Vacation rentals with a pool in Anne Arundel County

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Anne Arundel County

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Guest favorite

Guesthouse in Annapolis

5 out of 5 average rating, 154 reviews

Private Art-Filled Guesthouse near Naval Academy

Slip under a colorful quilt and get a great night's sleep in a secluded walk-up guesthouse. An intriguing blend of antique curios and Americana populates the room. The result is a comforting space that also has a modern kitchen and updated bathroom. Homeowners on site and available to book your Treetop Getaway! Key code access will be provided. Check in time is 3pm. Check out time is 11am. Contact me via phone or through messages here and I will respond as soon as possible. The guesthouse is in West Annapolis, a residential neighborhood bounded by Weems Creek and the Severn River. It's close to downtown, the Naval Academy, and the Stadium. Quaint shops and restaurants are just around the corner.

Guest favorite

Guest suite in Upper Marlboro

4.99 out of 5 average rating, 108 reviews

Basement Suite in Golf-course Community (DC metro)

A beautiful home in the Beech Tree Lake Presidential Golf Course community. Our cozy, spacious, new, private, basement suite is welcoming you. You can enjoy golfing on beautiful green rolling hills, Luxury Golf Course Clubhouse, restaurant & bar, walking trails around the Lake Presidential and morning coffee on the patio. Easy access to Washington, DC, Annapolis, AFB, Chesapeake Bay, Redskin FedEx Field and Baysox Baseball Stadiums, Six Flags Amusement Park, Show Place Arena & Equestrian Center.

Guest favorite

Home in Shady Side

4.88 out of 5 average rating, 181 reviews

Cattail Landing- Photographer's Waterfront Retreat

"Cattail Landing" Spring is here, with beautiful sunsets, new foliage on the trees, and our nest of Bald Eagles! Take a kayak out after breakfast to explore, or go fishing off our landing. In the afternoon enjoy the magnificent sunsets, a drink on the deck, our outdoor hot tub and/or fireplace. A waterfront retreat on 2 acre in a spacious, charming house on the Western Shore of the Chesapeake Bay. Great for a couples getaway, family reunion, or work from home (w. 1GB hi-speed internet).

Guest favorite

Rental unit in Stevensville

4.98 out of 5 average rating, 272 reviews

Boutique by the Bay

Completely renovated and exquisitely decorated, this one bedroom apartment has a private entrance from the main house and features a modern farmhouse vibe. Fully equipped kitchen with new glass top stove, large walk-in shower and queen sleeper sofa make this perfect for a couple or family. Located 9 miles south of the Bay Bridge, off of Route 8 on Kent Point Road ,this location is convenient for weddings at the Chesapeake Bay Beach Club or Swan Cove. Access to large in-ground pool included.

Guest favorite

Home in Severn

4.85 out of 5 average rating, 135 reviews

Large Home with Pool & 7 bedrooms; sleeps 21

Relax at this large 7-bedroom spacious top-quality home that is ideal for large gatherings where all can be together in one place. All will be comfortable in large open areas both inside (4,125 sq ft, tall ceilings) & outside (1 acre). Enjoy a huge first-class kitchen with all the granite countertop space, cooking & serving supplies you will ever need. Enjoy the large fenced-in backyard with pool, grill, & fire pit. Ideal for family events, quiet getaways, sports teams, & business meetings

Guest favorite

Home in Stevensville

5 out of 5 average rating, 123 reviews

Chesapeake Bay Waterfront ARTectural Home w/ Pool!

Welcome to this most relaxing home for your getaway. Perfect for vacations, retreats, meetings, anything that you can imagine. Travel just 4 short miles from the Bay Bridge to this 2 story home overlooking the Chesapeake Bay. Sunsets galore and constantly changing views of Ships, Sailboats, Osprey, Eagles, Heron and much more. Calm water and strong winds are all beautiful to watch from our two levels. 12' x 52' covered patio on main level and 12' x 52' three season room on the upper level.

Guest favorite

Guest suite in Arnold

4.89 out of 5 average rating, 113 reviews

Cozy Comfort- Fall Getaway- 7.5 Miles to Annapolis

Close to historic Annapolis, our cozy first floor guest apartment of our home in a quiet large single family home neighborhood. 'The Oasis' is private and spacious with 2-bedrooms, a living room, mini sit-in kitchen, bathroom, and laundry room. Close to waterfront restaurants, B & A trail, Sandy Point Public Beach and Park, festivals, shopping, bowling, miniature golf, wineries and more. Our guests are welcome to enjoy some time relaxing in our wooded backyard with gazebo and patio areas.

Guest favorite

Rental unit in Arnold

4.96 out of 5 average rating, 174 reviews

Fall Getaway

Lovely 2 acre waterfront lower level attached apartment with separate private entrance. Exceptional amenities include an inground pool, a pier with kayaks and paddle boards, pickleball and basketball courts, a swing set with a rock wall for kids, a gas grill, and a pool table. This amazing water front home is conveniently located only seven miles from the Naval Academy and downtown Annapolis. We do not host parties or events. Only registered guests are permitted on the property.

Guest favorite

Condo in Annapolis

4.96 out of 5 average rating, 250 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.

Guest favorite

Guesthouse in Stevensville

5 out of 5 average rating, 250 reviews

Waterfront Getaway - View of bay from your bed

Enjoy this newly renovated, waterfront private studio apartment with a beautiful view of the Chesapeake Bay. It's a perfect getaway for anyone looking for rest and relaxation amidst a quiet, breath-taking location. Enjoy swimming in the pool, fishing off the point, sitting around an evening gas fire, visiting any of the local sandy beaches, or simply watching stunning sunsets from a private patio. Ample parking, WiFi, TV, boat-ramp access. One pet is welcome.

Guest favorite

Home in Harwood

4.94 out of 5 average rating, 126 reviews

Luxury Home, Sleeps 15, Private Pool, Close to DC

Stunning 6 bedroom, 5½ bath home on 34 acres with panoramic woodland views and private salt water pool, perfect for that special gathering. Secluded yet just 35 minutes from Capitol Hill and 20 minutes from Annapolis. The home, with its high ceilings, huge windows and expansive decks comprises over 8000 square feet, so there is plenty of room to stretch out. *** IMPORTANT Please send AN INQUIRY with a little about you PRIOR to requesting a booking.

Guest favorite

Guest suite in Arnold

4.94 out of 5 average rating, 151 reviews

Coastal Comfort Suite Near Annapolis, Hottub, EV

Yes, the hot tub IS open! 24/7/365 :-) Ideal for a couple's retreat, this king suite guest room has a massive bedroom with a seating area, mounted TV, and coffee bar with microwave/mini-fridge. An ensuite bathroom provides a luxurious shower with dual shower heads and a spacious closet. The pool and hot tub are seasonal. Please don’t hesitate to reach out with any questions, concerns, or expectations so that we can address them prior to your stay.