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Holiday rentals with a pool in Chesapeake

Find and book unique homes with a pool on Airbnb

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Popular amenities for Chesapeake rentals with a pool

House rentals with a pool

Top guest favourite
Home in Corolla
5 out of 5 average rating, 21 reviews

New fully loaded, Firepit, pool/hottub, ocean view

JenniferRating, 5 stars1 week ago
My family came together for a 3-day stay at Nomad Dunes. It was everyone's 1st time to the OBX. There's 16 of us ranging in age from 9-74! There are 3 levels to this home with sleeping areas on all levels which was great for us. I think we used every entertaining and relaxing spot in this house!! You can see the ocean from the top floor and it truly is easy enough to walk to the beach or hop in the car and drive back and forth. Having the pool was perfect for our family. It is about 5ft deep at most so all the kids could access the pool without worry. And the hot tub was VERY popular with our group! Hardly anyone picked up a phone or devise other than to take photos or videos and we watched one movie. The drive on the beach to get to the home was a LOT more than we expected!! Videos do not do this justice. It's long, and bumpy, and feels out of control at times. SHOP beforehand!! Beds and furnishings are comfy and pretty. I suggest mentioning if you plan to use the bunks and sofa bed.
Guest favourite
Home in Corolla
5 out of 5 average rating, 32 reviews

Aloha Beaches OBX

RebeccaRating, 5 stars2 days ago
This home was incredible! The 4x4 experience was really fun and we saw horses everyday, at one point the horses were under the house cooling off in the shade. It’s hard to put into words 🙂 Sarah was responsive and helpful throughout the trip!
Top guest favourite
Home in Gloucester Point
4.99 out of 5 average rating, 185 reviews

York River Vacation Home

AdamRating, 5 stars1 week ago
We had a wonderful stay here! Everything was exactly as described. Eugene was really responsive when communicating and super friendly! I would highly recommend staying here if you get the chance. Thank you again for such a relaxing place to stay!
Guest favourite
Home in Sandbridge
4.93 out of 5 average rating, 14 reviews

New! Boat Dock /Pool /HotTub/ Waterfront/ Beach

Keya Rating, 5 stars1 month ago
I had a fantastic experience staying at Sandbridge Stay. The property was exactly as described—clean, cozy, and well-equipped with everything I needed. The location was perfect, close to beach, but still quiet and peaceful for a good night’s rest.
Superhost
Home in Sandbridge
4.84 out of 5 average rating, 129 reviews

Stunning Views of Back Bay & Seconds to the Beach

GregRating, 5 stars2 weeks ago
Great location and host. The home was the perfect size for my family and friends.
Top guest favourite
Home in Virginia Beach
4.97 out of 5 average rating, 203 reviews

Sunrise, North End Beach

CraigRating, 5 stars3 days ago
Mark is a great host. The house is immaculate. Every little detail is perfect. By far the nicest AirBNB I have ever rented. Mark made sure everything was perfect for our visit with our son in the Navy.
Top guest favourite
Home in Corolla
5 out of 5 average rating, 20 reviews

Splash of Lime Carova 4x4 Beach Cottage

KristenRating, 5 stars1 week ago
What a great place to stay. Splash of lime worked great for our group. The house is set up nicely and has lots of storage available. We were lucky enough to get daily visits from the wild horses throughout the day. Martin is an excellent host and responded very quickly to answer any questions we had.
Top guest favourite
Home in Sandbridge
5 out of 5 average rating, 21 reviews

Coconut Cottage-Sleeps 2,Pool,Beach

LoriRating, 5 stars1 week ago
The Pool House was exactly as described — clean, comfortable, and welcoming! Denise had thoughtful touches like snacks, water, and coffee ready for us when we arrived. Both she and her sweet dog Murphy made us feel right at home. We were also able to check in when we arrived in Sandbridge a little early. The Pool House was ready and waiting. We were in town for a wedding, and when a last-minute issue came up with the newlyweds’ accommodations, Denise was incredibly gracious and allowed us to turn the Pool House over to them. It ended up being the perfect space for the couple to relax for a couple of days before leaving on their honeymoon. The couple and their parents were very grateful for Denise’s kindness and willingness to help. The stress of not having a place to stay on their wedding night melted away. I would absolutely recommend staying here — Denise is a wonderful host, and Murphy is a joy! God bless you, Denise.

Apartment rentals with a pool

Guest favourite
Apartment in Virginia Beach
4.84 out of 5 average rating, 286 reviews

Beautiful Beachfront Condo

JeffreyRating, 5 stars1 week ago
The only issue we had was our code for the building and parking did not work at first! Pam was very quick to resolve! There are no elevators in parking garage, I would take my stuff in at the entrance and then park! Dolphin run staff was not much help! We had a second car that we were supposed to get a parking permit for. They just told us to park and not worry about signs that clearly stated towed with no permit. Our car did NOT get towed!
Guest favourite
Apartment in Virginia Beach
4.91 out of 5 average rating, 56 reviews

Beach Luxury Beachfront

SarahRating, 5 stars2 weeks ago
We frequently go to Virginia Beach and now that our boys are grown, it was nice to have the space of an apartment on the beach instead of 2 hotel rooms. The location is right where we usually stay when we go to Virginia Beach. Walkable to all of our favorite restaurants, clean, comfortable beds… just perfect!
Superhost
Apartment in Virginia Beach
5 out of 5 average rating, 4 reviews

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

AldoRating, 5 stars11 months ago
We stayed a week at Kerri’s place in Virginia. She went above and beyond our expectations, very communicative and organized. She offered a ton of information and insights before and during our stay. Her place offers a delightful and relaxing getaway experience. The resort's picturesque location by the ocean provides stunning views and a serene atmosphere. The rooms are spacious, well-appointed, and comfortable, ensuring a pleasant stay. The resort amenities such as the pool, spa, and on-site restaurants add to the overall wonderful experience. The staff is friendly, accommodating, and dedicated to providing top-notch service to guests. Whether you're looking to relax by the beach or explore the nearby attractions, Boardwalk Resort is a fantastic choice for a vacation in Virginia. I would definitely recommend and revisit Kerri’s place.
Guest favourite
Apartment in Virginia Beach
4.87 out of 5 average rating, 86 reviews

Good Vibes at the Beach

BevRating, 5 stars3 weeks ago
Colin is an impeccable host! He’s caring-he’s honest- he answers all concerns immediately- His “home” is one of the nicest beautifully decorated homes we have stayed in-and so clean!!! Thank you for the privilege of staying at your place
Superhost
Apartment in Sandbridge
4.92 out of 5 average rating, 132 reviews

Ocean & Bay Views - Local Family Owned & Operated

MarieRating, 5 stars2 weeks ago
We had a lovely stay at Crystal’s while in town for a graduation. Crystal was proactive with directions, recommendations, and instructions, and she responded quickly to questions. The place was nicely decorated, and well-stocked with kitchen gadgets, beach chairs, games, and other necessities. This is a nice place for a getaway.
Guest favourite
Apartment in Virginia Beach
4.97 out of 5 average rating, 93 reviews

Oceanfront Studio: Boardwalk, Beach, & Pool Views

HannahRating, 5 stars3 weeks ago
Frances’ condo was in a great location right at the end of the boardwalk. We were able to get up in the morning and walk to breakfast with multiple other restaurants within walking distance. The view of the pool and ocean was nice and the condo felt bright and sunny. There was one dedicated parking spot which was nice. Everything in the condo was clean and nicely decorated. We enjoyed our stay and highly recommend!
Guest favourite
Apartment in Virginia Beach
4.98 out of 5 average rating, 92 reviews

Paradise at the Beach

BlakeRating, 5 stars3 days ago
Overall this a great find, close to the beach, nice pool, easy access. Kattia was very fast to respond and had some great suggestions. She left us water bottles and rain ponchos which thankfully we didn't need. We found the unit to be very clean and fresh and she has thought of everything. The only issue we had was the TV in the master would not connect to the wifi but we didn't really need it. Loved having access to the pool from the sliding door in the master bedroom. We met some of the other owners and they were all very nice. It was also nice to be so close to Harris Teeter.
Guest favourite
Apartment in Virginia Beach
4.86 out of 5 average rating, 138 reviews

Oceanfront, beach, boardwalk, fun, dolphin, sunris

AnitaRating, 5 stars2 months ago
We enjoyed staying at Kelly's place in VB. Its an ideal location for anyone who wants to stay right at the boardwalk. We witnessed amazing sunrises and moonrises. The ocean was right in front of us and from the 6th floor, the view was expansive. A lot of restaurants were also nearby. Kelly was always very communicative, polite and professional. The apartment was clean with the kitchen well stocked with utensils The bedrooms were of a pretty large size. And parking was on the premises. Overall, it was a wonderful experience and holiday for us. We strongly recommend Kelly's place.

Quick stats about holiday rentals with a pool in Chesapeake

  • Total rentals

    130 properties

  • Nightly prices starting at

    $26 SGD before taxes and fees

  • Total number of reviews

    2.8K 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

  1. Airbnb
  2. United States
  3. Virginia
  4. Chesapeake
  5. Rentals with pools