Holiday rentals with a pool in Howard County

The Blissful House

Welcome to The Blissful House, a serene retreat designed for relaxation and convenience. Nestled in Western Howard County. This memorable home with 3 spacious bedrooms & 3 full B. Spacious & stylish home with modern interior touches. Ample parking space for your convenience Prime location – just few minutes away from Turf Valley Resort, restaurants, and Patapsco Valley State park. Easy access to Route 70 & Route 32 for effortless travel. We will be closing the pool at the end of September.

Family · Location · Getting around

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.

Value · Location · Comfort

Spacious Upscale Townhome Near Hanover and BWI

Spacious property 5 minutes from Arundel Mills Mall and Fort Meade, 20 minutes from Merriweather Post Pavilion and 25 minutes from Baltimore — the ideal base for group and family travel. Full kitchen, community pool and amenities, in-unit washer/dryer, and room for up to 8 across 3 levels. Self-contained studio suite spanning first level included. Walkable to shops, grocery stores, and eateries. Also ideal for professionals on extended assignment near Fort Meade (9 min) and BWI (12 min)

Location · Family · Indoor spaces

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.

Location · Family · Layout

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.

Family · Value · Accuracy

Pets Welcome: Quiet Silver Spring Retreat!

Recently Renovated | Spacious Yard | Seasonal Outdoor Pool Gather your crew for a family retreat at this inviting 3-bedroom, 2-bath vacation rental! Whip up breakfast in the updated kitchen, then head out for some excitement at The Adventure Park at Sandy Springs or enjoy a peaceful paddle on nearby lakes. Return home to unwind in the backyard oasis, where kids can play, pets can explore, and you can kick back on the patio. Make Silver Spring your family’s next adventure — book today!

Family · Location · Access

Hidden Gem w/ Heated Pool/ Hot Tub

This stylish place 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, a heated Olympic size pool, hot tub and massive deck with an out door cook space. You won’t go wrong this one, it has all of the bells and whistles. There is an apartment attached to the house with a separate entrance that can be rented also

Value · Location · Kitchen

Beautiful Clarksville guest suite - monthly rental

Spacious, airy, well-lit, and private basement apartment offering privacy and comforts of home. Lots of storage. Wifi, space to work. Large private en-suite bathroom with shower and his&her sinks. Private kitchenette including small two-burner stove, microwave, fridge, pantry space, dishwasher, sink, tea & coffee facilities. Linens, towels, and basic toiletries provided. Private laundry facilities including washer and dryer. Private entrance with keyless entry.

Family · Value · Quiet

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!

Value · Location · Decor

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. BRAND NEW HOT TUB DECK! Ideal for both relaxing escapes and extended stays. Owners do live on property in main house.

Location · Family · Laundry

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.

Location · Amenities · Bathroom

Hilltop Retreat: Pool, Games & Sunroom

Welcome to your elevated escape — literally. Nestled atop a peaceful hill, this spacious 5-bedroom, and 3-bathroom home offers a cozy, restful stay for families, groups, or anyone craving comfort with a splash of fun. From our midcentury-modern touches to our backyard poolside vibes, this retreat was designed with both connection and relaxation in mind. Pool is open

Value · Family · Indoor spaces