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

Ocean Escape
Ocean Escape, 4th floor condo in the luxuriously upscale Sanctuary Resort at False Cape in Virginia Beach, Virginia, breathtaking views of both the Atlantic Ocean and Back Bay and is a leisurely 100 step stroll to the beautiful beach and surf. Beach chairs, coolers, umbrellas, sand toys for the kids, boogie boards and two beach cruiser bikes. Community pool area, complete with Jacuzzi tub, lounge furniture, and stainless steel gas grills. The elevator is just across from dedicated parking spot.

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.

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!

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.

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.

Walk to Beach! Dogs OK, Backyard, Hot Tub, Pool
Welcome to Coral Cove in Corolla! Take it easy at this nearly new, well-appointed condo and relax under the stars in your own private hot tub! - 2bed, 2 bth, sleeps 6, 2 king beds + Queen sleeper sofa - Easy 8-10min walk to beach. - Dogs OK! (fee applies) - Beach Gear included w/wagon. - Linens and Beach towels included! - Single level with no steps to enter or leave. - Private Hot Tub - Private backyard with seating

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 Chesapeake rentals with a pool
House rentals with a pool

Chesapeake Bay Retreat Waterfront Indoor Pool

Waterfront, Stunning Views + Pool | Kayaks!

Private Pool at the Oceanfront in a Spacious Home

Stunning Views of Back Bay & Seconds to the Beach

Sunrise, North End Beach

MillerLight

4BD home w/ game room & pool near Langley & PTC!

Half house w/pool & new patio all to yourself
Condo rentals with a pool

OBC - 1BR/1BA - Amazing Oceanfront View!

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

Good Vibes at the Beach

Ocean & Bay Views - Local Family Owned & Operated

Oceanfront, beach, boardwalk, fun, dolphin, sunris

Paradise at the Beach

Boutique Oceanfront Condo - Boardwalk & Top Dining

Modern 2 bedroom, near beach and village
Other vacation rentals with a pool

The Green Bean Bungalow

Ava’s Estuary

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

Saltwater Seaclusion- Corolla-Walk to Everything!

Nates Nook on Back Bay

Oceanfront 2BR Luxury • Private Balcony

Coconut Cottage-Sleeps 2,Pool,Beach

Baja Daydreamer; 2 room Spacious Glamper
When is the best time to visit Chesapeake?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | € 84 | € 92 | € 92 | € 94 | € 97 | € 104 | € 109 | € 97 | € 92 | € 92 | € 84 | € 92 |
| Avg. temp | 6°C | 7°C | 10°C | 16°C | 20°C | 25°C | 27°C | 26°C | 23°C | 18°C | 12°C | 8°C |
Quick stats about vacation rentals with a pool in Chesapeake

Total vacation rentals
Explore 130 vacation rentals in Chesapeake

Nightly prices starting at
Chesapeake vacation rentals start at € 25 per night before taxes and fees

Verified guest reviews
Over 3,760 verified reviews to help you choose

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

Pet-friendly vacation rentals
Find 50 rentals that welcome pets

Rentals with dedicated workspaces
60 properties have a dedicated workspace

Wi-Fi availability
130 of Chesapeake vacation rentals include wi-fi access

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

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

Nearby attractions
Chesapeake's top spots, include Chrysler Museum of Art, Nauticus, and Cinemark Chesapeake Square
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- Rentals with pools United States
- Virginia Beach Oceanfront
- Busch Gardens Williamsburg
- Corolla Beach
- Carova Beach
- Water Country USA
- First Landing State Park
- Jamestown Settlement
- Buckroe Beach
- Cape Charles Beachfront
- Norfolk Botanical Garden
- Outlook Beach
- Ocean Breeze Waterpark
- Chrysler Museum of Art
- Currituck Beach Lighthouse
- Chrysler Hall
- The NorVa
- First Landing Beach
- Nauticus
- Virginia Zoological Park
- Old Dominion University
- Hampton University
- Currituck Club
- Currituck Beach
- Town Point Park




