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Family-friendly holiday rentals in Anne Arundel County

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Top-rated family-friendly rentals in Anne Arundel County

Guests agree: These family-friendly homes are highly rated for location, cleanliness and more.

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Superhost
A large, two-story home with a welcoming front porch is set amidst a spacious green lawn. The house features a grey exterior with white trim and multiple windows, surrounded by trees and landscaping, creating a peaceful and private atmosphere.
Home in Severn

Large Home w/ Private Pool, Gym, Sauna, 7 Bedrooms

Relax at this spacious 4,125 sqft, top-quality home on 1 acre. This 7-bedroom, 2.5 bathroom home features a private pool, gym, sauna, and a massive family room with 10 ft ceilings, and a 67 " Smart TV. Enjoy the large 1st class chef's kitchen with all the cooking & serving supplies you will ever need. Enjoy the modern amenities, multiple workspaces, a wrap-around porch, a fire pit, & a grill. Ideal for family events, quiet getaways, sports teams, & business meetings. You are able to have your l

4.86 out of 5 average rating, 222 reviews
Guest favourite
An open layout living area features a kitchen equipped with stainless steel appliances and a breakfast bar with high stools. A dining table is visible in the background near large windows. The space is complemented by two leather couches and light hardwood flooring.
Home in Arnold

Rachel's BnB

A well outfitted home away from home! A fully stocked kitchen with everything you need to cook for yourselves and your guests. Close to historic downtown Annapolis, the US Naval Academy, St. John's College and MD Statehouse are less than 10 minutes away There are king and queen beds in the rooms, and the 3rd bed is a comfortable pullout couch in the living room. All linens are Egyptian cotton and the beds have real down duvets. Additional cot beds and linens (up to 4) can be provided ($20 each)

4.91 out of 5 average rating, 152 reviews
Top Guest favourite
A modern living area features a light-colored sofa adorned with a teal throw blanket. A round wooden table accompanied by metal chairs is positioned nearby. A decorative mirror and an abstract painting are displayed on the wall, while a stone fireplace adds a subtle touch of warmth.
Apartment in Stevensville

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.

4.97 out of 5 average rating, 312 reviews
Guest favourite
A spacious deck offers outdoor seating, including a large dining table and comfortable chairs, overlooking the serene waterfront. Lush trees frame the scene, and the calm water reflects the clear sky, creating a peaceful environment for relaxation.
Home in Riva

Waterfront Annapolis Getaway!

Escape to this serene waterfront house in Annapolis, perfect for couples seeking a peaceful retreat. Nestled on the picturesque South River, this charming home offers stunning waterfront views and tranquil decks where you can unwind and soak in the beauty. Enjoy cozy evenings by the water, dine alfresco on the deck, and explore nearby attractions. With its serene ambiance and beautiful surroundings, this is the ideal spot for a romantic getaway. Book now for an unforgettable escape!

4.92 out of 5 average rating, 100 reviews
Top Guest favourite
Apartment in Upper Marlboro

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

Have fun and relax! Near every amenity. Huge Pool w/multiple cabanas, hot tub, trampoline, playground, axe throwing, pool/ice hockey table, arcade,huge theater room, 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. Now offering RV for additional cost to add additonal sleeping space. Basement apt so there is some movement noise. 20 mins to DC & National Harbor

4.94 out of 5 average rating, 215 reviews
Top Guest favourite
Home in Shady Side

Iconic Chesapeake. Unparalleled Luxury.

Summer at The Cottage at Silver Water is effortless and indulgent. A sweeping waterfront lawn leads to a private shoreline for swimming, kayaking, and long days in the sun. Evenings bring golden skies, spectacular sunsets, and fires by the water’s edge. Inside, the cottage is beautifully designed with luxurious bedding, curated art, and thoughtful amenities that make every stay relaxed, refined, and unforgettable. See why all our guests only have a 5-Star experience.

5.0 out of 5 average rating, 214 reviews
Top Guest favourite
A living area features a comfortable sectional sofa and a modern accent chair, centered around a round coffee table. Light wood flooring complements the space, while tall windows are dressed with blue curtains. Decorative lamps and minimalist wall art enhance the room's design.
Home in Edgewater

3 BRs House+Patio+Playground

Newly renovated and furnished entire house for your family! Spacious 3 bedrooms 1.5 bathrooms house, large backyard patio with gas grill and your own private playground for your kids! Brand new designer furnitures with a sense of home! Fully functional kitchen and large dining space, perfect to enjoy a great evening with your friends and family! Fit 3 cars in our private driveway. Minutes away from restaurants and grocery stores! 15 mins drive to Downtown Annapolis!

4.93 out of 5 average rating, 103 reviews
Top Guest favourite
Home in Odenton

Train Tracks Getaway (Whole house)

All aboard for comfort and charm at Train Track Getaway! This cozy Odenton home is perfect for families and friends, with easy MARC train access to D.C. and Baltimore. Enjoy pancakes on the back porch and marshmallows by the firepit—yes, we’ve got the s’mores kit ready! Inside offers comfy beds, a full kitchen, and space to relax or play. Whether you're visiting Fort Meade or just unwinding, this is your laid-back home base for fun, family, and firepit vibes.

4.96 out of 5 average rating, 107 reviews
Top Guest favourite
The image captures a serene evening scene by the pool with a view of the setting sun over the water. Sunlight filters through trees, creating a warm glow. Poolside lounge chairs are visible, along with a clear pool reflecting the colorful sky.
Guesthouse in Stevensville

Waterfront-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.

4.99 out of 5 average rating, 364 reviews
Top Guest favourite
A spacious great room features large windows that offer sweeping views of the water. Comfortable seating arrangements with soft furnishings are complemented by a working fireplace. A staircase is visible in the background, leading to additional living spaces.
Home in Shady Side

Waterfront Sanctuary only 50 Min. From DC/Balt.

New full home renovation with gourmet kitchen, wide open floor plan, multiple guests rooms, and a bunk room that accommodates 12. An inviting space that welcomes any couple or a large extended family. This home sits with only three other homes on a private peninsula and has water access on both sides. It is conveniently located less than an hour from DC and Baltimore on the west coast of the Bay (no need to cross the Bay Bridge).

4.97 out of 5 average rating, 110 reviews
Guest favourite
A view of the sunset over Chesapeake Bay is captured from the deck, with warm hues reflecting on the water. The scene includes a grassy area leading to the shoreline and a subtle silhouette of a dock in the background.
Cottage in Deale

Chesapeake Bay Cottage

Cottage Located directly on the Chesapeake Bay. Includes sandy beach, yard, a screened in porch and deck. Two Kayaks to enjoy. Two bedroom plus den. Two full baths. Fully equipped kitchen.Kurig coffee maker and regular available. Master bedroom -queen size mattress. Second bedroom -a full-size mattress (double) third bedroom -a twin day bed with twin pullout. Both twin size mattresses.

4.96 out of 5 average rating, 182 reviews
Top Guest favourite
A spacious bedroom is showcased with a king bed dressed in neutral linens and accented by two blue decorative pillows. Natural light filters through the two windows beside the bed, and a coastal-themed artwork adorns the wall above. Two bedside lamps provide additional soft lighting.
Guest suite in Arnold

Coastal Comfort Retreat near Annapolis, EV charger

Escape to a cozy, modern retreat just 4 miles from downtown Annapolis. This intimate king suite offers a private seating area, kitchenette, & TV. The ensuite bathroom features a luxurious shower. Relax in peace and comfort after exploring Annapolis or attending local events. Reach out anytime with questions or special requests—we’re happy to help make your stay memorable!

4.94 out of 5 average rating, 226 reviews

Popular amenities for Anne Arundel County family-friendly rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Family-friendly home rentals with a hot tub

Guest favourite
A spacious living area is highlighted by large windows allowing natural light. Modern furniture includes a sectional sofa and accent chairs, complemented by a sleek coffee table. A large television is mounted on the wall, while indoor greenery adds a touch of nature.
Home in Edgewater

Luxury Modern Home on Water+Hotub- Annapolis 25min

4.99 out of 5 average rating, 145 reviews
Guest favourite
Cottage in Deale

Waterfront Cottage@ChesapeakeParadise Hot Tub/Dogs

4.83 out of 5 average rating, 201 reviews
Top Guest favourite
A spacious backyard features a pool surrounded by a paved patio. Comfortable lounge chairs and umbrellas are positioned for relaxation. The two-story house with a deck overlooks the inviting pool area, flanked by lush greenery and colorful landscaping.
Home in Edgewater

Chesapeake Bay Beach House with Pool and Hot Tub

4.98 out of 5 average rating, 100 reviews
Guest favourite
A wooden pier extends over calm water, featuring two adirondack chairs positioned at the end. Sunlight reflects off the water's surface, surrounded by green foliage and trees. The view includes distant trees lining the shore.
Bungalow in Deale

Cozy waterfront getaway on the Bay

4.86 out of 5 average rating, 435 reviews
Top Guest favourite
Home in Deale

Chesapeake Waterfront-3 En Suites-Fire Pit-Kayaks

4.99 out of 5 average rating, 178 reviews
Top Guest favourite
A screened porch features a hanging bench swing with cushions in shades of blue and nautical motifs. A small chair stands nearby, adorned with a decorative pillow. Tall curtains frame the space, providing a relaxed and inviting atmosphere surrounded by greenery.
Cottage in Annapolis

Charming City Oasis. Walk to harbor, eateries.USNA

4.87 out of 5 average rating, 117 reviews
Top Guest favourite
Apartment in Arnold

Celebrate Summer In Your Private Pool & Hot Tub

4.96 out of 5 average rating, 196 reviews
Top Guest favourite
A Bullfrog hot tub is situated under a wooden gazebo, with water glistening in sunlight. A plush robe is draped over the edge alongside a straw hat and a rolled towel. A grassy area and wooden privacy fence complete the serene outdoor setting.
Home in Cape St. Claire

Beach Access, Hot Tub, Pet Friendly, Fully Fenced

4.99 out of 5 average rating, 142 reviews

Family- and pet-friendly home rentals

Top Guest favourite
The exterior of a two-story home is displayed, featuring a light-colored façade, white porch railings, and a chimney. A neatly manicured lawn surrounds the house, complemented by tall trees in the background and a clear blue sky above.
Home in West River

Cozy waterview home in West River!

4.97 out of 5 average rating, 168 reviews
Superhost
Home in Bowie

Modern 6BR • Close to DC & Annapolis

4.82 out of 5 average rating, 177 reviews
Guest favourite
A bright living room features a dark sofa adorned with decorative pillows, paired with a wooden coffee table on a patterned rug. A decorative wall with framed pictures adds character, while natural light enters through the large windows covered by light curtains.
Home in Edgewater

Relaxing Turkey Point Retreat-Steps to the marina!

4.94 out of 5 average rating, 125 reviews
Top Guest favourite
A single-level home in a serene setting is viewed from the water. The exterior is clad in light blue with large windows. A shaded area is present for outdoor seating. Kayaks are stored nearby, and a wooden dock extends into the calm water.
Home in Pasadena

Waterfront CHeerful 2 with Private home

4.98 out of 5 average rating, 101 reviews
Top Guest favourite
Home in Deale

8 Acre Waterfront Oasis! Pets are Free! 140ft Pier

4.98 out of 5 average rating, 151 reviews
Top Guest favourite
A spiral staircase leads to a lofted sleeping area in a well-lit living space. Warm wood tones are present in the furniture and flooring. A small kitchen area is visible, along with a dining table set for four. Lighting fixtures enhance the modern feel.
Guesthouse in Annapolis

Garden View, 1 Bedroom and a Loft.

4.99 out of 5 average rating, 165 reviews
Top Guest favourite
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.
Place to stay in Glen Burnie

The Crab House - a Private, Waterfront Guest House

4.94 out of 5 average rating, 408 reviews
Top Guest favourite
The living room features a light-toned couch centered in the space, complemented by a decorative coffee table. A reclined green chair and a lamp beside it provide additional seating. The open kitchen is visible in the background, with light cabinetry and full size appliances.
Home in Shady Side

Canary Pointe-A popular getaway for 2!

4.98 out of 5 average rating, 283 reviews

Family-friendly home rentals with a pool

Guest favourite
Guest suite in Annapolis

Annapolis Garden Suite

4.94 out of 5 average rating, 145 reviews
Top Guest favourite
An aerial view captures the waterfront cottage situated on the South River. The property is surrounded by water and greenery, featuring a manicured lawn with a patio area. A private dock is visible, leading from the house to the water, alongside a pool nestled within the landscaping.
Guesthouse in Annapolis

Coastal Waterfront 1 Bedroom Cottage

5.0 out of 5 average rating, 225 reviews
Top Guest favourite
A spacious living area features two comfortable sofas, one draped with a soft blanket. Natural light streams through large windows, highlighting the wooden flooring. A small wooden table is visible in the background, and a decorative piece hangs above the mantel.
Home in Tracys Landing

The Little Gypsy BoHome

4.99 out of 5 average rating, 251 reviews
Top Guest favourite
A living area features a gray couch adorned with decorative pillows against a light wall. A recliner is positioned nearby, and a wall-mounted Smart TV is visible. A dresser with a plant sits below the TV. Natural light streams in through nearby windows.
Condo in Annapolis

1st Floor Condo in Annapolis

4.96 out of 5 average rating, 173 reviews
Guest favourite
A cozy sleeping area features a spacious bed with cotton bedding and decorative pillows. Natural light enters through a window, highlighting the minimalist design. An ottoman rests at the foot of the bed, with a bedside table and a storage unit visible in the space.
Tiny home in Glen Burnie

Secluded Tiny House With your own Private Pool

4.87 out of 5 average rating, 117 reviews
Top Guest favourite
Condo in Annapolis

Annapolis Waterfront Condo - Unit #: A-203

4.97 out of 5 average rating, 345 reviews
Top Guest favourite
Condo in Annapolis

Captains Quarters | Waterfront & Pool

4.98 out of 5 average rating, 121 reviews
Guest favourite
A spacious living area is depicted with plush teal seating arranged around a coffee table. A modern entertainment unit is positioned against a wall, while large sliding doors open to a private balcony. Natural light enhances the warm tones of the decor.
Condo in Annapolis

Annapolis Condo-1 bedroom King

4.96 out of 5 average rating, 129 reviews

Destinations to explore