Vacation rentals with a pool in Anne Arundel County

5 out of 5 average rating, 156 reviews

A charming guesthouse is depicted, featuring a light-colored exterior with multiple windows and a red accent staircase leading to the upper floor. Cozy seating is provided on the porch, surrounded by greenery and set beside a covered area with a clock and decorative elements.

Guesthouse in Annapolis

Private Art-Filled Guesthouse near Naval Academy

CameronRating, 5 stars3 months ago

Came in from North Carolina for first time in Annapolis and was a great location to the Navy football stadium. Walking distance to great food and local stores. Linda has a great place and was very nice to chat with coming and going from the property. 10/10 stay!

Apartment in Upper Marlboro

A spacious swimming pool is surrounded by lush greenery, with colorful pool floats gently resting on the water's surface. A concrete deck provides access, and a handrail leads into the pool. A large screen for outdoor viewing is positioned nearby.

4.95 out of 5 average rating, 121 reviews

DC Oasis- hot tub, pool, theater/game rm, & more

MichaelRating, 5 stars1 week ago

Very quiet and peaceful home. Jennifer was very helpful and extremely responsive. The home was very clean and spacious, they provide plenty of activities for your entertainment or it’s extremely easy to watch a movie and just relax. The home was exactly like the pictures, check in and out was very easy.

4.87 out of 5 average rating, 132 reviews

Guest suite in Arnold

Cozy Comfort - only 7.5 Miles to Annapolis & USNA

DeborahRating, 5 stars2 weeks ago

A cozy and very clean retreat! I was so impressed with how comfortable and welcoming this place was. There are plenty of windows and sliding glass doors which offered sunlight by just opening the blinds and curtains. Temperature was perfect inside. A fan and heater were provided in each bedroom if extra coverage was needed. We only stayed one night to attend a local music event but wished we had booked the whole weekend! We will be back!

Apartment in Stevensville

A spacious backyard features a large in-ground pool surrounded by landscaped gardens. Comfortable seating areas with shaded pergolas are positioned nearby, offering a perfect spot for relaxation. The house stands in the background, complementing the serene outdoor environment.

4.98 out of 5 average rating, 273 reviews

Boutique by the Bay

MicheleRating, 5 stars5 months ago

Enjoyed our stay and appreciated all of the details like creamer in the refrigerator this morning. Tastefully appointed and very comfortable - exactly as pictured. We were in the area for a wedding and Diane was flexible and communicated throughout the reservation/stay. We would love to go back and stay longer.

Place to stay in Annapolis

An outdoor hot tub features a sleek design with built-in jets, illuminated by soft purple lighting. The surrounding area is draped with white curtains, creating a secluded atmosphere. Seasonal use is indicated, adding a touch of relaxation to the outdoor space.

4.94 out of 5 average rating, 119 reviews

Chesapeake Bay View 3BR/2BA Duplex*Hot Tub*

GregRating, 5 stars2 days ago

Very Peaceful neighborhood Pauls house is very close to the water end of the road with nearly no traffic when we were there. neighborhood is extremely walkable loved having the porch, large gas grill and hot tub next to the home with view of the bay. All 3 rooms had large comfortable beds. house was clean. well kept. There is a retail center about 2. 5 miles away with a GIant" Grocery store and a few doors down a quality wine and spirit shop. My family loved the city of Annapolis and Very Happy we chose to stay at Pauls home.

4.96 out of 5 average rating, 174 reviews

A well-maintained inground pool can be seen surrounded by a spacious deck featuring lounge chairs and shaded seating areas. Lush greenery and trees create a natural backdrop, enhancing the outdoor space’s tranquility with direct views of the water.

Apartment in Arnold

Celebrate Summer by Your Private Pool

JennaRating, 5 stars7 months ago

Absolutely amazing! The place had so much to do whether it was outside or in! Swimming in the pool, hot tub, kayaking and/or paddle boarding on the lake, giant yard games. Inside had a pool table, wide variety of board games, and many streaming services. Brenda was extremely friendly and helpful in many way. She had a binder full of local places for food and things to do! She truly showed us the best of Maryland.

4.98 out of 5 average rating, 64 reviews

A private backyard pool is surrounded by a white fence, featuring umbrellas and lounge chairs on a wooden deck. The water is clear and reflects the blue sky, while the house is visible in the background, creating an inviting outdoor space.

Home in Edgewater

Waterfront | Pool | Hot tub | Beach Access

LarryRating, 5 stars1 week ago

The moment we walked in we fell in love with this place. Clean newly appointed kitchen, open floor plan, fireplace, pool table, big TVs, children’s games, toys, and wonderful view of Big Pond. Great for bird watching. Beds were great, everything labelled and organized very smartly. Quick response to communications. We cooked a big meal and the kitchen was nicely stocked.

4.99 out of 5 average rating, 206 reviews

A serene outdoor area features a saltwater swimming pool surrounded by comfortable seating, including wicker chairs and side tables. Lush greenery frames the space, with a view of the water beyond. Lanterns are placed around the pool for added ambiance.

Home in Tracys Landing

The Little Gypsy BoHome

ToddRating, 5 stars2 weeks ago

The place was perfect, clean, homey, comfortable and really unique. Loved the pool, cold plunge, sauna, screen porch. We had everything we needed from fresh flowers and cookies to convenient multiple charging stations by the beds. Loved the outdoor lighting and overall coziness of this place. Quiet and peaceful, sounds of the water lapping the shore, beautiful place to drink morning coffee and watch the sunrise. Also found some great sea glass on the beach!! Love, love, loved staying here :)

A serene pool area is framed by lush planters and a wooden railing. Comfortable lounge chairs are arranged around the pool, with several umbrellas providing shade. Sailboats are anchored in the marina beyond, under a clear sky illuminated by the setting sun.

4.96 out of 5 average rating, 272 reviews

Annapolis Waterfront Condo - Unit #: A-203

CarolineRating, 5 stars1 week ago

The condo was great, and I felt right at home as soon as I walked in the door. I was very tired after a day of sightseeing, and the combination of a very comfortable bed and a quiet neighborhood made for a good night of sleep. The location is walkable to all of the sights in Annapolis. Jane is one of the best hosts that I have stayed with. She messaged me with very clear instructions to get into the unit, and checked in from time to time to make sure that I had everything I needed. I would love to stay with her again.

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What guests are saying

Rare Find 5 Star, No Cleaning fee, Salt Water Pool

5 out of 5 average rating, 37 reviews8 months ago

Katie’s place was a wonderful place for a weekend reunion with friends. The house was clean, comfortable and pretty - exactly as advertised and as shown in the pictures. The beds were comfortable and the kitchen well-stocked. The outdoor garden and pool were lovely and had lots of comfortable seating areas. The house was an easy drive to Annapolis for restaurants and shopping but had a great movie watching set up that would be great for a rainy day. Nearby nice grocery store.

Cottage in Arnold

What guests are saying

Updated North Beach Cottage: Pet Friendly!

4.75 out of 5 average rating, 32 reviews4 months ago

House is very cute and inviting. Couch was a little uncomfortable. Was able to host Thanksgiving for my family. My adult children stayed the whole time too. Which they enjoyed their private rooms. Close to restaurants and in a nice friendly area. Host was very responsive. I would recommend to anyone and would stay again.

Cottage in North Beach

What guests are saying

Annapolis Waterview Apartment

5 out of 5 average rating, 12 reviews4 months ago

This is one of our favorite Airbnbs due to proximity to activities and layout. Had great amenities for our month-long stay. Host was responsive and communicative any time we had a question. We would love to come back in the summer to enjoy the rooftop pool and view. Location- Best part! Located on the waterfront, great for walking to Main Street, restaurants, and exploring museums. You have a peek-a-boo view of the top of the state capital building from the living room window. Bedrooms- super comfy bed, couch/pull out bed in living room was convenient and very comfortable Kitchen & bathroom- Loved the open floor plan, very well stocked with dishes & shower got hot fast with great water pressure. Parking- loved having the dedicated parking and street parking

Apartment in Annapolis

What guests are saying

3-Level Luxury Near BWI, Casino, Mall & More!

5 out of 5 average rating, 9 reviews2 weeks ago

Absolutely gorgeous property - 8 of us came for a wedding in DC but using BWI for our airport - we had an very early flight out this morning (5:30am) and this location was literally 10 minutes away. Host was extremely responsive when I needed to reach out for an issue that had with Airbnb - she stayed on top of things and kept me informed. I would absolutely stay at this location again should the need arise.

Townhouse in Hanover

What guests are saying

Cozy Retreat in Laurel, MD!

4.88 out of 5 average rating, 8 reviews5 days ago

Here's a review you can use: --- I am incredibly grateful for the accommodations provided during my transition as I awaited my new home. The extended time offered me the flexibility and peace of mind I needed during this period. Thank you for your understanding and support. Wishing you all the best in your future endeavors! Rita Case

Apartment in Laurel

What guests are saying

Annapolis Garden Suite

4.94 out of 5 average rating, 89 reviews1 month ago

We enjoyed our stay at Laura's! My wife and I and our two small dogs stayed for a week and it worked out great. The kitchen was well-stocked, there were plenty of linens and pillows, and plenty of room. The dogs enjoyed the back yard and walks in the peaceful, tree-lined neighborhood. Laura was extremely responsive, communicative and friendly. The only issue that we had was that it was a bit tough walking down the stone path in the dark (my wife is still not 100% due to back surgery last year), but we communicated this concern to Laura, and by the next day, there was additional solar pathway lighting in place, which worked well. We would definitely stay there again!

Guest suite in Annapolis

What guests are saying

Cozy cottage with riverview and pool

4.98 out of 5 average rating, 40 reviews1 month ago

My stay was very peaceful—I stayed for six weeks, and everything went perfectly. The house is exactly as described in the listing. The waterfront view brought me peace and tranquility, allowing me to focus on my work. Cindi is an amazing host; she was always available throughout my stay, making sure I felt at home. I highly recommend this cottage for both short- and long-term stays. It was the perfect choice for the transition period I was going through. Thank you, Cindi, for the wonderful stay!

Guest suite in Arnold

What guests are saying

Nautical Newport Beautiful Water Front, Townhouse

4.86 out of 5 average rating, 22 reviews5 months ago

Great location! The master bedroom on the top floor has a great view of the yacht club and water below. Living room with open kitchen and large windows allow for a great hangout with beautiful views both day and night. Close to everything in downtown Annapolis but away from the traffic and main highway so very quiet. Host was very responsive and messaged to check on us before check in. Two parking spots available; one is under the building so recommend against bringing two big vehicles but street parking not too hard to find.

Townhouse in Annapolis

What guests are saying

Garage loft hideaway

5 out of 5 average rating, 15 reviews2 weeks ago

Mark is a very thoughtful host. He even picked me up and gave me a ride to the new place. Once there, he made me feel welcome and was right on top of anything I might need. Mark is a friendly, thoughtful and proactive host. Highly recommended and deserves the highest rating as well. 5 stars. Thanks Mark

Loft in Glen Burnie

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Popular amenities for Anne Arundel County rentals with a pool

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Free parking on premises

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House rentals with a pool

4.86 out of 5 average rating, 58 reviews

The entrance of the home features a set of brick steps leading to a solid front door. Flanking the door are two large windows, allowing natural light to brighten the entryway. The exterior showcases a warm brick facade, creating an inviting first impression.

Home in Pasadena

Beautiful Home Near Beach and Patapsco River

EvaRating, 5 stars3 weeks ago

This home is really nice! We stayed there because our daughter was getting married at a venue about 5 minutes away from the home. It was perfect! Plenty of space for our family and was great for the bridal party to get ready! Nice open floor plan. The beds a bedrooms were very large with comfortable beds. The home was well equipped. The outdoor area was nice and I’m sure the pool is nice in the summertime. Thank you for sharing your home with us on this very special occasion.

5 out of 5 average rating, 14 reviews

The backyard features a well-maintained lawn with colorful blooming flowers, surrounded by lush greenery. A hot tub is positioned nearby, and outdoor seating includes a set of chairs arranged around a fire pit. The house is visible in the background, with a spacious screened porch.

Home in Edgewater

Modern 4 bed | Swim spa | Chesapeake Bay

StephenRating, 5 stars6 months ago

10/10, 5-star experience. Christine and Will were wonderful hosts and their home was amazing. Don’t scroll past this listing!

4.94 out of 5 average rating, 16 reviews

Home in Deale

Modern Bay Dream

Olani Rating, 5 stars2 months ago

Rick was very supportive and his communication was superb. Great host with a beautiful cozy home. 5 star all across the board.

4.81 out of 5 average rating, 21 reviews

A serene outdoor area features a curved swimming pool surrounded by natural stone. White flowers are arranged nearby, and large windows reflect views of the waterfront. The house has a gabled roof and a screened porch, ensuring a blend of comfort and nature.

Home in Edgewater

South River Beach Front House

TammyRating, 5 stars6 months ago

Great location, beautiful home that was very comfortable.

4.93 out of 5 average rating, 80 reviews

Home in Bowie

Luxury 4 Bedroom - Pool/HotTub/Fire Pit

JessicaRating, 5 stars4 days ago

We had an amazing stay! Tons of space, amazing backyard and more. Perfect for a relaxing get away.

5 out of 5 average rating, 15 reviews

The exterior of the home is surrounded by trees, highlighting a private pool and spacious deck. Wood decking flows around the pool area, enhancing the connection to nature. Multiple levels of the house are visible, showcasing large windows and a variety of outdoor seating spaces.

Home in Severna Park

Luxury Home with Pool for 20

JanetRating, 5 stars2 weeks ago

This was a great place for our family of 13 to stay during the weekend of our niece's wedding in Baltimore. The home has plenty of large common areas, dining space, and super comfortable beds - even the queen-size bunk beds on the lower level had high-end mattresses. The kitchen is well-equipped. We had 4 additional family members drop in for dinner on our last night there, and it was no problem preparing food for, and serving, 17 people. Everyone was happy with this choice for our accommodations.

4.71 out of 5 average rating, 69 reviews

The image features a serene backyard area showcasing a pool surrounded by a stone patio. A wooden table with chairs is positioned nearby, while a two-story house is visible in the background, complemented by greenery and an outdoor staircase.

Home in Annapolis

Bay Poolhouse

KimberlyRating, 5 stars3 months ago

We really enjoyed staying here. It was a spacious home and we love the community. We were in town visiting family and It was so convenient being so close to family and friends. Very comfortable

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Condo rentals with a pool

A spacious living area features comfortable leather seating, a large smart TV, and artistic wall decor. An anchor-themed throw pillow adds character, while natural light flows in through the expansive windows, highlighting the warm hardwood floors and cozy atmosphere.

4.57 out of 5 average rating, 7 reviews

1BR water-view condo with rooftop pool & balcony

BennettRating, 5 stars2 weeks ago

First and foremost, Vacasa were extremely responsive to an issue that arose. The moment that I notified them of a problem with the unit (which wasn’t really their fault, nor ours), they moved quickly to resolve the issue. A+ there. Apart from that, the unit was great. Very clean, tastefully appointed and decorated. Only a 15 min walk to downtown, but there are other great restaurants even closer. Only negatives were minor: the view of the water was non-existent from inside the unit; the platform bed in the main BR may be too high for anyone with mobility issues (bring a stool); the other beds (a fold-out couch and a Murphy bed) don’t really offer any privacy; and the pool (that is literally in the title description) was inaccessible. I realize it’s not really pool season yet, but it WAS warm enough to swim when we visited, and my young daughter was looking forward to it. I just would’ve appreciated a heads-up in the ad that the pool was actually closed.

The kitchen features aqua and white cabinetry, complemented by a spacious granite countertop that houses four high-backed chairs. Stainless steel appliances are visible, with a window allowing natural light to enhance the warm tones of the space.

4.77 out of 5 average rating, 81 reviews

Amazing Views from Spa Creek 2BD Condo with Pool

ShellyRating, 5 stars3 months ago

Loved our stay at Marie’s condo. The place was clean, well-stocked and cute. Comfortable beds. Unbelievable view of the water and State House. A 10!

A comfortable living area is displayed, featuring a sectional sofa and a coffee table on a textured rug. A wall-mounted television is visible, alongside a stylish fireplace. The open layout connects to the kitchen area, with warm lighting illuminating the space.

4.99 out of 5 average rating, 73 reviews

Charming Annapolis Waterfront Condo

AnnaRating, 5 stars1 week ago

We really enjoyed our stay! The place was clean, comfy, and had everything we needed. Jared was super responsive and helpful. I highly recommend.

An aerial view reveals the marina along Spa Creek, showcasing numerous boats and yachts docked in calm waters. The charming waterfront area features picturesque buildings and green spaces, with the nearby drawbridge visible in the distance.

4.2 out of 5 average rating, 10 reviews

Upscale Waterfront Condo Annapolis

LaurieRating, 5 stars36 months ago

What a beautiful setting! As the others have said, it's in the perfect location with a beautiful view of St. Mary's church and the Maryland statehouse dome. Freshly renovated, you'll find a fully-tiled shower in place of the usual tub/shower combo. This is a perfect place for someone who does not like stairs. Easy access in and about the condo complex. The kitchen is fully equipped for anything you'd like to do, if cooking in. There are no curtains in the windows of the living space. There is a shade in the bedroom. The bed is comfortable, as are the sofa and loveseat. My husband and I stayed here for 6 months while our house was being renovated, and we felt quite at home.

An open living area is showcased, featuring a light-colored sofa against a wall adorned with framed photographs. A large rug anchors the space, complemented by a round dining table and chairs. Natural light floods in from large sliding doors leading to a balcony.

4.96 out of 5 average rating, 50 reviews

Cozy Annapolis Condo

JoeRating, 5 stars3 months ago

Host gave an accurate description. Also, gave clear and easy instructions for checking in to condo. Had everything we needed. Comfortable beds! Would highly recommend if you're visiting the Annapolis area.

A comfortable living space features a brown leather sofa and elegant dining table. A decorative sailboat is displayed on a sideboard, with light streaming through window blinds. Potted plants add a touch of greenery to the area, enhancing the inviting ambiance.

4.89 out of 5 average rating, 62 reviews

GREAT LOCATION ON SPA CREEK

LauraRating, 5 stars7 months ago

We’ve stayed here for a few years now. His place is always clean and quiet. Beautiful location and very comfortable.

The rooftop pool features vibrant blue water, surrounded by a spacious deck. Lounge chairs are positioned alongside the pool, providing a relaxing view of the marina and distant town structures. Clear blue skies enhance the serene ambiance of this outdoor space.

4.96 out of 5 average rating, 46 reviews

1st Floor Condo in Annapolis

AllieRating, 5 stars1 week ago

This place was amazing! Great location, you can walk to a lot of great restaurants.

A welcoming living area features a brown leather sofa and a light rug under a coffee table. A large television is mounted on the wall opposite the seating. Natural light enters through a window, complemented by a potted plant and artwork on the wall.