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

Relaxing Water Views - Mill Creek Cottage
Eclectic three level water view cottage in unique wooded location overlooking beautiful Mill Creek. Minutes from downtown Annapolis and the US Naval Academy; walk to Cantler’s Riverside Inn for crabs, convenient to US 50 and the Bay Bridge and Eastern Shore. Due to the stairs and loft, this accommodation may not be appropriate for toddlers and the mobility challenged Parties are not permitted. Please note that there is no water access on the property, but there is nearby public water access.

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!

Pool House -No Contact 24/7 Self Check-In- Private
Secluded Tiny Guest House Retreat with Private Pool – Near Baltimore & Annapolis As you pull into the driveway, the city noise melts away—replaced by the serenity of trees and the inviting sparkle of your private in-ground swimming pool. This 320 sq. ft. Pool House is cozy. A large window fills the space with natural light to the ever-changing views of the wooded setting. Completely private stay – no shared spaces Self check-in with no contact Private pool exclusively yours during your stay

Waterfront Cheerful 5 home
Welcome to this brand-new relaxing home with an 80ft pier by the water for your getaway. It is perfect for vacations, retreats, meetings, family reunion and business travelers’. Create memories and beautiful experiences while enjoying the beautiful 5 Bedrooms, 4 Bathroom .one bedroom on the first floor and four beds on the second floor. House has a large custom kitchen. It is located 11 miles from BWI airport,11.8 miles from downtown Baltimore,17 miles Naval academy and 40 miles to the DC .

Secluded acre near BWI and Baltimore
Secluded suburban acre 8 minutes from BWI Airport, 15 minutes from Baltimore's Inner Harbor and from Fort Meade, and 45 minutes from Washington DC. Private house attached to host house has 1220 square feet of cozy comfort--4 times the size of a hotel room! House includes 2 bedrooms (one queen, one double), 1.5 baths, living room, foyer, dining room, full kitchen, and washer/dryer. The one-acre lot has hundreds of trees and is great for pets. Level 2 charging station is good for all EVs.

Annapolis Garden Suite
Welcome to our oasis, tucked away on a forested residential street. ~7 minutes from the Annapolis Towne Centre, ~15m from the coast, and ~30m from Baltimore and DC. Tl;dr: This is a private ground-level guest suite. Inside, you’ll find 3 beds, 2 bedrooms, 1 desk, 1 kitchen with a dishwasher, oven, Nespresso/pour over, 2 TVs, a laundry room, fast wifi, a pool, patio and a forest view. We live on the top floor (separated by stairs and a deadbolt; no shared indoor spaces; separate entrances).

Home away from home
This is a small house with private parking close to Baltimore and Annapolis. I have one queen size Murphy bed, one single pull out couch. It has an updated kitchen, updated bathroom, walk-in closet, Internet and heating and cooling. I also have a pellet stove. my kitchen is fully stocked with dishes, knives, forks, pots and pans. The bathroom has towels and rugs. I tried to add all the amenities to make it as comfortable as home. Look at pet rules under the other things to note section.

Ft. Smallwood Overlook. Waterfront with Kayaks!
Delightful cottage at the confluence of Rock Creek, Patapsco River (Baltimore Inner Harbor) and the Chesapeake Bay. Adjoins Ft. Smallwood Park with its private coves and beaches. Secluded setting features water on 3 sides with beautiful relaxing views. Teeming with wildlife: ducks, geese, egrets, osprey, eagles, deer, foxes and other. Convenient to Annapolis, BWI Airport, Baltimore & Washington, D.C. Walk to the park. Cast a line, catch what you may! Total renovation 2018-2019.

Country House on the Bay
My home (owner occupied/shared) sports a spectacular view of the Chesapeake Bay with access to the beach. The home is spacious with a family, dining, breakfast and living room. Significant kitchen space is available with all of the cookware and place settings you would need for a meal. The master bath is handicapped accessible. My deck can be used for cookouts and relaxation. Hosting a gathering - lets talk- my home is perfect for celebrations. Close to Annapolis & Naval Academy.

Sea Dreamer
Tranquil TIDAL, riverfront, split-level home. Rent the spacious lower level with 2 bedrooms, full custom kitchen, large living room (TVs, sleeper sofas, massage chair), dining/office space, and full bath with luxury shower. Includes soaps, towels, hairdryer. Kitchen equipped for cooking, includes full fridge. Patio with grill/fire-pit, lounging and kayaks. Convenient: 25 min to BWI, 45min to Annapolis, 60min to DC. Ideal for relaxing and exploring!

Park View near BWI, Light Rail and I97.
Beautiful all new, cozy 1950's home completely remodeled. All hardwood floors, new paint, new kitchen, bath, everything! Clean and quiet home/duplex with a front porch to enjoy morning tea/coffee or evening cocktails. Huge empty park across the street to keep things still. Very quiet neighbors. Owners are onsite and live in the back house for any issues or questions. PLEASE NOTE: We require a 2-night minimum stay on weekends.

The Crab House - a Private, Waterfront Guest House
Privacy abounds at this waterfront one bedroom guest house with breathtaking water views throughout. The Crab House is located in the boating community of Stoney Creek. It is 20 minutes from BWI airport, 30 minutes north of Annapolis, 20 minutes from Baltimore's Inner Harbor and an hour from DC. Feel free to bring your boat, jetski, kayak or paddleboard, or use the kayak or paddleboards we have onsite. AA County 144190
Popular amenities for Pasadena family-friendly rentals
Family-friendly home rentals with a hot tub

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

Beautiful, quiet waterfront house. Lots of room!

Cottage on Solitude Creek, Hot Tub, Pool & Firepit

Waterfront Cottage@ChesapeakeParadise Hot Tub/Dogs

Waterfront, Dog-friendly, Hot Tub, Gas Fireplaces

Charming City Oasis. Walk to harbor, eateries.USNA

Parkfront Hot Tub Haven for Families & Pets

Celebrate Summer In Your Private Pool & Hot Tub
Family- and pet-friendly home rentals

Nautical Retreat 6 Guests • 3 BDR • 2 Baths

Rancher by Wash/Balt/Annap w/pool table, Kit, Deck

3BR Townhome Arcade + Kid Gear | Near Ft Meade/BWI

Historic Gatehouse Master Suite

Watch Deer from a Farm Cottage

Waterfront-View of Bay from your Bed

Garden View, a spacious 1 bedroom with loft.

Large yard - Quiet area - 15 min to DC
Family-friendly home rentals with a pool

Private Art-Filled Guesthouse near Naval Academy

Rollingside: Two-Room Guest Suite

Chesapeake Bay View 3BR/2BA Duplex*HOT TUB*

A home away from home

1st Floor Condo in Annapolis

LUXURY RESORT at National Harbor -1 BEDROOM DELUXE

La Casita on Harris Creek, St. Michaels

Beautiful Kent Island Getaway with Pool
When is the best time to visit Pasadena?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ764 | ﺩ.ﺇ830 | ﺩ.ﺇ775 | ﺩ.ﺇ735 | ﺩ.ﺇ852 | ﺩ.ﺇ867 | ﺩ.ﺇ841 | ﺩ.ﺇ837 | ﺩ.ﺇ845 | ﺩ.ﺇ863 | ﺩ.ﺇ870 | ﺩ.ﺇ852 |
| Avg. temp | 1°C | 3°C | 7°C | 13°C | 18°C | 23°C | 26°C | 25°C | 21°C | 14°C | 8°C | 4°C |
Quick stats about vacation rentals that are family-friendly in Pasadena

Total vacation rentals
Explore 40 vacation rentals in Pasadena

Nightly prices starting at
Pasadena vacation rentals start at ﺩ.ﺇ294 per night before taxes and fees

Verified guest reviews
Over 1,810 verified reviews to help you choose

Pet-friendly vacation rentals
Find 20 rentals that welcome pets

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wi-Fi availability
40 of Pasadena vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Pasadena rentals

4.8 Average rating
Pasadena stays are highly rated by guests—averaging 4.8 out of 5!
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- Family-friendly rentals Anne Arundel County
- Family-friendly rentals Maryland
- Family-friendly rentals United States
- Georgetown University
- Walter E Washington Convention Center
- National Mall
- The White House
- Nationals Park
- M&T Bank Stadium
- District Wharf
- Baltimore Convention Center
- National Museum of Natural History
- Capital One Arena
- Oriole Park at Camden Yards
- National Museum of African American History and Culture
- Arlington National Cemetery
- Howard University
- Sandy Point State Park
- Georgetown Waterfront Park
- Washington Monument
- Betterton Beach
- National Harbor
- Patterson Park
- Johns Hopkins University
- The Anthem
- Smithsonian American Art Museum
- CFG Bank Arena





