotel.brbr✦ Your room is 375 sq. ft, equipped with complimentary toiletries, TV.brbr✦ Cleaning services included in the nightly price.brbrThere are a few additional details to know before you book:brbr✦ The minimum age required for check-in is 21 years old.brbr✦ Please ensure you have a valid ID for check-in, as it is mandatory for entry.brbr———————————————brbrGuest Access:brDuring your stay, you will have access to the property and amenities according to the following schedule:brbr✦ Check-in is available from 04:00 pm.brbr✦ Fitness center is available.brbr✦ Pool is available.brbr✦ Paid valet parking – 1 space(s), available for $32.25 per day.brbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A mandatory resort fee of $51.00 per night will be collected upon check-in, not included in the daily rate.brbr✦ Pets are not allowed.brbr✦ We use multi-unit listings, so rooms are similar but may have small differences.

Beautiful Water Views! Minutes to Southernmost Point! Parking, Onsite Pools!

Key West, Florida, United States

Bed

Bath

Sleeps

$1074.35

Duval Street, Smathers Beach, & Old Town charm await—Key West escape begins herebrbrThis listing is for a room within a hotel.brbr✦ Your room is 1525 sq. ft, equipped with complimentary toiletries, TV.brbr✦ Cleaning services included in the nightly price.brbrThere are a few additional details to know before you book:brbr✦ The minimum age required for check-in is 21 years old.brbr✦ Please ensure you have a valid ID for check-in, as it is mandatory for entry.brbr———————————————brbrGuest Access:brDuring your stay, you will have access to the property and amenities according to the following schedule:brbr✦ Check-in is available from 04:00 pm.brbr✦ Fitness center is available.brbr✦ Pool is available.brbr✦ Paid valet parking – 1 space(s), available for $32.25 per day.brbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A mandatory resort fee of $51.00 per night will be collected upon check-in, not included in the daily rate.brbr✦ Pets are not allowed.brbr✦ We use multi-unit listings, so rooms are similar but may have small differences.

Family-friendly Villa! Near Key West Int'l Airport! Parking, Onsite Pools!

Key West, Florida, United States

Bed

Bath

Sleeps

$708.69

Duval Street, Smathers Beach, & Old Town charm await—Key West escape begins herebrbrThis listing is for a room within a hotel.brbr✦ Your room is 925 sq. ft, equipped with complimentary toiletries, TV.brbr✦ Cleaning services included in the nightly price.brbrThere are a few additional details to know before you book:brbr✦ The minimum age required for check-in is 21 years old.brbr✦ Please ensure you have a valid ID for check-in, as it is mandatory for entry.brbr———————————————brbrGuest Access:brDuring your stay, you will have access to the property and amenities according to the following schedule:brbr✦ Check-in is available from 04:00 pm.brbr✦ Fitness center is available.brbr✦ Pool is available.brbr✦ Paid valet parking – 1 space(s), available for $32.25 per day.brbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A mandatory resort fee of $51.00 per night will be collected upon check-in, not included in the daily rate.brbr✦ Pets are not allowed.brbr✦ We use multi-unit listings, so rooms are similar but may have small differences.

Enjoy the Tropics! Unit w/ Garden View & Kitchenette, Outdoor Pool

Key West, Florida, United States

Bed

Bath

Sleeps

$459.0

Duval Street, Smathers Beach, & Old Town charm await—Key West escape begins herebrbrThis listing is for a room within a hotel.brbr✦ Your room is 622 sq. ft, equipped with complimentary toiletries, TV.brbr✦ Cleaning services included in the nightly price.brbrThere are a few additional details to know before you book:brbr✦ The minimum age required for check-in is 21 years old.brbr✦ Please ensure you have a valid ID for check-in, as it is mandatory for entry.brbr———————————————brbrGuest Access:brDuring your stay, you will have access to the property and amenities according to the following schedule:brbr✦ Check-in is available from 04:00 pm.brbr✦ Fitness center is available.brbr✦ Pool is available.brbr✦ Paid valet parking – 1 space(s), available for $32.25 per day.brbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A mandatory resort fee of $51.00 per night will be collected upon check-in, not included in the daily rate.brbr✦ Pets are not allowed.brbr✦ We use multi-unit listings, so rooms are similar but may have small differences.

Lush Tropical Garden! Private Balcony, Onsite Parking! Near Southernmost Point!

Key West, Florida, United States

Bed

Bath

Sleeps

$1204.88

Duval Street, Smathers Beach, & Old Town charm await—Key West escape begins herebrbrThis listing is for a room within a hotel.brbr✦ Your room is 1525 sq. ft, equipped with complimentary toiletries, TV.brbr✦ Cleaning services included in the nightly price.brbrThere are a few additional details to know before you book:brbr✦ The minimum age required for check-in is 21 years old.brbr✦ Please ensure you have a valid ID for check-in, as it is mandatory for entry.brbr———————————————brbrGuest Access:brDuring your stay, you will have access to the property and amenities according to the following schedule:brbr✦ Check-in is available from 04:00 pm.brbr✦ Fitness center is available.brbr✦ Pool is available.brbr✦ Paid valet parking – 1 space(s), available for $32.25 per day.brbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A mandatory resort fee of $51.00 per night will be collected upon check-in, not included in the daily rate.brbr✦ Pets are not allowed.brbr✦ We use multi-unit listings, so rooms are similar but may have small differences.

Ideal Family Stay in Great Location, 4 Pools, Shuttle Service, Near Airport!

Key West, Florida, United States

Bed

Bath

Sleeps

$1064.23

Duval Street, Smathers Beach, & Old Town charm await—Key West escape begins herebrbrThis listing is for a room within a hotel.brbr✦ Your room is 1525 sq. ft, equipped with complimentary toiletries, TV.brbr✦ Cleaning services included in the nightly price.brbrThere are a few additional details to know before you book:brbr✦ The minimum age required for check-in is 21 years old.brbr✦ Please ensure you have a valid ID for check-in, as it is mandatory for entry.brbr———————————————brbrGuest Access:brDuring your stay, you will have access to the property and amenities according to the following schedule:brbr✦ Check-in is available from 04:00 pm.brbr✦ Fitness center is available.brbr✦ Pool is available.brbr✦ Paid valet parking – 1 space(s), available for $32.25 per day.brbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A mandatory resort fee of $51.00 per night will be collected upon check-in, not included in the daily rate.brbr✦ Pets are not allowed.brbr✦ We use multi-unit listings, so rooms are similar but may have small differences.

Experience Key West w/ Poolside Bar, Private Terraces & Free Shuttle Service!

Key West, Florida, United States

Bed

Bath

Sleeps

$1047.35

Zen Villa - A Luxe Retreat in the Heart of Old Key West! Tucked away on a quiet lane just steps from the vibrant heartbeat of Old Town, Zen Villa is where modern luxury meets island tranquility. Designed for those who crave both exhilaration and escape, this stunning contemporary retreat offers an effortless blend of indoor-outdoor living, lush tropical beauty, and refined elegance. Step inside to soaring 20-foot cathedral ceilings and an inviting lounge complete with a sleek wet bar, granite countertops, beverage cooler, and ice maker—because every great escape deserves a proper welcome. The open-concept living and dining areas flow seamlessly to multiple outdoor sanctuaries, framed by expansive sliding glass doors that invite Key West's natural beauty inside. Outside, the lush tropical landscape and Craig Reynolds-designed heated dipping pool with a cascading water feature, ambient lighting, and a refreshing outdoor shower set the scene for pure relaxation. Whether you're hosting under the stars or stealing a quiet moment in the sun, this tropical oasis delivers serenity at every turn. The first-floor primary suite is a spa-like haven, boasting a marble-clad en suite and indulgent steam shower. Upstairs, the second primary suite offers a private retreat with wide-plank hardwood floors, an en suite, and sliding glass doors leading to a covered porch and outdoor shower—the perfect spot for a slow morning or a sunset wind-down. A third (guest) bedroom features a day bed, soaking tub and a covered patio, ideal for unwinding in blissful solitude. All this, just moments from World-Famous Duval Street, the island's best restaurants, central shopping, and buzzing nightlife, as well as the sun-soaked shores of Fort Zachary Taylor Beach and Truman Waterfront Park. Zen Villa is more than a home—it's a lifestyle experience. A tranquil reprieve amidst the city's energy, waiting to welcome you in.

Villa

Zen Villa - A Luxurious 3-bedroom Sanctuary with WiFi & a Pool in Old Key West

Key West, Florida, United States

Bed

Bath

Sleeps

Select Dates for Price

Condo

A Place In Paradise | Key West Walkable w/ Shared Pool | Month-Long Stays

Key West, Florida, United States

*Please note that this home is available for 28+ night stays only.*brbr*This home has been recently upgraded with a remodeled kitchen, renovated upstairs bathrooms, new floors, and fresh furniture in the living room and outdoor area.*brbrLocated on Porter Lane of Truman Annex you can find your real PLACE IN PARADISE!brbrYou will experience true Key West living when you stay in this delightful 2 bedroom 2.5 bath Conch-Style town home in Truman Annex. One of the most desirable locations for vacationers, you will spend your vacation in a quiet gated community surrounded by historic buildings and tropical flora or wander just a few block over to all the excitement of Duval Street.brbrDecorated to reflect the spirit of Key West, this 2-story condo will help you unwind and feel right at home. On the main level this property features a fully equipped kitchen, dining area, half bath and living room with French doors that open to a sunny private patio. There you'll find an outside dining area ideal for your own personal happy hour. Upstairs are two bedrooms each with their own private bath and balcony, perfect for when a little quiet time is needed. A Place in Paradise also features a washer/dryer and WIFI. A beautiful shared swimming pool is just around the corner, to take a dip and cool down surrounded by plenty of lounge chairs for sunning, relaxing or reading.brbrConveniently located to all the best Key West has to offer, it is only a short walk to Duval Street where you will enjoy the finest restaurants, bars, galleries and great shopping. The Sunset Celebration at Mallory Square, The Tropic Cinema movie theater, and Fort Zachary Taylor State Park and beach are all within easy walking distance. Just park your car under the reserved covered parking when you get here and you won't need it again!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- This home has access to a shared pool and is part of a gated community.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 offers a sleeper sofa as an additional sleeping option.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:br- One parking space per unit, no guest parking.br- No vehicle over 18’ long or 80” wide allowed.br- No large trucks, trailers, mobile homes, vans, campers or similar vehicles shall be parked in the Truman Annex.br- Motorcycles and scooters must be parked in the parking lot and not on sidewalks or porches.br- All vehicles parked within the community must either have a permanent parking sticker or a temporary parking pass (obtained at the Security Guardhouse).br- All others will be subject to ticketing and towing.brbr---brbrThe room configuration is as follows:brbrPrimary Bedroom / Queen bed brBedroom 2 / Queen bedbrSleeper sofabrbr---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.

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.

Private Vacation Home

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.

Private Vacation Home

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

Key West, Florida, United States

Bed

Bath

Sleeps

$242.0

Summary:brbrPet Friendly! 2-Bedroom, 1-1/2 Bathroom Townhome at the Key West Golf ClubbrbrbrbrThe Space:brbr10brbrbrbrStep into our Island Oasis! A very spacious 2-bedroom, 1 1/2 -bathroom home, perfect for your island getaway, in the coveted gated community of the Key West Golf Club. With beach-style flooring throughout and charming shiplap accent walls in the living area and main bedroom. This home exudes the island life and Key West charm. The open concept living and dining areas flow seamlessly from the fully equipped kitchen to a large, screened deck. Looking through the glass wall with sliding doors is a peaceful view of the yard and serene butterfly garden. Upstairs, enjoy a private balcony off the front bedroom and another large screened in porch off the rear bedroom. Just around the corner is the expansive heated lagoon-style pool, perfect for a refreshing swim, enjoy your favorite book, or a cocktail. Our Island Oasis is just minutes away from some of the island's best hidden gem restaurants and island activities. Whether you're looking to explore the vibrant nightlife on Duval Street or enjoy the laid-back atmosphere of downtown, you're only a quick 10-minute drive away. Don’t forget your golf clubs or rent theirs. This is a perfect Oasis and ideal for those who want to be close to the action but still enjoy a peaceful retreat. Your island adventure awaits! Pet Friendly

Condo

2 Bedroom Townhome in Key West Golf Club

Key West, Florida, United States

Bed

Bath

5

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.

Private Vacation Home

Savor Margarita on Margaret w/ PRIVATE Pool

Key West, Florida, United States

Bed

Bath

Sleeps

$412.5

Turtle House. A Key West Artist's haven. Now available from January 8th through March 8th 2026! brbrDelight in the uniqueness of this property. It is a compound comprised of two former cigar maker’s cottages, redesigned and renovated by the artist and her late husband, an architect. Turtle House has been featured in several magazines, including the April 2009 edition of Coastal Living Magazine, and Design Within Reach summer catalogue 2019. Turtle House is located on a quiet lane in Old Town Key West near the cemetery. WAlk everywhere! brPrivate parking in front of the house.brbrCome finish your novel or work from home. A wonderful desk and computer monitor and printer set up for your use! brbrdip your body into the sunken black tiled jacuzzi. Dine under the covered breezeway beneath a bamboo pergola, protected from weather, with beautiful views of the garden illuminated at night by solar lighting. brbrFind magic and inspiration at Turtle House, along with all the comforts and amenities of modern living. Serenity abounds... br brFor those who seek elegant simplicity and a refuge in nature, this may be your dream come true! With privacy difficult to find in Key West... bike or walk to your favorite restaurant or cook at home on the gas grill and eat under the stars! Wake up to the song of birds and sleep peacefully to the sound of tree frogs and crickets. br brThe house is appointed with finr linens, dishes and cookware that offer a comfortable elegance to the rustic design of the cottages, The principle bedroom is its own cottage, furnished with a king size bed, an excellent mattress, a 24 x 68 desk and a bookshelf full of inspiration. brbrThere is a full indoor/outdoor bath attached to the cottage that can be accessed from the cottage or from the deck. The second bedroom is located in the main cottage. It is a cozy retreat, with a full size bed (brand new mattress) and its own bathroom which opens to both the bedroom and the living room. This bedroom faces the lane with a beautiful garden just outside the window. It is a wonderful place for an afternoon nap!brbrTurtle House is not for everyone! There are no marble countertops, no dishwasher, there are window aircondtioners, but no central air. But what there is cannot be overlooked or bought for all the money in the world....a magical oasis to provide a perfect retreat, a peaceful haven, for the sophisticated nature loving soul!brbr A perfect spot for a poet, or a poetic soul, a writer, an avid reader, an architect, a lover of architecture! a person who needs to continue working while on vacation. The lush gardens have been lovingly cultivated by the artist, herself. The owner, a well known Key West artist, hopes you will find inspiration and respite in this unique hide away!brbrCome and enjoy TURTLE HOUSE.brbrTurtle House has a 30 day minimum stay. Ideally, renting to a couple who would use the front bedroom (full size bed and private bath) as a guest room for friends or family to visit.brbr It is truly a little jewel. (Not for partiers, smokers, heavy drinkers, and revelers...sorry)

Cottage

LAST MINUTE AVAILABILITY! architect designed OASIS in OLD TOWNE on a quiet lane!

Key West, Florida, United States

Bed

Bath