
Condo vacation rentals in Annapolis
Find and book unique condos on Airbnb
Quick stats about condo rentals in Annapolis

Total vacation rentals
Explore 20 vacation rentals in Annapolis

Nightly prices starting at
Annapolis vacation rentals start at $84 CAD per night before taxes and fees

Verified guest reviews
Over 2,270 verified reviews to help you choose

Family-friendly vacation rentals
10 properties offer extra space and kid-friendly amenities

Vacation rentals with a pool
10 properties feature pools

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wifi availability
20 of Annapolis vacation rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Annapolis rentals

4.9 Average rating
Annapolis stays are highly rated by guests—averaging 4.9 out of 5!
Top-rated condo rentals in Annapolis
Guests agree: these condos are highly rated for location, cleanliness, and more.

Gorgeous, large, modern 1 BR on Hist. Logan Circle
Gorgeous, bright, open plan nearly 1,000 square foot 1 bedroom condo with space for an entire family in historic Logan Circle neighborhood on a quiet street. Short walk to White House, Mall & museums. Built in 1900, this brownstone was thoughtfully renovated to blend modern (in-ceiling lighting, stainless steel appliances, bamboo flooring) with historic features (original exposed brick & trim). Warm, spacious & comfortable for your stay. Logan is DC's hottest & hippest area with a 96 walk score.

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.

Newly Renovated & Modern 1BR Condo - Unit 3
Newly renovated, stylishly furnished condo unit in Arlington, VA just one stoplight from Washington DC, the Pentagon, Clarendon, Crystal City and 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 train. Comfortably accommodates the traveling professional, those on vacation. Sorry, NO parties.

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

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.

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.

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.

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.

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!

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!
Popular amenities for Annapolis condo rentals
Weekly condo rentals

Cozy Condo in Columbia Heights DC, with parking!

Modern Condo, 2 Bed/2 Bath, Rooftop - 6 PPL

Attractive one-bedroom unit on Capitol Hill

Sunny Apartment in Historic Capitol Hill

Cozy Annapolis Condo

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

Light-filled Private Oasis / Close to Capitol Bldg

Private Apt-Old Town Alexandria-Self Check In
Pet-friendly condo rentals

Spacious Bloomingdale 1BR; garage parking included

Semper Fi Condo

New 2BR - Cherry Blossom Suite - walk everywhere!

Sojourn in DuPont Circle: Modern Meets Historic

Family Friendly HQ - Historic DC 3BR & 3BA

Lux in heart of DC social scene, free parking!

Hill East BnB - Modern Style and Comfort 3BR/3BA

Modern Mt.Vernon studio in great central location
Condo rentals with a pool

Prime 2BR Urban Escape -Pool, Gym, Near Everything

Stylish 1BR Condo in Vibrant National Harbor, MD

2BDRM, 2BA near MGM, Gaylord, Top Golf & Shopping!

Wyndham National Harbor | 1BR/1BA King Bed Suite

National Harbor your D.C. Vacation Springboard.1br

Lovely 1-bedroom condo w/ 2 parking spots near DC

Wyndham National Harbor ツ 3 Bedroom Deluxe!

Club Wyndham National Harbor, 2 BR Deluxe
When is the best time to visit Annapolis?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $241 CAD | $259 CAD | $252 CAD | $238 CAD | $280 CAD | $255 CAD | $259 CAD | $271 CAD | $266 CAD | $282 CAD | $300 CAD | $285 CAD |
| Avg. temp | 1 °C | 3 °C | 7 °C | 13 °C | 18 °C | 23 °C | 26 °C | 25 °C | 21 °C | 14 °C | 8 °C | 4 °C |
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- Georgetown University
- M&T Bank Stadium
- National Mall
- The White House
- Nationals Park
- Walter E Washington Convention Center
- Baltimore Convention Center
- FedExField
- Oriole Park at Camden Yards
- Federal Hill Park
- Johns Hopkins University
- Arlington National Cemetery
- National Museum of African American History and Culture
- Washington Monument
- The Anthem
- Georgetown Waterfront Park
- Capital One Arena
- Betterton Beach
- CFG Bank Arena
- National Harbor
- Smithsonian National Zoological Park
- Howard University
- Merriweather Post Pavilion
- Patterson Park





