Historic Seaport Rentals USA Florida Key West Historic Seaport

NEW listing! Luxurious Island Pearl, 2 Bed/2 Bath Home near Duval - Pool | House in Key West

10.0 (31 Reviews) |   2 Bedrooms  2 Bathrooms  4 Guests  Stay&Play
Historic Seaport House | NEW listing! Luxurious Island Pearl, 2 Bed/2 Bath Home near Duval - Pool

2 Bedroom House in Historic Seaport, Key West

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!

NEW listing! Luxurious Island Pearl, 2 Bed/2 Bath Home near Duval - Pool is located in Historic Seaport. NEW listing! Luxurious Island Pearl, 2 Bed/2 Bath Home near Duval - Pool provides accommodation, featuring Barbecue/Outdoor Cooking, Child Friendly, Parking, among other amenities. This House features Barbecue/Outdoor Cooking, Child Friendly, Parking, to make your stay a comfortable one.

NEW listing! Luxurious Island Pearl, 2 Bed/2 Bath Home near Duval - Pool has 2 Bedrooms , 2 Bathrooms, and max occupancy of 4 people. The minimum rental for this property is 1 nights, but this can change depending on the season you plan on staying. Previous guests have given good rated it, and VRBO labeled it a top-rated House because of the excellent services rendered by the owner or manager of this House, and has consistently provided great experiences for their guests. Most families or guests that use it recommend it to their friends and some of them are repeat guests. House has a friendly neighborhood, and the Historic Seaport has interesting places to visit. If you want to learn more about the House in Historic Seaport, such as places to visit and things to do nearby, you can check below to learn more.

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Unique Amenities

  • Air Conditioner
  • Parking
  • Pool
  • TV
  • View
  • Ocean View
  • Balcony/Terrace
  • Oceanfront
  • Security/Safety
  • Sports/Activities
  • Bedding/Linens
  • Wellness Facilities
  • Guest Services
  • Barbecue/Outdoor Cooking
  • Child Friendly
  • Internet
  • Kitchen
  • Laundry
 
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Policies

Event Policy Events allowed
Check-in Check-in time starts at 4:00 pm contactless check-in available minimum check-in age: 25
Check-out Check-out before 10:00 am
Child Policy Children are welcome.
Pet Policy Pets not allowed
Smoking Policy Smoking is not permitted
Other Policy 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 host has indicated there is a smoke detector on the property host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip parties and events are allowed on site safety features at this property include a fire extinguisher, a first aid kit, and a deadbolt lock special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed 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
 
Key West, 33040, USA

What Our Guests say 500 + Reviews

Jun 25, 2025 11:21:00 AM
Summary: 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!
Gina W. Gina W.
Jun 3, 2025 09:26:53 PM
Summary: 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!
William William
May 30, 2025 01:22:00 PM
Summary: 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.
May 15, 2025 11:36:33 PM
Summary: 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.
Dianne T. Dianne T.
May 12, 2025 03:13:00 PM
Summary: 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).
Terry M. Terry M.
Apr 29, 2025 05:47:41 AM
Summary: right off of Duval, central location, communication with manager was prompt and fast..
James D. James D.
Apr 14, 2025 01:15:42 AM
Summary: The location was perfect! We walked everywhere! Very nice inside!
Julia C. Julia C.
Mar 28, 2025 10:52:47 PM
Summary: We loved our location, the house and Key West!
Stephanie M. Stephanie M.
Mar 18, 2025 05:08:42 AM
Summary: 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. Melissa W.
Mar 10, 2025 05:06:19 AM
Summary: 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. Jill M.

FAQ's

Is this Historic Seaport house pet-friendly for guests?

No, pets are not allowed at this property. Check the guest reviews to learn what guests had to share.

Does the Historic Seaport house have a swimming pool?

Yes, this Historic Seaport house has a swimming pool. Check the Facility Overview section for details about the pool and other available facilities.

How much does it cost per night to stay in Historic Seaport house?

Best-rates for the Historic Seaport house starts from $1,148 per night with includes TV, Oceanfront, Bedding/Linens, Wellness Facilities, Barbecue/Outdoor Cooking, Child Friendly, Parking, View, Ocean View, Security/Safety, Kitchen, Laundry, Sports/Activities, Balcony/Terrace, Guest Services, Internet, Air Conditioner, Pool StayAndPlay offers fully equipped golf villas, golf hotels, golf resorts, luxury golf cabins, and exclusive golf retreats, making it easier than ever to find your perfect golf escape — ideal for families, peaceful getaways, or pet-friendly retreats with the whole crew.

Is Historic Seaport house a family-friendly place to stay?

Based on the information we have received from the owner or our partner, this is considered to be a family-friendly property. Families have rated this house Good or guests have recommended them suitable for families. As reported by the owner or manager, the house has specified that children are welcome. Please see details about suitability for your family or inquire with the property to learn more.

Is the Historic Seaport house wheelchair accessible or offer services for disabled guests?

Based on the information received from our partner, the Historic Seaport house has not specified they are wheelchair accessible. Likewise, there is not an elevator specified as being available at the property. Specific accessibility details may be addressed in the property details section of this page.

What is the minimum night stay policy for the Historic Seaport house?

Based on the information reported by the owner or manager, the Historic Seaport house indicates 1 day stay policy at this house. Guests are cautioned that the minimum stay policy may differ based on seasonality or availability and may be at the discretion of the owner or manager.

What cancellation policy is in place for Historic Seaport house?

Based on the information reported by the owner or manager, details for the cancellation policy for the Historic Seaport house are as follows: Cancellation policy Guests are cautioned that the cancellation policy may differ based on seasonality, availability, or current travel restrictions. Guests should also be aware that this policy may be subject to change and should be confirmed prior to booking. More details may be available on this page in the property description. However, early check-in or late check-out can sometimes be negotiated between the guest and the owner or the manager of this property.

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