Condo holiday rentals in Anne Arundel County

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.

4.96 out of 5 average rating, 131 reviews

Annapolis Condo-1 bedroom King

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.

ValueFamilyKitchen

Superhost

A modern kitchen features dark cabinetry and a large island with granite countertops. Stainless steel appliances are integrated, and warm lighting illuminates the space. Seating for four is provided at the island, creating a cozy dining area. A staircase with wooden railings leads to the upper level.

Condo in Hanover

4.91 out of 5 average rating, 89 reviews

Parkside Retreat Brand New 3-bedroom condo

The Parkside Retreat is a new 2-story condo located in a resort-style community that features a spacious kitchen/dining area, a 75" HD TV with 5.1 surround sound, three thoughtfully decorated bedrooms and 2 full baths / 1 half. The sprawling master suite features a walk-in closet, a luxurious king-size bed and a bathroom with a double-sink vanity, a shower and luxurious white bath towels. Best part? It is truly central to unlimited historical sites, restaurants, shopping and more!

LocationFamilyBarbecue

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.

4.91 out of 5 average rating, 153 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.

ValueFamilyBreakfast

A spacious living area is presented with a blue reclining sofa facing a large wall-mounted television. Warm wood cabinetry complements the kitchen area in the background, illuminated by soft lighting. A cozy electric fireplace adds warmth, creating an inviting space for relaxation.

4.85 out of 5 average rating, 110 reviews

Anchors Away

Eastport: Spacious studio boasts high ceilings & lots of natural light with his and hers walk-in closets. Fully remodeled with fresh paint, new floors, bath & kitchen. Tempur-pedic Murphy bed & cozy electric fireplace below a 58” 4K television. Basement houses additional storage & full-size W/D. Grill area. Free off-on street parking. Walking distance to Eastport's finest restaurants, or take the water taxi across Spa Creek into down-town Annapolis or the Naval Academy.

ValueLocationCondition

A bright living area features a comfortable sofa and a patterned armchair, arranged around a wooden coffee table. A rug adds warmth to the hardwood floor, while ample natural light enters through multiple windows. The kitchen, adjacent to the living space, is equipped with modern appliances.

4.96 out of 5 average rating, 127 reviews

Funky Uptown Apt meets Downtown - Hist District

Location location location where Uptown meets Downtown in the Historic District. 1/2 block to Dinner Under The ✨ , First Sunday Arts. Tsu, 49 West, Level in the front yard Ramshead, Stan and Joes and Reynold's Tavern in the back. EVERYTHING Annapolis (USNA, Stadium, Statehouse, Ego Alley, Main St, Eastport) is walking distance from this unique 2nd floor unit w elevated deck for morning coffee as Jazz wafts in, full kitchen, w/d, clawfoot shower/tub, MBR with Queen.

ValueLocationQuiet

4.98 out of 5 average rating, 124 reviews

Captains Quarters | Waterfront & Pool

Welcome to Captains Quarters — your waterfront home in the Yacht Club Condominiums. Fall asleep to the sound of the water, wake up to views of Spa Creek, and walk to Eastport's best restaurants in minutes. Relax on the covered patio, swim in the community pool, or stroll across the Eastport Bridge to Downtown Annapolis. Two bedrooms, a full kitchen with Keurig and bean grinder, cable TV, and 2 free parking spots. Everything you need for an Annapolis stay on the water.

FamilyLocationView

4.89 out of 5 average rating, 35 reviews

Semper Fi Condo

Spacious and cozy 2BR/2BA condo in Annapolis just minutes from downtown, the Naval Academy, restaurants, and waterfront attractions. Pet-friendly with an additional fee. Features include a private balcony, smart TVs, high-speed Wi-Fi, full kitchen, free parking, pool, gym, and secure code-entry building access. The master bedroom includes a queen bed, private bath, and walk-in closet. Second bedroom has 2 queen beds, smart TV, pool view, and private bathroom access.

LocationFamilyAmenities

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.

4.94 out of 5 average rating, 453 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.

LocationValueHospitality

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.

4.96 out of 5 average rating, 178 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 (limited access) and a rooftop patio (with a seasonal pool) that offers beautiful views of downtown Annapolis.

FamilyValueGetting around

Superhost

A light-filled living area features a comfortable sectional sofa with pillows and a cozy throw. A round coffee table sits in the center, surrounded by a woven basket and a wooden armchair. The kitchen area is visible in the background, equipped with dark cabinetry and stainless-steel appliances.

4.75 out of 5 average rating, 85 reviews

Amazing Views from Spa Creek 2BD Condo with Pool

Welcome to your home away from home in Annapolis! Nestled in the charming neighborhood of Eastport, this beautifully appointed 2-bedroom condo offers breathtaking views overlooking the water and the iconic Annapolis skyline. Despite its serene setting, downtown Annapolis is just a quick half-mile walk or water taxi ride across Spa Creek, allowing you to easily explore all the attractions and amenities the city has to offer.

ValueFamilyTV

A bright living room features large windows dressed with light curtains, allowing natural light to fill the space. A comfortable sofa and armchair are arranged around a sleek coffee table, with shelves displaying books and decorative items, contributing to a welcoming atmosphere.