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Annapolis, MD villas
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238 Villa rentals in Annapolis, MD

Search Coastal Vacation Homes near Annapolis, MD

Experience relaxing coastal vibes at seaside vacation homes in Annapolis, MD, located short distances from popular beach-town shorelines.

Chapel Gate 3br Steps To City Dock & Naval Academy - Annapolis, MD
9.5 15 reviews

Chapel Gate 3br Steps To City Dock & Naval Academy

apartment, Annapolis
This top-floor apartment offers a prime location in Annapolis, situated just outside Gate 3 of the U.S. Naval Academy and a few blocks from City Dock, placing you within easy walking distance of downtown attractions.
This pet-friendly, three-bedroom, one-bathroom rental accommodates up to six guests and features a full kitchen, an outdoor grill and patio, and in-unit laundry for a comfortable stay.

Top-Rated Vacation Homes with a Pool in Annapolis, MD

On-site pool access in Annapolis, MD makes a refreshing swim to complement your beach day a wonderful part of your daily routine.

Captains Quarters Waterfront & Pool - Annapolis, MD
No reviews

Captains Quarters Waterfront & Pool

house, Annapolis
Captains Quarters Waterfront & Pool is a waterfront house in Annapolis, located a 13-minute walk from Annapolis Harbor and 26 miles from Baltimore's Inner Harbor.
This 650 square foot rental offers 2 bedrooms, 1 bathroom, and can accommodate up to 7 guests, featuring a full kitchen, a fireplace, a dishwasher, a washing machine, and direct access to an outdoor swimming pool.

Frequently Asked Questions about villa rentals in Annapolis, MD

Popular destinations

Best Annapolis, MD villas and beach houses with jacuzzi

Historic Row Home 1 Block From Gate 1 At Usna - Annapolis, MD
9.2 6 reviews

Historic Row Home 1 Block From Gate 1 At Usna

house, Annapolis
This Annapolis row house is located one block from the US Naval Academy's Gate 1, 1.1 miles from Annapolis Harbor, and 30 miles from Baltimore, offering easy access to these landmarks.
This 2000-square-foot property features three bedrooms, three bathrooms, accommodates up to 16 guests, and includes a fully equipped kitchen, free Wi-Fi, air conditioning, a private patio, and a garden.
The Goat Locker - Annapolis, MD
No reviews

The Goat Locker

house, Annapolis
The Goat Locker vacation rental is situated 2.5 miles from Annapolis Harbor and approximately 30 miles from Baltimore's attractions, offering easy access to both locations.
This one-bedroom, two-bathroom Annapolis house comfortably sleeps 21 guests and boasts a fully equipped kitchen with a dishwasher, a Jacuzzi, free Wi-Fi, parking, and air conditioning.

Neighborhoods and points of interest in Annapolis, MD

Best Annapolis, MD houses with a kitchen

Pet Friendly Retreat Near Downtown Annapolis - Annapolis, MD
No reviews

Pet Friendly Retreat Near Downtown Annapolis

house, Annapolis
This holiday home in Annapolis is situated 4.3 miles from Annapolis Harbor and 17 miles from Baltimore - Washington International Airport.
This 1360 square foot, two-bedroom, one-bathroom rental accommodates up to seven guests and features a fully equipped kitchen, fireplace, free WiFi, and private parking.
Secluded Cozy Cottage In Historic Downtown - Annapolis, MD
9.6 22 reviews

Secluded Cozy Cottage In Historic Downtown

cottage, Annapolis
This charming cottage, in the Historic District of Annapolis, offers immediate access to the city's iconic landmarks and attractions. The restored 1930s cottage has an open and airy interior with vaulted ceilings and an open floor plan.
The cottage has 2 bedrooms, 1 bathroom, and can accommodate up to 8 guests. It features a fully equipped gourmet kitchen, a comfortable living area with a large couch, chaise lounge chairs, a 55" Roku TV, and an electric fireplace. The cottage also has a private entrance and patio, and is pet-friendly.
Fisher House - Downtown Annapolis! - Annapolis, MD
No reviews

Fisher House - Downtown Annapolis!

house, Annapolis
House to rent. Your accommodation will be located in Annapolis.
Facilities and services include an iron, a fridge and a dish washer.
Unique Eastport Bungalow W Yard - Annapolis, MD
No reviews

Unique Eastport Bungalow W Yard

house, Annapolis
This Annapolis house rental in the Eastport district is 1.1 miles from Annapolis Harbor and 26-27 miles from Baltimore attractions like Camden Yards and the Inner Harbor.
The 10,760-square-foot property boasts four bedrooms, three bathrooms, and accommodates up to twelve guests, featuring a fully equipped kitchen, free Wi-Fi, air conditioning, and free private parking.

Traveler-Approved 5-Star Holiday Houses in Annapolis, MD

Upscale finishes and prime locations define these luxury vacation homes in Annapolis, MD, ensuring every detail of your stay is considered.

All Star Annapolis Retreat - Walk To Stadium - Annapolis, MD
10 2 reviews

All Star Annapolis Retreat - Walk To Stadium

house, Annapolis

Compare Family Vacation Homes in Annapolis, MD

Getting the vacation home right makes all the difference in Annapolis, MD, with easy access to the water and plenty of room to spread out.

Eastport Charmer - Annapolis, MD
No reviews

Eastport Charmer

house, Annapolis
Walk To Everything Historic Arts District - Annapolis, MD
9.0 12 reviews

Walk To Everything Historic Arts District

house, Annapolis
Pet Friendly Retreat Near Downtown Annapolis - Annapolis, MD
No reviews

Pet Friendly Retreat Near Downtown Annapolis

house, Annapolis
Around The Corner - Annapolis, MD
No reviews

Around The Corner

house, Annapolis

Search Dog-Friendly Holiday Houses in Annapolis, MD

Traveling with a pet to Annapolis, MD is easy in these vacation homes, featuring dog-friendly amenities.

Pet-friendly Eastport Yard & Fire Pit - Annapolis, MD
No reviews

Pet-friendly Eastport Yard & Fire Pit

house, Annapolis
Luxe Row Home Steps To Usna Gate 3! - Annapolis, MD
10 23 reviews

Luxe Row Home Steps To Usna Gate 3!

house, Naval Academy
Charming Rowhome In Downtown Annapolis - Annapolis, MD
No reviews

Charming Rowhome In Downtown Annapolis

house, Annapolis
Luxe Row Home Steps To Usna Gate 3 - Annapolis, MD
No reviews

Luxe Row Home Steps To Usna Gate 3

house, Annapolis

Check Out Vacation Homes with Spa in Annapolis, MD

Unwinding is effortless with an on-site spa. These vacation homes in Annapolis, MD deliver wellness by the water at its very best.

Historic Downtown Annapolis W Rooftop Deck - Annapolis, MD
No reviews

Historic Downtown Annapolis W Rooftop Deck

house, Annapolis

Best Annapolis, MD houses with air conditioning

Annapolis Vacation Home: 2 Mi To Quiet Waters Park - Annapolis, MD
No reviews

Annapolis Vacation Home: 2 Mi To Quiet Waters Park

house, Annapolis
The Annapolis Firehouse - Annapolis, MD
10 37 reviews

The Annapolis Firehouse

house, Annapolis
Charming Rowhome In Downtown Annapolis - Annapolis, MD
9.7 19 reviews

Charming Rowhome In Downtown Annapolis

house, Annapolis
Pet Friendly Park Free & Walk To Usna Stadium - Annapolis, MD
No reviews

Pet Friendly Park Free & Walk To Usna Stadium

house, Annapolis
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