Holiday rentals with a patio in Annapolis

The exterior of a charming historic building features a welcoming front porch adorned with seating. Lush green trees and blooming flowers enhance the inviting atmosphere. American flags are displayed, highlighting the traditional character of the neighborhood.

4.99 out of 5 average rating, 152 reviews

Elegant & Authentic Annapolis

Enjoy comfortable elegance in this historic beauty on one of the prettiest streets in Downtown Annapolis--Main Street and the Water only 2 blocks away. This private unit is the full main level with its own eat-in kitchen, living room, front porch and back patio. Bedroom features queen size bed, dresser and walk-in closet. Bathroom has shower/tub and counterspace for your comfort. Street parking is available or public garage parking is a short stroll away. Relish this quiet & convenient location.

ValueOutdoor spacesHospitality

4.95 out of 5 average rating, 255 reviews

Sailboats are moored in a serene marina, with soft waves reflecting the sunlight. The docks are lined with wooden posts, guiding the view to a lush green shoreline in the background. A peaceful atmosphere is created by the gentle ripples and warm evening light.

Home in Edgewater

Annapolis Area Waterside Retreat

This Rhode River home is your perfect getaway to the Annapolis area - whether you’re looking to get away to a unique home overlooking incredible sunsets, a fun weekend with friends along the water, a family trip to the Chesapeake, or a private work retreat away from the bustle of the city, this home has it all. The house is a short drive from DC or Baltimore and unlike any Airbnb this side of the Chesapeake - it is on a 3 acre marina just minutes from Annapolis but private and away from it all!

ViewValueAccess

4.95 out of 5 average rating, 107 reviews

A spacious bed is adorned with decorative orange pillows and flanked by elegant bedside lamps. Framed artwork featuring floral designs hangs above the headboard, complementing the soft color palette of the room.

Home in Fells Point

Luxury Fells Home w/Hot Tub, Poker Room, & Parking

Treat yourself to a luxury getaway with a 6-person hot tub, poker room with record player, and a gorgeously renovated bathroom with a freestanding soaking tub. This opulently decorated, spacious, renovated townhouse is located in the heart of very safe Fells Point. Sleeping arrangements for 6. Blazing fast 1GB Wifi, dedicated work space, 1 street parking permit, 65" Smart TV, and only 3 short blocks (3 min walk) to the bustling Fells Point waterfront. Just far enough to sleep undisturbed!

ValueComfortCheck-in

A spacious living area showcases a comfortable sectional sofa and a leather armchair beside a decorative rug. A modern fireplace is framed by a white mantel, while a large television is mounted on the wall. A view of the stylish kitchen is visible in the background.

4.98 out of 5 average rating, 99 reviews

Downtown Annapolis Luxury House

Our downtown luxury Annapolis getaway is located 1.4 miles from Church Circle, which is the heart of downtown Annapolis. We are walking distance to all the amazing attractions in Annapolis. Our house is a lovely blend of comfort and style, making it an ideal retreat for families, friends, or colleagues traveling together! We are happy to offer early check-in and late checkouts if our bookings allow. Please contact us today and reserve our house for your next Annapolis getaway!

Outdoor spacesValueBathroom

4.92 out of 5 average rating, 121 reviews

The entrance features a welcoming front door adorned with a decorative wreath, flanked by windows with shutters. A small stairway leads up to the door, with a concrete path that is surrounded by greenery.

Apartment in Annapolis

King George Hideaway

Perfect location for all that downtown Annapolis offers, right across from USNA gate 2. Super convenient, park your car and walk everywhere! Lots of shopping, restaurants, tours, cruises & nightlife. The unit is located on the 3rd floor. My place is perfect for couples, solo and business travelers. There is a large living room space with a full pull out couch, tv and dining table. The bedroom has a queen bed with a tv. There is a small full kitchen and updated bathroom.

ViewOutdoor spacesQuiet

4.97 out of 5 average rating, 100 reviews

Annapolis 3 BR Sleeps 8 Waterfront Dock & Firepit

Kick back and relax in this calm, charming newly renovated coastal farmhouse waterfront two-story home with private pier/dock! Gorgeous sunrises! Experience fresh Maryland Crabs & fish caught from your private pier & enjoy the peace, serenity, bay breezes & waterfront green space! Connect to nature and explore Meredith Creek on the Chesapeake Bay by kayak or boat! Super CLEAN & new with water views from dining, living room, kitchen and bedroom! 1.5 miles to the Beach!

ViewOutdoor spacesKitchen

4.98 out of 5 average rating, 117 reviews

Condo in Annapolis

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.

ViewOutdoor spacesAccuracy

4.96 out of 5 average rating, 165 reviews

A living area features a gray couch adorned with decorative pillows against a light wall. A recliner is positioned nearby, and a wall-mounted Smart TV is visible. A dresser with a plant sits below the TV. Natural light streams in through nearby windows.

Condo in Annapolis

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.

ViewValueSleep quality

4.97 out of 5 average rating, 109 reviews

A spacious great room features large windows that offer sweeping views of the water. Comfortable seating arrangements with soft furnishings are complemented by a working fireplace. A staircase is visible in the background, leading to additional living spaces.

Home in Shady Side

Waterfront Sanctuary only 50 Min. From DC/Balt.

New full home renovation with gourmet kitchen, wide open floor plan, multiple guests rooms, and a bunk room that accommodates 12. An inviting space that welcomes any couple or a large extended family. This home sits with only three other homes on a private peninsula and has water access on both sides. It is conveniently located less than an hour from DC and Baltimore on the west coast of the Bay (no need to cross the Bay Bridge).

ViewOutdoor spacesHospitality

A tranquil bedroom features a spacious bed adorned with a patterned throw and neatly arranged pillows. A modern lamp and decorative mirror enhance the ambiance, while natural light enters through a unique shaped window. A soft towel is elegantly rolled on the bed.

4.94 out of 5 average rating, 202 reviews

The Navy House-Walk or Shuttle Downtown! 3 bd

Your family will be close to everything when you stay at this centrally-located home. 3 blocks from the Navy stadium and walking distance to amazing restaurants! Here is your Annapolis home away from home. Our 3 bedroom 2.5 bath bungalow retreat is perfect for 6-7 people wanting to relax and see all that beautiful Annapolis has to offer. There’s also a free shuttle that takes you downtown to the water. Come, enjoy!

ValueOutdoor spacesCleanliness

5.0 out of 5 average rating, 220 reviews

An aerial view captures the waterfront cottage situated on the South River. The property is surrounded by water and greenery, featuring a manicured lawn with a patio area. A private dock is visible, leading from the house to the water, alongside a pool nestled within the landscaping.

Guesthouse in Annapolis

Coastal Waterfront 1 Bedroom Cottage

This waterfront cottage is located 2 miles from Historic Downtown Annapolis and the United States Naval Academy, making it easy to plan your visit. It is located right on the South River in a quiet neighborhood. There is a full outdoor seating and patio area with a grill and fire pit. It has a full kitchen, 1 bedroom, washer/dryer and can sleep up to 4 with the pull-out sleeper couch.

ViewOutdoor spacesGetting around

A modern kitchen is presented with white cabinetry and grey accents. Stainless steel appliances, including a refrigerator and microwave, are integrated. A large island with a light stone countertop serves as a central feature, complemented by overhead pendant lights that illuminate the workspace.

4.87 out of 5 average rating, 109 reviews

Chic Renovation On Fleet Street

We welcome you at our newest listing in the heart of downtown Annapolis . This chic renovation is a stylish landing spot for anything that brings you to downtown Annapolis . We feature an open floor plan, 2 bedrooms, 1.5 baths and a small city patio . Walkable to everything ! Our guests use Hillman city garage for parking ( pay )

Outdoor spacesSolo travelKitchen

Popular amenities for Annapolis Holiday Houses with Outdoor Verandahs

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Apartment rentals with a patio

Apartment in St. Michaels

A bright yellow building features large blue shutters and a welcoming entrance. A sign is placed outside, and vibrant flowers border the steps. In the background, another structure is visible, along with flags proudly displayed.

4.97 out of 5 average rating, 155 reviews

Blue Crab Lodge

Outdoor spacesValueAccess

Superhost

The exterior of a two-story beach house is shown, featuring white siding and dark shutters. A welcoming front porch is visible, adorned with a small American flag. A pathway leads through green grass to the entrance, surrounded by landscaped shrubs.

Apartment in North Beach

4.88 out of 5 average rating, 109 reviews

Spacious Beach House Top Floors - Walk Everywhere!

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Apartment in Sparrows Point

A spacious living area features a large sectional sofa arranged around a central area rug. The open layout includes a kitchen with modern appliances visible in the background. Ambient lighting and ceiling fans enhance the room's comfort and functionality.

4.97 out of 5 average rating, 109 reviews

Safe, quiet neighborhood close to downtown!

ViewOutdoor spacesCheck-in

4.97 out of 5 average rating, 156 reviews

Apartment in Takoma Park

Steps from D.C. | Peaceful 3BR Apt in Takoma Park

Outdoor spacesViewDecor

Apartment in Northwest Washington

A living area features a blue velour chaise lounge sofa and a stylish coffee table atop a light rug. A flat-screen TV is mounted on a wooden cabinet, which contrasts with the white brick walls. Natural light from windows illuminates the space, creating a welcoming ambiance.

4.99 out of 5 average rating, 431 reviews

Blue House by the Zoo- Mt. Pleasant-AdMo-CoHi

Outdoor spacesValueLocation

4.98 out of 5 average rating, 219 reviews

Apartment in Del Ray

Cute room, kitchenette & deck! Heart of Del Ray

ValueOutdoor spacesAccess

Apartment in Columbia Heights

A handcrafted figurine dressed in vibrant colors stands amid a shell chandelier. The figurine is surrounded by colorful shells hanging above. A couple of books are visible on the shelf beneath the window, adding to the decorative ambiance.

4.93 out of 5 average rating, 120 reviews

Casa Culturas

Outdoor spacesViewAccess

Apartment in Upper Marlboro

4.94 out of 5 average rating, 211 reviews

Kone Oasis- hot tub, pool, theater/game rm.

ViewOutdoor spacesNearby

Holiday House Rentals with a Verandah

The front exterior of the home features vibrant, blooming flowerbeds with a variety of blue and pink flowers. Two hanging planters with yellow flowers adorn the entryway, while a charming red door stands out against the yellow walls. A small seating area with dark chairs is visible on the porch.

5.0 out of 5 average rating, 200 reviews

Historic & sunny home steps from USNA/downtown

Outdoor spacesValueCheck-in

A newly renovated home is presented with light grey siding and blue accents. Two spacious decks with white railings create inviting outdoor spaces. Flower beds with blooming plants enhance the entryway, while leafy trees provide shaded areas around the property.

4.98 out of 5 average rating, 106 reviews

Captain’s Retreat! Newly Renovated - Beach House!

Outdoor spacesViewCheckout

4.95 out of 5 average rating, 104 reviews

USNA downtown house with garage parking EV 3bd/2ba

ViewOutdoor spacesKitchen

5.0 out of 5 average rating, 116 reviews

A spacious living area, featuring a small sectional couch facing a TV mounted on the wall. A foosball table occupies the foreground, while a dining nook with a round table and chairs is visible in the background. Soft artificial lighting enhances the relaxed setting.

Home in Crownsville

"Hilltop Hideaway"- Private basement suite

Outdoor spacesViewParking

Superhost

A relaxing hot tub is positioned surrounded by lush greenery and soft grass. Two wine glasses and a bottle are placed on a wooden tray, suggesting a tranquil atmosphere. The bubbling water is gently steaming under a clear blue sky.

4.9 out of 5 average rating, 170 reviews

The Naval Nook 1.3 mi. from Downtown Annapolis

Outdoor spacesValueIndoor spaces

4.99 out of 5 average rating, 140 reviews

A Bullfrog hot tub is situated under a wooden gazebo, with water glistening in sunlight. A plush robe is draped over the edge alongside a straw hat and a rolled towel. A grassy area and wooden privacy fence complete the serene outdoor setting.

Home in Cape St. Claire

Beach Access, Hot Tub, Pet Friendly, Fully Fenced

Outdoor spacesViewParks

4.96 out of 5 average rating, 119 reviews

Home in Edgewater

Waterfront Cheerful 6 BR Home with Private Pier

ViewOutdoor spacesDecor

4.94 out of 5 average rating, 110 reviews

A single-story home is featured with a light grey exterior. A wooden front door complements the facade, while a short pathway leads to the entrance. Lush green grass surrounds the house, and trees provide a backdrop against a clear blue sky.

Home in Riviera Beach

Cheerful 2 Home

Outdoor spacesViewQuiet

Holiday condos with a patio

4.97 out of 5 average rating, 126 reviews

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.

Condo in Annapolis

Annapolis Condo-1 bedroom King

Outdoor spacesValueCheck-in

5.0 out of 5 average rating, 124 reviews

A spacious living room features two comfortable armchairs positioned near a round coffee table, which holds a decorative bowl and a selection of books. Warm light from a floor lamp complements natural light streaming through the large window, with framed artwork enhancing the walls.

Condo in Capitol Hill

Attractive one-bedroom unit on Capitol Hill

ValueOutdoor spacesComfort

Condo in Northwest Washington

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.

4.9 out of 5 average rating, 276 reviews

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

ValueOutdoor spacesLaundry

4.95 out of 5 average rating, 192 reviews

A bright living room features a textured brick wall and a cozy gray sofa adorned with decorative pillows. A glass coffee table sits atop a soft rug near a modern armchair. Natural light fills the space through large windows, enhancing the inviting atmosphere.

Condo in Capitol Hill

Light-filled Private Oasis / Close to Capitol Bldg

Outdoor spacesValueSleep quality

Condo in Columbia Heights

The living area features a comfortable sofa adorned with decorative cushions, facing a television set atop a wooden console. A round coffee table is centered on a patterned area rug, complemented by a decorative pouf. Natural light enters through a window, softly illuminating the space.

4.94 out of 5 average rating, 113 reviews

Cozy Condo in Columbia Heights DC, with parking!

ValueOutdoor spacesSolo travel

4.87 out of 5 average rating, 233 reviews

A small dining setup is present featuring a round table and two gray chairs. A framed black-and-white photograph decorates the wall, adding a modern touch. Natural light enters from a nearby window, illuminating the clean and simple design.

Condo in Capitol Hill

Sunny Apartment in Historic Capitol Hill

ValueOutdoor spacesTV

4.88 out of 5 average rating, 108 reviews

A modern studio space is presented, featuring a spacious bed with a dark comforter. A large wall-mounted television is positioned across from the bed, with a wooden media console below it. The kitchenette is equipped with white cabinets and stainless steel appliances, adding a functional element to the inviting layout.

Condo in Mount Vernon

Modern Mt.Vernon studio in great central location

ViewValueGetting around