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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

  • Dryer
  • Washer
  • Parking available
  • Kitchen
  • Barbecue grill

Explore the area

Map
Key West, Florida
  • Duval Street
    ‪1 min walk‬
  • South Beach
    ‪5 min walk‬
  • Southernmost Point
    ‪6 min walk‬
  • 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
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.***

Property manager

Historic Key West Vacation Rentals
Premier Host

Languages

English

Add dates for prices

Amenities

Pool
Kitchen
Washer
Dryer
Free WiFi
Air conditioning

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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
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 indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a first aid kit

About the area

Key West

Located in Key West, this holiday home is in the city centre. Southernmost Point and Ernest Hemingway Home and Museum are notable landmarks, and the area's natural beauty can be seen at Fort Zachary Taylor Historic State Park and South Beach. 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 snorkelling nearby, or enjoy the great outdoors with ecotours.
Map
Key West, Florida

What's nearby

  • Duval Street - 1 min walk - 0.2 km
  • South Beach - 5 min walk - 0.5 km
  • Southernmost Point - 6 min walk - 0.6 km
  • Ernest Hemingway Home and Museum - 7 min walk - 0.7 km
  • Mallory Square - 4 min drive - 1.9 km

Getting around

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

Restaurants

  • ‪Old Town Tavern Key West - ‬6 min walk
  • ‪Southernmost Beach Café - ‬5 min walk
  • ‪Southernmost Point Bar In the USA - ‬5 min walk
  • ‪Rum Bar at the Speakeasy Inn - ‬2 min walk
  • ‪Banana Cafe - ‬2 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.

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

No, pets are not allowed at this 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!?

Checkout 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 holiday home is steps away from City Zoo Gallery and Duval Street. South Beach and Florida Keys Beaches are also within 10 minutes.

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 24 out of 25 reviews
Rating 8 - Good. 1 out of 25 reviews
Rating 6 - Okay. 0 out of 25 reviews
Rating 4 - Poor. 0 out of 25 reviews
Rating 2 - Terrible. 0 out of 25 reviews

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

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

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
This review comes from a trusted partner site and has not been verified.

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

10/10 Excellent

Kathleen A.

Stayed 7 nights in Mar 2025

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
This review comes from a trusted partner site and has not been verified.

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

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
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Abe P.

Wawaweewa, great success!

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: A wise man once told me, “the sign of a great hotel (or Airbnb), is if you walk in, and it feels like you’re the 1st person to ever stay there”. Lilly’s Pad passed the test with flying colors! My group of advanced scuba divers, had an amazing stay. Everything in town was just a short meander away. Shop’s, restaurants, bars, the beach, the “scary bar on the corner of rainbow lane”.....quiet location, but close enough to the action. The communication with the staff was easy & immediate. The house was not just immaculate, but beautifully furnished, well stocked, with very comfortable beds. The outdoor area was very private and chill. I would highly recommend this home. A shout out to the Key West crew, Rhonda, Bella, “Sloppy Johnny”, Dumpster Band, Girl on the Bike at 3AM, Gorilla Girl, Traveling, Dancer with the bad contract, Stalker Sally and all the great characters we met in Key West. Amazing trip!

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
This review comes from a trusted partner site and has not been verified.

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
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

A guest from Cordele, GA

The Lilly’s pad vacation Home

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 Lilly Pad is a beautiful relaxing vacation home. The house was very clean and the perfect size for the 6 adults. The Concierge at historic Key West vacation rentals made all the arrangement for me. She contacted the golf cart company to make sure it was delivered to their office waiting on us when we arrived. She also reserved our sunset tour and snorkeling trip for us. They do an excellent job. We had a problem with the hot water and their Maintance department came out quickly and replaced the water heater Johnny on the spot. And the 2 repairmen were very nice to talk to while they worked, he even gave us some mangos that were growing close by. We all highly recommend Historic Key West vacation rentals and their staff.
This review comes from a trusted partner site and has not been verified.

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.
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Gary D.

Our Lilly's Pad Experience

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 experience from the start. Information on web was on point. Communication was great with management company and I cannot say enough about the property. Fully stocked with everything you can think of, in great condition, nicely furnished and in a great location. Property was spotless when we arrived.
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Kati M., Brookings, SD

March 2024 Stay

Great location! Very easy to work with!
Stayed 4 nights in Mar 2024
This review comes from a trusted partner site and has not been verified.

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
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Julie B., Carmel, IN

Lilly's Pad - An Idyllic 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: Spent 2 glorious weeks at Lilly's Pad and loved every minute. The accommodations are so nice and new, the location is just perfect, just steps to the quiet end of Duval, and a quick bike ride to ANYwhere. Bikes, golf cart and a private boat charter were all arranged by HKWV concierge, planned seamlessly. The idyllic and tropical back porch and pool setting cannot be beat. This home is a true winner.
This review comes from a trusted partner site and has not been verified.

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.

10/10 Excellent

Marianne T.

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

Amazing house!

Lilly's Pad was the perfect house for our 3 couples! Great location, plenty of space for 6 people, and very well appointed....beds are comfy and each bedroom has its own bathroom! The pool and patio area was relaxing and comfortable as well....spent some nice evenings out there! Communication with property management was excellent! Again location was perfect...everything is walkable and super close to Duval but not too loud or too busy. Great Cuban coffee shop across the street and The Rum Bar is right around the corner! (maybe TOO close sometimes!LOL). We will definitely be back! Thanks for a great stay!
Stayed 7 nights in Jan 2024
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Traci B.

Lily's Pad the perfect Key West paradise!

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 can't say enough about this experience! the property is absolutely beautiful and perfectly located with all the amenities. We will stay here again! Not to mention that Key West Historic Vacation Rentals were so wonderful to do business with, so kind, friendly and thoughtful with all the communications and information. Our only critique is that the upstairs suite was a bit hot.
Stayed 5 nights in Jan 2024
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Kimberly B.

Great location!

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: What you see is what you get! This house was perfect for our get away w/our college girls before the holiday. Fantastic location, nice pool, we really enjoyed the porch in the early mornings, slept well, couldn't ask for more :-) I even began to like the rooster that shocked me bright and early on the first morning...lol!

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
This review comes from a trusted partner site and has not been verified.

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.
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Chris F.

Couldn't have been more pleased

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 couldn't have been more pleased by this rental. It was clean, renovated, charming, and super close to Duval (the sane side). You're only a short golf cart jaunt to the madness, though. The pool and back patio area were awesome. And aside from the roosters letting themselves be heard early in the morning, this property is really quiet. We'd love to stay there again.
Stayed 4 nights in Jul 2023

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
This review comes from a trusted partner site and has not been verified.

8/10 Good

Kent S.

Wonderful Location!

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was more than satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: We have been attending the Songwriter's Festival for 9 years - first time in this home. With the festival moving more toward this end of Duvall the location is perfect. Multiple King Size beds makes it great for two couples sharing the house. The parking space is awesome and quite large compared to others we have rented. There are a few things that I would suggest for the property: (1) Love the outdoor area, but the deck around the pool is not acceptable. There are a couple of soft, rotten boards and the deck coating is extremely hot in the sun...too hot to walk on with bare feet. (2) Front bedroom lacks storage...needs a chest of drawers or wardrobe. (3) As one who likes to cook, a knife sharpener would be appreciated.

About the host

Hosted by Historic Key West Vacation Rentals

Host profile image

Languages:

English

Premier Host

They consistently provide great experiences for their guests