Condo vacation rentals in Anne Arundel County

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Top-rated condo rentals in Anne Arundel County

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Guest favorite

Condo in Annapolis

4.99 out of 5 average rating, 136 reviews

New Downtown Annapolis Condo With Free Parking

This newly constructed property brings chic, low-maintenance living to the heart of the Arts District in Annapolis. No parties, events, or large gatherings! Week long stay discount is 20%! Month long stay discount is 30%! Pets are only $100 per stay! Additional guests are $15 per person per night :) For stays greater than 90+ days, ask host about leasing to avoid service fees. Monthly rates start at $5,000! We would be happy to accommodate flexible check in and check out times if available

Guest favorite

Condo in Annapolis

4.94 out of 5 average rating, 375 reviews

Brand New Reno in Historic Dist w 2 Parking spots

Spotless / sanitized !! Renovated upstairs unit two bedroom with TWO parking spots in the Historic District . Everything is high end ,brand new and used exclusively as a short term rental. Private entrance, cute small custom kitchen, ceiling fans, mini split A.C/ heat in every room for year round comfort. Hardwood floors, quality linens , lucid matresess, 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 10.

Guest favorite

Condo in Annapolis

5 out of 5 average rating, 13 reviews

1st Floor Condo in Annapolis

This newly renovated, first 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) & the USNA's Gate 1 entrance (14 min), our studio includes a full kitchen, high speed wifi, free onsite parking and a secure building entrance, as well as dock access & a rooftop patio (with a seasonal pool) that offers beautiful views of downtown Annapolis.

Guest favorite

Condo in Annapolis

4.94 out of 5 average rating, 17 reviews

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!

Guest favorite

Condo in Annapolis

4.98 out of 5 average rating, 91 reviews

Fall into Annapolis-very low cleaning fee

Brand New**Great Location See the best of Annapolis when you book this open concept 1 bedroom with a king bed vacation rental! NO CHORE LIST. Newly renovated and newly furnished, this condo is equipped with all the essentials, relax on the private balcony, and enjoy the bright modern interior, this condo is key to a memorable vacation. Begin your morning with a scenic walk thru Truxton Park trails or head down to the boat ramp and catch a water taxi to downtown Annapolis. Perfect spot!

Guest favorite

Condo in Hanover

4.91 out of 5 average rating, 75 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!

Guest favorite

Condo in Annapolis

4.86 out of 5 average rating, 74 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.

Condo in Annapolis

4.8 out of 5 average rating, 60 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.

Guest favorite

Condo in Annapolis

4.95 out of 5 average rating, 80 reviews

Funky Uptown Apt meets Downtown - Hist District

Location location location where Uptown meets Downtown in the Historic District. Tsunami, 49 West, Level in the front yard with Ramshead, Stan and Joes and Reynold's Tavern in the back. EVERYTHING Annapolis (USNA, Stadium, Statehouse, Ego Alley, Main St, Maryland Hall, Eastport) is walking distance from this unique 2nd floor unit w full kitchen, washer/dryer, clawfoot tub, deck, BR with full size bed, LR w/sofa. Short term parking to unload, garage pass for long term

Guest favorite

Condo in Sparrows Point

5 out of 5 average rating, 7 reviews

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'!!

Guest favorite

Condo in Annapolis

5 out of 5 average rating, 52 reviews

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.

Guest favorite

Condo in Annapolis

4.96 out of 5 average rating, 255 reviews

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.