Apartment holiday rentals in Annapolis

Find and book unique apartments on Airbnb

Top-rated apartment rentals in Annapolis

Guests agree: these apartments are highly rated for location, cleanliness and more.

%{current} / %{total}1 / 1
Top guest favourite
A comfortable seating area features a large sectional sofa adorned with colorful throw pillows. A round table sits in the center atop a decorative area rug. Natural light streams in through wide windows, complemented by a floor lamp and a touch of greenery from plants.
Apartment in Logan Circle
4.9 out of 5 average rating, 564 reviews

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.

Top guest favourite
A framed artwork featuring three dogs against a dark backdrop is displayed on a textured brick wall. The image includes a full moon positioned above the dogs. A leather tufted sofa is situated below the artwork, accompanied by patterned cushions.
Apartment in Dupont Circle
4.96 out of 5 average rating, 135 reviews

Lux in heart of DC social scene, free parking!

Unit #2. We have a fun, modern decor that showcases a love of our pet friendly home! One parking spot. There are two bedrooms: the primary and a second bedroom room (that we use as a dressing room) both are small rooms with deluxe memory foam Murphy beds - both with attached full bathrooms. Special note: this is our full-time home. We live here and our personal things remain here throughout your stay. Please think of yourself as close friends who have come for a visit - we’ll do the same!

Superhost
The living area showcases a comfortable gray sofa paired with a matching armchair, accented by a patterned area rug. Natural light floods through the large windows, highlighting a decorative coffee table and stylish wall art. Bar seating is visible in the adjoining kitchen.
Apartment in Penrose
4.88 out of 5 average rating, 256 reviews

Newly Renovated & Modern 1BR Condo - Unit 1

Completely renovated, stylishly furnished condo unit in Arlington, VA just one stoplight from Washington DC, the Pentagon, Clarendon, Crystal City & 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 trains. Comfortably accommodates the traveling professional, those on vacation and is kid friendly.

Guest favourite
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.
Apartment in Annapolis
4.94 out of 5 average rating, 425 reviews

Renovated Apt 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 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 10.

Guest favourite
A scenic view is captured from the balcony, showcasing a blend of rooftops and greenery with a gentle road winding through the neighborhood. The sunset casts a warm hue, illuminating the buildings and trees, providing a serene atmosphere.
Apartment in Chevy Chase
4.97 out of 5 average rating, 134 reviews

BRIGHT 1 BD w/ LARGE BALCONY in PRIME BETHESDA LOC

Location, location, location. Bright one bedroom condo in prime downtown Bethesda location with designer furnishings. One of the best 1 bedrooms in the building with the best balcony location right off Bethesda Row. Easy walking distance to Metro and includes one of the best underground parking spaces by elevator. Lobby was recently renovated and gym has all new gym equipment. NOTE - key is provided through a lockbox (rather than in person) and will need to be returned back to lockbox.

Top guest favourite
A welcoming living area features a light-colored sofa and an upholstered armchair, positioned around a central wooden coffee table. A unique area rug with intricate patterns adds warmth. The kitchen area, visible in the background, is equipped with modern appliances and a breakfast bar with stools.
Apartment in Annapolis
4.96 out of 5 average rating, 110 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, BR2 with Full. LR w/sofa

Guest favourite
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.
Apartment in Annapolis
4.97 out of 5 average rating, 118 reviews

Welcome to Annapolis-very 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.

Top guest favourite
A round swimming pool is centrally located, surrounded by lounge chairs and a wooden deck. Sailboats are visible in the marina beyond, with lush greenery lining the water's edge. An umbrella provides shade over a seating area, adding to the tranquil outdoor setting.
Apartment in Annapolis
4.96 out of 5 average rating, 313 reviews

Annapolis Waterfront Condo - Unit #: A-203

BOOK NOW SUMMER 2026 SPRING and FALL BOAT SHOW 1 bed/bath condo, sleeps 4 max, covered comfortable water facing deck, reserved parking! .5 mile walk to dwnt Annapolis and the Naval Academy, 1.9mi to the Navy Football, .25 mi. to boatshows! Great views - 2nd flr. condo (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 location.

Superhost
A cozy living area is highlighted by a large 65" TV on a white media console, flanked by tall speakers. A soft sofa is paired with a round dining table set for two, complemented by a potted plant and framed artwork on the wall.
Apartment in Petworth
4.91 out of 5 average rating, 234 reviews

New, Sunny, 2BR - Parking, Patio, Firepit

Sunny, newly renovated, pet friendly 2BR apartment available in the trendy Petworth neighborhood with full designer kitchen and bathroom, home theatre surround sound setup with 65" TV, washer/dryer, and permit parking included! Safe, friendly, picturesque neighborhood; it's tree-lined streets are mere blocks from the award winning restaurants on Upshur St. Located only .9 miles from the Petworth and Fort Totten Metro stations, and 3 miles from the White House and downtown DC.

Guest favourite
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.
Apartment in Annapolis
4.88 out of 5 average rating, 117 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.

Top guest favourite
A cozy sleeping area is featured with a spacious bed adorned with an abstract circular accent design. Soft blue pillows enhance the bedding, while warm orange walls add vibrancy. Soft lighting from two bedside lamps illuminates the space, complemented by a framed artwork and a small wardrobe.
Apartment in Hampden
4.94 out of 5 average rating, 193 reviews

Sun House in Hampden Private Apartment no stairs

Artists and creatives are welcomed! Stay at our 1920 rowhouse with its mix of 70's era textiles and contemporary style. Only two steps to a welcoming porch and keyless entry to our foyer/Shared hall. Straight ahead is Sun Apartment, private studio with stocked kitchen, comfiest 5 star bed, private bath, laundry and back yard access. Yoga room/ office located in shared hall. No need for a car in the heart of Hampden's Avenue just a block away. LGBTQ+ friendly

Top guest favourite
Apartment in Annapolis
4.98 out of 5 average rating, 103 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.

Popular amenities for Annapolis apartment rentals

When is the best time to visit Annapolis?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. price$222 SGD$201 SGD$208 SGD$219 SGD$257 SGD$234 SGD$238 SGD$248 SGD$244 SGD$280 SGD$219 SGD$212 SGD
Avg. temp1°C3°C7°C13°C18°C23°C26°C25°C21°C14°C8°C4°C

Quick stats about apartment rentals in Annapolis

  • Total holiday rentals

    Explore 20 holiday rentals in Annapolis

  • Nightly prices starting at

    Annapolis holiday rentals start at $77 SGD per night before taxes and fees

  • Verified guest reviews

    Over 2,110 verified reviews to help you choose

  • Family-friendly holiday rentals

    10 properties offer extra space & child-friendly amenities

  • Holiday rentals with a pool

    10 properties feature pools

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    20 of Annapolis holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Annapolis rentals

  • 4.8 Average rating

    Annapolis stays are highly rated by guests – averaging 4.8 out of 5!

Destinations to explore