
Holiday 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.

Va Beach Oceanfront Studio, Boardwalk, Pool, Beach
Nestled in the heart of the coastal city of Virginia Beach where all of the area’s greatest attractions will be right at your fingertips. This coastal beach studio offers a space-maximizing layout which includes kitchenette with full size appliances. All on the desirable north end of the Virginia Beach boardwalk. This small oceanfront complex is one of a kind, a great place for couples or a small family. Enjoy an early morning cup of coffee while enjoying beautiful views of the Atlantic Ocean.

Oceanfront Building Boardwalk Pool Beach 3 Beds
Welcome to the Cozy Crab – updated, comfort-focused & steps from the sand! Located in a quiet corner of a beachfront building on the Virginia Beach boardwalk with a seasonal pool (open mid-May–mid-Oct). Sleeps 4 with 3 real beds: one queen and two singles, all with real mattresses. Features a large, updated bathroom with full vanity and a kitchen. Just a few steps up—no elevator needed. No chore checkout, pro cleaning, fresh linens/towels, WiFi. 2nd-floor grills. Eat! restaurant is downstairs!

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.

Oceanfront Gem VaB Studio Exceptional Views
Newly renovated modern studio condo, owners personal getaway now open to guests. This corner unit, the largest and most private in Oceans ll Condominium complex, is on the 3rd floor and offers beautiful, expansive views at both sunrise and sunset. Just off the boardwalk with community pool, this unit sleeps three. Right on the oceanfront, you won't find a more peaceful getaway! Beach chairs and towels provided. Please note: due to the open layout of the building, there is no elevator.

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.

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!

Designer Beach House | Pool, Hot Tub, Walk to Sand
Breaker Bay is a fully renovated 5BR, 3BA beach cottage in the heart of Sandbridge. With a private pool, hot tub, spacious deck, and open living space, it’s perfect for families or groups. Just minutes from the sand, it offers the ideal blend of comfort and coastal charm. Wake up to ocean sunrises, unwind with bay sunsets, and enjoy all that this peaceful beach community has to offer. Your perfect coastal getaway starts here.

4BD home w/ game room & pool near Langley & PTC!
Welcome Home! Be the next to rent this beautifully renovated, modernized home with beautiful kitchen, amazing bathrooms and generous bedrooms and closets. Come in and relax in this centrally located neighborhood - convenient ten minute trip for shopping, restaurants and military bases. Great for families coming in town for Boo Williams tournaments! This is the one! DONT FORGET TO ASK ABOUT OUR YACHT RENTAL OPTIONS!!!

WOW Location! Beach Paradise on Boardwalk w/Pool
Enjoy a piece of the Oceanfront with this gorgeous updated condo! Walk out your front door to the beach, pool, boardwalk, the historic Cavalier hotel, restaurants, shops and many entertainments on the beach! Newly renovated, this beachy North End paradise is the perfect getaway for a couple. One parking spot, deck area , a lawn on the beach with lounge chairs and coin operated laundry available on premises.

Beautiful and Chic Studio Apartment
Chic private apartment is located in a quiet neighborhood at the end of the peninsula were the Indian River flows into the Elizabeth River. Centrally located, we are nestled in the heart of Hampton roads with Virginia Beach 1 mile to the east and Norfolk 1 mile to the north. Twenty minutes from everywhere you'll want to go: the airport, the beach, multiple shopping centers and several universities.
Popular amenities for Portsmouth rentals with a pool
House rentals with a pool

Nautical Cottage

The Blue Octopus~Private Pool~HotTub~Beach~FirePit

Artful Retreat with a Private Pool

Modernist Oasis | 2 Luxury Homes & Private Pool

Private Pool at the Oceanfront in a Spacious Home

Sunrise, North End Beach

Star by The Sea

Ocean Pearl- Canal View and Minutes to the beach
Apartment rentals with a pool

Beach Luxury Beachfront

Boardwalk Resort & Villas - 1BR/1BA - Oceanfront!

Good Vibes at the Beach

Ocean & Bay Views - Local Family Owned & Operated

Paradise at the Beach

Oceanfront, beach, boardwalk, fun, dolphin, sunris

Coastal Beach condo-amazing view and indoor pool

OBC - 2BR/2BA Suite - City View
Other holiday rentals with a pool

Coastal Retreat @ Coliseum| Bonus Room, Gazebo

The Green Bean Bungalow

Ava’s Estuary

8br, Pool, Lzy Rvr, Pier, Pool, Hot Tub (Sandbridge)

Oceanfront 2 bedroom condo

Barclay Towers Resort Direct Oceanfront Unit

Nates Nook on Back Bay

Coconut Cottage-Sleeps 2,Pool,Beach
Quick stats about holiday rentals with a pool in Portsmouth

Total holiday rentals
Explore 20 holiday rentals in Portsmouth

Nightly prices starting at
Portsmouth holiday rentals start at £37 per night before taxes and fees

Verified guest reviews
Over 660 verified reviews to help you choose

Family-friendly holiday rentals
10 properties offer extra space & child-friendly amenities

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wifi availability
20 of Portsmouth holiday rentals include wifi 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
- Buckroe Beach
- Corolla Beach
- Water Country USA
- First Landing State Park
- Haven Beach
- Buckroe Beach
- Jamestown Settlement
- Grandview Beach
- Bethel Beach
- Kiptopeke Beach
- Outlook Beach
- Norfolk Botanical Garden
- Ocean Breeze Waterpark
- Virginia Beach National Golf Club
- Golden Horseshoe Golf Club
- Chrysler Museum of Art
- Cape Charles Beachfront
- Wilkins Beach
- James River Country Club
- Red Wing Lake Golf Course




