Entire home

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

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A heated pool - Oversized home for the whole family w/private pool & dock (Key West)
Smart TV, DVD player - Oversized home for the whole family w/private pool & dock (Key West)
Interior - Oversized home for the whole family w/private pool & dock (Key West)
Exterior - Oversized home for the whole family w/private pool & dock (Key West)
5 bedrooms, iron/ironing board, free WiFi, bed sheets - Oversized home for the whole family w/private pool & dock (Key West)
Located close to Duval Street and Ernest Hemingway Home and Museum, Oversized home for the whole family w/private pool & dock provides golfing on-site, laundry facilities and babysitting service. Treat yourself to a massage or other spa services. Stay connected with free in-room WiFi.

Reviews

9.8 out of 10
Exceptional

Entire home

5 bedrooms4 bathroomsSleeps 12335 sq m

Popular amenities

  • Ocean view
  • Kitchen
  • Washing machine
  • Dryer
  • Pet-friendly

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.

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.

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

  • Golf
  • 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

Similar properties

Policies

Check-in

Check-in time starts at 4:00 PM
Contactless check-in and check-out are 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 allowed
Service animals are welcome, and 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

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 indicated that there is a carbon monoxide detector on the property
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

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

About the area

Located by the ocean, this holiday home is in Meadows, a neighbourhood in Key West. Ernest Hemingway Home and Museum and Southernmost Point are notable landmarks, and the area's natural beauty can be seen at Fort Zachary Taylor Historic State Park and Florida Keys Beaches. The Kite House and Sails To Rails Museum at Flagler Station are also worth visiting. Jet skiing and scuba diving offer great chances to get out on the surrounding water, or you can seek out an adventure with ecotours and cycling nearby. Visit our Key West travel guide
View more Holiday homes in Key West
Map
Key West, FL

What's nearby

  • #TroveOn
A couple miles north of Key West, on the right is Boca Chica Rd, follow that road as far as you can and you'll get to the beach at Geiger Key.  The road comes to an abrupt stop, the rest of it was destroyed in a hurricane years ago but you can park there and walk out.  The beach is secluded and quiet, except when the Navy is holding flight practices. The planes are so close, you can see the pilots!
    Key West Naval Station
    1 min walk - 0.2 km
  • Duval Street featuring signage
    Duval Street
    18 min walk - 1.6 km
  • Ernest Hemingway Home and Museum featuring heritage elements and a house
    Ernest Hemingway Home and Museum
    6 min drive - 2.4 km
  • Southernmost Point featuring signage
    Southernmost Point
    7 min drive - 2.4 km
  • South Beach featuring a sandy beach and general coastal views as well as a small group of people
    South Beach
    7 min drive - 2.4 km

Getting around

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

Restaurants

  • Circle K
    9 min walk
  • Dions Truman & White
    8 min walk
  • Square Grouper Key West
    17 min walk
  • Sandy's Café
    10 min walk
  • The Dive Bar Shirt Club - Grub House
    16 min walk

Frequently asked questions

Is Oversized home for the whole family w/private pool & dock pet-friendly?

Yes, pets are allowed at this property.

How much is parking at Oversized home for the whole family w/private pool & dock?

On-site parking is available at the property.

What time is check-in at Oversized home for the whole family w/private pool & dock?

Check-in begins at 4:00 PM.

What time is check-out at Oversized home for the whole family w/private pool & dock?

Checkout is at 10:00 AM.

Where is Oversized home for the whole family w/private pool & dock located?

Located in Meadows, this holiday home is within 1 mile (2 km) of Bayview Park, Duval Street and Ernest Hemingway Home and Museum. Florida Keys Beaches and Southernmost Point are also within 2 miles (3 km).

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Oversized home for the whole family w/private pool & dock 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. 126 out of 140 reviews
Rating 8 - Good. 12 out of 140 reviews
Rating 6 - Okay. 2 out of 140 reviews
Rating 4 - Poor. 0 out of 140 reviews
Rating 2 - Terrible. 0 out of 140 reviews

10

Cleanliness

9.8

Location

Reviews

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

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

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

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

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

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

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

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

10/10 Excellent

Melinda H.

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

60th Birthday party weekend

House was amazing! The house was clean and stocked with basic necessities even found a few tide pods for laundry. Perfect for a girls weekend party of 12. We will definitely rent this house again on our next trip to Key West!
Stayed 4 nights in Oct 2024

10/10 Excellent

Jackie J.

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

Great Location

House was clean, comfortable and described accurately. Communication was easy and precise. Party of 11 never felt crowded.
Stayed 7 nights in Jun 2024
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Daniel A.

Summer Family Vacation

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 from cleanliness to communications to customer service to location was excellent
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Marybeth B.

Awesome 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: The Captain's Daughter in Key West was absolutely perfect for my family in every way. My elderly mom loved the Master suite on the first floor, my husband and kids loved the pool and the overall layout and space gave everyone enough room for privacy and a great area for family gathering. Just a short walk to Duval street and all the great shops and restaurants. We would definitely go back!

10/10 Excellent

Yvonne M.

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

Birthday bash

We celebrated my husband’s birthday. The house was very clean and comfortably accommodated our party of 10 adults. We were able to check in early which was perfect. The website description did include a hot tub, however there was not hot tub but a jetted tub. Manager apologized and stated it is a software issue. Overall, very nice house. We enjoyed our stay.
Stayed 3 nights in Dec 2024
This review comes from a trusted partner site and has not been verified.

8/10 Good

Cindy V.

Nice large home fir group.

Rating Details: The property manager was more than helpful. The vacation rental was spotless. I was happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Really nice area just over a Mike from Duvall. House was equipped with everything (except coffee). Pool was heated which was great. Beds were comfortable.
Stayed 3 nights in Nov 2023
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Tracy L.

Great 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: We had a wonderful time in this beautiful home. The home was substantial. Extremely clean. The kitchen was stocked very well with everything we needed. We would recommend to friends and family.
Stayed 7 nights in Dec 2023

10/10 Excellent

Kelly R.

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

Great for Large Group

We were a group a women on a friends trip and had plenty of space. House was very clean. We walked, took the KW Free Shuttle and Ubered to Duval. All are reasonable options. Pool was clean and neighbors were very nice. We used Kelly “ The Concierge Girl” to prestock our fridge before arrival which was very helpful to get our trip started. She was recommended by the management company.
Stayed 4 nights in Apr 2024

10/10 Excellent

jocelyn i.

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

Bday celebration

We had a fantastic time! Location is perfect for getting away from party area, but close enough to walk about a mile or so. The house included everything we needed for our two large families. The pool was nice and warm after we turned up the warmer due to chilly weather. Lots of beds to sleep everyone and plenty of beach towels too! We even stored our luggage at Office until our time to leave, which was a nice amenity! Our party was ages from 15-66 and everyone had a blast! Will be back!
Stayed 5 nights in Dec 2023

10/10 Excellent

Debbie P.

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

Captains Daughter

When the listing said property had a dock I assumed it would have a water view. It didn’t. That being said the pool and backyard were very nice. The house was well appointed and very clean. Lots of towels, extra pillows and blankets available. Water pressure and warm water was adequate. Two off street parking spots at the front door and plenty of off street parking always available. Would rent this property again
Stayed 4 nights in Mar 2024
This review comes from a trusted partner site and has not been verified.

8/10 Good

Kyle T.

Nice house, bad beds

Rating Details: The property manager was very helpful. The vacation rental was very clean. I was very happy with the location. I was somewhat dissatisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Very Large and beautiful home with plenty of space, and clean. The only thing I can complain about is the beds. All of the beds inside this house were very stiff, and cheap feeling. I figured that by paying $4200 for a two night stay, I would atleast have a bed that didn’t feel like plywood
Stayed 2 nights in Sep 2023
This review comes from a trusted partner site and has not been verified.

6/10 Okay

Jimmy L.

Great place! Unfortunate AC issue

Rating Details: The property manager was more than helpful. The vacation rental was spotless. I was very happy with the location. I was satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Great property and we really enjoyed our stay. Host was accommodating and communicative up until the trip. We had an issue with the AC where it broke a few days into our stay and caused us some problems — made the top two of three floors untenable. Unfortunately we haven’t heard back from them after we complained after the fact asking for some sort of refund. Seems to be a recurring problem for the unit. All in all tho a great property that I would recommend were it not for that issue.
Stayed 3 nights in Sep 2023
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Leah B.

Fantastic weekend!

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 rental was awesome. There is so much space, very clean and a great location. Can’t wait to go back!
Stayed 3 nights in Sep 2024
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Debra G.

Lots of Room for Family; Mini Lobster week

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: Had plenty of room for all of us-beds comfy, and enjoyed having our boat slip nearby and swimming in the pool. Microwave was a little complicated to start, and is a need for a can-opener in the kitchen.
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Ryan H.

Memorial Day Weekend 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: Everything we expected and then some. Great trip
Stayed 3 nights in May 2024
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Bryan H.

Great 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: We’ve rented from Key West vacation homes multiple times, and it continues to be a great experience. The house is just as described, everything was spotless, and their service level is fantastic.
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Nicholas S.

Great Holiday Weekend in a Spacious Hom

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 in a great location with plenty of space for all the guests. We would definitely seek this place out again next time traveling down to Key West
Stayed 3 nights in Feb 2024