Luxurious Island Pearl - June 1st-July 15th 15% Off!-Private Pool - 2BD/2Bath
Looking for the perfect spot to soak up some sunshine and unwind in Key West? You’ve found it. Island Pearls is a stylish and comfy 2-bedroom, 2-bath vacation rental located right on charming Fleming Street—just one block from all the action on Duval and directly across from the local favorite, Fausto's grocery store. You’ll be close to everything, so no need for a car (though there’s a driveway if you have one).
Step inside and you’ll feel instantly at home. The kitchen is modern and fully equipped, with sleek white finishes and custom cabinets that keep everything looking clean and polished. Whether you’re whipping up breakfast or sharing cocktails at the island, it’s a space that makes cooking and gathering easy and fun.
The living area is cozy yet modern, with hardwood floors, comfy seating, and just the right amount of Key West charm. Throw open the plantation shutters and let in that sweet Florida sunshine—it’s the perfect spot to kick back after a day of exploring.
Both bedrooms are en-suites, thoughtfully designed with comfy beds, soft linens, and fun, tropical wallpaper that’ll remind you you’re on island time. Each has its own private bathroom, making it great for couples, friends, or a small family traveling together.
Outside, the private pool and deck are where you’ll probably spend most of your time. Whether you’re sunbathing, taking a dip, or just enjoying the breeze with a drink in hand, it’s a peaceful spot that feels like your own slice of paradise.
Island Pearls is all about comfort, convenience, and that laid-back Key West vibe. It’s not just a place to stay—it’s a place to relax, recharge, and make some great memories.
P.S. The pool is all yours—no sharing here! Pool heat available when requested.
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.
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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, a first aid kit and a deadlock
About the area
Key West
Located by the sea, this holiday home is in Key West Historic District, a neighbourhood in Key West. Ernest Hemingway Home and Museum and Fort Zachary Taylor Historic State Park are notable landmarks, and the area's natural beauty can be seen at Florida Keys Beaches and South Beach. The Kite House and Sails To Rails Museum at Flagler Station are also worth visiting.
Oldest House Museum and Garden - 1 min walk - 0.2 km
Harry S. Truman Little White House - 8 min walk - 0.7 km
Mallory Square - 10 min walk - 0.9 km
Ernest Hemingway Home and Museum - 12 min walk - 1.1 km
Getting around
Key West, FL (EYW-Key West Intl.) - 14 min drive
Restaurants
‪Margaritaville - ‬2 min walk
‪La Concha Bar - ‬3 min walk
‪Kermit’s Key West Key Lime Shoppe - ‬3 min walk
‪Caroline's Cafe - ‬7 min walk
‪Wendy's - ‬3 min walk
Frequently asked questions
Does Luxurious Island Pearl - June 1st-July 15th 15% Off!-Private Pool - 2BD/2Bath have a pool?
Yes, this property has a pool. Pool types include heated pools.
How much does it cost to stay at Luxurious Island Pearl - June 1st-July 15th 15% Off!-Private Pool - 2BD/2Bath?
As of 16 May 2026, prices found for a 1-night stay for 2 adults at Luxurious Island Pearl - June 1st-July 15th 15% Off!-Private Pool - 2BD/2Bath on 17 June 2026 start from AU$1,013, 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 Luxurious Island Pearl - June 1st-July 15th 15% Off!-Private Pool - 2BD/2Bath pet-friendly?
No, pets are not allowed at this property.
How much is parking at Luxurious Island Pearl - June 1st-July 15th 15% Off!-Private Pool - 2BD/2Bath?
On-site parking is available at the property.
What time is check-in at Luxurious Island Pearl - June 1st-July 15th 15% Off!-Private Pool - 2BD/2Bath?
Check-in begins at 4:00 PM.
What time is check-out at Luxurious Island Pearl - June 1st-July 15th 15% Off!-Private Pool - 2BD/2Bath?
Checkout is at 10:00 AM.
Where is Luxurious Island Pearl - June 1st-July 15th 15% Off!-Private Pool - 2BD/2Bath located?
Located in Key West Historic District, this holiday home is steps away from San Carlos Institute - Casa Cuba and Duval Street. Florida Keys Beaches and Ernest Hemingway Home and Museum are also within 15 minutes.
Reviews
10
Exceptional
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Well stocked with kitchen appliances and utensils. Great location for restaurants, bars, beach and entertainment. Can walk to everything. Management company was very responsive and attentive.
The house is beautiful and is centrally located in Old Town. It had everything we needed and more, beautiful kitchen, two en suite bedrooms and a beautiful private pool in the backyard. The hosts were super-responsive, answered all of our questions, and could not have been more helpful. We would stay here again in a heartbeat!
Perfect house for our stay in Key West. Exceptionally clean, open living area. The 2 bedrooms are on each side do the house, giving privacy. The private pool and tranquil backyard are added bonuses
The house was wonderful. Very clean and provided everything we needed. The host was extremely communicative and responded to our questions within minutes. The location is great, but great in Key West usually means busy and loud. That was the only downside, but definitely not the fault of the host - Key West can just be loud! We would definitely stay again!
Great house, yard and pool and location. The communication with the rental staff was spot on and check in check out seamless.
Judy O.
Stayed 5 nights in Sep 2025
From a partner site
10/10 Excellent
Bruce W.
17 Jan 2026
Island pearl more like diamond
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:
Everything was great! Comfortable beds, clean and well taken care of. Property management was quick to respond to our needs. Truly enjoyed this property.
Bruce W.
From a partner site
10/10 Excellent
Jim D.
21 Dec 2025
Great place in perfect 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:
Had a wonderful time and the rental was like new and good location. Property mgr was easy to communicate with.
Great updated house in the perfect location. Super easy communication with the host, who were very accommodating to our needs in the trip. Would definitely stay here again!
In the heart of everything...yet removed enough to enjoy our vacation. Rental is not the full house but the area you are granted access is fantastic (worked well for us). Home is well finished with two ensuites that worked perfectly for us, a beautiful kitchen and private pool. Comfortable and convienent, tough to beat.
This unit was amazing!!! Appliances were very high quality. Unit was immaculate. Location was perfect - 2 blocks off Duval St., about 3/4 mile from the marina and less than a mile from Southernmost Point. Pool out back and a grocery store across the street. We plan to book this unit again!
Verified traveller
Stayed 7 nights in Dec 2025
From a partner site
10/10 Excellent
Laura T.
7 Oct 2025
Awesome Ley West House
Rating Details:
The property manager was very helpful.
The vacation rental was spotless.
I was more than happy with the location.
I was satisfied with the condition of the vacation rental.
Overall, I recommend this vacation rental.
Reviewer Comments:
The place was beautiful and location superb!Perfect place to stay in Key West
Laura T.
From a partner site
10/10 Excellent
David f.
12 Dec 2025
location location 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:
Amazing location, luxury accommodations. Everything you needed is supplied. Fantastic communication and service. Very clean and comfortable. see you next year!!!
The house was beautiful, so comfortable and well thought out. Perfect location to all the action on Duval st, but out of the way enough to be quiet and peaceful. Would stay again in a heartbeat.
The location was perfect! We walked everywhere! Very nice inside!
Julia C.
Stayed 3 nights in Apr 2025
From a partner site
10/10 Excellent
Terri A.
14 Feb 2026
Another Great Stay In KW
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:
The Property Management was very great about communicating prior to our stay. The house has recently been renovated and is comfortable. I gave 4 stars for maintenance since the pool deck has some boards that need replacing. The pool itself is wonderful. The property is across the street from the grocery store-great for running over for a forgotten item. But, being across the street they get a lot of traffic and noisy early morning deliveries. Nothing that would prevent us from staying here again.
Terri A.
From a partner site
10/10 Excellent
Dan Y.
30 Nov 2025
Fantastic gem in Old Town
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:
Everything about this rental was top notch. House seems recently renovated and rooms are tastefully decorated. Location is perfect as you can walk down either direction in Duval Street. Our little one loved the heated pool. Last but not least, Preferred Properties was very accommodating and super responsive!
Dan Y.
About the host
Hosted by The Team at Preferred Properties
Languages:
English
Premier Host
They consistently provide great experiences for their guests