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~LILLY'S PAD~ Upscale elegance with a private pool and parking!

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Key West life!
A tropical vacation awaits you!
Welcome to Key West living!
Enter through the sunny yellow door.
Plenty of Key West charm!

Reviews

10 out of 10
Exceptional
3 bedrooms3+ bathroomsSleeps 6

Popular amenities

  • Pool
  • Kitchen
  • Washer
  • Dryer
  • Free WiFi
  • Air conditioning

Explore the area

View in a map
Key West, FL
  • Place, Duval Street
    ‪1 min walk‬
  • Place, South Beach
    ‪3 min walk‬
  • Place, Southernmost Point
    ‪5 min walk‬
  • Airport, Key West, FL (EYW-Key West Intl.)
    ‪12 min drive‬

Rooms & beds

3 bedrooms (sleeps 6)

Bedroom 1

1 King Bed

Bedroom 2

1 King Bed

Bedroom 3

1 Queen Bed

3 bathrooms, 1 half bathroom

Bathroom 1

Toilet

Bathroom 2

Toilet · Shower only

Bathroom 3

Toilet · Shower only

Bathroom 4

Toilet · Shower only

Spaces

Deck or patio
Porch or lanai
Kitchen

About this property

~LILLY'S PAD~ Upscale elegance with a private pool and parking!

THE PROPERTY: Awarded the Florida Keys Preservation Star, this stunning home and outdoor space will entice you to live like a local. From its covered front porch to its rear entertaining area, you won’t want to leave. As you enter via the sunny yellow doors you will be captivated by the gingerbread balustrade, staircase book nook and beautiful Dade County pine walls.

Moving into the open concept kitchen and living room, high ceilings, designer finishes and natural light will greet you. The sleek white kitchen is equipped with stainless steel appliances and everything you need to prepare meals or snacks. The oversized island has seating for six and allows you to mingle with guests in the comfortably furnished living room. You will be drawn to the outdoors via the double set of sliders that spill onto the lanai. Unlike other lanais this one is generously furnished and includes a large screen TV and an air conditioned half bath. From here you can take a dip in the pool, sip cocktails or simply relax with a good book. The pool includes a water feature, and the entire area enjoys privacy via fencing and lush landscaping. Nap on a lounger while surrounded by palm trees and sunshine. A wonderful island option is alfresco dining. The chef in your group will enjoy the gas grill and large dining table.

All three bedrooms in this home have ceiling fans and en suite baths with walk in showers. Two king bedrooms are located on the first floor, and one has direct access to the pool. You will appreciate the beautiful linens, natural light, and closet space. The third bedroom is located on the second floor. It has a queen bed and provides a bit of privacy for those who may need it. This room also has a vaulted ceiling, closet, TV, and plenty of natural light.

This lovingly restored home has unique island charm and is in a fabulous location. If modern amenities, outdoor living, and walk-ability are on your Key West bucket list, Lilly's Pad is the vacation home for you!

BED CONFIGURATION: There is a king en suite bedroom on the first floor. The second king en suite bedroom is also on the first floor. The third queen en suite bedroom is located on the second floor.

OUTDOOR AMENITIES: The covered lanai provides an outdoor living space with TV and plenty of seating. The dip pool with water feature is delightful after a day exploring the island. Dine alfresco on your large outdoor dining table. The pool is heated seasonally (November through April) for an additional fee which will be assessed at the time of booking. A grill is available for cooking up the catch of the day. A convenient and air conditioned half bath is located off the lanai. Sunshine, palm trees and lounge chairs on the sun deck await you.

PARKING: There is a convenient off-street parking space with this home, which is a rarity in Key West.

LOCATION: Old Town just a half block from Duval Street. Near the Key West Butterfly Museum and Southernmost Point. You will enjoy this quieter yet walkable side of town near finer shops, galleries, and restaurants.

PETS: This home is NOT pet friendly. (If you have pets, please browse through our many homes that are pet-friendly).

SMOKING: This is a non-smoking home and property.

***Guests must be 25 years of age or older unless accompanied by an adult.

***Managed by Historic Key West Vacation Rentals.***
Our prices include all fees. No hidden fees.

Add dates for prices

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House Rules

Check in after 4:00 PM
Minimum age to rent: 25
Check out before 10:00 AM
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Children

Children allowed: ages 0-17
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Events

No events allowed
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Pets

No pets allowed
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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
Onsite 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 indicated there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a first aid kit
This property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children; if you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room

About the neighborhood

Key West

Located in Key West, this vacation home is in the city center. Southernmost Point and Ernest Hemingway Home and Museum are notable landmarks, and the area's natural beauty can be seen at Florida Keys Beaches and Fort Zachary Taylor Historic State Park. Key West Butterfly and Nature Conservatory and MLK Community Pool & Community Center are also worth visiting. Discover the area's water adventures with jet skiing, scuba diving, and snorkeling nearby, or enjoy the great outdoors with ecotours.
View more Vacation Homes in Key WestOpens in a new window
Map
Key West, FL

What's nearby

  • Duval Street - 1 min walk - 0.2 km
  • South Beach - 3 min walk - 0.3 km
  • Key West Butterfly and Nature Conservatory - 3 min walk - 0.3 km
  • Southernmost Point - 5 min walk - 0.4 km
  • Ernest Hemingway Home and Museum - 6 min walk - 0.5 km

Getting around

  • Key West Intl. Airport (EYW) - 12 min drive

Restaurants

  • ‪Circle K - ‬3 min walk
  • ‪Cuban Coffee Queen (Duval) - ‬2 min walk
  • ‪Rum Bar at the Speakeasy Inn - ‬2 min walk
  • ‪Banana Cafe - ‬2 min walk
  • ‪Southernmost Point Bar in the USA - ‬5 min walk

Frequently asked questions

Does ~LILLY'S PAD~ Upscale elegance with a private pool and parking! have a pool?

Yes, this property has a pool.

How much does it cost to stay at ~LILLY'S PAD~ Upscale elegance with a private pool and parking!?

As of Apr 19, 2026, prices found for a 1-night stay for 2 adults at ~LILLY'S PAD~ Upscale elegance with a private pool and parking! on Aug 6, 2026 start from $1,311, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

Is ~LILLY'S PAD~ Upscale elegance with a private pool and parking! pet-friendly?

No, pets are not allowed at this property.

How much is parking?

Onsite parking is available at the property.

What time is check-in at ~LILLY'S PAD~ Upscale elegance with a private pool and parking!?

Check-in begins at 4:00 PM.

What time is check-out at ~LILLY'S PAD~ Upscale elegance with a private pool and parking!?

Check-out is at 10:00 AM.

Where is ~LILLY'S PAD~ Upscale elegance with a private pool and parking! located?

Located in Old Town Key West, this vacation home is steps from City Zoo Gallery and Duval Street. Florida Keys Beaches and South Beach are also within 10 minutes.

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labeled.
Learn moreOpens in a new window
Rating 10 - Excellent. 35 out of 36 reviews
Rating 8 - Good. 1 out of 36 reviews
Rating 6 - Okay. 0 out of 36 reviews
Rating 4 - Poor. 0 out of 36 reviews
Rating 2 - Terrible. 0 out of 36 reviews

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

Verified

10/10 Excellent

Jane S.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Wonderful cottage home with easy access to shops, restaurants, and all the fun Key West has to offer. The host was very communicative and goes extra step to help schedule activities around the island.
Stayed 4 nights in Dec 2025
Verified

10/10 Excellent

Lisa D.

Liked: Cleanliness, check-in, communication, location, listing accuracy
The property was wonderful. Updated beautifully with all the charm and practicality necessary for what we like in a rental. The location was a block off of Duval which made going for a coffee or perusing the shops very convenient. The property management was excellent at responding to the questions we had during our stay. Highly recommend!
Sheltering the frog statue from the rain
Stayed 8 nights in Jan 2026
From a partner site

10/10 Excellent

Steve E.

Lilly’s Pad

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: Excellent place to stay - very clean, comfortable and terrific location!
Verified

10/10 Excellent

Heather B.

Liked: Cleanliness, check-in, communication, location, listing accuracy
We had a fantastic stay at Lilly’s Pad. The home is beautifully designed, spotless, and truly feels like a little luxury retreat in Key West. The private pool was a highlight, perfect for relaxing after a day out, and the outdoor space felt very peaceful and private.The location was excellent: close to everything but still quiet at night. Easily walkable. Having dedicated parking was also a huge plus in Key West and made getting around so easy.The host was incredibly helpful and even coordinated with the baby equipment rental company so everything we needed for our baby was set up and ready when we arrived, which made traveling so much easier for us.Everything was seamless from check-in to check-out. We would absolutely stay here again and highly recommend it to anyone visiting Key West.
Stayed 6 nights in Feb 2026
Verified

10/10 Excellent

Darlene W.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Perfect spot off Duval Street. Pool is a bit small but was nice to cool off on hot Key West days. Grill was very nice to have.
Stayed 5 nights in Sep 2025
Verified

10/10 Excellent

Andrea L.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Fun vacay

Great central location to see all Key West has to offer and house has good layout for relaxing
Stayed 5 nights in Mar 2025
Verified

10/10 Excellent

David D.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Excellent location, wonderful backyard

Wife and I stayed with another couple, really enjoyed the backyard, was great setting and privacy for us to hang out after the day on the town. Easy access to all of key west and had parking onsite.
Stayed 4 nights in Apr 2025
Verified

10/10 Excellent

Dean R.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great stay

This is an upscale home in a great central location The pool was well maintained and very relaxing. The parking space is a big plus. Highly recommend
Stayed 5 nights in Apr 2025
From a partner site

10/10 Excellent

Rigo H.

Phenomenal!

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: Amazing house, great location! I always stay here while visiting Key West. A block from duval, couple blocks from the beach, but hidden away from all the foot traffic. I can’t recommend Lilly’s Pad enough!
Verified

10/10 Excellent

Caroline G.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect location and charming house

We had a great vacation in this rental. It was clean, well appointed and a fantastic location. The property manager was attentive and responsive and made our stay there a breeze. It was perfect for the five of us. The outside and inside couldn't have been better.
Stayed 4 nights in May 2025
From a partner site

10/10 Excellent

Karen K.

Perfect Vacation Spot

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 house was perfect for our family vacation and the concierge team was fabulous. I highly recommend renting this beautiful home to be in the heart of Key West!
Verified

10/10 Excellent

Jane P.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Lovely property

We really enjoyed our stay at Lillys Pad, and the convenience of the location. Everything was perfect!
Stayed 4 nights in Jun 2024
Verified

10/10 Excellent

Jennifer M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great birthday celebration

We loved staying at this house in this location. Loved being near a bus stop and right off Duval St. The rental company was so helpful in sharing great restaurants, shopping and more, it was a great spot.
Stayed 4 nights in Nov 2023
Verified

10/10 Excellent

Heather A.

Liked: Cleanliness, check-in, communication, location, listing accuracy

FirstTimers

Loved the location for proximity to restaurants, shopping and water. Parking spot was essential. Pool was amazing at the end of the day. On the bus route for easy commute to other end for touristy things. Home interior was fresh and fun. Would come back!
Stayed 4 nights in May 2025
From a partner site

10/10 Excellent

Barry B.

Perfect spot for Key West family vacation home base

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: Lilly's Pad is just as advertised, and just what we hoped for. Near the quieter end of Duval, beautifully furnished, immaculately clean, 4 baths, 3 bedrooms, and the delightful 'cool off' pool in the back couldn't have been better for our trip. We'd stay again in a heartbeat.
Verified

10/10 Excellent

Lindsay L.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Grown Ups Celebrating

This home was perfect. We had 6 adults (3 couples). It had plenty of space. Extremely clean. Would definitely be coming back to this property.
Stayed 4 nights in Apr 2025
From a partner site

10/10 Excellent

Pam M.

Lilly Pad

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: Great stay for our daughter’s wedding. Convenient to everything, clean and cozy
Verified

10/10 Excellent

Lisa R.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Lily’s Pad

Great place! Four friends enjoyed all that Lily’s Pad had to offer. The house was just as it looked in the listing! Close to all that key west has to offer. Check in was a breeze & the parking space was an added bonus!! Would definitely stay here again.
Stayed 5 nights in Jul 2024
From a partner site

10/10 Excellent

Roderick J.

Key West Vacation

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: Astor meets Key West
From a partner site

10/10 Excellent

Gary S.

Cute, cozy retreat.

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: Nice hone, met all our requirements. Well stocked.
From a partner site

10/10 Excellent

Wes F.

A Fabulous Key West Vacation Rental

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: Super clean, well equipped vacation rental in a fantastic location. We would definitely rent it again on our next Key West vacation. The management staff is also wonderful. Highly recommend.
From a partner site

10/10 Excellent

Erin R.

Perfect 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: The layout, furnishings and decor in this home is all well thought out and perfect! Historic Key West Vacation Rentals goes above and beyond with communication.
From a partner site

10/10 Excellent

Thomas F.

Couldn’t be better

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: Exactly as described on line. Management company communications were perfect. Location made it walkable to the Hemmingway House, Mallory Square, the Truman Little White Hoyse, Duval Street shopping, and several great restaurants.
Stayed 4 nights in Sep 2024
Verified

10/10 Excellent

Kenneth A.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Key West at its Best

The property was fantastic. Has the feel of old Key West with all the modern amenities. The property is very quiet inside and in the pool area, yet just a 1/2 block off of Duval! I almost hate to brag on the property so it will be available for us again! We are returning soon! The staff is fantastic and extremely helpful in every aspect. Beautiful office close by, cant say enough good things. Absolutely no downside!
Stayed 4 nights in May 2023
From a partner site

10/10 Excellent

Joseph M.

Lilly’s Pad

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: Lilly’s Pad and my experience with Vacation Homes of Key West was exceptional. The house was extremely clean, well-equipped, and very comfortable. The outdoor patio and pool area were outstanding. Its location close to Duval was also great! Aubrey at Vacation Homes of Key West was exceptional in meeting all of our needs, ensuring our stay was perfect, and keeping us well-informed.
Stayed 7 nights in Mar 2024

About the host

Hosted by Historic Key West Vacation Rentals

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