In the heart of Old Town Key West, this 3 bedroom retreat offers a serene escape amidst island excitement. Unwind in the private oasis with heated pool and lush landscaping or indulge in gourmet delights within the elegant kitchen. With comfortable seating arrangements and tranquil bedrooms, this residence caters to relaxation and entertainment.
Reviews
1010 out of 10
Exceptional
Entire home
3 bedrooms4 bathroomsSleeps 6163 sq m
Popular amenities
Pool
Kitchen
Washing machine
Dryer
Free Wi-Fi
Air-conditioning
Add dates for prices
About this property
Ashe St Serenade - A Luxury Island Oasis - 3BD/3.5Bath - Private Pool
Welcome to your dream getaway in the charming Old Town Key West, where the tranquility of island living meets the excitement of tropical adventures. This enchanting 3 bedroom, 3.5 bathroom monthly vacation rental offers a serene retreat amidst the vibrant atmosphere of the island, ensuring an unforgettable experience for you and your loved ones.
As you enter this magnificent residence, you'll be captivated by the dramatic ceiling heights, elegant wood flooring, and designer accents that exude sophistication and coastal elegance. The open-concept gourmet kitchen invites you to indulge in Key West's culinary delights, featuring a 48" gas range, an expansive island with seating, quartz countertops, stainless steel appliances, and a wine chiller. The telescoping door wall connects the indoor dining area to the outdoor seating, creating the perfect ambiance for memorable meals and tropical libations.
For entertaining purposes, the residence offers comfortable seating arrangements that cater to socializing and dining. In addition to the living room, there is a separate dining room that accommodates up to six people. Furthermore, the kitchen is equipped with an island that offers additional seating for up to four people.
The primary suite, situated on the first level, provides a tranquil retreat for relaxation and rest. It features a spacious king-size bed, ensuring a comfortable and luxurious sleeping experience. Within the master suite, you'll find the ensuite, a private bathroom attached exclusively to the primary bedroom. The ensuite is designed to enhance your indulgence and rejuvenation. It boasts a large soaker tub, inviting you to immerse yourself in a soothing bath or enjoy a sizable walk-in shower.
On the second floor of the residence, you will find two additional guest bedrooms, each equipped with a king-size bed and ensuite bathrooms with showers. These guest bedrooms are designed to provide a comfortable and private space for your family and friends during their stay. Moreover, the second floor also features a bonus space, dedicated to providing a comfortable area for family and friends to relax and unwind.
Step outside to your private oasis, where the lush landscaping and gentle sounds of the waterfall create a soothing backdrop for leisurely afternoons by the heated pool. The composite decking offers an inviting space for sunbathing, lounging poolside, or enjoying the island breeze.
Nestled on a peaceful street just a short stroll from Duval Street and the Historic Seaport, you'll be ideally positioned to explore Key West's famous attractions, delightful shops, world-class dining, and vibrant nightlife. With its walkable and bike-friendly location, your island adventures are just steps away from your luxurious retreat.
Immerse yourself in the enchanting atmosphere of Key West and create lasting memories with your loved ones at this stunning vacation rental. From its exquisite design and modern amenities to its unbeatable location, your unforgettable island getaway awaits. Book your stay at this luxurious Key West oasis today.
Important Notice: Some booking platforms may not correctly display our security deposit requirements. This contract is based on a $125 non-refundable damage protection plan in place of a $5000.00 refundable security deposit; if you prefer to pay the $5000.00 deposit instead, please let us know.
Guests are subject to a 2% credit card processing fee. In order to avoid that fee, we encourage you to pay by check.
Property amenities
Pool/Spa
Communal pool
Heated pool
Private pool
Internet
Available in the house: Free WiFi
Parking and transport
Parking on site
Kitchen
Coffee/tea maker
Cookware, dishware, and utensils
Dishwasher
Hob
Ice maker
Kitchen island
Microwave
Oven
Refrigerator
Toaster
Dining
Dining table
Bedrooms
3 bedrooms
Bedsheets provided
Bathroom
3.5 bathrooms
Bathtub
Hair dryer
Shower
Towels provided
Living spaces
Dining table
Living room
Entertainment
Smart TV with cable/satellite channels
Outdoor areas
Barbecue grill
Fenced yard
Patio
Laundry
Laundry facilities
Washing machine
Comfort
Air conditioning
Pets
No pets allowed
Suitability/Accessibility
Hardwood flooring in public areas
Smoke-free property
Services and conveniences
Concierge services
Housekeeping on request
Iron/ironing board
Meal delivery service
Location highlights
In a village
Near a hospital
Near the marina
Near the sea
Things to do
Heated pool
Birdwatching nearby
Cycling nearby
Ecotours nearby
Fishing nearby
Golfing nearby
Jet skiing nearby
Sailing nearby
Scuba diving nearby
Snorkelling nearby
Swimming nearby
Windsurfing nearby
Safety features
Carbon monoxide detector not reported (host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector)
Smoke detector not reported (host has not indicated whether there is a smoke detector on the property)
General
Housekeeping (on request)
Unit size: 1,750 square feet
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You will receive an email from the host with check-in and check-out instructions
Information provided by the property may be translated using automated translation tools
Pets
Pets not allowed
Children and extra beds
Children are welcome
Events
No events allowed
Smoking
Smoking is not permitted
Important information
You need to know
Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip
Host has not indicated whether there is a smoke detector on the property
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation
About the area
Located by the sea, this holiday home is in Old Town Key West, a neighbourhood in Key West. Ernest Hemingway Home and Museum and Southernmost Point are notable landmarks, and the area's natural beauty can be seen at Florida Keys Beaches and Fort Zachary Taylor Historic State Park. The Kite House and Sails To Rails Museum at Flagler Station are also worth visiting. Jet skiing and scuba diving offer great chances to get out on the surrounding water, or you can seek out an adventure with cycling and ecotours nearby. Visit our Key West travel guide
Does Ashe St Serenade - A Luxury Island Oasis - 3BD/3.5Bath - Private Pool have a pool?
Yes, this property has a pool. Pool types include heated pools.
Is Ashe St Serenade - A Luxury Island Oasis - 3BD/3.5Bath - Private Pool pet-friendly?
No, pets are not allowed at this property.
How much is parking at Ashe St Serenade - A Luxury Island Oasis - 3BD/3.5Bath - Private Pool?
On-site parking is available at the property.
What time is check-in at Ashe St Serenade - A Luxury Island Oasis - 3BD/3.5Bath - Private Pool?
Check-in begins at 4:00 PM.
What time is check-out at Ashe St Serenade - A Luxury Island Oasis - 3BD/3.5Bath - Private Pool?
Checkout is at 10:00 AM.
Where is Ashe St Serenade - A Luxury Island Oasis - 3BD/3.5Bath - Private Pool located?
Located in Old Town Key West, this holiday home is within a 15-minute walk of Key West Burlesque Theater and Duval Street. Florida Keys Beaches and Ernest Hemingway Home and Museum are also within 1 mile (2 km).
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Ashe St Serenade - A Luxury Island Oasis - 3BD/3.5Bath - Private Pool Reviews
Reviews
Exceptional
All reviews shown are from real guest experiences. Only travellers who have booked a stay with us can submit a review. We verify reviews according to our guidelines and publish all reviews, positive or negative.
Rating Details:
The property manager was very helpful.
The vacation rental was spotless.
I was very happy with the location.
I was very satisfied with the condition of the vacation rental.
Overall, I recommend this vacation rental.
Reviewer Comments:
Preferred is a good company with attentive service. We were very pleased.
Christine B.
From a partner site
10/10 Excellent
A guest from New York, NY
15 Apr 2025
Serenaded by Ashe Street
Rating Details:
The property manager was very helpful.
The vacation rental was spotless.
I was very happy with the location.
I was very satisfied with the condition of the vacation rental.
Overall, I recommend this vacation rental.
Reviewer Comments:
This is a very special house on a very special street. Spacious & extremely well-appointed it was the perfect property for us for a three-month stay. We are returning again next year. Having lived in Key West for 24 years, this was our first time renting and it lived up to our expectations.
A guest from New York, NY
From a partner site
10/10 Excellent
Beth A M.
15 Dec 2025
Great house!
Rating Details:
The property manager was very helpful.
The vacation rental was spotless.
I was very happy with the location.
I was very satisfied with the condition of the vacation rental.
Overall, I recommend this vacation rental.
Reviewer Comments:
We chose to stay for the month of November and found Ashe Street Serenade to be available. We’re so glad that it was! The house was wonderful in so many ways: 3 bedrooms, each with its own bathroom plus an additional powder room on the first floor, which made things even more convenient. The living room/dining room and kitchen were perfect for entertaining, open and comfortable. The back deck is a bit crowded because of all of the furniture but it was sufficient and very nice. The pool is perfect for cooling off after a nice, long walk. The location was great for us, just under a mile from Duval. We like to patronize mostly places off Duval so the location worked out wonderfully! Don’t hesitate to rent here, you’ll love it! We only needed the management team once and they responded quickly! It was just a reset button on the water heater that needed to be hit!