Condo holiday rentals in Annapolis

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Top-rated condo rentals in Annapolis

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Guest favourite
A charming street view showcases a two-story building with black shutters and bright red umbrellas over outdoor seating. Lush greenery decorates planters lining the patio, inviting guests to enjoy the vibrant atmosphere in the heart of Old Town Alexandria.
Condo in Old Town
4.83 out of 5 average rating, 267 reviews

HEART of OLD TOWN! Historic 2 BR! Walk to KING ST

Step into our historic 2-bedroom loft in the heart of Old Town Alexandria, set in a charming 1790 building. This desired location offers a unique stay with a cozy loft area and modern amenities. Nearby public parking and less than a block from King St, you're surrounded by local cafes, bars, and shops. The perfect blend of historical ambiance and urban convenience awaits you. Explore, unwind, and enjoy the best of Alexandria from this prime spot. Ready for an amazing stay? Book with us today!

Superhost
A bright living area features a gray sofa with patterned cushions, complemented by a cozy armchair. A trio of small, round tables sits on a soft area rug. Floor-to-ceiling windows allow natural light to illuminate the space, framed by light blue curtains.
Condo in Penrose
4.89 out of 5 average rating, 295 reviews

Newly Renovated & Modern 1BR Condo - Unit 4

Completely renovated, stylishly furnished condo unit in Arlington, VA just one stoplight from Washington DC, the Pentagon, Clarendon, Crystal City & National Airport. Spacious unit with free cable TV, secure Internet/Wi-Fi, FREE reserved PARKING space in private lot, in-unit Washer/Dryer, Full Kitchen. Steps away from public transit buses that route to multiple Orange/Blue/Silver line Metro trains. Comfortably accommodates the traveling professional, those on vacation and is kid friendly.

Top Guest favourite
A modern kitchen showcases a marble-topped island with bar seating for three. Natural light illuminates the space, highlighting the wooden stools and kitchen essentials arranged on the shelves. A potted plant in the foreground adds a touch of greenery, enhancing the inviting decor.
Condo in Ellicott City
4.88 out of 5 average rating, 112 reviews

Historic Schoolhouse Condo

Perched on a hill in Historic Ellicott City, this charming 1800s schoolhouse condo is perfect for long-term stays (30+ nights). Bright, spacious, and thoughtfully designed, it features a fully equipped kitchen, in-unit laundry, high-speed internet, and a dedicated workspace. Walk to Main Street, explore Trolley Trail #9 and Patapsco State Park, or easily access Columbia (10 min), Baltimore (20 min), and Washington D.C. (40 min) - historic charm meets modern comfort for an ideal extended stay.

Guest favourite
A spacious living area is depicted with plush teal seating arranged around a coffee table. A modern entertainment unit is positioned against a wall, while large sliding doors open to a private balcony. Natural light enhances the warm tones of the decor.
Condo in Annapolis
4.97 out of 5 average rating, 117 reviews

1 bedroom -king in Annapolis- low cleaning fee

Brand New Vacation Rental – Prime Annapolis Location! 1 bedroom. Experience the best of Annapolis in this newly renovated, beautifully furnished 1-bedroom condo with a king bed and NO chore list! This open-concept retreat offers a bright, modern interior and a private balcony to unwind. Start your day with a scenic walk through Truxton Park trails or head to the boat ramp to catch a water taxi to downtown Annapolis! Whether you're here for relaxation or adventure, this is the perfect spot.

Top Guest favourite
Condo in Annapolis
4.97 out of 5 average rating, 319 reviews

Annapolis Waterfront Condo - Unit #: A-203

Cozy, comfortable condo. Great views - 2nd flr. Fireplace 1 bed/bath condo, sleeps 4 max, covered, water front deck, reserved parking! .5 mile walk to dwnt Annapolis and the Naval Academy, 1.9mi to the Navy stadium. Book NOW for the Summer! Easy access to Spring/Fall boatshows. 12 stairs, no elevator. Pool Memorial to Labor Day: MWTh 4pm-8 Tues: Closed FSS and Holidays: 12pm-8 The pool is one of the best places to be on a hot summer day. If hours are unacceptable, pls select another

Guest favourite
A wooden walkway extends along the water, bordered by low posts and a railing. Boats are docked in the distance, with a gentle curve of the marina visible. Potted plants and striped decor can be seen, contributing to the waterfront atmosphere.
Condo in Annapolis
4.89 out of 5 average rating, 127 reviews

Annapolis @Gate 1 steps to the Harbor Free parking

Parking included. The heart of Annapolis 1 street from the harbor, fun restaurants & backs to the Naval Academy. This 1st floor 2 bed / 1 ba condo has been fully renovated with new paint, floors, bath & kitchen. 1 Parking space included & additional paid parking on street. Queen Bed & sleeper couch is a full size. Linens included. Kitchen includes refrigerator, stove/oven, microwave, keurig, dishes silverware, pots and pans. High speed internet included & separate work area.

Top Guest favourite
A cozy sleeping area is featured with a spacious bed adorned with an abstract circular accent design. Soft blue pillows enhance the bedding, while warm orange walls add vibrancy. Soft lighting from two bedside lamps illuminates the space, complemented by a framed artwork and a small wardrobe.
Condo in Baltimore
4.95 out of 5 average rating, 204 reviews

Sun House in Hampden Private Apartment no stairs

Artists and creatives are welcomed! Stay at our 1920 rowhouse with its mix of 70's era textiles and contemporary style. Only two steps to a welcoming porch and keyless entry to our foyer/Shared hall. Straight ahead is Sun Apartment, private studio with stocked kitchen, comfiest 5 star bed, private bath, laundry and back yard access. Yoga room/ office located in shared hall. No need for a car in the heart of Hampden's Avenue just a block away. LGBTQ+ friendly

Guest favourite
A bright living area features stylish seating arrangements with two blue sofas and a central ottoman. A wall-mounted television is positioned beneath decorative shelving. An open kitchen space is visible, showcasing modern bar stools and a dining area bathed in natural light from a nearby window.
Condo in Annapolis
4.94 out of 5 average rating, 433 reviews

Renovated Apt In Historic Dist w/2 Parking Spots

Renovated upstairs unit two bedroom with TWO parking spots in the Historic District. Everything is high end and used exclusively as a short term rental. Private entrance, cute small custom kitchen, ceiling fans, mini split AC/ heat in every room for year round comfort. Hardwood floors, quality linens , lucid mattresses, Keurig coffee bar, toiletries. Walk to town in 10 min or less or take the free trolley to Main St, USNA, Churches, AYC. No children under 12.

Guest favourite
Condo in Trinidad
4.94 out of 5 average rating, 191 reviews

Modern, spotless 1br for families or work

Bright and unique basement gem in the heart of DC! This thoughtfully renovated private space gets sunlight in the front and rear through real windows and glass doors. Enjoy your morning coffee on your own private patio. Come and go easily with your dedicated gated parking spot (free parking, off street!). Enjoy a full kitchen. Working during your stay? We have fast wi-fi. Live like a local in a (relatively) quiet residential neighborhood.

Top Guest favourite
A living area features a gray couch adorned with decorative pillows against a light wall. A recliner is positioned nearby, and a wall-mounted Smart TV is visible. A dresser with a plant sits below the TV. Natural light streams in through nearby windows.
Condo in Annapolis
4.96 out of 5 average rating, 125 reviews

1st Floor Condo in Annapolis

This newly renovated, 1st floor studio is perfectly located just across Spa Creek from historic Annapolis in Eastport. Within easy walking distance of restaurants (3 min), Main Street/City Dock (10 min) & USNA's Gate 1 entrance (14 min), our studio includes a full kitchen, high-speed wifi, free onsite parking lot, a secure building entrance, dock and a rooftop patio (with a seasonal pool) that offers beautiful views of downtown Annapolis.

Top Guest favourite
The spacious master bedroom features a large bed with decorative pillows and a coordinating gold bedspread. A patterned rug lies beneath, while a stylish lamp and a plant add warmth. An elegant mirror and chair provide additional functionality, and soft lighting enhances the serene ambiance.
Condo in Alexandria
4.99 out of 5 average rating, 100 reviews

Cozy Old Town Apartment

Welcome to our charming condo in the heart of historic Old Town Alexandria! Enjoy a fully equipped kitchen, cozy living room with a 55” smart TV, and a peaceful master bedroom with en-suite bathroom. With two private entrances, dedicated parking, and easy access to King Street’s dining, shopping, and metro, this home offers comfort and convenience. Perfect for relaxing after exploring D.C., or enjoying the charm of Old Town on foot!

Guest favourite
A modern living area features a light grey sectional sofa and a blue accent chair. A dark coffee table sits in front of the seating, while built-in shelves display books and decor. A large window provides natural light and offers access to a private balcony.
Condo in Pentagon City
4.92 out of 5 average rating, 125 reviews

Stylish Condo, DC Views, Free Parking

Chic 1-BR apt with private balcony & stunning views of the DC skyline, including the Washington Monument. Perfect for 2 guests. Features a queen bed, dedicated workspace, full kitchen & fast WiFi. Enjoy building amenities like free parking, a gym & club room. Prime location, steps from the Metro, Pentagon Row & Fashion Center Mall, offering easy access to DC & DCA. Your home base for exploring the capital region!

Popular amenities for Annapolis condo rentals

When is the best time to visit Annapolis?

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Avg. price$245 AUD$221 AUD$229 AUD$241 AUD$283 AUD$258 AUD$262 AUD$273 AUD$269 AUD$284 AUD$303 AUD$287 AUD
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Quick stats about condo rentals in Annapolis

  • Total holiday rentals

    Explore 20 holiday rentals in Annapolis

  • Nightly prices starting at

    Annapolis holiday rentals start at $85 AUD per night before taxes and fees

  • Verified guest reviews

    Over 2,070 verified reviews to help you choose

  • Family-friendly holiday rentals

    10 properties offer extra space and kid-friendly amenities

  • Holiday rentals with a pool

    10 properties feature pools

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    20 of Annapolis holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Annapolis rentals

  • 4.8 Average rating

    Annapolis stays are highly rated by guests—averaging 4.8 out of 5!

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