
Pet-friendly holiday rentals in Anne Arundel County
Find and book unique pet-friendly homes on Airbnb
Top-rated pet-friendly home rentals in Anne Arundel County
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Annapolis Area Waterside Retreat
This Rhode River home is your perfect getaway to the Annapolis area - whether you’re looking to get away to a unique home overlooking incredible sunsets, a fun weekend with friends along the water, a family trip to the Chesapeake, or a private work retreat away from the bustle of the city, this home has it all. The house is a short drive from DC or Baltimore and unlike any Airbnb this side of the Chesapeake - it is on a 3 acre marina just minutes from Annapolis but private and away from it all!
4.95 out of 5 average rating, 262 reviews
8 Acre Waterfront Oasis! Pets are Free! 140ft Pier
Waterfront Enjoyment: A 3-bedroom, 2-bathroom home! This charming one-story house in Churchton, Maryland, is perfect for families. It includes 8 acres of land and over 700 feet of waterfront on Broadwater Creek, ideal for fishing, crabbing, paddleboarding, and kayaking. Discover the charming town of Deale, Maryland, with its easy entry to the Chesapeake Bay. Relax and enjoy this property! There's a brand-new 140-foot dock with beautiful views of the bay, ideal for catching crabs and fish!
4.98 out of 5 average rating, 151 reviews
Luxury Modern Home on Water+Hotub- Annapolis 25min
Waterside mid-century modern home, perfectly appointed. Join with colleagues, family, and friends. Paddleboard, roast marshmallows, watch fireworks, take a hot tub or team building. Our "Flight Deck" is perfect for meetings and retreats. Breathtaking, peaceful grounds with an abundance of space. Approximately 2800 SF sits on a 3/4 acre property - perfect for lawn games and zip lining. 20x20 furnished deck + dock Mayo Beach and Beverly Triton 1 mile away. Within an hour of the DMV
4.99 out of 5 average rating, 145 reviews
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
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, 213 reviews
Cozy waterview home in West River!
Your family will be close to everything when you stay at this centrally-located place. This home is located just 15 miles to Annapolis, 18 miles to the Naval Academy, and 30 miles to the heart of Washington, DC. Less then 8 miles to Rt 214, providing direct access to beltway, and other major highways. This charming home has as spacious fenced in yard, High Speed Internet, TV (Netflix & Hulu), outdoor seating and a fire pit. Want to get away? Bring the whole family!
4.97 out of 5 average rating, 168 reviews
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
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, 363 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
4.94 out of 5 average rating, 408 reviews
Captains Quarters Oasis Near Annapolis, Sleeps 4
This updated suite is designed for comfort & convenience. Enjoy a king bed and a (queen bed) LoveSac sofa perfect for 2-4 guests. The suite includes a private en-suite bathroom, high-speed internet, a fully furnished kitchen, and a coffee bar to make you feel right at home. Located just 4 miles from Annapolis, you're close to all the best spots. Whether you’re here to relax or explore, this suite has everything you need!
4.95 out of 5 average rating, 214 reviews
Modern 6BR • Close to DC & Annapolis
Bright and spacious 6 bedroom, 5.5 bathroom home with a gym and sauna in a quiet, safe Largo neighborhood. Perfect for families and relaxed groups. Woodmore Town Center is under 5 minutes for groceries, dining, and shopping. About 20 minutes to DC and Silver Spring, with the Largo Town Metro only 7 minutes away for easy access to all major lines. Fast Wi-Fi, comfy beds, friendly neighbors, and plenty of space to unwind.
4.82 out of 5 average rating, 177 reviews
Relaxing Cabin Get Away Near Annapolis & DC
This is a 1,000 sq foot open concept rustic cabin. There are 4 "rooms" including a fully equipped kitchen, a dining room, a family room with a TV for movies and streaming, and a bedroom full of windows. It is located down a 1/3 mile gravel driveway in the woods on 72 acres of land that has been dedicated in perpetuity to not being developed.
4.91 out of 5 average rating, 188 reviewsPopular amenities for Anne Arundel County pet-friendly home rentals
Pet-friendly house rentals

Nautical Luxe Retreat 6 Guests • 3 BDR • 2 Baths
4.96 out of 5 average rating, 150 reviews
Hannah’s Hideaway
4.99 out of 5 average rating, 161 reviews
Relaxing Turkey Point Retreat-Steps to the marina!
4.94 out of 5 average rating, 125 reviews
The Navy House-Walk or Shuttle Downtown! 3 bd
4.93 out of 5 average rating, 206 reviews
Modern Escape | Near DC, Dining & Entertainment!
4.98 out of 5 average rating, 122 reviews
Historic Downtown in-law suite
4.96 out of 5 average rating, 260 reviews
Riverside | 15 mins to USNA
5.0 out of 5 average rating, 22 reviews
A Happy Place
5.0 out of 5 average rating, 31 reviewsPet-friendly home rentals with a pool

Annapolis Garden Suite
4.94 out of 5 average rating, 145 reviews
The Little Gypsy BoHome
4.99 out of 5 average rating, 251 reviews
Secluded Tiny House With your own Private Pool
4.87 out of 5 average rating, 117 reviews
Private Resort! 100" TV Home Theater, Pool, Hotub
4.74 out of 5 average rating, 19 reviews
*Waterfront* 5BR w/ Pool + Firepit on Kent Island!
5.0 out of 5 average rating, 20 reviews
The General's House-Spacious Home w/Pool & Hot Tub
4.96 out of 5 average rating, 45 reviews
Waterfront | Pool | Hot tub | Beach Access
4.99 out of 5 average rating, 94 reviews
Pool & Yard Retreat | 4BR | 20 Min to Annapolis
4.9 out of 5 average rating, 21 reviewsPrivate, pet-friendly home rentals

Boatyard Bungalow, 6 beds; 2 Full Baths-Waterfront
4.95 out of 5 average rating, 168 reviews
Garden View, 1 Bedroom and a Loft.
4.99 out of 5 average rating, 165 reviews
Home away from Home
4.89 out of 5 average rating, 165 reviews
Relaxing Water Views - Mill Creek Cottage
4.97 out of 5 average rating, 470 reviews
Ft. Smallwood Overlook. Waterfront with Kayaks!
4.97 out of 5 average rating, 194 reviews
Walk to Beach| Yard Games, Fire Pit in South River
5.0 out of 5 average rating, 25 reviews
Chessie Cottage - Chesapeake Bay
5.0 out of 5 average rating, 36 reviews
Waterfront Cottage with Private Pier
4.93 out of 5 average rating, 92 reviewsDestinations to explore
- Waterfront rentals Anne Arundel County
- Rentals with a hot tub Anne Arundel County
- Beachfront rentals Anne Arundel County
- Hotel rooms Anne Arundel County
- Rentals with pools Anne Arundel County
- Rentals with lake access Anne Arundel County
- Boat rentals Anne Arundel County
- Rentals with beach access Anne Arundel County
- Private suite rentals Anne Arundel County
- Rentals with breakfast Anne Arundel County
- Family-friendly rentals Anne Arundel County
- Flat rentals Anne Arundel County
- House rentals Anne Arundel County
- Guest house rentals Anne Arundel County
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- Apartment rentals Anne Arundel County
- Rentals with a kayak Anne Arundel County
- Pet-friendly rentals Maryland
- Pet-friendly rentals United States
- M&T Bank Stadium
- National Mall
- The White House
- Walter E Washington Convention Center
- Nationals Park
- FedExField
- Johns Hopkins University
- Oriole Park at Camden Yards
- Federal Hill Park
- Arlington National Cemetery
- Capital One Arena
- Georgetown Waterfront Park
- Washington Monument
- National Museum of African American History and Culture
- Betterton Beach
- CFG Bank Arena
- National Harbor
- Howard University
- Smithsonian National Zoological Park
- Baltimore Convention Center
- Museum of the Bible
- Smithsonian National Air and Space Museum
- Patterson Park
- Smithsonian American Art Museum





