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Vacation rentals with a pool in Stevensville

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Quick stats about vacation rentals with a pool in Stevensville

  • Total vacation rentals

    Explore 10 vacation rentals in Stevensville

  • Nightly prices starting at

    Stevensville vacation rentals start at €78 per night before taxes and fees

  • Verified guest reviews

    Over 560 verified reviews to help you choose

  • Wi-Fi availability

    10 of Stevensville vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Stevensville rentals

  • 4.9 Average rating

    Stevensville stays are highly rated by guests—averaging 4.9 out of 5!

Top-rated rentals with a pool in Stevensville

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

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Top guest favorite
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
Top guest favorite
The custom-built home features a blend of stone and siding, set within a grassy landscape. A covered front porch invites relaxation, while large windows allow ample natural light. Solar panels are visible on the roof, integrating sustainable energy solutions.
Farm stay in Centreville

3 bedroom home with pool and game room

Forget your worries in this spacious and serene space. 5 miles outside of the town of Centreville. 15 miles to Chestertown. Custom built home sits on 4 acres in the middle of a 200 acre farm. First floor master bedroom and master bath. Living room, half bath, kitchen and dining area. Large back porch facing pool. Second story has full bathroom and two bedrooms. Each bedroom has an extra room inside. Also upstairs is a game room with a pool table. 1-king bed 1-full bed 1- queen bed 1- twin

4.93 out of 5 average rating, 130 reviews
Top guest favorite
A modern guesthouse features a peaked roof and large windows, set against a vibrant sunset sky. The surrounding landscape includes wild grasses and a paved pathway, suggesting a serene connection to nature.
Cottage in St. Michaels

La Casita on Harris Creek, St. Michaels

La Casita on Harris Creek is an architecturally unique guest house situated on a private 40-acre farm in the heart of the Chesapeake Bay, 5 min by car to Saint Michaels, MD. The guesthouse, adjacent to the owner's main farm house, features an upstairs loft, open plan first floor TV/WiFi, full bath/shower, galley kitchen/ cook top stove, microwave, stainless refrigerator, microwave, stainless refrigerator. An adjacent private pool is available for guests. TALBOT COUNTY LICENSE NUMBER STRN 26-39

4.98 out of 5 average rating, 200 reviews
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
Top guest favorite
The outdoor area features a spacious concrete saltwater pool surrounded by lounge chairs and tables. The house showcases a light-colored façade with multiple entrances, large windows, and umbrellas providing shade, all set against a backdrop of lush greenery.
Home in Stevensville

Beautiful Kent Island Getaway with Pool

PRIME LOCATION! This home offers 4 bedrooms 3 1/2 baths with a spacious bonus room for all your family entertaining. You will love the open floor plan with cathedral ceilings with a beautiful stone fireplace. The Master bedroom with jacuzzi tub. Surround sound music system. Desk with computer. Separate pool house with kitchen and bathroom great for entertaining. Outside features includes a Concrete saltwater pool (not heated) with huge fenced in backyard and KOI pond. Porches back and front.

4.97 out of 5 average rating, 131 reviews
Guest favorite
Guest suite in Annapolis

Annapolis Garden Suite

Welcome to our oasis, tucked away on a forested residential street. ~7 minutes from the Annapolis Towne Centre, ~15m from the coast, and ~30m from Baltimore and DC. Tl;dr: This is a ground-level guest suite. Inside, you’ll find 3 beds, 2 bedrooms, 1 desk, 1 kitchen with a dishwasher, oven, Nespresso/pour over, 2 TVs, a laundry room, fast wifi, a pool, patio and a forest view. We live on the top floor (separated by stairs and a locked door; separate entrances).

4.94 out of 5 average rating, 145 reviews
Top guest favorite
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, 363 reviews
Top guest favorite
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

This newly renovated, 1st floor studio is perfectly located just across Spa Creek from historic Annapolis in Eastport. Within easy walking distance of restaurants (3 min), Main Street/City Dock (10 min) & USNA's Gate 1 entrance (14 min), our studio includes a full kitchen, high-speed wifi, free onsite parking lot, a secure building entrance, dock (limited access) and a rooftop patio (with a seasonal pool) that offers beautiful views of downtown Annapolis.

4.96 out of 5 average rating, 172 reviews
Top guest favorite
An aerial view captures a spacious home set on a wooded parcel adjacent to a serene body of water. The exterior features a large swimming pool surrounded by decking, with a manicured lawn and tall trees creating a natural boundary.
Home in Cambridge

Gorgeous, Waterfront Home Is Perfect for Families!

Looking for a large, beautiful house for a big family get-away? Casey's Porch is the place to go. Come and see for yourself. Bring your extended Family. Bring your friends. Enjoy the pool. Kayaks and paddle boards and bikes await you at this beautiful home on Hudson Creek. Fish from the dock. Pull crabs from the creek. Walk down quiet country lanes. Sit around the fire pit. So many fun, outdoor things to do. Casey's Porch has it all.

4.96 out of 5 average rating, 140 reviews
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

Cottage on Solitude Creek, Hot Tub, Pool & Firepit

Cottage on Solitude Creek, Hot Tub (open), Fire Pit, Pool (Not Heated -closed Oct-June) Convenient to St. Michaels, Easton, Oxford - this beautiful cottage has a fully equipped kitchen, patio with private hot tub and gas grill. Waterfront. Host resides on property, but will give you your privacy. *PLEASE NOTE: property complies with zoning of Talbot County which enforces a 3-night minimum and 4 guest max. NO DOGS ALLOWED No Parties #STRN-23-51

5.0 out of 5 average rating, 125 reviews
Guest favorite
Guest suite in Arnold

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
Top guest favorite
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

Escape to a private Chesapeake Bay retreat with stunning water views and sunsets. Located in peaceful Tracy’s Landing, this coastal home offers relaxed charm and resort-style amenities. Enjoy a saltwater pool, private beach, sauna, steam shower, canoe, and outdoor spaces. Perfect for families, couples, or friends, with easy access to Annapolis and D.C. Relax, recharge, and make unforgettable memories.

4.99 out of 5 average rating, 251 reviews

Popular amenities for Stevensville rentals with a pool

KitchenWifiPoolFree parking on premisesAir conditioning

House rentals with a pool

Superhost
Home in Waldorf

*Brand New | Modern Farmhouse | Lux 4 BR | Near DC

4.83 out of 5 average rating, 119 reviews
Guest favorite
A charming blue cottage is depicted with a gabled roof and white columns framing the entrance. Lush green bushes line the pathway, providing an inviting approach. Clear blue skies and tall trees are visible in the background, enhancing the peaceful setting.
Home in St. Michaels

SM's Premier Rental Heated Pool (closes 10/27)

4.97 out of 5 average rating, 116 reviews
Top guest favorite
The exterior of the house features a combination of natural stone and shingle siding. A well-maintained garden with flowering shrubs borders the walkway. A small porch is visible, providing access to the entrance, all under a clear blue sky.
Home in Stevensville

Bay Bliss House

5.0 out of 5 average rating, 40 reviews
Top guest favorite
Home in Stevensville

*Waterfront* 5BR w/ Pool + Firepit on Kent Island!

5.0 out of 5 average rating, 21 reviews
Top guest favorite
The outdoor pool area features a spacious salt-water pool surrounded by a stone patio. Comfortable seating is arranged on either side, with colorful landscape visible in the background and an umbrella providing shade. The skyline is adorned with hues of sunset across the bay.
Home in Stevensville

Bayside Escape

5.0 out of 5 average rating, 44 reviews
Top guest favorite
An inground pool is surrounded by a spacious patio, featuring a pergola with a shaded dining area. Lush greenery provides a natural backdrop, while lounge chairs are positioned nearby for relaxation. The clear water invites enjoyment on warm days.
Home in Stevensville

The Pool House in Romancoke on the Bay

4.99 out of 5 average rating, 74 reviews
Top guest favorite
Home in Stevensville

Waterfront | Swim Spa + Sauna + Beach + Game Room

5.0 out of 5 average rating, 26 reviews
Guest favorite
A spacious exterior of a two-story home is presented, showcasing a brick facade and a covered balcony above the entrance. The driveway is paved, leading to a gravel area, with a fenced yard visible in the background, offering ample outdoor space.
Home in Pasadena

Beautiful Home Near Beach and Patapsco River

4.87 out of 5 average rating, 95 reviews

Condo rentals with a pool

Top guest favorite
Condo in Annapolis

Annapolis Waterfront Condo - Unit #: A-203

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

Captains Quarters | Waterfront & Pool

4.98 out of 5 average rating, 121 reviews
Top guest favorite
Condo in Annapolis

Semper Fi Condo

4.94 out of 5 average rating, 32 reviews
Guest favorite
An open living area is showcased, featuring a light-colored sofa against a wall adorned with framed photographs. A large rug anchors the space, complemented by a round dining table and chairs. Natural light floods in from large sliding doors leading to a balcony.
Condo in Annapolis

Cozy Annapolis Condo

4.96 out of 5 average rating, 77 reviews
Superhost
Condo in Annapolis

Waterfront Eastport Condo w Pool & Parking

4.83 out of 5 average rating, 12 reviews
Superhost
A light-filled living area features a comfortable sectional sofa with pillows and a cozy throw. A round coffee table sits in the center, surrounded by a woven basket and a wooden armchair. The kitchen area is visible in the background, equipped with dark cabinetry and stainless-steel appliances.
Condo in Annapolis

Amazing Views from Spa Creek 2BD Condo with Pool

4.75 out of 5 average rating, 85 reviews
Superhost
A dining area features a modern table set for four, with red napkins and a vase of flowers at the center. Ambient lighting is provided by a stylish pendant fixture above the table. A large window with blinds allows natural light to brighten the space.
Condo in Greenbelt

Lovely 1-bedroom condo w/ 2 parking spots near DC

4.77 out of 5 average rating, 61 reviews

Other vacation rentals with a pool

Top guest favorite
The facade of a historic farmhouse is presented with a covered porch, featuring white railings and columns. An American flag is displayed prominently. Yellow chrysanthemums are placed near the entrance, with a brick pathway leading to the front door, framed by large green shutters.
Farm stay in Chestertown

Piney Grove Farm

4.97 out of 5 average rating, 110 reviews
Top guest favorite
Apartment in Upper Marlboro

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

4.94 out of 5 average rating, 215 reviews
Top guest favorite
Apartment in Arnold

Celebrate Summer In Your Private Pool & Hot Tub

4.96 out of 5 average rating, 196 reviews
Top guest favorite
A spacious lawn is surrounded by tall trees, leading to a two-story house with a porch. Soft evening light casts a gentle glow, while a hammock can be seen suspended between two trees, inviting relaxation in the outdoor space.
Casa particular in Chestertown

Red, White & Waterview Studio Apt with pool

4.92 out of 5 average rating, 191 reviews
Top guest favorite
An aerial view showcases a large grassy area surrounding a heated pool, with several lounge chairs positioned nearby. A fire pit is set with white adirondack chairs. Two properties are visible, featuring balconies and umbrellas enhancing the outdoor space.
Apartment in Stevensville

Heron Roost

5.0 out of 5 average rating, 94 reviews
Top guest favorite
A spacious outdoor area is shown, featuring a well-maintained saltwater pool surrounded by lounge chairs and umbrellas. Lush green landscaping, including plants and rocks, enhances the setting. The guest house is visible in the background, offering a welcoming atmosphere.
Guesthouse in Stevensville

22 Acre Waterfront Retreat.

5.0 out of 5 average rating, 65 reviews
Guest favorite
Guest suite in Queenstown

River Guest Suite w/ Pool, Beach, Private BoatSlip

4.98 out of 5 average rating, 44 reviews
Guest favorite
An aerial view captures an expansive property surrounded by water, showcasing vibrant green trees and a swimming pool nestled among the foliage. A long pier extends into the water, emphasizing the natural beauty of the estate and the serene landscape.
Villa in Centreville

Blake House Historic Estate with Private Inn

5.0 out of 5 average rating, 61 reviews

Destinations to explore