Entire home
Ahoy! Game Room, Screened Porch, Yard Mins to DTA
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Reviews
9.8 out of 10
Exceptional
3 bedrooms2 bathroomsSleeps 91272 sq ft
Popular amenities
Explore the area

Annapolis, MD
- Place, Maryland Quiet Waters Park3 min drive
- Place, Annapolis Landing Marina3 min drive
- Place, Annapolis Maritime Museum4 min drive
- Airport, Baltimore, MD (BWI-Baltimore Washington Intl. Thurgood Marshall)36 min drive
Rooms & beds
3 bedrooms (sleeps 9)
Family Room
1 Queen Sofa Bed
Main Floor Bedroom
1 Queen Bed
Upstairs Bunk Room
1 Single Bunk Bed
Upstairs King
1 King Bed
2 bathrooms
Main Floor
Bathtub or shower · Toilet
Upstairs Hall Bath
Bathtub or shower · Toilet
Spaces
Deck or patio
Kitchen
Number of living rooms
About this property
Ahoy! Game Room, Screened Porch, Yard Mins to DTA
Experience the Difference: Professionally Managed by iTrip Annapolis
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
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
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House Rules
Check in after 4:00 PM
Minimum age to rent: 25
Check out before 11:00 AM
Children
Children allowed: ages 0–17
Events
No events allowed
Pets
Pets 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
This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room
About the area
Annapolis
Annapolis is home to this holiday home. Historical Society of Talbot County and Kunta Kinte Plaque & Alex Haley Memorial are local landmarks, and travellers looking to shop may want to visit Bay Bridge Market Place Shopping Center and Annapolis City Dock. Looking to enjoy an event or a game while in town? See what's happening at Tose Family Tennis Center or Alumni Hall.

Annapolis, MD
What's nearby
- Bay Bridge Market Place Shopping Center - 19 min walk - 1.6 km
- Maryland Quiet Waters Park - 3 min drive - 1.4 km
- Annapolis Sailing School - 3 min drive - 1.8 km
- Annapolis Landing Marina - 3 min drive - 1.8 km
- Annapolis Maritime Museum - 4 min drive - 2.5 km
Getting around
Restaurants
- McDonald's - 20 min walk
- Bay Ridge Wine & Spirits - 3 min drive
- Carrol's Creek Cafe - 7 min drive
- Boatyard Bar & Grill - 7 min drive
- Starbucks - 16 min walk
Frequently asked questions
Reviews
9.8
Exceptional
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window9.8/10
Cleanliness
10/10
Check-in
10/10
Communication
10/10
Location
10/10
Listing accuracy
Reviews
Verified
16 Jul, 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Stayed 3 nights in Jun 2025
Verified
10/10 Excellent
Kelly S.
23 Jun, 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Adorable Home Perfect for Families
Kelly S.
Stayed 4 nights in Jun 2024
Verified
10/10 Excellent
Dina C.
16 Mar, 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Buccaneer Review
Dina C.
Stayed 4 nights in Mar 2025
Verified
10/10 Excellent
Ronald V.
21 Jun, 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Wonderful Property
Ronald V.
Stayed 4 nights in Jun 2024
From a partner site
10/10 Excellent
Katie C.
28 Mar, 2024
Great trip!
Katie C.
Stayed 4 nights in Mar 2024
Verified
8/10 Good
Whitney W.
19 Oct, 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Family Vacay
Whitney W.
Stayed 5 nights in Oct 2024
From a partner site
10/10 Excellent
Linda M.
2 Aug, 2024
The Buccaneer
Linda M.
Stayed 4 nights in Jul 2024
Verified
10/10 Excellent
Missy F.
3 Jun, 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
great
Missy F.
Stayed 4 nights in May 2024
Verified
10/10 Excellent
Rosemary H.
10 Sept, 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Great Annapolis Visit
Rosemary H.
Stayed 3 nights in Sep 2024
Verified
8/10 Good
Margaret H.
7 Aug, 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Family vacation friendly
Margaret H.
Stayed 4 nights in Aug 2024
Verified
10/10 Excellent
Debra W.
4 Apr, 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Family Trip
Debra W.
Stayed 4 nights in Mar 2025
From a partner site
10/10 Excellent
Nicole H.
29 Jul, 2024
12 Pirates!
Nicole H.
Stayed 5 nights in Jul 2024
From a partner site
10/10 Excellent
Brenna J.
25 Nov, 2024
Perfect Place
Brenna J.
Stayed 2 nights in Nov 2024
Verified
10/10 Excellent
Dennis K.
6 Jul, 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Annapolis, DC and Ocean City!
Dennis K.
Stayed 5 nights in Jun 2024
Verified
10/10 Excellent
Sandra M.
21 Jul, 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Wonderful Property!
Sandra M.
Stayed 2 nights in Jul 2024
Verified
10/10 Excellent
Dean D.
1 Jul, 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Awesome in Annapolis
Dean D.
Stayed 3 nights in Jun 2024
About the host
Hosted by iTrip Vacations Annapolis - Sean Degnan
Languages:
English
Premier Host
They consistently provide great experiences for their guests
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