
Family-friendly vacation rentals in Parole
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Parole
Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

New Loft w/South River view from treehouse deck!
Enjoy the quiet Sylvan Shores neighborhood and a view of the South River and bridges in this new modern apartment that has a treehouse style deck for relaxing and enjoying the outside. The unit is served by a separate entrance and free street parking. Bring your kayak or stand-up-paddleboard, or try your luck at fishing! The TV is upgraded to a 55". Downtown Annapolis is just 6 miles away and offers cultural attractions, bars and restaurants, historical tours and access to the Naval Academy.

Old Bay Bungalow
This in-law apartment located in the lower level of my occupied home is just moments outside of Annapolis, mere blocks from the Magothy River. I enjoy inviting guests into the space, and take pride in treating new friends like family. Come rest your weary bones in your private retreat with its own separate entrance, relaxing sunporch, and stocked kitchenette. Reach into the fridge and enjoy cold soda or a local beer on me! Sit around our fireplace and relax. Settle into the Old Bay Bungalow!

4 bedrooms, 7 beds, 3 bath completely updated
Not your typical Airbnb. This is our vacation house too and we have it stocked so you can enjoy all of the amenities of home, without having to bring them yourself. Full kitchen with fresh coffee beans, K cups, and tea provided for starters. Breakfast starters provided too. Everything you need if you want to cook. Games for inside (including PS5), and backyard games too. 3 bedrooms on ground floor so no constantly having to go up and down steps. We love our place and know you will too.

Calico Cottage Guest House, king bed, free parking
Cute-as-a-bugs ear West Annapolis guest cottage just 1.5 miles from the Navy Stadium and less than 2 miles from Academy's Gate 8. Cottage features: high speed WiFi, EZ free parking, washer & dryer, kitchenette, air conditioning, self check-in and laptop friendly workspace. Park 10 feet from front door. Only 1 step to enter. No stairs to negotiate while carrying luggage! 15 min. walk to Weems Creek with scenic, serene waterviews and a few more minutes walk to popular Bean Rush Cafe.

Spacious 3 Bedrooms House+Patio+Playground
Spacious 3 bedrooms house with functional patio + private playround located in Edgewater, only 15 mins drive to downtown Annapolis. Fully equipped with designer furnitures, with a sense of home! Huge dining room and fully functional kitchen, perfect to enjoy a great evening with your friends and family! Bedrooms are equipped with your own desks if you want to do some works even in your vacation. Easily fit 2 cars in private driveway. Very quiet neighborhood with proximity to everything!

Lil’ House - A Serene Tiny Home Experience
Newly renovated, immaculate two room tiny home. A stand-alone gem nestled against a wooded backdrop - well back from the main home - and wrapped in a huge, teak-furnished, blue stone patio with fire pit situated in a sunny opening in the mature tree canopy. Super comfy queen Murphy bed offers easy conversion of the well lit and modern main living space from living room & kitchen by day to main sleeping quarters at night. The adjoining room is a well appointed full bath and dressing area.

Annapolis Garden Suite
Welcome! We’re tucked away on a forested residential street, roughly a 7 minute drive from restaurants, coffee shops and all that Annapolis has to offer. 15m from the coast, 30m from Baltimore and 35m from DC. Tl;dr: this is a private ground-level guest suite with 3 beds, 2 bedrooms, 1 desk (optional standing desk), 1 kitchen with oven, dishwasher + Nespresso/pour over, 2 tvs, laundry room with washer/dryer, fast wifi, a pool, patio and a forest view. We live on the top floor.

Chesapeake Comfort, Annapolis.
Veteran Superhost! Annapolis Bungalow Home that is professionally cleaned and is a full time Airbnb. I have been a Superhost with my listings for over 5 years. Walking distance to Navy Stadium and to Park Place where you can jump on the trolley and take a ride through town.There is a kayak/paddle launch at the bottom of the street. Enjoy the spacious backyard deck and yard. Bring your kayaks and store on our rack and walk it down to the launch.

Coastal Comfort Suite Near Annapolis, Hottub, EV
Our pool is closed for the season; however, our hot tub is open! Ideal for a couple's retreat, this king suite guest room has a seating area, mounted TV, and coffee bar, microwave, and mini-fridge. An ensuite bathroom provides a luxurious shower 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.

Garden View, a spacious 1 bedroom with loft.
Relax and unwind at this peaceful and charming retreat, nestled in a quiet neighborhood. Located just minutes from Route 50, I-95, and Downtown Annapolis, Garden View is ideally situated for exploring Naval Academy sports, the Renaissance Festival, Boat Shows, and golf at The Preserve. If you prefer staying in, the fully equipped kitchen and free Wi-Fi make it easy to work or cook from the comfort of your space.

South River Park Apartment
Located minutes from Annapolis, the in-law apartment offers access to Baltimore and DC in under an hour. The apartment offers its own entrance, full kitchen, one bathroom, one bedroom, tile floors, pullout sofa, Wifi, and parking. The apartment is registered with the Anne Arundel County Dept. of Inspections & Permits, #STR-15, for short term rentals.

Historic Downtown in-law suite
This special place is close to everything. One block to the Naval Academy and one block to all the historic and downtown attractions. This in-law suite has a queen bed, full bath, sauna, kitchenette, seating area, and desk/dining table. Welcoming separate, quiet entrance with access to a lovely patio with seating and firepit.
Popular amenities for Parole family-friendly rentals
Family-friendly home rentals with a hot tub

Cozy Retreat: Immaculate Clean, private place

Pet Friendly Bright In Law suite w Outdoor HangOut

Charming Annapolis Water View Home

Beautiful 2BR/1BA Renovated Condo near DC

Celebrate Summer by Your Private Pool

TheAzalea: Cozy, private basement suite w/ jacuzzi

Luxury Oasis - hot tub, fire pit, fully fenced

Cozy waterfront getaway on the Bay
Family- and pet-friendly home rentals

Quiet Cozy 1 Bdr Apt at BWI Airport

* Beautiful Oasis w/ No Detail Spared

Private guest suite in a newly remodeled home

Renovated Apt In Historic Dist w 2 Parking Spots

Relaxing Water Views - Mill Creek Cottage

Carriage House near Navy Stadium, parking, pets

Charming Annapolis Retreat with Hidden Wine Room

Fox Cottage *Pet Friendly*
Family-friendly home rentals with a pool

Red, White & Waterview Studio Apt with pool

Private Art-Filled Guesthouse near Naval Academy

#3 Foggy Bottom/Georgetown Apartment

Sophisticated Studio Apartment, Metro DC

Cozy, Cute and Clean rowhouse w/ 2 Masters!

Rollingside: Two-Room Guest Suite

Waterfront Farmhouse Meets Modern Luxury

Patuxent River View
Quick stats about vacation rentals that are family-friendly in Parole
Total rentals
250 properties
Nightly prices starting at
€ 51 before taxes and fees
Total number of reviews
10K reviews
Pet-friendly rentals
90 properties allow pets
Rentals with a pool
10 properties have a pool
Rentals with dedicated workspaces
150 properties have a dedicated workspace
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- Family-friendly rentals Anne Arundel County
- Family-friendly rentals Maryland
- Family-friendly rentals United States
- Nationals Park
- The White House
- National Mall
- Georgetown University
- M&T Bank Stadium
- District Wharf
- Oriole Park at Camden Yards
- Smithsonian National Museum of Natural History
- Betterton Beach
- National Museum of African American History and Culture
- Hampden
- Sandy Point State Park
- Arlington National Cemetery
- Georgetown Waterfront Park
- Caves Valley Golf Club
- National Harbor
- Washington Monument
- Great Falls Park
- Crystal Beach Manor, Earleville, MD
- Six Flags America
- The Pentagon
- Patterson Park
- Smithsonian American Art Museum
- Library of Congress