Vacation Rentals By Owner In Key West, FL

$1260.0

2 Charming Oceanfront Rooms w/ Full-Service Marina & Bike Rentals - Pets Welcome

Key West, Florida, United States

This listing is for 2 separate rooms within a hotel. The price shown in the listing covers all 2 rooms.brbr✦ Each room is 570 sq. ft, equipped with complimentary toiletries, high definition 49-inch TV, available with Hulu.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✦ You may keep your luggage at the front desk if you arrive early.brbr✦ Public or shared fitness center open 24/7, available in the property.brbr✦ Outdoor shared pool is available, opened from 7:00AM to 10:00PM.brAdditional features:br • Heated poolbr • Saltwater poolbrbr✦ Paid parking lot – 1 space(s), available for $27 per day.brbr✦ Shuttle service operates according to a schedule, available every hour between 9:00AM and 11:00PM.brbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A credit/debit card is required at check-in for a $200 refundable deposit, returned after check-out if no damages occur.brbr✦ A mandatory resort fee of $59.63 per night will be collected upon check-in, not included in the daily rate.brbr✦ Pets are welcome with an additional charge of $75.00 (per pet per night). Up to two dogs under 60 lbs. allowed per room.brbr✦ We use multi-unit listings, so rooms are similar but may have small differences.brbr✦ The maximum number of days that you may book per reservation is only 28 days.brbr✦ Six temperature-controlled swimming pools and a marina are available on-site.brbr✦ Up to two dogs under 60 lbs. allowed per room with a nightly fee per pet. Pets must be supervised and are not allowed on the pool deck or in the pool.

2

Bed

2

Bath

12

Sleeps

$1013.65

/ Nightly

Hotel

2BR Apt in Oceanview Resort w/ Sunset Cruises & Poolside Relaxation

Key West, Florida, United States

This listing is for 2 separate rooms within a hotel. The price shown in the listing covers all 2 rooms.brbr✦ Each room is 570 sq. ft, equipped with complimentary toiletries, high definition 49-inch TV, available with Hulu.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✦ You may keep your luggage at the front desk if you arrive early.brbr✦ Public or shared fitness center open 24/7, available in the property.brbr✦ Outdoor shared pool is available, opened from 7:00AM to 10:00PM.brAdditional features:br • Heated poolbr • Saltwater poolbrbr✦ Paid parking lot – 1 space(s), available for $27 per day.brbr✦ Shuttle service operates according to a schedule, available every hour between 9:00AM and 11:00PM.brbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A credit/debit card is required at check-in for a $200 refundable deposit, returned after check-out if no damages occur.brbr✦ A mandatory resort fee of $59.63 per night will be collected upon check-in, not included in the daily rate.brbr✦ Pets are welcome with an additional charge of $75.00 (per pet per night). Up to two dogs under 60 lbs. allowed per room.brbr✦ We use multi-unit listings, so rooms are similar but may have small differences.brbr✦ The maximum number of days that you may book per reservation is only 28 days.brbr✦ Six temperature-controlled swimming pools and a marina are available on-site.brbr✦ Up to two dogs under 60 lbs. allowed per room with a nightly fee per pet. Pets must be supervised and are not allowed on the pool deck or in the pool.

2

Bed

2

Bath

8

Sleeps

$1014.79

/ Nightly

Hotel

2 Suites Oceanview Balcony King at Oceans Edge Key West, Full Service Marina

Key West, Florida, United States

This listing is for 2 separate rooms within a hotel. The price shown in the listing covers all 2 rooms.brbr✦ Each room is 570 sq. ft, equipped with complimentary toiletries, high definition 49-inch TV, available with Hulu.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✦ You may keep your luggage at the front desk if you arrive early.brbr✦ Public or shared fitness center open 24/7, available in the property.brbr✦ Outdoor shared pool is available, opened from 7:00AM to 10:00PM.brAdditional features:br • Heated poolbr • Saltwater poolbrbr✦ Paid parking lot – 1 space(s), available for $27 per day.brbr✦ Shuttle service operates according to a schedule, available every hour between 9:00AM and 11:00PM.brbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A credit/debit card is required at check-in for a $200 refundable deposit, returned after check-out if no damages occur.brbr✦ A mandatory resort fee of $59.63 per night will be collected upon check-in, not included in the daily rate.brbr✦ Pets are welcome with an additional charge of $75.00 (per pet per night). Up to two dogs under 60 lbs. allowed per room.brbr✦ We use multi-unit listings, so rooms are similar but may have small differences.brbr✦ The maximum number of days that you may book per reservation is only 28 days.brbr✦ Six temperature-controlled swimming pools and a marina are available on-site.brbr✦ Up to two dogs under 60 lbs. allowed per room with a nightly fee per pet. Pets must be supervised and are not allowed on the pool deck or in the pool.

2

Bed

2

Bath

8

Sleeps

$507.33

/ Nightly

Hotel

Serene Retreat w/ Waterfront Balcony & Easy Access to Paddleboarding

Key West, Florida, United States

This listing is for a room within a hotel.brbr✦ Your room is 570 sq. ft, equipped with complimentary toiletries, high definition 49-inch TV, available with Hulu.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✦ You may keep your luggage at the front desk if you arrive early.brbr✦ Public or shared fitness center open 24/7, available in the property.brbr✦ Outdoor shared pool is available, opened from 7:00AM to 10:00PM.brAdditional features:br • Heated poolbr • Saltwater poolbrbr✦ Paid parking lot – 1 space(s), available for $27 per day.brbr✦ Shuttle service operates according to a schedule, available every hour between 9:00AM and 11:00PM.brbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A credit/debit card is required at check-in for a $100 refundable deposit, returned after check-out if no damages occur.brbr✦ A mandatory resort fee of $59.63 per night will be collected upon check-in, not included in the daily rate.brbr✦ Pets are welcome with an additional charge of $75.00 (per pet per night). Up to two dogs under 60 lbs. allowed per room.brbr✦ We use multi-unit listings, so rooms are similar but may have small differences.brbr✦ The maximum number of days that you may book per reservation is only 28 days.brbr✦ Six temperature-controlled swimming pools and a marina are available on-site.brbr✦ Up to two dogs under 60 lbs. allowed per room with a nightly fee per pet. Pets must be supervised and are not allowed on the pool deck or in the pool.

1

Bed

1

Bath

4

Sleeps

$507.33

/ Nightly

Hotel

Oceanview Balcony King Suite at Oceans Edge Key West, Sunset Cruises

Key West, Florida, United States

This listing is for a room within a hotel.brbr✦ Your room is 570 sq. ft, equipped with complimentary toiletries, high definition 49-inch TV, available with Hulu.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✦ You may keep your luggage at the front desk if you arrive early.brbr✦ Public or shared fitness center open 24/7, available in the property.brbr✦ Outdoor shared pool is available, opened from 7:00AM to 10:00PM.brAdditional features:br • Heated poolbr • Saltwater poolbrbr✦ Paid parking lot – 1 space(s), available for $27 per day.brbr✦ Shuttle service operates according to a schedule, available every hour between 9:00AM and 11:00PM.brbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A credit/debit card is required at check-in for a $100 refundable deposit, returned after check-out if no damages occur.brbr✦ A mandatory resort fee of $59.63 per night will be collected upon check-in, not included in the daily rate.brbr✦ Pets are welcome with an additional charge of $75.00 (per pet per night). Up to two dogs under 60 lbs. allowed per room.brbr✦ We use multi-unit listings, so rooms are similar but may have small differences.brbr✦ The maximum number of days that you may book per reservation is only 28 days.brbr✦ Six temperature-controlled swimming pools and a marina are available on-site.brbr✦ Up to two dogs under 60 lbs. allowed per room with a nightly fee per pet. Pets must be supervised and are not allowed on the pool deck or in the pool.

1

Bed

1

Bath

4

Sleeps

$364.54

/ Nightly

Hotel

Ocean View Balcony King Room at Oceans Edge, Panoramic Water Views, Pets Welcome

Key West, Florida, United States

This listing is for a room within a hotel.brbr✦ Your room is 380 sq. ft, equipped with complimentary toiletries, high definition 49-inch TV, available with Hulu.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✦ You may keep your luggage at the front desk if you arrive early.brbr✦ Public or shared fitness center open 24/7, available in the property.brbr✦ Outdoor shared pool is available, opened from 7:00AM to 10:00PM.brAdditional features:br • Heated poolbr • Saltwater poolbrbr✦ Paid parking lot – 1 space(s), available for $27 per day.brbr✦ Shuttle service operates according to a schedule, available every hour between 9:00AM and 11:00PM.brbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A credit/debit card is required at check-in for a $100 refundable deposit, returned after check-out if no damages occur.brbr✦ A mandatory resort fee of $59.63 per night will be collected upon check-in, not included in the daily rate.brbr✦ Pets are welcome with an additional charge of $75.00 (per pet per night). Up to two dogs under 60 lbs. allowed per room.brbr✦ We use multi-unit listings, so rooms are similar but may have small differences.brbr✦ The maximum number of days that you may book per reservation is only 28 days.brbr✦ Six temperature-controlled swimming pools and a marina are available on-site.brbr✦ Up to two dogs under 60 lbs. allowed per room with a nightly fee per pet. Pets must be supervised and are not allowed on the pool deck or in the pool.

1

Bed

1

Bath

2

Sleeps

$806.63

/ Nightly

Hotel

Ocean View Balcony 2 Queen at Oceans Edge Key West, Saltwater Pools - 2 Units

Key West, Florida, United States

This listing is for 2 separate rooms within a hotel. The price shown in the listing covers all 2 rooms.brbr✦ Each room is 380 sq. ft, equipped with complimentary toiletries, high definition 49-inch TV, available with Hulu.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✦ You may keep your luggage at the front desk if you arrive early.brbr✦ Public or shared fitness center open 24/7, available in the property.brbr✦ Outdoor shared pool is available, opened from 7:00AM to 10:00PM.brAdditional features:br • Heated poolbr • Saltwater poolbrbr✦ Paid parking lot – 1 space(s), available for $27 per day.brbr✦ Shuttle service operates according to a schedule, available every hour between 9:00AM and 11:00PM.brbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A credit/debit card is required at check-in for a $200 refundable deposit, returned after check-out if no damages occur.brbr✦ A mandatory resort fee of $59.63 per night will be collected upon check-in, not included in the daily rate.brbr✦ Pets are welcome with an additional charge of $75.00 (per pet per night). Up to two dogs under 60 lbs. allowed per room.brbr✦ We use multi-unit listings, so rooms are similar but may have small differences.brbr✦ The maximum number of days that you may book per reservation is only 28 days.brbr✦ Six temperature-controlled swimming pools and a marina are available on-site.brbr✦ Up to two dogs under 60 lbs. allowed per room with a nightly fee per pet. Pets must be supervised and are not allowed on the pool deck or in the pool.

2

Bed

2

Bath

8

Sleeps

$401.65

/ Nightly

Hotel

Oceanview Balcony 2 Queen Room at Oceans Edge Resort, Six Saltwater Pools

Key West, Florida, United States

This listing is for a room within a hotel.brbr✦ Your room is 380 sq. ft, equipped with complimentary toiletries, high definition 49-inch TV, available with Hulu.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✦ You may keep your luggage at the front desk if you arrive early.brbr✦ Public or shared fitness center open 24/7, available in the property.brbr✦ Outdoor shared pool is available, opened from 7:00AM to 10:00PM.brAdditional features:br • Heated poolbr • Saltwater poolbrbr✦ Paid parking lot – 1 space(s), available for $27 per day.brbr✦ Shuttle service operates according to a schedule, available every hour between 9:00AM and 11:00PM.brbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A credit/debit card is required at check-in for a $100 refundable deposit, returned after check-out if no damages occur.brbr✦ A mandatory resort fee of $59.63 per night will be collected upon check-in, not included in the daily rate.brbr✦ Pets are welcome with an additional charge of $75.00 (per pet per night). Up to two dogs under 60 lbs. allowed per room.brbr✦ We use multi-unit listings, so rooms are similar but may have small differences.brbr✦ The maximum number of days that you may book per reservation is only 28 days.brbr✦ Six temperature-controlled swimming pools and a marina are available on-site.brbr✦ Up to two dogs under 60 lbs. allowed per room with a nightly fee per pet. Pets must be supervised and are not allowed on the pool deck or in the pool.

1

Bed

1

Bath

4

Sleeps

$806.63

/ Nightly

Hotel

2 Cozy Resort Rooms Perfect for Family Vacations, Enjoy Pools & Water Activities

Key West, Florida, United States

This listing is for 2 separate rooms within a hotel. The price shown in the listing covers all 2 rooms.brbr✦ Each room is 380 sq. ft, equipped with complimentary toiletries, high definition 49-inch TV, available with Hulu.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✦ You may keep your luggage at the front desk if you arrive early.brbr✦ Public or shared fitness center open 24/7, available in the property.brbr✦ Outdoor shared pool is available, opened from 7:00AM to 10:00PM.brAdditional features:br • Heated poolbr • Saltwater poolbrbr✦ Paid parking lot – 1 space(s), available for $27 per day.brbr✦ Shuttle service operates according to a schedule, available every hour between 9:00AM and 11:00PM.brbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A credit/debit card is required at check-in for a $200 refundable deposit, returned after check-out if no damages occur.brbr✦ A mandatory resort fee of $59.63 per night will be collected upon check-in, not included in the daily rate.brbr✦ Pets are welcome with an additional charge of $75.00 (per pet per night). Up to two dogs under 60 lbs. allowed per room.brbr✦ We use multi-unit listings, so rooms are similar but may have small differences.brbr✦ The maximum number of days that you may book per reservation is only 28 days.brbr✦ Six temperature-controlled swimming pools and a marina are available on-site.brbr✦ Up to two dogs under 60 lbs. allowed per room with a nightly fee per pet. Pets must be supervised and are not allowed on the pool deck or in the pool.

2

Bed

2

Bath

8

Sleeps

$401.65

/ Nightly

Hotel

Elegant Resort Room w/ Paddleboards, Kayaks & Breathtaking Oceanviews

Key West, Florida, United States

This listing is for a room within a hotel.brbr✦ Your room is 380 sq. ft, equipped with complimentary toiletries, high definition 49-inch TV, available with Hulu.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✦ You may keep your luggage at the front desk if you arrive early.brbr✦ Public or shared fitness center open 24/7, available in the property.brbr✦ Outdoor shared pool is available, opened from 7:00AM to 10:00PM.brAdditional features:br • Heated poolbr • Saltwater poolbrbr✦ Paid parking lot – 1 space(s), available for $27 per day.brbr✦ Shuttle service operates according to a schedule, available every hour between 9:00AM and 11:00PM.brbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A credit/debit card is required at check-in for a $100 refundable deposit, returned after check-out if no damages occur.brbr✦ A mandatory resort fee of $59.63 per night will be collected upon check-in, not included in the daily rate.brbr✦ Pets are welcome with an additional charge of $75.00 (per pet per night). Up to two dogs under 60 lbs. allowed per room.brbr✦ We use multi-unit listings, so rooms are similar but may have small differences.brbr✦ The maximum number of days that you may book per reservation is only 28 days.brbr✦ Six temperature-controlled swimming pools and a marina are available on-site.brbr✦ Up to two dogs under 60 lbs. allowed per room with a nightly fee per pet. Pets must be supervised and are not allowed on the pool deck or in the pool.

Bed

Bath

Sleeps

$348.96

/ Nightly

Private Vacation Home

Ocean Front, Private home with Boat Dock, 3 bedroom

Key West, Florida, United States

Welcome to your dream home in the Keys/ Big Coppitt! This stunning single-family home boasts 3 bedrooms, 2 bathrooms, and a spacious 3-car garage, perfect for all your storage needs. The modern kitchen features stainless steel appliances and sleek tile flooring, creating a stylish and functional space for cooking and entertaining. Step outside to your private boat dock with Gulf access, ideal for enjoying the beautiful waters of Key West. With under house parking and close proximity to a public boat ramp, this home is a boater's paradise. The stilt design of the home offers breathtaking views from the three stories with Balconies from each floor, allowing you to take in the beauty of the surrounding area from every angle. Additionally, enjoy kayaking with the included kayak use and convenient boat trailer parking. Whether you're looking for a peaceful retreat or a waterfront oasis, this home has it all. Don't miss your chance to rent this incredible property in one of the most sought-after locations in Key's. Vacation in the Florida lifestyle you've always dreamed of in this exceptional home. 28 Day minimum and Pet Friendly! Third Floor has a Large Primary suite with King bed and private Bathroom and Balcony. Second bedroom on the third floor with Queen bed. Second floor has living room, kitchen and one bedroom with queen bed and bathroom. House is on the Gulf of Mexico, Great Balcony with Views of the Gulf of Mexico and in the Florida Keys. MM 12brbr

Bed

Bath

Sleeps

$298.1

/ Nightly

Private Vacation Home

FLAMINGO ROSE ~ Midtown 3 Bedroom, 2 Bathroom Home w/ Pool & Parking!

Key West, Florida, United States

ISLAND NIRVANA AWAITS…brImagine your perfect island oasis for indoor/outdoor entertaining and gathering with friends and family. You'll love the vibrant backyard hideaway for relaxation and pleasure under the Key West sunshine. This wonderful 3 bedroom/2 bath home is nestled in a quiet Midtown neighborhood, but is only a brief walk to the picturesque sandy beaches and all the fun the Southernmost City has to offer!br***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGEbrbrDETAILS AND AMENITIES...brStep inside to the bright and cheery open concept floor plan, showcasing terrazzo flooring throughout and casual coastal decor that will soothe your senses and mesmerize your island soul. The living area greets you first and invites you to stay a while. Sink down into cozy couches and indulge in your favorite shows on the giant smart tv. Ready to tackle some culinary creations The adjoining kitchen is fully stocked and equipped for elaborate meals and adult concoctions, with modern stainless appliances, granite counters, a kitchen island that seats 2, and a dining table for 6. There is an office located off the kitchen and is a perfect space when you need to plug in with work remotely. A full bath with a glass door shower is next to the office for your convenience.brbrSLEEPING ARRANGEMENTS...brThe primary bedroom offers a plush king bed and ensuite bathroom with a glass door shower. Abundant natural light spills in from French doors that lead to the backyard area. A hanging/storage closet and clothing dresser will accommodate all of your vacation belongings. A TV provides enjoyment while you sink down into crisp bedding. There is another cozy king bedroom that offers a clothing dresser and a tv. The last bedroom has twin beds, a TV and a clothing dresser for storage. A queen sofa sleeper lies in the living area for visiting guests. brbrOUTDOOR LIVING...brThe magnificent backyard is the centerpiece of this delightful island abode and will provide hours of enjoyment and relaxation. Lush tropical foliage surrounds a spacious heated pool with beautiful decking and a festive Chickee hut with a wrap-around bar, kitchenette, TV, hammock, outdoor shower, gas grill and ample cushioned loungers and chairs throughout the playful space. There is ample seating around the bar as well as an outdoor table so you can dine under the sultry stars!brbrPARKING...brThere is off street parking available for this home.brbrPETS...brThis is a dog friendly home only and a pet fee is required.brbrBOOKING DATES...brThis home is offered only as a monthly rental (28 night minimum). We prefer to book by the calendar month (first day of the month to the last). We may consider alternate dates if the calendar allows or if the owner will make an exception.brbrCANCELLATION...brBookings canceled at least 90 days before the start of stay will receive a 100% refund. brbrCancellations inside of 90 days may receive a refund if we are able to re-rent any or all of the dates of the stay. The refund amount is dependent upon the rate of the new reservation. For multi-month reservations for January through March, a refund will only be offered in the event we are able to re-rent. The refund amount is dependent upon the rate of the new reservation(s).brbrCONCIERGE SERVICES...brEnjoy our concierge service to assist you with planning activities for your trip, from bike/scooter/golf cart rentals to any excursion you can think of including snorkeling and sunset cruises, jet ski rentals, parasailing, kayaking, fishing, paddle boarding and much more. They can also have your fridge stocked with all the necessities in advance of your arrival!brbrYOUR ISLAND ZEN IS HERE…

3

Bed

2

Bath

8

Sleeps

$444.38

/ Nightly

Condo

2 bedroom Beach House Key West

Key West, Florida, United States

Welcome to the Hyatt Beach House, a Hyatt Residence Club, your own private sanctuary in Key West with crystal-clear water views and direct beach access. Enjoy the private beach, furnished with thick-cushioned chairs, picnic tables, barbeque grills and a private dock. Soak up the sun in the zero-entry lagoon shaped pool and hot tub.brbrWalk down stairs and enjoy the complimentary kayaking, gorgeous beach area and pool. Spend a wonderful week in the sunny Florida Keys!brbrThe space:brThis condo is 2 bedroom, 2 bathrooms and comes with a full kitchen, dining area and living room with balcony. The master bedroom has a King bed and the guest bedroom has a Queen bed. There is also a sleeper sofa in the living room. Max occupancy is 6 guests per unit.brbrComplimentary Wi-Fi access, in room washer and dryer, and on-site parking are also included.brbrHyatt typically offers complimentary, freshly brewed Starbucks coffee and an assortment of teas from 7:00 to 9:00 AM each morning in the lobby.brbrSpend your days relaxing by the lagoon-shaped pool with zero-entry end for easy access, or on Hyatt's private on-site beach. The heated pool is wheelchair accessible and open year-round.brbrThe Hyatt Beach House’s convenient location puts you just minutes from the free-spirited art, music and entertainment scene of Old Town. Or head over to nearby Smathers Beach, the biggest white sand beach in Key West to rent windsurfers or go parasailing. The keys are also a haven for anglers - shallow flats, mangrove islands, inland channels and open blue waters offer world-class fishing opportunities.brbrWhether you choose to spend your days simply relaxing by the lagoon pool or setting off on a diving adventure, Key West delivers a dream vacation of your own design. Your island home is just minutes away from celebrating the sunset each evening at Mallory Square and taking in the renowned dining, shopping and nightlife of Duval Street.brbrComplementary onsite parking is available at the Hyatt Beach House. Hyatt will issue a parking permit to you at Check-in. Parking is limited to one car per reservation. Reservations of less than 7 nights will be charged a fee of $80 payable to the resort for split week cleaning.brbrTrailer parking is available for a fee if you reserve a boat dock. The boat dock and trailer parking must be reserved directly with Hyatt Beach House in advance. I am not involved with the boat docks and/ or trailer parking.brbrThe Hyatt Beach House is located about 3 Miles from Key West's Historic Seaport District, Duval Street, Mallory Square, and the Sunset Pier. You can drive downtown and park. Alternately, you can take a taxi, Uber, or Lyft or you can rent a scooter or an electric vehicle.

2

Bed

2

Bath

6

Sleeps

$1260.0

/ Nightly

Hotel

2 Suites 2 Queen w/ Oceanview at Oceans Edge Resort, Kayak Rentals, 6 Pools

Key West, Florida, United States

This listing is for 2 separate rooms within a hotel. The price shown in the listing covers all 2 rooms.brbr✦ Each room is 570 sq. ft, equipped with complimentary toiletries, high definition 49-inch TV, available with Hulu.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✦ You may keep your luggage at the front desk if you arrive early.brbr✦ Public or shared fitness center open 24/7, available in the property.brbr✦ Outdoor shared pool is available, opened from 7:00AM to 10:00PM.brAdditional features:br • Heated poolbr • Saltwater poolbrbr✦ Paid parking lot – 1 space(s), available for $27 per day.brbr✦ Shuttle service operates according to a schedule, available every hour between 9:00AM and 11:00PM.brbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A credit/debit card is required at check-in for a $200 refundable deposit, returned after check-out if no damages occur.brbr✦ A mandatory resort fee of $59.63 per night will be collected upon check-in, not included in the daily rate.brbr✦ Pets are welcome with an additional charge of $75.00 (per pet per night). Up to two dogs under 60 lbs. allowed per room.brbr✦ We use multi-unit listings, so rooms are similar but may have small differences.brbr✦ The maximum number of days that you may book per reservation is only 28 days.brbr✦ Six temperature-controlled swimming pools and a marina are available on-site.brbr✦ Up to two dogs under 60 lbs. allowed per room with a nightly fee per pet. Pets must be supervised and are not allowed on the pool deck or in the pool.

2

Bed

2

Bath

12

Sleeps

$630.0

/ Nightly

Hotel

Room in Coastal Resort w/ Oceanview - Six Pools & Pvt Oceanview Balcony

Key West, Florida, United States

This listing is for a room within a hotel.brbr✦ Your room is 570 sq. ft, equipped with complimentary toiletries, high definition 49-inch TV, available with Hulu.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✦ You may keep your luggage at the front desk if you arrive early.brbr✦ Public or shared fitness center open 24/7, available in the property.brbr✦ Outdoor shared pool is available, opened from 7:00AM to 10:00PM.brAdditional features:br • Heated poolbr • Saltwater poolbrbr✦ Paid parking lot – 1 space(s), available for $27 per day.brbr✦ Shuttle service operates according to a schedule, available every hour between 9:00AM and 11:00PM.brbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A credit/debit card is required at check-in for a $100 refundable deposit, returned after check-out if no damages occur.brbr✦ A mandatory resort fee of $59.63 per night will be collected upon check-in, not included in the daily rate.brbr✦ Pets are welcome with an additional charge of $75.00 (per pet per night). Up to two dogs under 60 lbs. allowed per room.brbr✦ We use multi-unit listings, so rooms are similar but may have small differences.brbr✦ The maximum number of days that you may book per reservation is only 28 days.brbr✦ Six temperature-controlled swimming pools and a marina are available on-site.brbr✦ Up to two dogs under 60 lbs. allowed per room with a nightly fee per pet. Pets must be supervised and are not allowed on the pool deck or in the pool.

1

Bed

1

Bath

6

Sleeps

$364.54

/ Nightly

Hotel

Comfortable Family Resort Room w/ Ocean Views, Kayak Rentals & Six Pools

Key West, Florida, United States

This listing is for a room within a hotel.brbr✦ Your room is 380 sq. ft, equipped with complimentary toiletries, high definition 49-inch TV, available with Hulu.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✦ You may keep your luggage at the front desk if you arrive early.brbr✦ Public or shared fitness center open 24/7, available in the property.brbr✦ Outdoor shared pool is available, opened from 7:00AM to 10:00PM.brAdditional features:br • Heated poolbr • Saltwater poolbrbr✦ Paid parking lot – 1 space(s), available for $27 per day.brbr✦ Shuttle service operates according to a schedule, available every hour between 9:00AM and 11:00PM.brbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A credit/debit card is required at check-in for a $100 refundable deposit, returned after check-out if no damages occur.brbr✦ A mandatory resort fee of $59.63 per night will be collected upon check-in, not included in the daily rate.brbr✦ Pets are welcome with an additional charge of $75.00 (per pet per night). Up to two dogs under 60 lbs. allowed per room.brbr✦ We use multi-unit listings, so rooms are similar but may have small differences.brbr✦ The maximum number of days that you may book per reservation is only 28 days.brbr✦ Six temperature-controlled swimming pools and a marina are available on-site.brbr✦ Up to two dogs under 60 lbs. allowed per room with a nightly fee per pet. Pets must be supervised and are not allowed on the pool deck or in the pool.

Bed

Bath

Sleeps

$421.88

/ Nightly

Hotel Resort

Hyatt Beach House - 2 Bedroom Waterfront Condo

Key West, Florida, United States

Hyatt Beach House offers an elevated island retreat where refined coastal living meets the quiet beauty of Key West’s waterfront. Tucked away in a serene, private enclave surrounded by lush tropical landscaping, the resort feels like a secluded hideaway designed for guests who appreciate space, comfort, and a more relaxed, upscale experience. Gentle breezes drift across the shoreline, and the calm waters create a soothing backdrop that sets the tone for a truly restorative stay.brbrThe residence blends understated luxury with the warmth of a well‑appointed coastal home. Sunlight fills the spacious living areas, highlighting thoughtful finishes and inviting textures that create a sense of effortless elegance. A fully equipped kitchen with full‑size appliances makes it easy to enjoy leisurely breakfasts or intimate dinners at home, while the in‑suite washer and dryer add convenience for longer stays. The private balcony becomes a personal sanctuary—perfect for morning coffee, afternoon reading, or unwinding with a glass of wine as the day fades into a soft island evening.brbrThe resort’s lagoon‑style pool is framed by swaying palms and tranquil water views, offering a peaceful place to relax in the sun or cool off in the shade. The property’s location provides a quiet, residential feel while still giving you quick access to the best of Key West. Within minutes, you can explore waterfront dining, enjoy sunset cruises, or venture into Old Town for shopping, galleries, and the vibrant energy of Duval Street. Whether you’re seeking a serene escape or a luxurious home base for island adventures, Hyatt Beach House delivers a refined and memorable Key West experience.brbrNOTE brThis property is available for a 3 or 4 night stay on select dates.brbrPlease send an inquiry before a booking request to confirm availability. . brbrA $125 housekeeping fee will be charged by Hyatt upon check out

2

Bed

2

Bath

6

Sleeps

$669.38

/ Nightly

Condo

WATERFRONT PENTHOUSE! Galleon Resort Key West, Sleeps 6, Private Beach

Key West, Florida, United States

WEEK 39 PENTHOUSE UNIT D-51 ! 9/26--10/3/26.brEnjoy 7 nights in downtown Key West at The Galleon Resort!brbrThe Galleon Resort is located in the heart of Old Town Key West in the Historic Seaport District. This resort overlooks the Gulf of Mexico with a private marina, private beach, pool, hot tub, with a restaurant and tiki bar. Relax in the hot tub or workout in the onsite fitness center. Enjoy fishing off the dock, or rent bicycles and take in all that Old Town Key West has to offer.brbrMel Fisher Museum, Mallory Square and Duval St are just a 5 minute walk from this conveniently located resort. The Ernest Hemingway Home & Museum is 1 mile away.br.brWe have one week to offer in 2026 with guaranteed unit number as follows:brWeek 39, 9/26--10/3 is Unit D51 PENTHOUSE marina side unit. The 2nd bdrm here has two twins that can be pushed together to make a queen.brbrOverlooking the marina and historic seaport. This two bedroom condo sleeps six, and features a fully equipped kitchen. The primary suite has a king size bed, jetted tub, shower, two vanity sinks and large closets. The guest bedroom features either two twins and has access to the full guest bathroom with a shower. The living room has a TV with cable, dining area for six, and a queen sleeper sofa. Large balcony from the living room overlooking all of the boats & restaurants in the marina.brbrOther than the rent paid to VRBO, there will be a $80 resort fee to be collected by the front desk upon check in. This is in addition to the rent already paid. A $150 refundable security deposit is also secured on your credit card and is released by resort after checkout as long as no damages occur during your stay.brbrOne free mid week cleaning! Housekeeping changes linens and towels on Wednesday only at no additional charge. If daily housekeeping is desired, there is an additional fee imposed by the resort.brbrParking for one vehicle, per unit only. No oversized vehicles, RV's or trailers are allowed to park on property. Parking is extremely limited and multiple vehicles are not able to be accommodated.brbrMinimum Age: 21 years oldbrPet Policy: No PetsbrAn ID and credit card for a refundable security deposit will be required.brCheck-in is after 4 pm;brcheck-out by 10 am.brNo Smoking. Penalties will apply.brNon-Refundable Cancellation and Refund Policy:br$80 Resort Fee Due at Check-in *Pricing Subject to changebrGuest check-in certificate will be email to you directly from the resort once VRBO releases full payment to me, the owner.brPlease look over the lease document uploaded in VRBO.brbrNote that we do not accept liability for any inconveniences beyond our control including but not limited to temporary defects or outage of utilities, closures of resort amenities, or limitation of any other service. We will not provide refunds, reimbursements, or compensation for inconvenience or interruption of utilities, resort amenities, or any other service. Trip/Vacation insurance is highly recommended and may be included as part of VRBO's fees.brbrPictures are representative of the unit, layout and decor may vary.

Bed

Bath

Sleeps

$531.78

/ Nightly

Condo

VILLA SERENA@DUVAL SQUARE - A peaceful retreat in the heart of Old Town.

Key West, Florida, United States

Open the door to Villa Serena and find yourself transported to a peaceful sanctuary. Villa Serena is the perfect space for your relaxing Key West vacation. Duval Square is located in the heart of Old Town Key West, yet is secluded away upstairs from the crowds. Delicious restaurants and unique shops are located in the quaint bricked courtyard below. A bright and sunny rooftop pool and pavilion area are just few steps from your front door. This home also offers one reserved parking space in the gated garage. brbrThe downstairs living area is decorated in soothing cobalt and beachy sand tones and provides plenty of space for entertaining. French doors lead out to a covered and private patio area. The kitchen features modern appliances and granite countertops.brbrUpstairs, the main bedroom is a calming oasis of dramatic wood tones and Caribbean blue accents. A spa-like ensuite bath features a large step in, pebble-tiled shower and generous vanity. A second balcony provides a private outdoor space to enjoy your morning coffee. The second bedroom features a queen size bed and another ensuite bath.brbrBedding: 1 King, 1 Queen.brbrElevator access from ground level to the first floor of the condos. Stairs to the unit's second floor bedrooms.brbr**Construction Disclaimer** From mid May through the month of June, 2026, the pool area will be under construction. This will create noise and dust that could impact your stay and may lead to pool closure as well.

Bed

Bath

Sleeps

$512.75

/ Nightly

Condo

PARADISE PLACE:A tastefully decorated space in the heart of Old Town Key West

Key West, Florida, United States

Open the door to Paradise Place and find yourself transported to a peaceful sanctuary. brbrThe downstairs living area is decorated with warm wood floors, blue and sand accents and provides plenty of space for entertaining. French doors lead out to a large covered and private patio area. The kitchen features modern appliances, clean white cabinets and a dramatic granite countertop that seats four for dining.brbrUpstairs, the main bedroom is a calming oasis of ocean blue green accents. A spa-like ensuite bath features a large step in shower and generous vanity. A second balcony provides a private outdoor space to enjoy your morning coffee. The second bedroom features a queen size bed and another ensuite bath.brbrDuval Square is located in the heart of Old Town Key West, yet is secluded away upstairs from the crowds. Delicious restaurants and unique shops are located in the quaint courtyard below. A bright and sunny rooftop pool and pavilion area are just few steps from your front door. This home also features one reserved parking space in the secure, gated garage.brbrBedding: 1 King, 1 Queen.brbrDuval Square Retreat is In the heart of Old Town. Duval Square is located at the artistic and quieter end of Duval Street. This recently upgraded unit is tastefully decorated with design elements from around the world. The first floor offers a well- equipped kitchen, and an open living and dining concept, French doors to a private balcony and a half bath powder room. brbrUpstairs, the main bedroom suite has a private balcony and ensuite bath. The second second bedroom also has an ensuite bath. brbrThere is central air conditioning and Wi-Fi internet. The complex's shared pool and sunning area overlooks world famous Duval Street. On the street level you will find a unique tree lined courtyard with restaurants and shops. While gated garage parking is provided here, all you really need is a bicycle for your main mode of transportation as you can walk or bike everywhere from Duval Square. brbrBedding: 2 QueenbrA shared, sun-drenched, rooftop pool and pavilion are just steps from your door.brbrThis is an unbeatable location offering easy pedestrian access to dozens of shops and restaurants, the Ernest Hemingway Home Museum and other notable local attractions, and of course the serene, turquoise ocean that the island is famous for. brbrGather your friends and family together and book a Key West vacation you will never forget at Duval Square Penthouse.brbrBeds: 3 Kings, 2 Twins, 1 Sleeper SofabrDuval Square is a charming community with shops and restaurants downstairs and secure, quiet, private residences, pool and pavilion upstairs. Although the condo includes one assigned parking space in the gated garage, you can stroll anywhere from this conveniently located condo. All of the shops, galleries, restaurants, and attractions on and around Duval Street and nearby beaches are just a leisurely stroll away. brbrWhen you enter the home you will find a fully equipped kitchen, dining area, spacious living room and a convenient half bath. French doors let in the natural sunshine and open to the private back deck with dining table and chairs perfect for outdoor entertaining. brbrOn the second floor, you will find 2 bedroom suites, each with their own private bathroom and an additional private balcony off the main suite.brbrBedding: 1 king, 1 queen, 1 queen sleeper sofa.brbrElevator access from ground level to the first floor of the condos. Stairs to the unit's second floor bedrooms.brbr1 Reserved Parking Space in the Gated Garage.brbr**Construction Disclaimer** From mid May through the month of June, 2026, the pool area will be under construction. This will create noise and dust that could impact your stay and may lead to pool closure as well.

2

Bed

2

Bath

6

Sleeps

Vacation Rentals By Owner In Key West, FL

$1260.0

$1013.65

$1014.79

$507.33

$507.33

$364.54

$806.63

$401.65

$806.63

$401.65

$348.96

$298.1

$444.38

$1260.0

$630.0

$364.54

$421.88

$669.38

$531.78

$512.75

Rent a place that suits your needs

Most popular vacation rentals in Key West

$2606.88

$2168.85

$2179.76

$2193.75

$2377.08

$2433.36

$2489.04

$2519.19

$4253.21

$3363.07

Most Popular Cities in Florida