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Book for CW 2025 Ahoy! The Buccaneer with 3-seasons room, fenced-in yard and rec room

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Fridge, microwave, oven, stovetop
Smart TV, video games, DVD player, table football
Outdoor dining
Interior
Aerial view

Reviews

9.8 out of 10
Exceptional

Entire home

3 bedrooms2 bathroomsSleeps 9

Popular amenities

  • Barbecue grill
  • Washer
  • Dryer
  • Kitchen
  • Pet-friendly
  • Parking available

Explore the area

Map
Annapolis, MD
  • Maryland Quiet Waters Park
    ‪5 min drive‬
  • Annapolis City Dock
    ‪7 min drive‬
  • U.S. Naval Academy
    ‪9 min drive‬
  • Washington, DC (DCA-Ronald Reagan Washington National)
    ‪47 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.

Book for CW 2025 Ahoy! The Buccaneer with 3-seasons room, fenced-in yard and rec room

Still available for Commissioning Week 2025!

Welcome to The Buccaneer, a family-friendly home located just 3 miles from Historic Downtown Annapolis and Eastport. This charming and fun home has a four-season patio, with adjustable plexiglass windows, overlooking the fenced-in backyard and full entertainment room in the basement, complete with foosball, an arcade and a theater room.

This home's full kitchen, dining area, family room, bedroom with Queen bed and full bath are on the main floor. The kitchen is fully-stocked with cookware, stainless steel appliances and a chef's butcher block built into the countertop. The custom dining room table is built in to allow up to 8 guests to gather and enjoy a family meal. Head out to the 4-seasons room/screened-in porch and private backyard.

The 2nd bedroom, located upstairs, has a bunk bed with a Full bed over 2 Twin beds. The 3rd bedroom, also located on the 2nd floor, has a King bed.

The home is just a short walk through a quiet neighborhood to Capital SUP on Back Creek, where paddle boards and kayaks are available for rent. Looking for a fun adventure on the water? You will be conveniently located within walking distance to Ellen Moyer Park, Annapolis Maritime Museum and Bert Jabin Yacht Yard. Or, take a water taxi into Annapolis! Just 2 blocks away at the waterfront of King James Landing, you can hire a water taxi.

SLEEPING ARRANGEMENTS 3 BR / 2 BA / Sleeps 9:
Main Floor Bedroom:
-Queen Bed
-Full bathroom in the hall with shower/bath combo

King Bedroom
-2nd Floor
-Full bath in the hall with shower/bath combo

Upstairs family guest room
-Full bed over Two Twins bunk bed
-Full bath in the hall with shower/bath combo

Family Room
Queen sleeper sofa

HIGHLIGHTS:
-Large screened-in patio overlooking the big private backyard
-Built-in kitchen dining table seats 6-8
-High Speed Internet and WiFi
-Coffee maker with starter pack of coffee/creamers
-BBQ gas grill (propane included)
-Luxury bed and bath linens, complimentary toiletries Starter Kit, and boutique-level service
-Parking for 2-3 cars in driveway
-Full-sized washer & dryer
-Private fenced-in backyard
-Dogs allowed with $150 non-refundable fee paid prior to checkin
-Keyless entry. Drive straight to your rental home and enter the front door with an electronic lock code. Prior to your visit, we will send you our mobile app with directions and full instructions.
***************
Property Distance to:
-Downtown Annapolis – 2.5 miles (10 mins)
-U.S. Naval Academy – 3 miles (10 mins)
-Washington, DC – 33 miles
-Baltimore - 34 miles
***************
* Amenity pack with starter coffees, sweeteners, soap, shampoo, conditioner, lotion and hand sanitizer, paper towels, toilet paper, dish soap, scrubber and dishwashing liquid to get you going
* All beds are made for you with freshly-laundered sheets & towels in the baths.

House Rules
Reservations made for teenagers or young single groups will not be honored without any accompanying adult staying in the unit at ALL times. We require at least one member of the party to be 25 (twenty-five) years of age. No smoking. Be respectful of the house and contents. Please respect the neighbors and neighborhood. No parties. Quiet neighborhood hours are 9pm-8am!
Check-in time: 4:00 pm
Check-out time: 11:00 am
During your stay at this vacation home, you'll be within walking distance of Sparrows Beach. You'll find features like laundry facilities and an arcade/game room. The vacation home offers free WiFi and a kitchen.
  • Air-conditioned home with kitchen, washing machine, and 2 bathrooms
  • Free WiFi
  • Amenities include laundry facilities
  • Onsite recreation includes a playground
  • Just a 3-minute drive from Annapolis Sailing School and a few minutes from Sparrows Beach
This vacation home offers its guests barbecue grills, an arcade/game room, and a garden. The front desk is open around the clock.

Property manager

iTrip Vacations Annapolis - Sean Degnan

Languages

English

Property amenities

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
  • Paper towels
  • Refrigerator
  • Toaster

Dining

  • Dining table

Bedrooms

  • 3 bedrooms
  • Bedsheets provided
  • Sofa bed

Bathroom

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

Living spaces

  • Dining table
  • Living room

Entertainment

  • DVD player
  • Games
  • Smart TV
  • Video games
  • Video library

Outdoor areas

  • Barbecue grill
  • Garden
  • Outdoor furniture
  • Patio

Laundry

  • Laundry facilities
  • Washing machine

Work spaces

  • Desk
  • Desk chair

Comfort

  • Air conditioning
  • Heating

Pets

  • Pet friendly

Suitability/Accessibility

  • Smoke-free property

Services and conveniences

  • Iron/ironing board

Location highlights

  • Near a health/beauty spa
  • Near a hospital
  • Near an outlet shopping centre
  • Near the marina

Things to do

  • Arcade/game room
  • Bicycle parking
  • Bicycle storage
  • Foosball table
  • Basketball nearby
  • Birdwatching nearby
  • Casino nearby
  • Cycling nearby
  • Ecotours nearby
  • Fishing nearby
  • Golfing nearby
  • Hiking/biking trails nearby
  • Horseback riding nearby
  • Ice skating nearby
  • Jet skiing nearby
  • Kayaking nearby
  • Motor boating nearby
  • Parasailing nearby
  • Sailing nearby
  • Swimming nearby
  • Water skiing nearby
  • Wildlife walks nearby
  • Winery tours 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)

General

  • At least 80% lighting from LEDs
  • Bicycle parking
  • Bicycle storage
  • Garden
  • Recycling

Policies

Check-in

Check-in time starts at 4:00 PM
Minimum check-in age: 25

Check-out

Check-out before 11:00 AM

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions

Pets

  • Pets are welcome
  • Service animals are exempt from fees

Children and extra beds

  • Children are welcome.

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
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.

Property is also known as

14071

Book for CW 2025 Ahoy! The Buccaneer with 3-seasons room, fenced-in yard and rec room Reviews

Reviews

9.8

Exceptional

Rating 10 - Excellent. 13 out of 15 reviews
Rating 8 - Good. 2 out of 15 reviews
Rating 6 - Okay. 0 out of 15 reviews
Rating 4 - Poor. 0 out of 15 reviews
Rating 2 - Terrible. 0 out of 15 reviews

9.8/10

Cleanliness

Reviews

10/10 Excellent

Debra W.

Liked: Cleanliness

Family Trip

I have to say that my family and I had a wonderful stay at this house. It was a perfect location to visit both Washington DC and Annapolis. The house is in a quiet neighborhood with a great fenced in yard for small children or “canine children“. The theater room and game area were just the right space for my sons to have their own area of the house.My personal favorite spot was the enclosed back porch. With the table, seating and tv it was the perfect spot to relax on a warm evening.This home would definitely be at the top of my list if I were to visit the area again.
Stayed 4 nights in Mar 2025

10/10 Excellent

Dina C.

Liked: Cleanliness

Buccaneer Review

Enjoyable stay & quick proximity to USNA.
Stayed 4 nights in Mar 2025

8/10 Good

Whitney W.

Liked: Cleanliness

Family Vacay

Overall the house was very accommodating and spacious! The highlights were the theater downstairs, the back patio, and bunk beds! It was in a great location for easy access to downtown Annapolis and food/shopping. The place had plenty of towels and kitchen items.
Stayed 5 nights in Oct 2024

10/10 Excellent

Rosemary H.

Liked: Cleanliness

Great Annapolis Visit

We really enjoyed our weekend in Annapolis and staying at the Buccaneer. The home was very comfortably furnished and fully equipped. We especially enjoyed the porch and the basement game and TV room. The kitchen was well stocked with good quality cookware and I was able to prepare the meals as planned. The beds were comfortable and the plush towels were great too. Our grandchildren have already asked to return next year!
Stayed 3 nights in Sep 2024

8/10 Good

Margaret H.

Liked: Cleanliness

Family vacation friendly

Great house in a great location. My kids (12 and 14 years old) enjoyed the theatre room and foosball table in the basement. I appreciated the newer appliances in the kitchen. Comfy seating in the kitchen and living room. Nice sized backyard with playset and outdoor games.
Stayed 4 nights in Aug 2024

10/10 Excellent

Sandra M.

Liked: Cleanliness

Wonderful Property!

We were in town for husband/father's funeral. The house was perfect for our stay. The kids loved the home theater soace and games in the basement. After a very long and difficult day, we were able to relax. They owners supplied all towels, linens and small bags of toiletries for our stay. The porch was large and peaceful. The kitchen was stocked well with all needed dishes, utensils, and pots and pans. If we need to stay in the area again, I would definitely choose this property!
Stayed 2 nights in Jul 2024

10/10 Excellent

Dennis K.

Liked: Cleanliness

Annapolis, DC and Ocean City!

We had a great time and enjoyed the home. The kids loved the arcade game, foosball, and movie theater. My 78 yo dad had his own bath and a first floor bedroom. Everything was perfect. A few minor things but nothing even worth mentioning. Everyone was more than satisfied! Would stay here again o. A heartbeat!
Stayed 5 nights in Jun 2024

10/10 Excellent

Dean D.

Liked: Cleanliness

Awesome in Annapolis

It is safe to say we scored when we booked the Buccaneer! The home was perfect. It was spacious enough for a few old friends and their boys to hang and reminisce. It was clean, in a great location and roomy. Despite our stay being in the middle of a heat wave we enjoyed the back patio. Speaking of a heat wave, when we arrived it was quite warm inside and we could not get the AC to stay set to a cooler temp. Melissa and her team were awesome when I brought this to their attention and worked with me until 11 PM to get the temp dropping! Who does that? We enjoyed our stay thoroughly and when back in Annapolis we will look to book the Buccaneer first!
Stayed 3 nights in Jun 2024

10/10 Excellent

Kelly S.

Liked: Cleanliness

Adorable Home Perfect for Families

We were very pleased with our stay and would stay here again.
Stayed 4 nights in Jun 2024

10/10 Excellent

Ronald V.

Liked: Cleanliness

Wonderful Property

It’s an amazing house, near everything . Everything you need is available at the property We had a great time
Stayed 4 nights in Jun 2024

10/10 Excellent

Missy F.

Liked: Cleanliness

great

This is a great house with amazing outdoor space
Stayed 4 nights in May 2024