Vacation rentals with a pool in Parole

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Parole

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

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Top guest favorite

A modern kitchen area showcases a wooden countertop with two stools, complemented by a colorful floral arrangement. In the background, a cozy sleeping area features a quilted bedspread. Natural light streams through multiple windows, illuminating the space.

Guesthouse in Annapolis

5 out of 5 average rating, 160 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

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.

Apartment in Upper Marlboro

4.95 out of 5 average rating, 135 reviews

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

Have fun and relax at this stylish oasis! Packed w/ amenities. Huge Pool w/multiple cabanas, HOT TUB, trampoline, playground, axe throwing, pool/ice hockey table, arcade,huge theater room and outdoor projector too, basketball court, grill, spa/library with sauna and full gym!! 5 comfy beds. Rooms split for privacy. Open kitchen/dining/living room. Cold DeerPark water fountain. Basement apt so there is some movement noise. Updated bath and an outdoor shower. 20 mins from Downtown DC & 6Flags.

Top guest favorite

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.

Apartment in Stevensville

4.98 out of 5 average rating, 278 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

The image highlights a spacious backyard featuring a pool with bright blue water. A well-maintained fence surrounds the area, while a two-story house with multiple windows and a staircase is visible in the background. Lush greenery and pink flowering shrubs add a touch of natural beauty.

Guest suite in Arnold

4.94 out of 5 average rating, 176 reviews

Coastal Comfort Suite Near Annapolis, Hottub, EV

Hot tub is open for the season. Pool will be open May 12 through Labor Day weekend. 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.

Guest favorite

Two adirondack chairs flank a small table beside an unheated pool, surrounded by a lush wooded area. Sunlight filters through the trees, creating a serene atmosphere for relaxation. The pool is partially shaded, inviting guests to unwind in a private setting.

Guest suite in Arnold

4.88 out of 5 average rating, 136 reviews

The Oasis - Cozy Comfort Close to Annapolis & USNA

Private first-floor guest apartment, a quiet retreat in a lovely residential neighborhood 7.5 miles to downtown Annapolis & USNA. Two bedrooms, living room, mini sit-in kitchen, bathroom, and laundry room. It’s ideal for travelers who want privacy, and a little more space than the usual stay. Sip your morning coffee in the gazebo and unwind after day trips fireside on the comfy sectional. The kitchen is ideal for enjoying light cooking or take outs. Comfy queen sized beds with crisp linens.

Top guest favorite

A fenced-in pool area is surrounded by lush greenery, with tall plants and trees creating a natural backdrop. The pool features calm blue waters, and a small paved pathway leads toward it. A black chair is positioned near the entrance of the pool gate.

Guest suite in Catonsville

4.94 out of 5 average rating, 527 reviews

Rollingside: Two-Room Guest Suite

Two-room guest suite with private entrance located in picturesque Catonsville, MD on a pre-Colonial road originally used for rolling tobacco to the harbor. Downtown Baltimore is 20 minutes away, BWI airport and Amtrak station 15 minutes, and our street is located on a bus route. Beautiful 3.5 mile walk to historic Ellicott City and an hour from Washington, D.C. Individuals and families with children are welcome, but the Airbnb member renting the property must be over the age of 25.

Top guest favorite

A serene swimming pool is illuminated by soft lighting, surrounded by trees. Lounge chairs are positioned beside the pool, offering a tranquil space for relaxation in the evening ambiance. The mid-century modern guesthouse is partially visible among the foliage, enhancing the secluded atmosphere.

Guesthouse in Highland

4.98 out of 5 average rating, 290 reviews

Woodland Retreat

Welcome to our private woodland retreat! This stylish and secluded mid-century modern guesthouse is nestled on five acres in horse country in Highland, Maryland. Totally separate from our owners home, our guesthouse combines the serenity, privacy, and safety you crave with all the conveniences of modern life including: a full bath; kitchenette; internet; and a screened porch with access to our beautiful lighted and heated swimming pool (weather permitting) and adjacent walking trails.

Top guest favorite

Home in Perry Hall

4.99 out of 5 average rating, 99 reviews

Gunpowder Retreat

Unwind and relax with friends & family at this peaceful mid-century modern home. Nestled along the Gunpowder Falls State Park you can enjoy long summer days lounging in the pool under a canopy of trees or take an adventure along the hiking trails easily accessible from the back yard. Although there is no reason to leave this oasis, shopping and restaurants are only a five-minute drive away. Enjoy the beauty of nature without giving up modern comforts in this 4 bedroom, 3 bath home.

Guest favorite

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

4.96 out of 5 average rating, 174 reviews

Celebrate Summer by Your Private Pool

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

Cottage in Saint Michaels

4.97 out of 5 average rating, 164 reviews

La Casita on Harris Creek, St. Michaels

Newly constructed architecturally unique guesthouse inspired by the historic barns of the Chesapeake. Stay in luxury on a secluded 40 acre farm on Harris Creek, be at one with nature & still only 5 min from town's fine dining, shops & charm . With 360 views, TV/Wi-fi, full bath/shower, galley kitchen w/ microwave, fridge w/ice maker, washer/drier, patio fire pit, private pool & kayaks. We comply with Talbot County's zoning that requires a 3 night minimum ST-934-HUD 2020.

Top guest favorite

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

4.99 out of 5 average rating, 214 reviews

The Little Gypsy BoHome

Welcome to our Little Gypsy BoHome on the bay! The house is situated in Southern Anne Arundel County, MD in the quaint waterfront town of Tracy's Landing. Our home sits directly on The Chesapeake Bay with breathtaking views from every window. We offer a saltwater swimming pool, two corn hole game sets, a basketball hoop, beach access, canoe, 2 Paddle Boards, a gas grill, and a steam shower, an outdoor redwood panoramic barrel sauna and a redwood cold plunge!

Top guest favorite

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.

Condo in Annapolis

4.96 out of 5 average rating, 281 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.