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Waterfront Beach Houses with Dock & Heated Pool

Summerland Key vacation home with private pool

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A large house with a swimming pool surrounded by lush greenery and a dock.
A pool area with a fenced deck, lounge chairs, and a small inflatable pool.
A spacious living area with a dining table, chairs, and a ceiling fan.
A modern living room with a glass dining table, a blue sofa, and a ceiling fan.
A modern kitchen with white cabinets, granite countertops, a built-in oven, and a large window offering a view.

Reviews

10 out of 10
Exceptional

Entire home

8 bedrooms5 bathroomsSleeps 203400 sq ft

Popular amenities

  • Ocean view
  • Pool
  • Kitchen
  • Washer
  • Dryer
  • Pet friendly

Explore the area

View in a map
Little Torch Key, FL
  • Place, Big Pine Key Flea Market
    ‪3 min drive‬
  • Place, National Key Deer Refuge Visitor Center
    ‪4 min drive‬
  • Place, Coupon Bight Aquatic Preserve
    ‪4 min drive‬
  • Airport, Key West, FL (EYW-Key West Intl.)
    ‪47 min drive‬

Room options

About the neighborhood

Summerland Key

Seaside stay .You'll find Boondocks Grille & Draft House and Big Pine Key Flea Market within 3 miles (5 km) of this vacation home. Also, National Key Deer Refuge Visitor Center is within 3 miles (5 km) and Key West Visitors Center is within 6 miles (10 km).
View more Vacation Homes in Summerland KeyOpens in a new window

What's nearby

  • Boondocks Grille & Draft House - 3 min drive - 2.3 miles
  • Big Pine Key Flea Market - 3 min drive - 2.5 miles
  • National Key Deer Refuge Visitor Center - 4 min drive - 2.9 miles
  • Coupon Bight Aquatic Preserve - 4 min drive - 2.7 miles
  • Key West Visitors Center - 5 min drive - 3.9 miles

Getting around

  • Marathon, FL (MTH-Florida Keys Marathon) - 33 min drive

Restaurants

  • ‪No Name Pub - ‬9 min drive
  • ‪Boondock's Grille & Drafthouse - ‬3 min drive
  • ‪Morning Joint - ‬9 min drive
  • ‪Kiki's Sandbar - ‬2 min walk
  • ‪Looe Key Tiki Bar & Restaurant - ‬3 min drive

About this property

Entire place

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

Waterfront Beach Houses with Dock & Heated Pool

Welcome to Paradise!

Stay in the amazing Keys and beautiful waterfront homes with 200 foot dock for your boat. Two exclusive heated pools to relax and enjoy the surrounding ocean view - just breath taking! The private lot is almost an acre with two homes and still very spacious. Stunning panoramic water views, sunrise, sunset, steps from ocean water. Bring or rent fishing and snorkel gear nearby to fish off the dock and enjoy the underwater scenery!

Similar properties

A bar area with a long counter, bar stools, and a view of the water.
Fairfield Inn & Suites by Marriott Marathon Florida Keys
Marathon
  • Pool
  • Breakfast included
  • Pet friendly
  • Free WiFi
4.6 out of 5, Wonderful, 1,220 reviews
$134 nightly
The price is $151
Oct 4 - Oct 5
Total with taxes and fees
Fairfield Inn & Suites by Marriott Marathon Florida Keys

Property amenities

Beach

  • Beach loungers
  • Beach towels

Pool/Spa

  • Heated pool
  • Private pool

Internet

  • Available in the house: Free WiFi

Parking and transportation

  • Car recommended
  • Parking on site

Kitchen

  • Blender
  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Electric kettle
  • Ice maker
  • Kitchen island
  • Microwave
  • Oven
  • Paper towels
  • Refrigerator
  • Stovetop
  • Toaster

Dining

  • Dining table

Bedrooms

  • 8 bedrooms
  • Bedsheets provided

Bathroom

  • 5 bathrooms
  • Bathtub
  • Bathtub or shower
  • Hair dryer
  • Shampoo
  • Shower
  • Soap
  • Toilet paper
  • Towels provided

Living spaces

  • Dining table

Entertainment

  • Books
  • DVD player
  • Games
  • Stereo
  • TV with cable/satellite channels

Outdoor areas

  • Outdoor furniture
  • Patio

Laundry

  • Laundry facilities
  • Washing machine

Comfort

  • Air conditioning
  • Heating

Pets

  • Pet friendly
  • 2 pets total (up to 999 lbs per pet)

Suitability/Accessibility

  • Smoking not allowed
  • Note from host: Please use the outdoor sand pots for disposal.

Services and conveniences

  • Iron/ironing board

Location highlights

  • Near a health/beauty spa
  • Near a hospital
  • Near an outlet shopping mall
  • Near the marina
  • Near the ocean
  • On the waterfront

Things to do

  • Heated pool
  • Basketball nearby
  • Birdwatching nearby
  • Cycling nearby
  • Ecotours nearby
  • Fishing nearby
  • Golfing nearby
  • Hiking/biking trails nearby
  • Jet skiing nearby
  • Kayaking nearby
  • Parasailing nearby
  • Rafting nearby
  • Scuba diving nearby
  • Snorkeling nearby
  • Surfing/bodyboarding nearby
  • Swimming nearby
  • Water skiing nearby
  • Water tubing nearby
  • Wildlife walks nearby
  • Windsurfing nearby

Safety features

  • No carbon monoxide detector (host has indicated there is no carbon monoxide detector on the property; consider bringing a portable detector)
  • Smoke detector (host has indicated there is a smoke detector on the property)
  • Deadbolt lock
  • Fire extinguisher
  • First aid kit

General

  • Unit size: 3,400 square feet

Policies

Check-in

Check-in time starts at 3:00 PM
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

Check-out instructions

The host requires you complete the following before checking out:
Start the dishwasher
Strip any used beds and gather used towels
Remove personal items, remove leftover food and drinks, and take out the trash
Turn off the lights, lock the doors, and return the keys
Failure to complete these may result in a negative review from the host.

Rules

Maximum occupancy is 20 and strictly enforced by law. Your stay will be terminated if the guest count exceeds the occupancy limit.
Confirm your home address, vehicle plate #, watercraft registration # (county required) and e-sign before arrival via pre check-in email/text.
Quiet hours 9 pm - 9 am (events, gatherings, etc. not allowed). No smoking inside, please use the outdoor sand pots near entrance doors for disposal.

Pets

  • Pets are welcome
  • Maximum 2 (weight limit: 999 lbs per pet)
  • Service animals are exempt from fees

Children and extra beds

  • Children are welcome.

Events

No events allowed
Quiet time is 9 pm - 9 am.

Smoking

Smoking is not permitted
Please use the outdoor sand pots for disposal.

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
Note from host: Quiet time is 9 pm - 9 am.
Long-term renters welcome
Host has indicated there is no 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, a first aid kit, and a deadbolt lock
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
Charges for extra guests may apply and vary according to property policy.
A cash deposit, credit card, or debit card for incidental charges and government-issued photo identification may be required upon check-in.
Special requests are subject to availability at the time of check-in. Special requests can't be guaranteed and may incur additional charges.
    This property is managed by a private host, not a professional engaged in trade or business. 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. Onsite parties or group events are strictly prohibited. Note from host: Quiet time is 9 pm - 9 am. Long-term renters welcome. For guests' safety, the property includes a fire extinguisher, a smoke detector, a first aid kit, and a deadbolt lock in each accommodation.

Property is also known as

Barry Beach Waterfront Cozy House Dock
Barry Beach Waterfront Cozy Dock
Barry Waterfront Cozy Dock
Barry Beach Waterfront Beach House Dock Little Torch Key
Barry Beach Waterfront Beach House Dock
Barry Beach Waterfront Beach Dock Little Torch Key
Barry Beach Waterfront Beach House Dock Little Torch Key
Barry Beach Waterfront Beach House Dock
Barry Beach Waterfront Beach Dock Little Torch Key
Barry Beach Waterfront Beach Dock
Barry Beach Waterfront Cozy House With Dock Heated Pool!
Barry Waterfront House Dock
Barry Beach Waterfront Beach House With Dock Heated Pool!
Barry Beach Waterfront Cozy House With Dock Heated Pool!
Barry Waterfront House Dock
305049

Frequently asked questions

How close is Waterfront Beach Houses with Dock & Heated Pool to the airport?

This vacation home is 23.3 mi (33-min drive) away from the Marathon, FL (MTH-Florida Keys Marathon) airport, the closest popular airport to the property.

Does Waterfront Beach Houses with Dock & Heated Pool have an airport shuttle?

Airport shuttle services are not available at this vacation home.

How close is Waterfront Beach Houses with Dock & Heated Pool to the beach?

This vacation home is 7.1 mi (15-min drive) from Florida Keys Beaches and 9 mi (15-min drive) from Loggerhead Beach. Don't forget your sunscreen!

Does Waterfront Beach Houses with Dock & Heated Pool offer free breakfast?

This vacation home does not offer free breakfast.

Is there a casino at Waterfront Beach Houses with Dock & Heated Pool?

No, there is no casino at this vacation home.

What time is check-in at Waterfront Beach Houses with Dock & Heated Pool?

Check-in begins at 3:00 PM.

Is there free parking at Waterfront Beach Houses with Dock & Heated Pool?

Free parking is not available at this vacation home.

Does Waterfront Beach Houses with Dock & Heated Pool have a pool?

Yes, there's a private pool.

Does Waterfront Beach Houses with Dock & Heated Pool have a spa?

There are no spa services available at this vacation home.

How close is Waterfront Beach Houses with Dock & Heated Pool to downtown Summerland Key?

This vacation home is 3.7 mi away from Summerland Key.

Barry Beach & Guesthouse Reviews

Reviews

10

Exceptional

Rating 10 - Excellent. 77 out of 82 reviews
Rating 8 - Good. 4 out of 82 reviews
Rating 6 - Okay. 1 out of 82 reviews
Rating 4 - Poor. 0 out of 82 reviews
Rating 2 - Terrible. 0 out of 82 reviews

9.6/10

Cleanliness

10/10

Amenities

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Ideal setup for large groups who want to relax and socialize. Very clean, well equipped property with a beautiful view and an accommodating but not intrusive host.
Stayed 3 nights in May 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Lots of space, clean rooms (bedrooms, bathrooms), it was nice to have laundry detergent, clean pools, loved the dock!
Stayed 10 nights in Feb 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Excellent stay again. Will be back
Stayed 5 nights in Sep 2025
Verified review

10/10 Excellent

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

Beautiful House

Family had a great stay. We will come again.
Stayed 7 nights in Aug 2024
Verified review

10/10 Excellent

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

Fantastic place

Fantastic place a truly Florida Keys experience. Beautiful view and location. The only thing that could be improved is the boat dock could be accessible to get in and out of a boat.
Stayed 7 nights in May 2025
Verified review

10/10 Excellent

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

Company Trip

Everything was fantastic, just as we saw on the website. We appreciate the hospitality and will book our annual trip for next year very soon, so we don't miss out on the dates!
Stayed 2 nights in Sep 2024
Verified review

10/10 Excellent

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

Senior spring break

we could not have enjoyed our time more at this house! It was well stocked, wonderfully located, and well maintained.Communication with the owners was fabulous!
Stayed 7 nights in Mar 2025
Verified review

10/10 Excellent

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

FAVORITE KEYS RENTAL PROPERTY

ALWAYS A GREAT STAY HERE. THANKS AGAIN
Stayed 7 nights in Aug 2023
Verified review

10/10 Excellent

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

Little Torch Prize

The house and property are very nice, is advertised, it is the perfect setting for families who want privacy but yet only a couple miles away from restaurants, shopping, etc. The dock is great and having Kikis next door was a plus.
Stayed 9 nights in Mar 2025
Verified review

10/10 Excellent

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

Fun times

Every thing was great had a good time!
Stayed 3 nights in Oct 2023
Verified review

10/10 Excellent

Beautiful home and view

Great house with open living area and wall of windows for an excellent view! Great dock for boats and some fishing. Rooms had very comfortable beds and were clean and modern. Pool was perfect with afternoon shade and plenty of seating. There is a great waterfront Nextdoor as well (Kiki’s). Had cool iguana visitors in the back and plenty of parking. Would definitely stay again!
Stayed 7 nights in Jul 2018
Verified review

10/10 Excellent

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

The place was great

The location and the size of the property was amazing. It could’ve used a better cleaning. There were hairs in the bathroom sinks and some garbage was left under the kitchen sink.
Stayed 5 nights in Sep 2024
Verified review

10/10 Excellent

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

Family vacation

Great property and location for Lower Keys activities. Access to both homes is nice with a large group. View, dock, parking, outside bait freezer and pools are great! The only suggestion would be to add an ice maker to keep up with larger crowds. Property manager and owners are very responsive. Definitely recommend this property!
Stayed 7 nights in May 2023
Verified review

10/10 Excellent

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

Great location plenty of room beautiful property

Owners and maintenace staff were all friendly and helpful. Noticeable small upkeep projects such as light bulbs, chalking around tubs, clean up under house and in wooded area around house due to ocean debris in the main house could be better maintained. Otherwise, house’s are 100 percent as discribed
Stayed 9 nights in Jan 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
We had an amazing vacation at Barry Beach House and Guest House. What a great vibe! Loved the location, close to Key West, on the water with stunning sunrises and great fishing from the dock. Caught mangrove snapper, pinfish, grunt, shark and missed several other large bites. Barely needed to leave the house. The pools were great. Loved being able to walk over to Kiki's to grab a bite to eat. Great trip with family and friends and the houses had everything we needed. Could use a little more general maintenance and slightly more attention to cleaning/details, but we were still thrilled with the total property and with our stay. All minor things like the blinds in master didn't reach bottom of window for privacy, found a piece of clothing from past guests still in bureau and the drawer underneath the oven was off track and wouldn't fully close. We will be back!
Stayed 7 nights in Apr 2026
Verified review

10/10 Excellent

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

Reclining

Wasnt sure on reclining process
Stayed 4 nights in Dec 2023
Verified review

6/10 Okay

Liked: Check-in, communication, location
Disliked: Listing accuracy

Nice Property but not as Listed

Property is nice but listing is confusing the listing says it sleeps 20 but that is if you rent both homes. Had several issues that had to resolve myself. Make sure you ask plenty of questions. Main property sleeps 6 adults and 4th room has twin beds.
Stayed 7 nights in Dec 2023
Verified review

8/10 Good

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

Perfect for a multiple family vacation with kids :)

Thank you so much for welcoming us for our friends and family vacation. The houses and location were exactly what we were looking for. The property manager Walt was amazing - responsive and helpful. The cleanliness, especially in the guest house, could use some work. The alarm on the sliding doors and the very secure fence around the pool gave us parents such a peace of mind with all of our kids running around. The kitchen could use some plastic dishes for kids and eating lunch by the pool. We will definitely be back next year! The staff at Kiki’s was so welcoming and the kids had a blast dancing to the band. Thank you.
Stayed 2 nights in Oct 2023
Verified review

8/10 Good

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

Great space and view

The space for the amount of people was great. Views and amenities were nice. Place could have been cleaner, needs a deep clean but not terrible. The ants on the pool deck were really bad so unless you were in pool or on chair you couldn’t sit on side of pool with feet in. The restaurant/bar next door is literally next door and the music is on until 9 pm so if you want quiet or sleep before that it’s not going to happen. Property manager showed up on day 2 without notice which was strange but he was very nice and left quickly. Plenty of towels and seating, all in all good for a large groups.
Stayed 6 nights in Oct 2023
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great place, and wonderful place stay
Stayed 7 nights in Apr 2026
Verified review

10/10 Excellent

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

Perfect vacation!!!

Instalaciones perfectas, todo limpo y bello. Atención constante a todas nuestras necesidades y la zona muy buena tambien. Sin dudas volveriamos a repetir. Gracias
Stayed 2 nights in May 2024
Verified review

8/10 Good

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

Celebration

My family gathered to celebrate 25 years of me surviving stage 3 breast cancer. I also celebrated one of my grandsons 21st birthday. We had a wonderful time and was sad to see the week end.
Stayed 7 nights in Oct 2022
Verified review

10/10 Excellent

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

Fantastic stay

Everything about the accommodation is perfect. The house was beautiful and incredibly well equipped , absolutely everything you need. The rooms are individual and a good size with all the comforts you could need. The outside is amazing, one of our best vacations. Thank you
Stayed 3 nights in Oct 2022
Verified review

10/10 Excellent

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

Nice place

Great family vacation, the place was nice and comfortable, awesome host.
Stayed 2 nights in Oct 2022
Verified review

10/10 Excellent

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

Family Vacation

Barry Beach and guesthouse had plenty of room for our family. Did not bring kiddos but had the space to do so. Plenty of room for family. Loved big open layout for kitchen and living room. Comfy couches. We spent our time lounging by pool. Would book again. We wanted to stay longer but weather happened and hosts were accommodating.
Stayed 3 nights in Sep 2022

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