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Poolside Paradise - Heated Pool & Steps to Duval St

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Pool
Pool
Exterior
3 bedrooms, iron/ironing board, WiFi, bed sheets
Shower, hair dryer, towels, shampoo

Reviews

8.8 out of 10
Excellent

Entire home

3 bedrooms2 bathroomsSleeps 101075 sq ft

Popular amenities

  • Pool
  • Kitchen
  • Washer
  • Dryer
  • Pet friendly
  • Air conditioning

Explore the area

View in a map
Key West, FL
  • Place, Duval Street
    ‪2 min walk‬
  • Place, Ernest Hemingway Home and Museum
    ‪5 min walk‬
  • Place, Key West Lighthouse and Keeper's Quarters Museum
    ‪5 min walk‬
  • Airport, Key West, FL (EYW-Key West Intl.)
    ‪10 min drive‬

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About the neighborhood

Key West

Located in Old Town Key West, this vacation home is next to popular attractions like Duval Street and Ernest Hemingway Home and Museum. The vacation home includes a private pool, a kitchen, and a furnished balcony.
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What's nearby

  • Duval Street - 2 min walk - 0.1 miles
  • Ernest Hemingway Home and Museum - 5 min walk - 0.3 miles
  • Key West Lighthouse and Keeper's Quarters Museum - 5 min walk - 0.3 miles
  • South Beach - 9 min walk - 0.5 miles
  • Southernmost Point - 11 min walk - 0.6 miles

Getting around

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

Restaurants

  • ‪Moondog Cafe & Bakery - ‬3 min walk
  • ‪Mangoes Restaurant - ‬4 min walk
  • ‪801 Bourbon Bar - ‬3 min walk
  • ‪Old Town Tavern - ‬1 min walk
  • ‪Bourbon Street Pub - ‬4 min walk

About this property

Entire place

You'll have the entire home to yourself and will only share it with other guests in your party.

Poolside Paradise - Heated Pool & Steps to Duval St

Summary:

This 3 bed 2 bath home with an amazing HEATED pool is located right off the quieter end of Duval St. The home consists of 2 separate units "Poolside Suite" and "Poolside Retreat" which are side-by-side and have their own living rooms and kitchens. This property is perfect for larger groups looking for a memorable time in Key West and is walking distance to popular restaurants, attractions, shops and bars!



The Space:

Bring the whole family together for a reunion or holiday celebration at this spacious, Key West home located just a block from the non-stop fun of Duval Street. This rental, with space for up to 10 guests, features an enclosed yard, a private pool, a furnished patio, two full kitchens, and off-street parking for two vehicles (a real rarity in Key West). And dogs up to 40 pounds are welcome for a small nightly fee.



Poolside Retreat Bed Layout:

Bedroom 1: Queen

Living Room: Queen pullout couch

Poolside Suite Bed Layout:

Bedroom 1: King

Bedroom 2: Queen

Living Room: Queen pullout couch



Ideal for an extended family or a few couples traveling together, this home offers free WiFi, four cable TVs, two full kitchens, and a gas grill for a family cookout on the furnished patio.



Guest Access:

Our contactless check-in procedure makes check-in easy. Guests will receive a personalized access code prior to arrival.



The Neighborhood:

This home is located one block from Duval Street, the most popular street in all of Key West, where you'll find fantastic restaurants, unique local shops, and year-round special events and festivals. Play on the sand and people-watch at Southernmost Beach, just a half-mile away. Visit the many historic sites including the Ernest Hemingway Home & Museum and the Key West Lighthouse, both only a couple blocks from your front door, as well as the Truman Little White House and the Mel Fisher Maritime Museum, just under a mile away over on Front Street.



Getting Around:

Parking Information: There are 2 private off street parking spots on the Olivia St side of the property. They are labeled "Poolside Retreat" & "Poolside Suite."



There are a variety of great ways to explore Key West including by bicycle, pedi-cab, moke, scooter, golf cart, Uber, Taxi, or by feet. As this unit is located in downtown Key West, many attractions are within walking distance. Feel free to ask us for recommendations!



Other Things to Note:

- Private washer/dryer located outside.

- This unit is pet friendly. Our requirements are as follows:

•40lb maximum per pet

•$25/per night

•2 pet maximum

Please let us know if you plan on bringing your pet.

- Are you within 90 days of your check in date a & have a smaller group? Rent just Poolside Retreat or Poolside Suite!
The vacation home is air-conditioned and features a kitchen, 2 bathrooms, and a furnished balcony or patio, and there's space to spread out with 3 bedrooms. Other standard amenities include a private pool, a washing machine, and a sofa bed.

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Property amenities

Pool/Spa

  • Communal pool
  • Private pool

Internet

  • Available in the house: WiFi

Parking and transportation

  • Parking on site

Kitchen

  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Microwave
  • Refrigerator
  • Stovetop
  • Toaster

Bedrooms

  • 3 bedrooms
  • Bedsheets provided
  • Sofa bed

Bathroom

  • 2 bathrooms
  • Hair dryer
  • Shampoo
  • Shower
  • Towels provided

Living spaces

  • Living room

Entertainment

  • TV with cable/satellite channels

Outdoor areas

  • Furnished patio
  • Garden
  • Gas grill
  • Yard

Laundry

  • Laundry facilities
  • Washing machine

Work spaces

  • Office

Comfort

  • Air conditioning
  • Heating

Pets

  • Pet friendly

Suitability/Accessibility

  • Smoking not allowed

Services and conveniences

  • Iron/ironing board

Location highlights

  • In the city center
  • Near the sea

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)
  • Fire extinguisher

General

  • Garden
  • Unit size: 1,075 square feet

Policies

Check-in

Check-in time starts at 4:00 PM
Contactless check-in available
Minimum check-in age: 18

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

Rules

-Damages to the property or additional cleaning due to excessive mess are subject to charges. -Pets are welcome! Requirements include: Less than 40...

Pets

  • This property welcomes pets
  • Service animals exempt from fees
  • Note from host: Charge may apply

Children and extra beds

Children allowed: ages 0-17

Events

No events allowed

Smoking

Smoking is not permitted

Important information

You need to know

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
Onsite 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 there is a smoke detector on the property
Safety features at this property include a fire extinguisher
This property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children; if you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room
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
  • Check-in: 4:00 PM
  • Check-out: 10:00 AM
  • Minimum check-in age: 18

We should mention

Details about charges, deposits, or other important information:

  • This property is managed by a professional host. The provision of housing is linked to their trade, business, or profession.
  • This property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children. If you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room.
  • Charges for extra guests may apply and vary depending on the property's policy.
  • A cash deposit, credit card, or debit card for incidental charges, as well as a government-issued photo ID, may be required at check-in.
  • Special requests are subject to availability at the time of check-in and can't be guaranteed. Certain requests may come with additional charges.
  • Onsite parties or group events are strictly prohibited.
  • Onsite safety features include a fire extinguisher and a smoke detector.

Property is also known as

618ac09879046e0034cc47a8

Frequently asked questions

What's there to see around this vacation home?

This vacation home is situated in Old Town Key West, just steps from Duval Street and Ernest Hemingway Home and Museum, and within a short walk of Florida Keys Beaches. You'll also find South Beach and Southernmost Point less than a mile away.

How much does it cost to stay at Poolside Paradise - Heated Pool & Steps to Duval St?

As of Aug 1, 2026, prices found for a 1-night stay for 2 adults at Poolside Paradise - Heated Pool & Steps to Duval St on Aug 31, 2026 start from $948, 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 there parking available at Poolside Paradise - Heated Pool & Steps to Duval St?

No, there isn't parking at this vacation home.

Is this vacation home associated with a casino?

No, this vacation home is not connected to a casino.

Is there an indoor pool at this vacation home?

No, there is no indoor pool at this vacation home; however, the accommodation features a private pool.

What do couples enjoy most about Poolside Paradise - Heated Pool & Steps to Duval St?

Amenities that appeal to couples at this historic vacation home include a private pool and a kitchen along with a garden.

Does Poolside Paradise - Heated Pool & Steps to Duval St have a hot tub?

No, this vacation home doesn't have a spa tub.

Does this vacation home offer breakfast?

No, this vacation home doesn't offer breakfast.

Does this vacation home allow pets to stay free of charge?

Although pets can't stay for free, they are welcome at this vacation home.

Does Poolside Paradise - Heated Pool & Steps to Duval St have connecting rooms available?

No, this vacation home doesn't feature connecting guestrooms.

Where is the closest airport to this vacation home?

The closest major airport to this vacation home is Key West Intl. Airport (EYW), which is 3.8 mi away (14 minutes by car).

Are there rooms with balconies at Poolside Paradise - Heated Pool & Steps to Duval St?

Yes, every house at Poolside Paradise - Heated Pool & Steps to Duval St comes with a furnished patio.

Poolside Paradise - Heated Pool & Steps to Duval St Reviews

Reviews

8.8

Excellent

Rating 10 - Excellent. 14 out of 24 reviews
Rating 8 - Good. 6 out of 24 reviews
Rating 6 - Okay. 3 out of 24 reviews
Rating 4 - Poor. 1 out of 24 reviews
Rating 2 - Terrible. 0 out of 24 reviews

9.0/10

Cleanliness

Reviews

Verified review

10/10 Excellent

Peter S.

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

Great Spot

Great location
Stayed 3 nights in Apr 2025
Verified review

8/10 Good

michael w.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Very convenient location. Property management was extremely helpful and responsive.
Stayed 9 nights in May 2025
Verified review

10/10 Excellent

Jenny M.

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

Awesome location with parking!

8 of us stayed for 1 night and we loved the location! The on-site parking was super convenient. Pool was clean, rooms were clean, overall a really great place to stay. We’d recommend this VRBO!
Stayed 1 night in Oct 2023
Verified review

10/10 Excellent

William D.

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

Perfect

Very great property excellent location will stay again.
Stayed 3 nights in Feb 2024
Verified review

10/10 Excellent

Sydney R.

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

Great location

Right off of duval street, but pretty quiet considering.
Stayed 3 nights in Apr 2022
Verified review

10/10 Excellent

Kerrie B.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Location was spot on. The house was simple to keep clean and was so dang cute. Would like to see some door locks up high on door so I know my kids can’t get out
Stayed 4 nights in Nov 2025
Verified review

10/10 Excellent

paul g.

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

Nice

Nice place
Stayed 3 nights in Apr 2024
Verified review

10/10 Excellent

Judd S.

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

Nice, clean, great location,

Above plus lots of towels
Stayed 2 nights in Jul 2023
Verified review

6/10 Okay

Chris a.

Liked: Cleanliness, check-in, location
Amenities were average. Details such as the advertised pool heater... which did not work... and empty bbq gas tanks were not appreciated. Broken lounge chair around left out for use.Wouldn't recommend.
Stayed 3 nights in Jan 2026
Verified review

10/10 Excellent

Frances D.

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

Low Key Bachelorette

This was a great place for our whole crew to stay with kitchens and spaces outdoor and indoor to gather. There were 6 of us, so sharing two bathrooms wasn’t a problem. We could have slept up to 8 but more than that would have been a squeeze!
Stayed 3 nights in May 2025
Verified review

10/10 Excellent

Jonathan H.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Thank you for the accommodations. This is a duplex so keep that in mind when booking. Our initial check-in had a slight hiccup due to an access code issue to unlock both doors (duplex), but a phone call with Brightwind and all was well. My friends and family enjoyed our stay. Nice location within walking distance of Duval and all its attractions. Parking is tight so be mindful of the size of vehicles you have.
Stayed 1 night in Aug 2025
Verified review

6/10 Okay

Tina C.

Liked: Cleanliness, location
Disliked: Check-in, communication, listing accuracy
The listing included baby/toddler items like crib, high chair, toys, and dishes. We checked in very late at night after a long day of travel to find that NONE of the listed items were in the unit. We had a sleepy toddler with no appropriate sleeping accommodations. Numerous calls and texts and more than a day later the resolution was that I rent the things I needed myself and they would reimburse me. Additionally, the pool heater never worked properly and the pool seemed to be leaking water. The walls and windows were very thin. You could hear every noise and voice inside and out. The only real positive about the property was the location.
Stayed 5 nights in Apr 2026
Verified review

8/10 Good

David T.

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

Key West After Christmas Getaway

We picked this property because of its prime location and heated pool. Walkable to everything. Hemingway house two blocks away. Duval street one block away. Golf cart, scooter, bicycle rental two blocks away. The air conditioning in both homes worked very well. Plenty of room and beds for 6 of us. We would stay here again!
Stayed 2 nights in Dec 2024
Verified review

10/10 Excellent

Michelle M.

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

Perfect location!

I was fortunate to celebrate my 40th birthday with friends at this rental in Key West, and it was great! The home is very close to great restaurants, shops and museums - Duvall St is very close and fun to explore. The home had everything we needed, including pool towels and linens for our party of 6. The home was clean, and the beds were comfortable! Olivia with the property management team was very kind when I reached out to her with questions during our stay. I would stay at this location again!
Stayed 3 nights in Nov 2022
Verified review

8/10 Good

Billie H.

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

Fun weekend

Good location, nice property. Said it sleeps up to 10. That’s if everyone can double up. It sleeps 5 if you want to sleep alone. Otherwise it’s a nice place!
Stayed 3 nights in Dec 2024
Verified review

8/10 Good

Jennifer D.

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

Great place, great location!

Great location close to lots of stuff. We were able to walk to most places we wanted to go, which was really nice. The property was very nice, and we really enjoyed the pool. We just had a minor issue with cleanliness. The floors were so dirty that all of our feet were instantly black from walking the house barefoot the whole trip, which was a little frustrating. Otherwise, a really wonderful stay in a great house!
Stayed 3 nights in Sep 2023
Verified review

10/10 Excellent

George G.

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

A fabulous time right next to Duval!

We had a fabulous time at the house! The location couldn't be better right next to Duval street and just a couple blocks from the major attractions like the Hemingway House, the Lighthouse, and the little White House. The pool is small but very clean and the water temperature was perfect. The interiors were very nice and they made the check in and check out process very easy. Only a couple minor grumbles, the exterior needs a little work as the deck had some plywood patches on it and the canopy tarp is starting to fall apart. I didn't know the house has two completely separate suites and there's no interior passage between the suites. Again, that is minor as it's all about living outside in Key West. I definitely recommend this place and stay again!
Stayed 2 nights in Mar 2024
Verified review

6/10 Okay

steve d.

Liked: Cleanliness, check-in, location, listing accuracy
Disliked: Communication

Access to property

The code to get in the units kept changing, one unit we were locked out of for a whole day, the property manager would not repsond
Stayed 1 night in Mar 2023
Verified review

8/10 Good

curtis h.

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

Excellent location with angry neighbors

The property was great for what we needed. However, there were a few cosmetic issues around the pool area with the deck having a piece of plywood put down to cover I’m assuming a hole. The first full day we were at the property we were harassed by a pretty rude code enforcement guy who threatened to give us a noise violation at 12pm on a Friday over spring break for very minimum noise. The property management team did a good job on handling this as they came out and saw that we were not being crazy and luckily we never heard from the angry little code person again. The location is great to walk anywhere worth walking to in key west.
Stayed 3 nights in Mar 2024
Verified review

8/10 Good

TINA C.

Liked: Check-in, communication, location

Loved the little pool!

Great location 1/2 block from Duval. Lots of great towels, and pillows! I didn’t know this is two units connected but no connecting door, you access back unit via the pool. We needed both sofa beds but one had broken springs and was unusable. The floors hadn’t been mopped and all of my kids had black feet from walking around barefoot. If you are planning to cook you might want to bring a decent frying pan and a sharp knife. They have plenty of knives but none sharp. The grill didn’t work and there was no grill tools even if it did. The fire alarm went off at 5:00 am and it wouldn’t stop. If you go it’s a cute place with lots of tVs and a great location, the owner should just stay there a weekend to check it out. Oh, bring your own salt and pepper!
Stayed 3 nights in May 2024
Verified review

4/10 Poor

Parthasarathi P.

Disliked: Cleanliness, check-in, communication, listing accuracy
Stayed 1 night in Mar 2026
Verified review

10/10 Excellent

Tim C.

Stayed 2 nights in Feb 2026
Verified review

10/10 Excellent

Brittany Y.

Stayed 4 nights in Oct 2025

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