
Vacation rentals with a pool in Portsmouth
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Portsmouth
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

All About Amanzi (Water in Zulu)
Recently refurbished and refitted with all the mod-cons our fully equipped townhouse offers you the perfect haven in the heart of Ole Town Hampton and within 30 yards of the Hampton River with its ever changing tranquility. The 2nd floor has an open plan layout with a large deck and water views from every space to make the most of this asset. The 3rd floor has the master bedroom and bathroom with a private balcony for those early morning coffees while watching the changing colors of Amanzi.

The Seaglass Cottage
A charming and quiet space with lovely natural lighting. The cottage is situated in a hidden garden,just a seven minute walk ( 2 blocks )to a our beautiful beach. The beach is becoming a beloved summer destination but ,the “off season”is when we really shine! The bay waters sparkle from the warm sunshine and the water stays a comfortable temperature far into the autumn! Our Sunsets are unforgettable! Fisherman enjoy surf casting year round.Kayaking and paddle boarding are popular year round.

Elegance Escape on Saunders Dr
Experience all that Portsmouth has to offer from this 3-bed, 2-bath vacation rental! This home features 5 Smart TVs, a fully equipped kitchen, and an awesome outdoor space fit for the whole group. Get outside and enjoy a morning stroll through Portsmouth City Park, then hit the links at Elizabeth Manor Golf and Country Club! For the art fanatics, visit the Chrysler Museum of Art. Following your leisure, cool down with a dip in the pool or gather around the fire pit for stargazing and s’mores.

Wooded Wonderland Miniature Golf Hot tub Pool
Make yourself at home! This property offers a warm and welcoming environment for guests, located in a quiet and established neighborhood in the middle of Portsmouth, VA. Guests should expect a clean space equipped with modern technology and appliances. Attractions aren’t too far; 41mi from Busch Gardens, 24 mi from Virginia Beach Ocean Front, 7.3 mi from Waterside District Norfolk, and 2.9 mi from Rivers Casino Portsmouth. Peaceful mornings and a comfortable stay awaits at Wooded Wonderland!

"Shangri-La", of Hampton, Virginia
2nd story 1200 square foot apartment with 2 BR's, Wi-Fi, microwave, fridge and bar with sink. Walk in glass enclosed shower & soaker tub. Private deck with gas grill down the spiral stairs below on ground level patio. Pool table in BnB. We share our pool with our BnB guests seasonally. Please inquire about pool availability if important to your booking. Local history, sites, nature and beaches abound. Security cameras surround the exterior of our home for our protection as well as yours!

Gorgeous Vacation House
This is is the perfect home away from home! Enjoy cozy furnishings and modern amenities in this 3bed/2.5 bath house located in the vibrant city of Norfolk oceanview. The house is renovated with top notch material and artistic touch. The kitchen, living room, and private backyard with deck/patio swimming pool make it the ideal place to relax. Shopping, restaurants, and entertainment are all within minutes; plus onsite parking and self-check-in make this an ideal destination for travelers.

𓂃Tidal Creek Retreat: Near CNU, JLab and Busch𓂃
Relax at this serene & unique water getaway! 🏞️ This cozy two-story home on a cul-de-sac is ideal for nature lovers & wildlife spotting. Enjoy the panoramic tidal creek views from chef's kitchen or play board games by the gas fireplace. Need to work? A cute desk, extra monitor, & ergonomic chair are waiting for your next project. With a full dining room, luxurious body jet/rainfall showers, pool + outdoor hot tub, it's a great spot for family reunions or unwinding after a busy day!

Half house w/pool & new patio all to yourself
PLEASE READ TO THE END!!!!!! Our home is close to restaurants, parks, the resort oceanfront and art and culture. You’ll love our place because of the location and the ambiance. Our space is good for couples, solo adventurers, business travelers or small families. Please know that my wife and I live in the other half of the house. There is NO shared space!!! You have a private entrance with full & private access to all amenities. Our home is LGBTQ+ friendly because LOVE IS LOVE!

Sweet Suite!
Private attached MOTHER IN LAW suite (not the whole house) in a quiet neighborhood in the heart of Hampton Roads. We offer keyless entry and a private parking space, private pool and backyard grill area. All are welcome here, including pets. We ask that you tell us if you are bringing a pet(s) and I'll message you about the added pet fee. We are minutes away from all major attractions and less than 5 minutes from major highways. Our location gives you easy access to the Outer Banks.

The Blue Octopus~Private Pool~HotTub~Beach~FirePit
Welcome to the Blue Octopus! This charming coastal retreat offers comfort and convenience for your seaside escape. Just a short walk to the beach, it's perfect for families, couples, or solo travelers. Location Highlights: 3 minutes to the beach 10 minutes to restaurants & Norfolk Naval Base 15 minutes to outlets 20 minutes to VA Beach Features: Private Pool Hot Tub Outdoor Movie Projector BBQ Grill Home Office Smart TV & Wi-Fi Kid-Friendly Book your stay today!

Perfect Getaway!
Home away from home!! Beautiful 2 story house with 3 bedrooms, 3 bathrooms, and a huge playroom over the garage. The master suite has a beautiful bathroom with a jacuzzi tub, and huge walk in shower. The fenced in backyard has plenty of space to run around, and has an awesome saltwater inground pool for fun! In addition, there is a 2 level, new deck, and patio furniture to sit and relax on. There is something for everyone to do here.. I’m positive you will love it!

Positano Villa
This recently remodeled home build in 1933 and located on the Chesapeake Bay is a perfect place to vacation. Direct private beach access with a beautiful salt water pool to enjoy. Around the pool there is plenty of space for games, grilling, and relaxing. Use the newly renovated kitchen or visit one of several local restaurants serving fresh local seafood to satisfy your appetite. Williamsburg, Jamestown and Yorktown are only a short drive away.
Popular amenities for Portsmouth rentals with a pool
House rentals with a pool

Cozy Pool Home w/ Sun Porch!

Nautical Cottage

The Perfect NORF/VA Beach Oasis

ShowTyme's Hampton Oasis

Coastal Retreat @ Coliseum| Bonus Room, Gazebo

Chesapeake Bay Retreat Waterfront Indoor Pool

Waterfront home with heated pool available!

Chic 2 En Suite Condo! Family & Pet Friendly
Other vacation rentals with a pool

Perfect Getaway in Chesapeake

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4 Mi to Dtwn: Home w/ Fenced Yard in Portsmouth!

Charming Home

Amazing Grace

The Cove House
Quick stats about vacation rentals with a pool in Portsmouth

Total vacation rentals
Explore 20 vacation rentals in Portsmouth

Nightly prices starting at
Portsmouth vacation rentals start at ﺩ.ﺇ184 per night before taxes and fees

Verified guest reviews
Over 700 verified reviews to help you choose

Family-friendly vacation rentals
10 properties offer extra space & kid-friendly amenities

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wi-Fi availability
20 of Portsmouth vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Portsmouth rentals

4.7 Average rating
Portsmouth stays receive an average rating of 4.7 out of 5 from guests

Nearby attractions
Portsmouth's top spots, include Chrysler Museum of Art, Nauticus, and Cinemark Chesapeake Square
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- Chesapeake Bay
- Virginia Beach Oceanfront
- Busch Gardens Williamsburg
- Carova Beach
- Corolla Beach
- Water Country USA
- First Landing State Park
- Buckroe Beach
- Jamestown Settlement
- Outlook Beach
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- The NorVa
- Currituck Beach Lighthouse
- Nauticus
- First Landing Beach
- Old Dominion University
- Colonial Williamsburg's Merchants Square
- The Mariners' Museum
- Virginia Living History Museum
- Sandy Bottom Nature Park




