Condo holiday rentals in Anne Arundel County

Stylish Annapolis Retreat | Personalized Gift

Every stay includes a thoughtful, personalized gift! Stylish top-floor condo located in Spa Creek outfitted with king sized beds, espresso bar, 65” 4K smart TV, Nintendo Switch, vinyl listening station, full kitchen, dedicated workplace, book nook, and covered balcony. Community perks include pool, gym, and grills. Walk to parks, courts , water & trails nearby. Just 7 mins to downtown Annapolis & the Naval Academy. Perfect for work or play—resort-style amenities and cozy comfort all in one.

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.

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

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!

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.

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.

The Industrial Suite

The Industrial R&R Suite is a wonderful, modern live/work space located in a commercial/residential building. Influenced by the historic Bethlehem Steel Mill. This unique place has a style all its own. Minutes from Tradepoint Atlantic, 695, 95, and Baltimore City however located in Baltimore County's best kept secret, the North Point Peninsula. Cave like bathroom is decked out in slate, antique brick, stone, concrete, and tile! Note: Rain Shower Head Height is only 6'!!

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.

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.

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.

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.

New Downtown Annapolis Condo With Free Parking

This newly constructed property brings chic, low-maintenance living to the heart of Annapolis. No parties, events, or large gatherings! The week-long stay discount is 20%! The month-long stay discount is 40%! Pets are $100 per stay! We would be happy to accommodate flexible check-in and check-out times if available!