Island Pearls in Key West offers a sophisticated retreat on Fleming Street. Enjoy the culinary masterpieces in your kitchen, unwind with plush seating and tasteful wooden accents, or relax by the tranquil pool area with glorious sunshine.
Reviews
1010 out of 10
Exceptional
Entire home
2 bedrooms2 bathroomsSleeps 4
Popular amenities
Pool
Kitchen
Washing machine
Dryer
Free Wi-Fi
Air-conditioning
The current price is €1,100
€1,100
includes taxes & fees
3 May - 4 May
Add dates for prices
About this property
Entire place
You'll have the entire home to yourself and will only share it with other guests in your party.
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.
Property amenities
Pool/Spa
Communal pool
Heated pool
Internet
Available in the house: Free WiFi
Parking and transport
Parking on site
Kitchen
Coffee/tea maker
Cookware, dishware, and utensils
Dishwasher
Hob
Kitchen island
Microwave
Oven
Refrigerator
Toaster
Dining
Dining table
Bedrooms
2 bedrooms
Bedsheets provided
Bathroom
2 bathrooms
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
Location highlights
Near the marina
Things to do
Golf
Heated pool
Tennis
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 (host has indicated there is a smoke detector on the property)
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
This property is managed by a professional host. The provision of housing is linked to their trade, business or profession.
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
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
If you cancel your booking, you'll be subject to the host's cancellation policy. In accordance with EU regulations about consumer rights, property booking services are not subject to the right of withdrawal.
Property is also known as
2302-262609
About the area
Key West Historic District, a neighbourhood in Key West, is home to this holiday home. 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. Visit our Key West travel guide
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 1 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 3 May 2026 start from €1,100, 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.
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Luxurious Island Pearl - June 1st-July 15th 15% Off!-Private Pool - 2BD/2Bath 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.
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
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!
The interior was beautifully done. Well laid out and good amenities. Exterior needs work to compliment the inside.
joseph c.
Stayed 14 nights in Feb 2025
From a partner site
10/10 Excellent
30 May 2025
First time Key West visit
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:
Beautiful historic home one block off Duval. Beautiful renovation appears to be very recent. The pool is great to take a break from the heat.
This house was perfect for our couples weekend! Two master king suits with their own private bathrooms. Location was excellent, we were in walking distance to Duval and the marinas. The rental company was great at letting us know about early check in and let us store our bags in their office when needed. There is a grocery store right across the street from the house.
Melissa W.
Stayed 4 nights in Mar 2025
From a partner site
8/10 Good
Terry M.
12 May 2025
Nice updated unit 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:
This was a great property in the perfect location! The updates to this unit really make it feel special. And Angela was very accommodating and communication was timely. The only issue we had was the upstairs renters could be heard walking all hours of the night (midnight and 3am).
I can't speak highly enough of this property. The furnishings are fantastic. The rooms luxurious. The bathrooms indulgent. The location is unbelievable. The pool was delightful.
11/10 blew me away. Possibly the only time I've ever enjoyed ALL of my keys trip.
Christopher P.
Stayed 4 nights in Jun 2024
From a partner site
10/10 Excellent
CPL I.
24 Jul 2024
Beautiful oasis near everything
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 2 bed/2 bath home is in impeccable condition and perfectly decorated with high-end appliances and furnishings. Three, count them, three coffee makers to cover all your early morning needs (espresso, drip, or Keurig). Great places to eat within 50 yrds, and a quick walk to Duval or Historic Seaport. Do not hesitate to book a stay at Island Pearls!
Classy, high quality and upscale place to stay with the whole Key West vibe. Our husbands were high fiving us and telling us we hit it out of the park with our selection. The kitchen had all the right amenities and was easy to cook in. We never used the pool because the front porch is the sitting zone and place you want to hang out at. The tenants above were always gracious and never a bother and we left with new friends. Each bedroom had a huge, built in closet with plenty of hanging or drawer space. The bathrooms were gorgeous with luxury showers. The front bedroom was noisy at first with late night revelers but once you knew what it was it no longer bothered you. If you need TV's, there are four. One in each bedroom, then kitchen and living room. There was room to park our car and then the golf cart we rented too. As yes, the large store directly across was very convenient. Not just a mini mart, but full grocery. We can't wait to come back and stay here again.
Jill M.
Stayed 3 nights in Feb 2025
From a partner site
10/10 Excellent
Angie G.
16 Sept 2024
Beautiful property!
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:
This is a beautiful newly renovated property. It was perfectly located within walking distance of Duvall Street. It has a great front porch for people watching. Is directly across the street from a great little grocery store, which is super convenient. The kitchen is great if you like to cook and it has an awesome set up for coffee. The backyard is perfect for relaxing, but you should know there is also a small cottage behind the house that is a separate rental property. Apparently, if it is rented at the same time as this property, you would be sharing the swimming With strangers. That did not happen to us, but we also did not know it was a possibility until we were already there. The listing should be very clear about this, but it’s not. The property management company was very helpful with any questions we had and super responsive. I would definitely stay here again.
This was the perfect spot to walk to most places in old town! The beds were very comfortable and the rooms were spacious.
We loved being able to enjoy the quiet back yard and pool.
There is a resident rooster who does a great job of patrolling the parking lot and may be an alarm clock for some.
We did have a hiccup with checking in- we were provided the wrong code and it took a few times to get ahold of the host. But the host was always very friendly and helpful. We also found small bugs around the coffee pots- we found moldy coffee grounds that were causing them.
We did find that drunk folks gravitate to the porch every so often but didn’t cause any issues. There is also a dumpster right next to the house and with the smell that makes it unenjoyable to sit out front.
Overall though the house was very comfortable and beautiful. The appliances were amazing and the decor really tied everything together
There are definitely more pros than cons with this rental. We will definitely be back again.
Macenzie W.
Stayed 4 nights in Sep 2024
From a partner site
10/10 Excellent
Jared & Nichole V.
5 Sept 2024
Excellent 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:
We had an absolutely wonderful stay at Island Pearls. The location could not have been better to enjoy the nightlife of Key West. The home was absolutely immaculate with very comfortable and top-of-the-line amenities. We didn't have a chance to use the pool but that and the driveway are a major bonus! The grocery store across the street came in quite handy as well. Note to the owner: This appears to be a newer rental and clearly a lot of thought went into the comfort of your guests. A few things to make their stay easier would be beach/pool towels. There was only one in the house. An iron/steamer combo would be great as most traveling are dressing out of a suitcase. And also some baking sheets for the oven would be a nice addition to the kitchen. This truly was the best home we've rented and we travel ALOT! We will definitely seek out this home again when we visit Key West. Thank you for the great accomodations!
We recently had the pleasure of staying at this exquisite Key West home and were absolutely blown away by the experience. A stone's throw from Duval Street, this house offered the perfect blend of tranquility and convenience.
From the moment we stepped through the door, we were greeted by a meticulously clean and beautifully decorated interior that immediately made us feel at home. The layout was spacious yet cozy, with every room exuding a charming blend of Key West character and modern comfort.
The kitchen was a dream for anyone who loves to cook, fully stocked with high-end appliances and all the tools we needed to prepare meals with ease. We enjoyed leisurely breakfasts on the back patio, surrounded by lush tropical foliage that provided a serene backdrop for our morning routines.
The bedrooms were nothing short of luxurious, each offering plush bedding and ample closet space. The bathrooms were pristine, with sparkling clean fixtures and plenty of fluffy towels – a true treat after a day spent exploring the island.
One of the highlights of our stay was the outdoor space. The beautifully landscaped backyard oasis was our own private sanctuary, complete with a refreshing pool and comfortable loungers where we could unwind under the swaying palm trees. Evenings were spent sipping cocktails by the poolside, soaking in the warm Key West.
The location of the house couldn't have been better – just a short walk or bike ride to the nightlife of Duva
Christopher F.
Stayed 4 nights in Jun 2024
From a partner site
10/10 Excellent
Jeffrey V.
2 Nov 2024
Florida National Park Trip
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 Home is Beautiful inside & out! Incredible Family Room, Kitchen and two bedrooms all decorated beautifully! In a great area, walkable to everything including a grocery store across the street! Would definitely stay here again!
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!
Beth G.
Stayed 5 nights in Jan 2026
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.
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
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.