Entire home

Oversized home for the whole family w/private pool & dock

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A heated pool
Smart TV, DVD player
5 bedrooms, iron/ironing board, free WiFi, bed sheets
Exterior
Interior

Reviews

9.8 out of 10
Exceptional

Entire home

5 bedrooms4 bathroomsSleeps 12335 sq m

Popular amenities

  • Kitchen
  • Washing machine
  • Dryer
  • Pet-friendly
  • Free Wi-Fi

Explore the area

View in a map
Key West, FL
  • Place, Key West Naval Station
    ‪1 min walk‬
  • Place, Duval Street
    ‪18 min walk‬
  • Place, Ernest Hemingway Home and Museum
    ‪7 min drive‬
  • Airport, Key West, FL (EYW-Key West Intl.)
    ‪10 min drive‬

Room options

Similar properties

About this property

Entire place

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

Oversized home for the whole family w/private pool & dock

"Captain's Daughter” is a spacious home with the ability to sleep a large group comfortably, a private pool and tropically furnished yard, a prime Old Town location, and a private 43’ boat slip.

Through the sliding glass doors of the living area is the private back yard complete with a large deck and a private pool. There are chaise lounges by the heat-optional pool when it’s time for a swim and some sun. A full outdoor dining set by the pool can comfortably sit 6. Cross the parking lot of this private complex to the docks where you will find your own boat slip.

The perks of this little-known location are many: walking distance to the family friendly Bayview Park and Fausto's a local grocery store. All while still being tucked away in your own quiet neighborhood. This home includes plenty of off-street parking.

The master bedroom is on the second level and has a King-sized bed, a large flat-screen TV, plenty of dresser space, and a private balcony overlooking the water. The master bathroom is en-suite with dual sinks, a large soaking tub, a glass and marble shower. The second bedroom is also on the second living level, and has a Queen sized bed, a flat-screen TV, and a private balcony. The second bathroom is also en-suite and has a tub/shower. The third level can sleep a total of 6: there is a private bedroom with two twin beds that can convert to a King upon request, and an open room with another 4 twin beds, which can convert to 2 King sized beds upon request. The third level accommodations share one full bathroom with a tub/shower. The fifth bedroom is on the main floor and has a King size bed and is also en-suite with access to the bathroom through the hallway as well. Additional sleeping area is available in the living room, as the sofa pulls out into a Queen bed. There is also a full bath off the living room next to the bedroom on the main floor.

Amenities: Washer & Dryer, Central Heat and A/C, Ceiling Fans, Off-Street Parking, Flat Screen State-of-the Art HD TVs in all bedrooms and main living area, Fully Equipped Chef’s Kitchen with Gourmet Appliances, Private Heated Pool, Private Boat Slip, Large BBQ Grill, Linens and Towels provided. Interim housekeeping provided upon request. Wireless high-speed Internet access and full cable is included. This property will accommodate 10-12 adults.

2023: New custom dining table, new couches and chairs, new carpeting as well as new LVT on stair treads and landings!

RATES: we have 3 night (not always available) and 4 night rates available. We also have a 7 night and 21+ night discounted rate (automatically provided with dates).

DOG FRIENDLY. Please contact us to confirm specific pet policies.
This vacation home's great location gets high marks from our customers. During your stay, you're just a quick walk from Bayview Park. Features include concierge services and laundry facilities. The vacation home offers free WiFi and a private pool.
  • Air-conditioned home with private pool, kitchen, and washer/dryer
  • Free WiFi (speed: 250+ Mbps (good for 3–5 people or up to 10 devices))
  • Services include a concierge and babysitting
  • Onsite recreation includes tennis courts
  • Guests have great things to say about the helpful staff and the location
  • Just a 3-minute drive from Florida Keys Beaches and a few minutes from Duval Street
As a guest of this vacation home, you'll find barbecue grills, concierge services, and laundry facilities. The front desk is open around the clock.

Property amenities

Pool/Spa

  • Heated pool
  • Massage
  • Private pool

Internet

  • Available in the house: Free WiFi

Parking and transport

  • Parking on site

Kitchen

  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Hob
  • Ice maker
  • Microwave
  • Oven
  • Refrigerator
  • Toaster

Dining

  • Chef service
  • Dining table

Bedrooms

  • 5 bedrooms
  • Bedsheets provided

Bathroom

  • 4 private bathrooms
  • Bathtub
  • Bathtub or shower
  • Bidet
  • Hair dryer
  • Shower
  • Towels provided

Living spaces

  • Dining table
  • Living room

Entertainment

  • DVD player
  • Smart TV with cable/satellite channels

Outdoor areas

  • Balcony
  • Barbecue grill
  • Yard

Laundry

  • Laundry facilities
  • Washer/dryer

Comfort

  • Air conditioning

Pets

  • Pet friendly

Suitability/Accessibility

  • Smoke-free property

Services and conveniences

  • Concierge services
  • Housekeeping on request
  • Iron/ironing board
  • Meal delivery service
  • Phone

Location highlights

  • Near a hospital
  • Near the marina
  • Near the ocean

Things to do

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

Safety features

  • Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property)
  • Smoke detector (host has indicated there is a smoke detector on the property)
  • First aid kit
  • Fire extinguisher
  • Deadbolt lock

General

  • Housekeeping (on request)
  • Unit size: 3,605 square feet

Policies

Check-in

Check-in time starts at 4:00 PM
Contactless check-in available
Minimum check-in age: 31

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 are welcome
  • Service animals are exempt from fees

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
Onsite parties or group events are strictly prohibited
Host has indicated there is a carbon monoxide detector on the property
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 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
You will receive an email from the host with check-in and check-out instructions. You will also receive an email from Vrbo with a link to a Vrbo account which will enable you to manage your booking.
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

Oversized Oldtown Home Whole Family Dock House Key West
Oversized Oldtown Home Whole Family Dock House
Oversized Oldtown Home Whole Family Dock Key West
Oversized Oldtown Home Whole Family Dock
Oversized Oldtown Home Whole Family Dock House Key West
Oversized Oldtown Home Whole Family Dock House
Oversized Oldtown Home Whole Family Dock Key West
Oversized Oldtown Home Whole Family Dock House Key West
Oversized Oldtown Home Whole Family Dock House
Oversized Oldtown Home Whole Family Dock Key West
Oversized Oldtown Home Whole Family Dock
2328-139622

Oversized home for the whole family w/private pool & dock Reviews

Reviews

9.8

Exceptional

Rating 10 - Excellent. 130 out of 144 reviews
Rating 8 - Good. 12 out of 144 reviews
Rating 6 - Okay. 2 out of 144 reviews
Rating 4 - Poor. 0 out of 144 reviews
Rating 2 - Terrible. 0 out of 144 reviews

10/10

Cleanliness

Reviews

Verified

10/10 Excellent

Nichole G.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Amazing location and perfect space for large families. Very comfortable beds and quality towels, which is not very common.
Stayed 3 nights in Feb 2026
From a partner site

10/10 Excellent

MJ P.

Beautiful Home

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 Home with lots of room for the whole family! We loved the big dining room table, spacious rooms and pool area to relax in.
Verified

10/10 Excellent

Linda H.

Liked: Cleanliness, check-in, communication, location, listing accuracy
This was a great place to stay with family! We enjoyed the space and the amenities. Office staff were very helpful with all our questions.
Stayed 5 nights in Dec 2025
Verified

10/10 Excellent

Amog R.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great house with ample space and beds. The pool was a nice touch and both the kitchen and table were large enough for dinners with 12 adults and children. The host also accommodated us checking into the property earlier than normal, which was a welcome perk after our redeye flights.
Stayed 3 nights in Dec 2025
Verified

10/10 Excellent

Kelly M.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great place for large group! Clean, well maintained. Great location.
Stayed 6 nights in Aug 2025
Verified

10/10 Excellent

Jean K.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful and spacious home. It was perfect for our vacation. Wish the pool had a vacuum available.
Stayed 7 nights in Oct 2025
Verified

10/10 Excellent

LeAnn A.

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

Great Place!

Beautiful home with everything needed for a fun family vacation
Stayed 3 nights in Mar 2025
Verified

10/10 Excellent

Andrew B.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Large and clean home in a good location
Stayed 3 nights in Jul 2025
Verified

10/10 Excellent

Alicia H.

Liked: Cleanliness, check-in, communication, location, listing accuracy
The house was perfect for 11 of us…4 wonderful bedrooms…and an open room that slept the 3 extras. Four bathrooms was awesome…one suggestion is to add a full length mirror/big mirror in the open top room!
Stayed 4 nights in Oct 2025
From a partner site

10/10 Excellent

Robin S.

Great Key West Vacation Home!

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 exceptional. The staff were very friendly and accommodating. The house was exactly like the pictures, even better in person. The location was ok I would have liked to be a tad closer to Duval St but a mile away was not the worst. The house was very clean and so was the pool and the grounds. Highly recommend!
Verified

8/10 Good

Cheryl B.

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

Our Easrer weekend

The house was a perfect size for our family and the pool was a big hit with the kids.
Stayed 3 nights in Apr 2025
Verified

10/10 Excellent

Michael G.

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

Fantastic Place

Nice spacious property. Comfortable and clean. Plenty of space a great location if you prefer a little more quiet for evenings. Would definitely stay again.
Stayed 3 nights in Mar 2025
Verified

8/10 Good

Verified traveller

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

MC

It met all our needs. Loved the location!! Particularly loved the great room off the kitchen…great family times were had by all!
Stayed 5 nights in May 2025
Verified

10/10 Excellent

Carolyn L.

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

A Great Stay with Friends

The Captain's Daughter was the perfect venue for an extended weekend getaway with friends. The house was spacious, clean, and exactly what we needed! Would definitely stay there again for future trips.
Stayed 3 nights in May 2024
Verified

8/10 Good

Mike P.

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

Great for large group

Had a good time
Stayed 5 nights in Jun 2024
Verified

10/10 Excellent

Cori B.

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

Exactly what we were looking for!

Our stay was absolutely incredible. The condo was bigger than we were expecting so we had plenty of room to spread out and relax. The property management website was super helpful and the customer service was amazing as well! Nothing but good reviews from everyone who stayed there!
Stayed 3 nights in Jan 2025
From a partner site

10/10 Excellent

Debra G.

Awesome Stay Love this Place

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 love this unit so much--lots of room, comfortable, clean, and so relaxing. And we love to have our boat right near us in our boat slip, for fishing and sunset cruises. Was a great trip
Verified

10/10 Excellent

Jason R.

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

Great place to stay

The house was amazing. We will definitely booo this house again next year.
Stayed 3 nights in Jul 2023
Verified

10/10 Excellent

patsy w.

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

Beautiful home!

Location is excellent. Home is very spacious, and the pool area is a little oasis. Hope to be back next year!
Stayed 7 nights in Aug 2024
Verified

10/10 Excellent

Sally B.

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

Perfect location for a family gathering

Had so much fun in this idyllic location . House was spacious and well equipped .
Stayed 7 nights in Apr 2023
Verified

10/10 Excellent

Steve R.

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

Wonderful house in a great location.

All good. Easy in easy out. Great location, loved Macs bar and grill up the street. Beautiful home
Stayed 5 nights in Apr 2025
Verified

10/10 Excellent

James S.

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

Perfection!

Very large, modern, and quiet home, perfect for a large family vacation! It made our 7 days on Key West the best!
Stayed 7 nights in Nov 2024
From a partner site

10/10 Excellent

maggie C.

Amazing girls 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: The house was wonderful and very updated! All the amenities you could ask for. Very close to main stops in key west! Would definitely recommend for a girls trip!
Verified

10/10 Excellent

Jennifer C.

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

Third time

We've stayed at this property 3 times and we love it. Prefect size. Great communication
Stayed 4 nights in Mar 2025
Verified

10/10 Excellent

Peter S.

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

First time, we’ll be back

We were in town for a wedding with a group of friends and have a perfect stay at the house! Can’t wait to come back again. Good location, spacious main room and comfy beds
Stayed 3 nights in Feb 2024