Holiday rentals with a pool in Howard County

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Howard County

Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

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Guest favourite

Townhouse in Hanover

5 out of 5 average rating, 18 reviews

3-Level Luxury Near BWI, Casino, Mall & More!

Shops, restaurants, movie theater, gaming all 5 minutes or less away! BWI airport 12 minutes away! 5 minutes from the largest mall in MD. Casino and Entertainment center, Family dinner theater. Suburban family-friendly modern townhome central to major hubs in the Balt/Wash area. Close to Columbia/Annapolis and more. Equipped for cooking/entertaining. Space for privacy/relaxation. Great for group travel. Areas for working from home. Access to additional amenities at neighborhood community center

Home in Milford Mill

4.7 out of 5 average rating, 20 reviews

Hidden Gem w/ Pool

This stylish place to stay is perfect for group trips and family gatherings in style. Newly renovated and boasting in character is this very spacious property in a great location. The home includes 5 queen size beds , one king, 5 bathrooms rooms, an Olympic size pool with a massive deck with an out door cook space. You won’t go wrong this one, it has all of the bells and whistles any place has to offer. There is an apartment attached to the house with a separate entrance that can be rented also

Loft in Columbia

4.74 out of 5 average rating, 38 reviews

Lakefront Retreat w/ Sunroom, Patio & Kayak!

Wake up to shimmering lake views, sip coffee in a light-drenched sunroom, and paddle out from your own backyard at this Columbia vacation rental! Nestled on Wilde Lake, this thoughtfully curated 1-bathroom studio offers the perfect mix of peaceful retreat and luxury comfort, just minutes from Columbia’s best events, shops, and trails. Whether you’re attending a concert, working remotely, or simply craving quiet time by the water, you're sure to breathe deeply, sleep well, and enjoy the moment.

Top guest favourite

Flat in Woodstock

4.93 out of 5 average rating, 15 reviews

Resort studio apt w/ pool, hot tub, fire pit, gym

Resort living at it’s best! Everything you need in this studio apartment equipped with gym equipment (treadmill, Peloton bike, weights), large smart tv, WiFi, hot tub, firepit, full bath, kitchen, queen bed, washer/dryer on a golf course resort with free access to the community pool (Memorial Day through Labor Day) and community gym, walking distance to the public golf course (Waverly Woods), restaurants, shops, and grocery store. Walkable neighborhood just minutes from Patapsco state park.

Top guest favourite

Guest suite in Catonsville

4.94 out of 5 average rating, 528 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.

Top guest favourite

Guest house in Highland

4.98 out of 5 average rating, 292 reviews

Woodland Retreat

Welcome to our private woodland retreat! This stylish and secluded mid-century modern guesthouse is nestled on five acres in horse country in Highland, Maryland. Totally separate from our owners home, our guesthouse combines the serenity, privacy, and safety you crave with all the conveniences of modern life including: a full bath; kitchenette; internet; and a screened porch with access to our beautiful lighted and heated swimming pool (weather permitting) and adjacent walking trails.

Guest suite in Woodbine

4.68 out of 5 average rating, 199 reviews

Treetop Penthouse at Streit Manor

NEWLY REDECORATED! Our 2,500 sf penthouse has its own private parking, entrance, kitchen, full laundry. It has 3 inviting bedrooms and a large 1,000 sq ft bath suite with multi person Jacuzzi. Located 18 miles from Baltimore, 31 miles from the White House. Owners live in separate residences on the site. Fully furnished and well-appointed to ensure an enjoyable stay! NO PARTIES OR GATHERINGS WITHOUT PRIOR APPROVAL. NO SMOKING ALOWED INSIDE THE HOUSE!

Superhost

Flat in Laurel

4.78 out of 5 average rating, 18 reviews

Cozy Retreat in Laurel, MD!

Welcome to this comfortable, 2 bd, 2 bth, with sleeper sofa for additional guests-modern retreat in the heart of Laurel that offers the perfect blend of tranquility and convenience. You’ll have easy access to both DC and Baltimore, making it ideal for exploring the best of both cities! Inside: stocked kitchen, cozy living area with wood-burning fireplace, fast WIFI, not some, but all premium channels, and your own private balcony!

Guest house in Gaithersburg

5 out of 5 average rating, 3 reviews

Country Cabana

Welcome to your private retreat! This inviting guest house features two spacious bedrooms and a modern bathroom—perfect for families, couples, or small groups. The open-concept design connects a cozy living room with a fully equipped kitchen and a charming dining area, complete with a piano for a touch of musical enjoyment. Ideal for both relaxing escapes and extended stays. Owners do live on property in main house.

Guest favourite

Guest house in Spencerville

4.87 out of 5 average rating, 30 reviews

Adorable Guesthouse on Historic Farm.

Spring is upon us at Drayton! With excellent proximity to both Washington DC and Balitmore, enjoy peaceful respite in a lovely historic cottage (fully airconditioned) in Montgomery County, MD. Enjoy the grounds of Drayton Manor, built in 1834, boasting beautiful cherry trees, magnolias, massive oak and yew trees, as well as an inground swimming pool (seasonal), summer house, fire pit, and a children's playground.

Apartment in Columbia

4.63 out of 5 average rating, 16 reviews

TranquilNest 3BR Retreat w/ Pool | 5 Mins to Mall.

Peaceful 3BR retreat just 5 mins from Columbia Mall and Merriweather Post Pavilion. Features forest views, high ceilings, private entrance, cozy living space, and fast Wi-Fi. Includes kitchenette, clean bath, shared laundry, free driveway parking, and seasonal pool access. Pet-friendly with approval. Ideal for concert-goers, remote workers, or long-term guests seeking quiet comfort between Baltimore and DC.

Top guest favourite

Flat in Columbia

5 out of 5 average rating, 45 reviews

Chic style space near Columbia

Take it easy at this unique and tranquil getaway. I call it my THINK PAD. Take time to reorganize, plan and think about your next moves. This space is specifically designed for resetting and refreshing for the month. Mind map on the white board. Pull out the poster board and create a vision board that you can take with you. Enjoy small snacks and reminders to help you enjoy this moment.