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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.

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A cozy bedroom area is highlighted by a queen-sized bed with light blue linens and a decorative wall art piece. A small dining table is set for two, featuring plates and cups. A desk with a lamp and a television are also present in the room.

Guest suite in Millersville

4.82 out of 5 average rating, 159 reviews

The Lower Level Loft near BWI

Unwind in this tranquil, stylish in-law suite, updated for your comfort. Located on the lower level of a townhouse just minutes from BWI, this space offers a private entrance.Inside, you'll find an inviting dining area, a spacious bathroom, and a cozy bedroom featuring a brand-new queen-sized bed and a high-definition TV. There are two dedicated parking spaces that are well-lit. The kitchenette has a fridge, microwave, coffee maker, etc., providing all the essentials for a comfortable stay.

Top guest favorite

A well-lit living area features a black piano along one wall, with a wooden cabinet displaying books and decorations nearby. A fireplace is set within a white brick surround, and a flat-screen TV is mounted above. Comfortable seating is arranged for relaxation.

Guest suite in Arnold

4.96 out of 5 average rating, 685 reviews

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!

A serene backyard space features a rectangular pool surrounded by a spacious patio. Lounge chairs are positioned near the water, with a shaded gazebo offering seating nearby. The area is bordered by lush greenery, providing a sense of privacy and tranquility.

Guest suite in Arnold

4.94 out of 5 average rating, 184 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.

The entrance of the guest cottage is framed by a charming picket fence, featuring a blue door and a welcoming porch. A small table with two chairs and an umbrella is situated on a wooden deck, surrounded by lush greenery.

Guesthouse in Annapolis

4.9 out of 5 average rating, 296 reviews

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.

An 80-foot private pier extends over calm water, lined with posts and surrounded by greenery. Two personal watercraft and a yellow pedal duck are visible at the end of the dock. The tranquil scene is enhanced by a blue sky with scattered clouds.

Home in Riviera Beach

4.95 out of 5 average rating, 146 reviews

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, 3 Bathroom .one bed 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 .

A gazebo is nestled among tall trees and greenery, providing a serene outdoor space. The surrounding grass is well-maintained, and a stone pathway leads to the gazebo, enhancing accessibility. Sunlight filters through the trees, creating a calm and inviting atmosphere in the yard.

Apartment in Glen Burnie

4.83 out of 5 average rating, 476 reviews

Quiet Cozy 1 Bdr Apt at BWI Airport

Furbabies Welcome! Yard Oasis! 1 Bedroom Basement suite with private entrance - 12 min. to UM Baltimore Washington Hospital -15 min to Ft. Meade - Great for military - 6 min. drive to BWI Airport terminal -10 min. drive to Casino Live - Driveway parking for 2 vehicles or RV -Wifi/Smart TV with Netflix & YT -10 min drive to Downtown Baltimore -Fully equipped kitchen - Full bathroom w/Soap/Shampoo -Late checkout available w/Fee -Doggie basket -20 miles to Annapolis, Md NO CATS permitted.

The entrance features double glass doors framed by a wooden deck. Seasonal potted plants, including vibrant flowers and greenery, are arranged on either side, while a small pumpkin adds a festive touch. A decorative light fixture hangs nearby, enhancing the welcoming appearance.

Cottage in Glen Burnie

4.91 out of 5 average rating, 201 reviews

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.

A charming cottage is nestled among lush trees, featuring a spacious yard of green grass. Ample sunlight filters through the leaves, casting playful shadows. The exterior showcases a combination of windows and porch areas, offering a welcoming appearance in a serene environment.

Cottage in Pasadena

4.97 out of 5 average rating, 182 reviews

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.

Top guest favorite

A classic brick Colonial house is surrounded by well-maintained gardens and lush greenery. Large trees provide shade over the front lawn, which features manicured bushes and young saplings, contributing to the inviting exterior of the home.

Guest suite in Catonsville

4.94 out of 5 average rating, 531 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.

A serene waterfront scene is displayed, showcasing a calm body of water bordered by lush greenery. A pier extends into the water, with boats moored nearby. In the distance, various structures line the shore, surrounded by nature, under a softly lit sky.

Cottage in Pasadena

4.85 out of 5 average rating, 131 reviews

Chesapeake Cottages- 2 Quaint Waterfront Retreats

Our tastefully appointed cottages sit on almost an acre of waterfront property. Peaceful and tranquil, yet close to shops and restaurants, this property is perfect for serene getaways and family gatherings. With 2 separate cottages on one property, everyone will enjoy a unique and private space to relax. From peaceful mornings to magical sunsets on the 60-foot pier, this setting will quickly become a family favorite. This area is great for fishing, kayaking and paddle boarding!

Top guest favorite

A serene riverfront scene features a reflecting water surface, with the sky painted in soft pinks and purples at sunset. Lush greenery borders the water's edge, and silhouettes of trees frame the tranquil landscape.

Guest suite in Pasadena

4.98 out of 5 average rating, 630 reviews

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!

A wooden pier stretches into the water, flanked by lush greenery. A rainbow arcs above the serene landscape, with gentle waves lapping at the edge of the sandy shore. Trees and homes line the distant banks, completing the tranquil waterfront scene.

Guesthouse in Glen Burnie

4.93 out of 5 average rating, 353 reviews

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

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Popular amenities for Pasadena family-friendly rentals

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

Top guest favorite

A wooden pier extends into calm water, flanked by tall grasses and greenery. The sky features soft clouds, casting gentle light on the serene scene. Nearby structures are visible along the shoreline, enhancing the tranquil waterfront setting.

Home in Middle River

4.98 out of 5 average rating, 118 reviews

Beautiful, quiet waterfront house. Lots of room!

Top guest favorite

A charming cottage is visible beside a clear pool, surrounded by well-maintained green lawns. Two shaded umbrellas stand over cushioned lounge chairs by the water's edge, creating a comfortable outdoor space for relaxation. The inviting pool reflects the bright sky, enhancing the serene atmosphere.

Cottage in Easton

5 out of 5 average rating, 110 reviews

Cottage on Solitude Creek, Hot Tub, Pool & Firepit

Top guest favorite

A pet feeding station is set on a textured mat, featuring two stainless-steel bowls. A colorful pet toy stands playfully beside the bowls, and a glass jar labeled with treats is positioned nearby. Light fills the space, enhancing the warm wood flooring.

Townhouse in Canton

4.96 out of 5 average rating, 534 reviews

Parkfront Hot Tub Haven for Families & Pets

Top guest favorite

A serene waterfront scene is captured at dusk, featuring a dock illuminated by soft lighting. A swing sits beneath a large tree, providing a peaceful spot to relax while overlooking the calm water.

Home in Grasonville

4.95 out of 5 average rating, 275 reviews

River Front, Private Single Family Home

Top guest favorite

Home in Shady Side

5 out of 5 average rating, 176 reviews

Luxe Modern Chesapeake Waterfront Oasis - 5 Star

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, 179 reviews

Celebrate Summer by Your Private Pool

The living room features a high, wooden ceiling with large windows allowing natural light to fill the space. A comfortable arrangement of sofas and chairs offers ample seating, complemented by a stylish area rug. A modern fireplace adds warmth to the inviting design.

Home in Perry Hall

4.99 out of 5 average rating, 107 reviews

Gunpowder Retreat

Home in Edgewater

4.98 out of 5 average rating, 128 reviews

Luxury Modern Home on Water+Hotub- Annapolis 25min

Family- and pet-friendly home rentals

Top guest favorite

A spacious living area is highlighted by a mix of seating options, including a gray sofa and two blue armchairs. A wooden coffee table sits in the center, complemented by an area rug. The dining area features a round table, and the kitchen is visible in the background.

Townhouse in Fells Point

4.97 out of 5 average rating, 203 reviews

Fells Point - Close to Attractions

A serene swimming pool is featured in a private outdoor area, surrounded by a stone deck. Two white lounge chairs are positioned nearby, with trees providing a shaded atmosphere. The clear water glistens under a partly cloudy sky, inviting relaxation.

Home in Edgewater

4.91 out of 5 average rating, 158 reviews

House in Edgewater Maryland

A comfortable living area features a light grey sofa adorned with soft blankets, positioned near a wooden coffee table. Two nautical-themed art pieces hang on the white shiplap wall, while a lamp casts a warm glow beside a potted plant. Steps lead to an upper level.

Home in Timonium

4.88 out of 5 average rating, 254 reviews

* Beautiful Oasis w/ No Detail Spared

A cozy sleeping area is featured, with a comfortable bed dressed in a plaid blanket. Soft lighting from two bedside lamps creates a warm glow. Artwork hangs above the headboard, adding a touch of modern design to the space.

Apartment in Dundalk

4.9 out of 5 average rating, 103 reviews

Modern Independent Private Apartment#1 And Parking

A modern living room is presented with a large grey sofa and two armchairs, complemented by a glass coffee table. Natural light filters through the window treatments, highlighting the hardwood floors and fireplace. A neutral color palette enhances the inviting ambiance.

Townhouse in Annapolis

4.96 out of 5 average rating, 161 reviews

Historic 3 Bedroom Downtown Annapolis Townhome

Top guest favorite

A charming single-story house is presented with a light gray exterior and a prominent teal door. Symmetrical landscaping frames the entrance, featuring neatly trimmed hedges and colorful plants. A concrete pathway leads to the front steps, inviting guests into a welcoming atmosphere.

Home in Annapolis

4.95 out of 5 average rating, 103 reviews

Charming Annapolis Retreat with Hidden Wine Room

A single-story home is positioned at the end of a paved driveway, surrounded by greenery. The exterior features a brown roof, light-colored siding, and multiple windows. A white bench is located in front of the house, offering a place to relax in the garden-like setting.

Guesthouse in Annapolis

4.84 out of 5 average rating, 221 reviews

"The Cape Saint Claire Inn"

An open living area features hardwood flooring and large windows, allowing natural light to fill the space. A comfortable sectional sofa is positioned near a television. A kitchen island with seating complements the design, enhancing the inviting atmosphere of the home.

Home in Annapolis

4.93 out of 5 average rating, 430 reviews

New Hotel Chic

Family-friendly home rentals with a pool

An aerial view captures the expansive property, featuring a large home surrounded by lush green lawns and mature trees. A heated in-ground pool is visible in the backyard, adjacent to a serene water body, with an expansive landscape enhancing the tranquil setting.

Cabin in Saint Michaels

4.99 out of 5 average rating, 114 reviews

True St. Michaels 6 Acre Waterfront w/heated pool

Top guest favorite

A charming guesthouse exterior is showcased, featuring multiple entrances with glass doors. A staircase leads to the upper level. Two shaded seating areas adorned with potted plants and a clock are visible in a well-kept outdoor space, enhancing the inviting environment.

Guesthouse in Annapolis

5 out of 5 average rating, 162 reviews

Private Art-Filled Guesthouse near Naval Academy

Top guest favorite

A charming bungalow is surrounded by vibrant greenery, featuring a welcoming front porch with decorative railings. The well-kept garden includes various plants and trees, while a wooden trellis adds an element of structure to the outdoor space.

Guest suite in Silver Spring

4.96 out of 5 average rating, 279 reviews

Sophisticated Studio Apartment, Metro DC

A stylish swing chair with turquoise cushions is suspended in a bright living area. A round wooden coffee table occupies the center, adorned with a vase of fresh flowers and a decorative figurine. Large windows with sheer curtains allow natural light to enter the space.

Apartment in Patterson Park

4.95 out of 5 average rating, 131 reviews

Patterson Park Penthouse with Rooftop Deck!

A serene view of the Chesapeake Bay is captured from the backyard, featuring a pool surrounded by green lawn. Towering trees provide shade, while a patterned stone patio is visible in the foreground, enhancing the outdoor atmosphere.

Home in Chester

4.95 out of 5 average rating, 100 reviews

Waterfront Farmhouse Meets Modern Luxury

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, 293 reviews

Woodland Retreat

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, 223 reviews

The Little Gypsy BoHome

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

4.87 out of 5 average rating, 146 reviews

The Oasis - Cozy Comfort Close to Annapolis & USNA

Quick stats about vacation rentals that are family-friendly in Pasadena

Total rentals
40 properties
Nightly prices starting at
G$16,609 GYD before taxes and fees
Total number of reviews
1.5K reviews
Pet-friendly rentals
20 properties allow pets
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Wifi availability
40 properties include access to wifi

Destinations to explore