Condo holiday rentals in Anne Arundel County

Newly Renovated 1-Bedroom on Spa Creek

This newly renovated 1-bedroom condo overlooks Spa Creek & Annapolis skyline. Renovated last year, so be among the first to enjoy the space for the Boat Shows, USNA football games or for your Annapolis vacation! Available year round for your visit to Annapolis. This condo is located in the Newport Condo Building, with views of Spa Creek. You are just over the bridge from downtown Annapolis, but with the quiet and easy parking in a dedicated lot. Easy walk downtown, or take the water taxi!

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!

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 25%! The month-long stay discount is 40%! The early bird discount is 10% (12 months in advance) The last minute discount is 10% (28 days in advance) Pets are only $100 per stay! Additional guests are $15 per person per night :) We would be happy to accommodate flexible check-in and check-out times if available!

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.

1st Floor Condo in Annapolis

This newly renovated, 1st floor studio is perfectly located just across Spa Creek from historic Annapolis in the quiet yet hip neighborhood of 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, a secure building entrance, dock access & a rooftop patio (with a seasonal pool) that offers beautiful views of downtown Annapolis.

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'!!

Charming Annapolis Waterfront Condo

Discover the charm of CAPTAINS QUARTERS, your exclusive waterfront retreat in the prestigious Yacht Club Condominiums. Steps from Downtown Eastport and Annapolis, this gem offers stunning views, a community pool, and the essence of luxury. With 2 free parking spots, you're 1.6 miles from the Naval Academy and under a mile to Downtown Annapolis attractions. Perfectly positioned for exploration or relaxation, your stay promises an unmatched Annapolis experience.

Annapolis Waterfront Condo - Unit #: A-203

BOOK NOW FOR SUMMER 2025! SPRING and FALL BOAT SHOW AVAILABILITY! Free reserved parking! Walk to show in minutes! Great views - 2nd flr. condo (12 stairs, no elevator.) Pool hours are fixed: Mon: 4pm-8 Tues: Closed Wed: 4-8 Thurs: 4-8 Fri: 3-8 Sat/Sun/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 location. 15 min. walk to downtown Annapolis/USNA. MULTIPLE Free parking options.