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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.

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Home in Sandbridge

4.85 out of 5 average rating, 118 reviews

Stunning Views of Back Bay & Seconds to the Beach

Be our guest and enjoy some of the most spectacular views in all of Virginia Beach. Lounge in the pool and watch the sun set over Back Bay or enjoy exploring Back Bay with fishing and site seeing. With the beach being a block away, you can get your feet wet with surfing or snorkeling or simply relax on the beach with your favorite beverage. Little Island Park, Back Bay Wildlife Refuge & The Baja are just a few minutes away as well. This 6 bedroom home, with 11 beds will be the perfect get away.

Condo in Sandbridge

4.87 out of 5 average rating, 227 reviews

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.

Condo in Virginia Beach

4.84 out of 5 average rating, 121 reviews

Oceanfront, beachfront, boardwalk, fun, dolphins

Fantastic condo on the beach. Floor to ceiling windows in living-room, bedrooms. Watching waves, sunrise, dolphins. Enjoy the ocean, boardwalk, beach gym, playground right at downstairs. Extra-large end-unit with fully equipped kitchen, saves you $$$ on meals. One free parking. Walking distance to restaurants, bars, stores, beach concerts, activities, art shows, performance. New 65” QLED TV, new sofa and dining set. Ask for extended stay discount! Up to 45% off Winter Special Deals. Book now!

Home in Phoebus

4.85 out of 5 average rating, 181 reviews

Waterfront home with heated pool available!

This lovely, spacious waterfront home is full of things to do. It is the perfect get away! Enjoy views of the Hampton River while you relax in the heated salt water pool! You may have up to eight guests with our 4 bedroom 3 bath home. Additional guests are $30 per person and an air mattress can be provided upon request. Pets are welcome for $45 per pet, you must notify ahead of time. You may also have the pool heated during your entire stay for only $250. (DO NOT TOUCH THE POOL PUMP PLEASE)

Home in Virginia Beach

4.88 out of 5 average rating, 128 reviews

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!

Guest suite in Chesapeake

4.95 out of 5 average rating, 530 reviews

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.

Rental unit in Virginia Beach

4.87 out of 5 average rating, 145 reviews

VA Beach Oceanfront Studio, Beach, Boardwalk, Pool

This studio condo is located at the north end of Virginia Beach's famous boardwalk, just steps to the beach with an Atlantic Ocean view. Walking distance to area attractions, restaurants, and shopping. Ideal for couples with access to the salt water pool, lawn on the beach with lounge chairs and tables, and a reserved parking space. If you are visiting for a quiet getaway or for an event, you will love the boutique feel in an ideal location of this clean, newly renovated condo

Home in Virginia Beach

4.82 out of 5 average rating, 112 reviews

THE OLD BEACON 1 | Beach Living

The Old Beacon is the perfect vacation blend of beach time and poolside sunbathing. This is the downstairs unit of the front cottage and the largest of The Old Beacon units. Stylish and comfortable interior with access to the amazing outdoor common area - pool, cornhole, porch swings, outdoor dining area, and outdoor shower for when you return from the beach! Kick back and relax in this vacation home that’s two blocks to the beach and Virginia Beach boardwalk!

Condo in Virginia Beach

4.9 out of 5 average rating, 202 reviews

Va Beach Oceanfront Studio, Boardwalk, Pool, Beach

Nestled on the desirable north end of the boardwalk, close to the area’s best attractions, the top restaurants and bars. Just steps to the boardwalk, beach and ocean. Enjoy a nice meal or a early morning cup of coffee while enjoying a beautiful view of the Atlantic Ocean. Our studio includes a reserved parking space, saltwater pool, large BBQ deck area and a lawn on the beach. This small oceanfront complex is a great place for couples or a small family.

Cottage in Norfolk

4.97 out of 5 average rating, 231 reviews

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.

Home in Virginia Beach

4.96 out of 5 average rating, 186 reviews

Salida del Sol, North End Beach

The beach AND privacy! Wide open residential beaches, with plenty of "distancing space"! Best kept secret at the beach! Fully stocked, fully furnished, immaculate Vacation rental on Va Beach North End. 5 star rating says it all. Atlantic Ocean across the street. Public beach access. 3 flat screen TVs, Wifi, cable, beach cart, chairs &'umbrella. Outdoor grill. Private parking. 2024 Pool Season... May 10-September. 15. NO HAIR DYE!

Condo in Virginia Beach

4.85 out of 5 average rating, 137 reviews

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.

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Popular amenities for Chesapeake rentals with a pool

Free parking on premises

Air conditioning

House rentals with a pool

Home in Portsmouth

4.94 out of 5 average rating, 85 reviews

Wooded Wonderland Miniature Golf Hot tub Pool

Home in Sandbridge

4.99 out of 5 average rating, 77 reviews

Breathtaking Ocean views at Pinch Me, 8bdrm, 6bath

Home in East Ocean View

4.98 out of 5 average rating, 49 reviews

The Seaglass Cottage

Home in Norfolk

4.95 out of 5 average rating, 80 reviews

Gorgeous Vacation House

Home in Sandbridge

4.92 out of 5 average rating, 38 reviews

Silver Strand-Renovated 2022, Sandbridge/Bayfront

Home in Sandbridge

4.79 out of 5 average rating, 43 reviews

5BR Waterfront 350ft-Beach Salt Pool Reno 14 guest

Home in Corolla

4.88 out of 5 average rating, 32 reviews

Sandy Beaches OBX *New Pool and Hot Tub 2024*

Home in Hampton

4.92 out of 5 average rating, 88 reviews

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

Condo rentals with a pool

Condo in Virginia Beach

4.9 out of 5 average rating, 50 reviews

Ocean front best beach, boardwalk, dolphins!

Condo in Sandbridge

5 out of 5 average rating, 51 reviews

Sandbridge Beach - DeepSeaSide Retreat

Condo in Virginia Beach

4.99 out of 5 average rating, 72 reviews

Oceanfront Studio: Boardwalk, Beach, & Pool Views

Condo in Virginia Beach

5 out of 5 average rating, 12 reviews

Paradise Cove

Condo in Virginia Beach

4.83 out of 5 average rating, 53 reviews

Seas The Day of Virginia Beach

Condo in Virginia Beach

4.89 out of 5 average rating, 9 reviews

Beachfront Oasis

Condo in Virginia Beach

4.94 out of 5 average rating, 80 reviews

Oceanfront/Boardwalk Complex, Beach, Pool, Balcony

Quick stats about vacation rentals with a pool in Chesapeake

Total rentals
130 properties
Nightly prices starting at
$20 before taxes and fees
Total number of reviews
3.3K reviews
Family-friendly rentals
50 properties are a good fit for families
Pet-friendly rentals
40 properties allow pets
Rentals with dedicated workspaces
60 properties have a dedicated workspace

Destinations to explore