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Luxurious Island Pearl, 2 Bed/2 Bath Home near Duval - Pool

Holiday home with kitchen, steps from Duval Street

Photo gallery for Luxurious Island Pearl, 2 Bed/2 Bath Home near Duval - Pool

Fridge, microwave, oven, stovetop - Luxurious Island Pearl, 2 Bed/2 Bath Home near Duval - Pool (Key West)
2 bedrooms, iron/ironing board, free WiFi, bed sheets - Luxurious Island Pearl, 2 Bed/2 Bath Home near Duval - Pool (Key West)
Smart TV - Luxurious Island Pearl, 2 Bed/2 Bath Home near Duval - Pool (Key West)
A heated pool - Luxurious Island Pearl, 2 Bed/2 Bath Home near Duval - Pool (Key West)
Terrace/patio - Luxurious Island Pearl, 2 Bed/2 Bath Home near Duval - Pool (Key West)
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

10 out of 10
Exceptional

Entire home

2 bedrooms2 bathroomsSleeps 4

Popular amenities

  • Pool
  • Kitchen
  • Washing machine
  • Dryer
  • Free Wi-Fi
  • Air-conditioning

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, 2 Bed/2 Bath Home near Duval - Pool

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.

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.

P.S. The pool is all yours—no sharing here! Pool heat available when requested.

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

  • In a village
  • In the city centre
  • Near a hospital
  • Near the marina
  • Near the sea

Things to do

  • Golf
  • Heated pool
  • Tennis
  • Birdwatching nearby
  • Cycling nearby
  • Ecotours nearby
  • Fishing nearby
  • Golfing nearby
  • Jet skiing nearby
  • Sailing nearby
  • Scuba diving nearby
  • Snorkelling nearby
  • Swimming nearby
  • Windsurfing nearby

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)
  • First aid kit
  • Fire extinguisher
  • Deadbolt lock

General

  • Housekeeping (on request)

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Key West Dreamin' - Private Pool Steps Off Duval
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  • Kitchen
  • Washing machine
  • Dryer
9.8 out of 10, Exceptional, 52 reviews
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Policies

Check-in

Check-in time starts at 4:00 PM
Contactless check-in and check-out are available
Minimum check-in age - 25

Check-out

Check-out before 10:00 AM

Special check-in instructions

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

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. Discover the area's water adventures with jet skiing and scuba diving nearby, or enjoy the great outdoors with cycling and ecotours.
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Map
Key West, FL

What's nearby

  • Duval Street - 1 min walk - 0.2 km
  • Harry S. Truman Little White House - 6 min walk - 0.5 km
  • Key West Aquarium - 7 min walk - 0.7 km
  • Mallory Square - 9 min walk - 0.8 km
  • Ernest Hemingway Home and Museum - 9 min walk - 0.8 km

Getting around

  • Key West, FL (EYW-Key West Intl.) - 14 min drive

Restaurants

  • ‪Margaritaville - ‬2 min walk
  • ‪Willie T's - ‬3 min walk
  • ‪Jack Flats - ‬2 min walk
  • ‪Hard Rock Cafe - ‬5 min walk
  • ‪Kermit’s Key West Key Lime Shoppe - ‬3 min walk

Frequently asked questions

Does Luxurious Island Pearl, 2 Bed/2 Bath Home near Duval - Pool have a pool?

Yes, this property has a pool. Pool types include heated pools.

Is Luxurious Island Pearl, 2 Bed/2 Bath Home near Duval - Pool pet-friendly?

No, pets are not allowed at this property.

How much is parking at Luxurious Island Pearl, 2 Bed/2 Bath Home near Duval - Pool?

On-site parking is available at the property.

What time is check-in at Luxurious Island Pearl, 2 Bed/2 Bath Home near Duval - Pool?

Check-in begins at 4:00 PM.

What time is check-out at Luxurious Island Pearl, 2 Bed/2 Bath Home near Duval - Pool?

Checkout is at 10:00 AM.

Where is Luxurious Island Pearl, 2 Bed/2 Bath Home near Duval - Pool 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, 2 Bed/2 Bath Home near Duval - Pool 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.
More informationOpens in a new window
Rating 10 - Excellent. 42 out of 44 reviews
Rating 8 - Good. 2 out of 44 reviews
Rating 6 - Okay. 0 out of 44 reviews
Rating 4 - Poor. 0 out of 44 reviews
Rating 2 - Terrible. 0 out of 44 reviews

9.8

Cleanliness

10

Location

Reviews

10/10 Excellent

michelle s.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great location nice place
Stayed 4 nights in Jul 2025

10/10 Excellent

Judy O.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great house, yard and pool and location. The communication with the rental staff was spot on and check in check out seamless.
Stayed 5 nights in Sep 2025

10/10 Excellent

Mike D.

Liked: Cleanliness, check-in, communication, location, listing accuracy
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!
Stayed 3 nights in Aug 2025
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Laura T.

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

10/10 Excellent

John H.

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

Great Property

Outstanding location with beautiful features! Very comfortable!
Stayed 3 nights in Jul 2025
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Randi D.

Wonderful!!!! 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: This house is perfect for 2 couples. The bedrooms and bathrooms are large. Kitchen has new appliances and the pool is beautiful! Perfect location to walk to attractions and restaurants. On a quiet street across from a grocery. Loved this house!!!!

10/10 Excellent

Stephanie M.

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

Great location and customer service

We loved our location, the house and Key West!
Stayed 4 nights in Mar 2025

10/10 Excellent

Dianne T.

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

Wonderful property

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.
Stayed 2 nights in May 2025

10/10 Excellent

Julia C.

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

Perfect house and location!

The location was perfect! We walked everywhere! Very nice inside!
Stayed 3 nights in Apr 2025
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Nancy T.

Great place to stay

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 home was beautifully decorated and a great location. We were able to walk to everything. There was even a grocery store across the street. The property management company was very helpful. I would definitely recommend staying at this beautiful home!
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

David B.

Best Rental Property in Key West

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 house was modern with new appliances. The king size beds were comfortable. The walk in showers were spacious. The private pool was an oasis at the end of a busy day. And the location was perfect. Definitely staying here again.
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Patti S.

Everything and More!

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: Not often are our expectations exceeded when renting a vacation home, but oh my goodness this place is the best. Two couples stayed comfortably. The location is fabulous, especially the grocery store across the street. Several area restaurants were all great. And the bookstore - well let's just say it became my new favorite place. The cherry on top was a dedicated parking space adjacent to the home. We would all give this location 10 stars if possible!

10/10 Excellent

Eric S.

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

Great Place

Place was perfect and property management was great. Will definitely try to stay here again.
Stayed 3 nights in Aug 2024

10/10 Excellent

James D.

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

key west

right off of Duval, central location, communication with manager was prompt and fast..
Stayed 3 nights in Apr 2025

10/10 Excellent

William

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

Awesome place to stay!

Really convenient location, close to everything! Very clean and well appointed. Beds and linens were fantastic. The backyard pool is a nice touch on hot days. Upstairs long term residents are phenomenal, treated us like family and provided tons of tips only locals would know. One of the better trips we have made to key west and this location had a lot to do with the experience. We would certainly book here again!
Stayed 4 nights in May 2025
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Gina W.

Great house in 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: We loved the house. It was clean, well maintained, and in a great location! We loved having the grocery store across the street and walked or rode bikes to everything!

8/10 Good

joseph c.

Liked: Check-in, communication, location, listing accuracy

Island Retreat

The interior was beautifully done. Well laid out and good amenities. Exterior needs work to compliment the inside.
Stayed 14 nights in Feb 2025

10/10 Excellent

jean-michel d.

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

Inside is a 5*

First i have been impressed by the professionalism of the property manager ! When we arrive we are doubting because outside needs improvement… but when we open the door whoaa ! newly refurbished, with taste and confort .. A wonderful place to stay , the pool is a us … when the outside will be refurbished this place will be a all star !
Stayed 2 nights in Jul 2025
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

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.

10/10 Excellent

Melissa W.

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

Couples Getaway

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.
Stayed 4 nights in Mar 2025
This review comes from a trusted partner site and has not been verified.

8/10 Good

Terry M.

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).

10/10 Excellent

Christopher P.

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

Incredible...

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.
Stayed 4 nights in Jun 2024
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

CPL I.

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!
Stayed 3 nights in Jul 2024

10/10 Excellent

Jill M.

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

Paradise - Perfection

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.
Stayed 3 nights in Feb 2025
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Angie G.

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.