Lilly's Pad- Nightly Rental

3 Bedrooms

3.5 Bathrooms

6 Guests

5.0

Renovated with style, this bright and sunny home depicts enchanting island life. Three ensuite bedrooms, an open concept kitchen/living room, and a well-appointed lanai provide privacy and indoor-outdoor living for family and friends.



About the property

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.***


Sleeping Arrangements

Sleeping space 1

BEDROOM
KING (1)

Sleeping space 2

BEDROOM
KING (1)

Sleeping space 3

BEDROOM
QUEEN (1)

Features & amenities

  • Type: House
  • King Bed
  • Hair Dryer
  • Downtown
  • Private Pool
  • pets not allowed
  • Monthly: No
  • Nightly & Weekly
  • Air Conditioning
  • Internet Access
  • Washer / Dryer
  • Historic Old Town
  • Outdoor Dining
  • Walk in Shower

Get Quote

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Location

5.0 (19 reviews)

5.0

perfect vacation spot

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!

Submitted by Londonderry NH on Aug 18, 2025

Response from Historic Key West Vacation Rentals

Thank you for your fabulous review of Lilly's Pad and our Concierge Team! We love this gorgeous home and are so glad you enjoyed your time there. We hope to welcome you back to Key West soon~ The Team at HKWVR

5.0

perfect spot for key west family vacation home base

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.

Submitted by Sykesville MD on Jul 17, 2025

Response from Historic Key West Vacation Rentals

What a nice review and we thank you! Please come and make some more memories with us at Lilly's Pad! ~ The Team @ HKWVR

5.0

4 night weekend in key west

We were 3 couples in our 60's on a 4 day visit to Key West. The house was a tad smaller than we expected but it was extremely well appointed and centerally located so that we could walk everywhere. The onsite parking spot was great.

Submitted by Mendham NJ on Apr 29, 2025

Response from Historic Key West Vacation Rentals

We are so happy you enjoyed your time at Lilly's Pad! We hope you all will come back and stay with us again, and soon! ~ The Team @ HKWVR

5.0

lilly pad

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

Submitted by Richmond VA on Apr 02, 2025

Response from Historic Key West Vacation Rentals

Congratulations! We hope everyone will come back for their anniversary! ~ The Team @ HKWVR

5.0

spring break

My 4th time to stay book with this company. All have been 5 Star. Houses are gorgeous and VERY clean.

Submitted by Poteet TX on Mar 23, 2025

Response from Historic Key West Vacation Rentals

May the 4th visit be with you! We are so happy to have you come and stay with us and can't wait for your next visit. Thank you for reviewing us so kindly. ~ The Team @ HKWVR

5.0

couldn’t be better

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.

Submitted by Cumming GA on Oct 03, 2024

Response from Historic Key West Vacation Rentals

We are so happy you enjoyed your time at Lilly's Pad and can't wait for your return! Please make it soon. ~ Jennifer & Team @ HKWVR

5.0

wawaweewa, great success!

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!

Submitted by Cedarhurst NY on Jul 05, 2024

Response from Historic Key West Vacation Rentals

You do trips like I like to do trips. Fun with quick catchphrases to round up the whole thing! Please come and stay with us again and give us more soundbites to share. ~ Jennifer & Team HKWVR

5.0

key west vacation

Astor meets Key West

Submitted by Astor FL on Jun 11, 2024

Response from Historic Key West Vacation Rentals

What a beautiful way to describe Lilly's Pad! Thank you for that visual. Please come and stay with us again, anytime. ~ Jennifer & Team @ HKWVR

5.0

the lilly’s pad vacation home

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.

Submitted by Cordele GA on Jun 04, 2024

Response from Historic Key West Vacation Rentals

It's so nice to hear that you enjoyed your time at Lilly's Pad. Thank you for reviewing the home and our Team so nicely! ~ Jennifer & Team @ HKWVR

5.0

a fabulous key west vacation rental

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.

Submitted by Tyler TX on May 14, 2024

Response from Historic Key West Vacation Rentals

Thank you so much for the nice review of HKWVR and Lilly's Pad! We are here, eagerly awaiting your return! ~ Jennifer & Team @ HKWVR

5.0

our lilly's pad experience

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.

Submitted by Houma LA on Apr 08, 2024

Response from Historic Key West Vacation Rentals

Thank you so much for the kind review of Lilly's Pad ~ we are so happy you enjoyed your time and can't wait for you to come again! ~ Jennifer & Team @ HKWVR

5.0

lilly’s pad

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.

Submitted by Poland OH on Mar 11, 2024

Response from Historic Key West Vacation Rentals

Thank you so much for your kind review of Historic Key West Vacation Rentals (and Aubrey!). We love hearing kind words and hope you're already making plans to come and stay with us again! ~ Jennifer & Team @ HKWVR

5.0

lilly's pad - an idyllic rental

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.

Submitted by Indianapolis IN on Mar 04, 2024

Response from Historic Key West Vacation Rentals

It is so nice to hear that you had a great time. We love our Lilly's Pad and are glad you did too. We can't wait for your next stay. ~ Jennifer & Team @ HKWVR

5.0

cute, cozy retreat.

Nice hone, met all our requirements. Well stocked.

Submitted by Cincinnati OH on Feb 17, 2024

Response from Historic Key West Vacation Rentals

Thank you so much for the kind words about Lilly's Pad! We hope you'll come and stay with us again, and soon. ~ Jennifer & Team @ HKWVR

5.0

lily's pad the perfect key west paradise!

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.

Submitted by Port Deposit MD on Jan 08, 2024

Response from Historic Key West Vacation Rentals

Thank you for taking the time to review Lilly's Pad ~ we appreciate your taking the time and for letting us know about the upstairs. We will definitely look into that! Please come back and let us know how we did. ~ Jennifer & Team @ HKWVR

5.0

great location!

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!

Submitted by Lexington KY on Dec 22, 2023

Response from Historic Key West Vacation Rentals

You got to meet the bonus rooster? That's amazing! He only comes out for special guests! Come and stay with us again. We're always happy to have him crow for you again. Jennifer & Team @ HKWVR

5.0

perfect house!

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.

Submitted by Hendersonville NC on Nov 14, 2023

Response from Historic Key West Vacation Rentals

Well, that is just so nice to hear! We love our Lilly's Pad and can't wait for you to come and stay with us again. ~ Jennifer & Team @ HKWVR

5.0

couldn't have been more pleased

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.

Submitted by Tampa FL on Jul 23, 2023

Response from Historic Key West Vacation Rentals

Thank you for the kind words about Lilly's Pad! We love this home and are so glad you did too. Please come and stay with us again, soon! ~ Jennifer & Team HKWVR

5.0

wonderful location!

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.

Submitted by Mt Pleasant SC on May 10, 2023

Response from Historic Key West Vacation Rentals

Thank you kindly for the honest review of Lilly's Pad. You were our first guest in our new home so it is good for us to know what we can do differently and better. We will definitely look into your suggestions; the owners already have plans in place to replace the deck. We hope you will come back and see the improvements. ~ Jennifer & Team HKWVR

Sep 14-14, 2025
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  • The Vacation Rental Travel Guide - Most Outstanding Award for 2017
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