House
10.0(47 Reviews)
6 Bedrooms
18 Guests
Private Pool
Hot Tub
Parking
Pool
US $1,089/Night
7 Nights - US $7,623
Hampton Roads, VA Holiday Rentals
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Compare Holiday Rentals, Villas & Resorts in Hampton Roads
10.0
Bed & Breakfast
10.0(11 Reviews)
1 Bedroom
4 Guests
EV Charge Station- Parking
View
Air Conditioner
US $187/Night
7 Nights - US $1,312
US $826/Night
7 Nights - US $5,781
House
10.0(45 Reviews)
4 Bedrooms
10 Guests
- Parking
Ocean View
Balcony/Terrace- View
US $611/Night
7 Nights - US $4,276
Bed & Breakfast
10.0(8 Reviews)
1 Bedroom
6 Guests
- EV Charge Station
- Parking
- View
- Air Conditioner
US $275/Night
7 Nights - US $1,927
Condo
10.0(44 Reviews)
3 Bedrooms
8 Guests
Oceanfront- Parking
- Pool
- Ocean View
US $556/Night
7 Nights - US $3,893
House
10.0(43 Reviews)
3 Bedrooms
7 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $269/Night
7 Nights - US $1,882
House
10.0(42 Reviews)
6 Bedrooms
12 Guests
- Private Pool
- Oceanfront
- Hot Tub
- Parking
US $1,064/Night
7 Nights - US $7,447
House
10.0(42 Reviews)
4 Bedrooms
10 Guests
- Private Pool
- Hot Tub
- Parking
- Pool
US $525/Night
7 Nights - US $3,674
Luxury Holiday Rentals in Hampton Roads
Over 10000+ Luxury Holiday Rentals in or Near Hampton Roads
Apartment
4 Bedrooms
10 Guests
- Oceanfront
- Hot Tub
- Parking
- Pool
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Apartment
4 Bedrooms
10 Guests
- Oceanfront
- Hot Tub
- Parking
- Pool
Unlock the Best Price
Apartment
3 Bedrooms
8 Guests
- Oceanfront
- Hot Tub
- Parking
- Pool
Unlock the Best Price
Apartment
3 Bedrooms
8 Guests
- Oceanfront
- Hot Tub
- Parking
- Pool
Unlock the Best Price
Apartment
3 Bedrooms
8 Guests
- Oceanfront
- Hot Tub
- Parking
- Pool
Unlock the Best Price
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Top-Rated Holiday Rentals with a Pool in Hampton Roads
Over 10000+ The Best Private Villas and Holiday Rentals in Hampton Roads with a Pool
Condo
10.0(271 Reviews)
4 Bedrooms
8 Guests
- Oceanfront
- Hot Tub
- Parking
- Pool
US $392/Night
7 Nights - US $2,741
House
10.0(264 Reviews)
3 Bedrooms
8 Guests
- Private Pool
- Hot Tub
- Parking
- Pool
US $433/Night
7 Nights - US $3,033
House
10.0(200 Reviews)
6 Bedrooms
14 Guests
- Private Pool
- Hot Tub
- Parking
- Pool
US $369/Night
7 Nights - US $2,584
Condo
10.0(193 Reviews)
2 Bedrooms
6 Guests
- Private Pool
- Oceanfront
- Parking
- Pool
US $387/Night
7 Nights - US $2,707
Condo
10.0(192 Reviews)
3 Bedrooms
8 Guests
- Parking
- Pool
- Balcony/Terrace
- View
US $228/Night
7 Nights - US $1,598
Condo
10.0(188 Reviews)
2 Bedrooms
6 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
US $168/Night
7 Nights - US $1,173
House
10.0(185 Reviews)
2 Bedrooms
5 Guests
- Parking
- Pool
- Balcony/Terrace
Kitchen
US $193/Night
7 Nights - US $1,351
Condo
10.0(184 Reviews)
1 Bedroom
2 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
US $193/Night
7 Nights - US $1,349
Condo
10.0(181 Reviews)
1 Bedroom
4 Guests
- Private Pool
- Oceanfront
- Parking
- Pool
US $157/Night
7 Nights - US $1,097
Pet-Friendly Holiday Rentals in Hampton Roads
Over 8713+ Pet-Friendly Holiday Rentals in or Near Hampton Roads
House
10.0(42 Reviews)
3 Bedrooms
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $445/Night
7 Nights - US $3,114
House
10.0(7 Reviews)
3 Bedrooms
6 Guests
- Parking
- View
Internet
Pet Friendly
US $619/Night
7 Nights - US $4,333
House
4 Bedrooms
8 Guests
- Oceanfront
- Hot Tub
- Parking
- Ocean View
US $681/Night
7 Nights - US $4,765
House
10.0(38 Reviews)
4 Bedrooms
8 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $602/Night
7 Nights - US $4,216
US $597/Night
7 Nights - US $4,178
House
10.0(35 Reviews)
6 Bedrooms
14 Guests
- Private Pool
- Oceanfront
- Hot Tub
- Parking
US $676/Night
7 Nights - US $4,731
House
10.0(32 Reviews)
3 Bedrooms
9 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $263/Night
7 Nights - US $1,841
House
10.0(30 Reviews)
4 Bedrooms
10 Guests
- Hot Tub
- Parking
- Ocean View
- Balcony/Terrace
US $424/Night
7 Nights - US $2,968
House
10.0(29 Reviews)
4 Bedrooms
8 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $615/Night
7 Nights - US $4,304
Large Holiday Rentals and Private Villas in Hampton Roads
Over 9196+ Large Holiday Rentals and Private Villas in or Near Hampton Roads
House
10.0(35 Reviews)
6 Bedrooms
18 Guests
- Private Pool
- Hot Tub
- Parking
- Pool
US $1,131/Night
7 Nights - US $7,919
House
10.0(7 Reviews)
4 Bedrooms
10 Guests
- Hot Tub
- Parking
- Internet
Child Friendly
US $367/Night
7 Nights - US $2,569
US $466/Night
7 Nights - US $3,262
House
10.0(35 Reviews)
4 Bedrooms
10 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $749/Night
7 Nights - US $5,240
House
10.0(3 Reviews)
4 Bedrooms
10 Guests
- Parking
- Balcony/Terrace
- Internet
Sports/Activities
US $562/Night
7 Nights - US $3,934
House
10.0(34 Reviews)
3 Bedrooms
10 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $326/Night
7 Nights - US $2,282
House
10.0(32 Reviews)
4 Bedrooms
10 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $431/Night
7 Nights - US $3,018
House
10.0(15 Reviews)
4 Bedrooms
10 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $297/Night
7 Nights - US $2,079
House
10.0(14 Reviews)
4 Bedrooms
10 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $688/Night
7 Nights - US $4,817
Wheelchair Accessible Holiday Homes in Hampton Roads
Over 4437+ Wheelchair Accessible Holiday Homes in or Near Hampton Roads
Condo
10.0(12 Reviews)
3 Bedrooms
8 Guests
- Pool
- Ocean View
- Balcony/Terrace
- View
US $448/Night
7 Nights - US $3,139
US $988/Night
7 Nights - US $6,916
Hotel
9.8(415 Reviews)
- Hot Tub
Breakfast- Pool
Spa
US $582/Night
7 Nights - US $4,077
Apartment
10.0(12 Reviews)
1 Bedroom
2 Guests
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
US $250/Night
7 Nights - US $1,752
House
9.5(2 Reviews)
3 Bedrooms
6 Guests
- Parking
- Pool
- View
- Air Conditioner
US $406/Night
7 Nights - US $2,839
House
Shaken Not Stirred - 8 bedroom 10 bath oceanfront with pool, elevator, hot tub and spectacular views
10.0(7 Reviews)
8 Bedrooms
24 Guests
- Private Pool
- Oceanfront
- Hot Tub
- Parking
US $1,725/Night
7 Nights - US $12,073
House
10.0(4 Reviews)
9 Bedrooms
24 Guests
- Private Pool
- Oceanfront
- Hot Tub
- Parking
US $2,051/Night
7 Nights - US $14,357
House
10.0(3 Reviews)
9 Bedrooms
24 Guests
- Private Pool
- Hot Tub
- Parking
- Pool
US $1,696/Night
7 Nights - US $11,875
House
10.0(3 Reviews)
4 Bedrooms
12 Guests
- Private Pool
- Hot Tub
- Parking
- Pool
US $1,054/Night
7 Nights - US $7,380
Hampton Roads Private Villas and Holiday Homes Under $200
Over 5441+ Hampton Roads Private Villas and Holiday Homes Under $200
House
10.0(15 Reviews)
3 Bedrooms
8 Guests
- Hot Tub
- Parking
- Ocean View
- Balcony/Terrace
US $187/Night
7 Nights - US $1,311
House
10.0(6 Reviews)
2 Bedrooms
4 Guests
- Parking
- Internet
- Sports/Activities
Security/Safety
US $190/Night
7 Nights - US $1,332
House
10.0(232 Reviews)
1 Bedroom
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $185/Night
7 Nights - US $1,294
House
10.0(13 Reviews)
1 Bedroom
3 Guests
- Parking
- Ocean View
- View
- Kitchen
US $200/Night
7 Nights - US $1,399
House
10.0(4 Reviews)
2 Bedrooms
4 Guests
- Oceanfront
- Parking
- Spa
- Ocean View
US $101/Night
7 Nights - US $707
Apartment
10.0(12 Reviews)
2 Bedrooms
4 Guests
- Hot Tub
- Parking
- Kitchen
- Air Conditioner
US $166/Night
7 Nights - US $1,163
House
10.0(11 Reviews)
3 Bedrooms
9 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $182/Night
7 Nights - US $1,276
House
10.0(8 Reviews)
3 Bedrooms
9 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $156/Night
7 Nights - US $1,094
House
10.0(5 Reviews)
2 Bedrooms
2 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $186/Night
7 Nights - US $1,301
Instantly Bookable Holiday Homes in Hampton Roads
Over 16470+ Instantly Bookable Holiday Homes in or Near Hampton Roads
House
10.0(36 Reviews)
3 Bedrooms
7 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $354/Night
7 Nights - US $2,475
US $733/Night
7 Nights - US $5,129
House
10.0(30 Reviews)
2 Bedrooms
5 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- View
US $423/Night
7 Nights - US $2,961
House
10.0(30 Reviews)
4 Bedrooms
8 Guests
- Parking
- Balcony/Terrace
- View
- Kitchen
US $339/Night
7 Nights - US $2,370
Condo
10.0(28 Reviews)
3 Bedrooms
9 Guests
- Hot Tub
- Parking
- Ocean View
- Balcony/Terrace
US $607/Night
7 Nights - US $4,248
House
10.0(23 Reviews)
3 Bedrooms
7 Guests
- Hot Tub
- Parking
- Kitchen
- Air Conditioner
US $471/Night
7 Nights - US $3,298
House
10.0(23 Reviews)
3 Bedrooms
7 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $449/Night
7 Nights - US $3,141
House
10.0(19 Reviews)
1 Bedroom
2 Guests
- Hot Tub
- Parking
- Kitchen
- Air Conditioner
US $220/Night
7 Nights - US $1,541
House
10.0(16 Reviews)
3 Bedrooms
9 Guests
- Parking
- Ocean View
- View
- Kitchen
US $1,063/Night
7 Nights - US $7,442
Book a Last Minute Place to Stay in Hampton Roads
About Casai's Private Villas and Holiday Rentals in Hampton Roads
Discover more than 24955 vacation rentals available in Hampton Roads. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in Hampton Roads.
Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Hampton Roads, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near Hampton Roads. On average, places to stay near Hampton Roads offer 1208.9 ft², with nightly prices averaging US $491.
With Casai, finding and comparing holiday rentals in Hampton Roads is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.
Other Places to Stay in Hampton Roads, US
There are 24955 Hampton Roads, US Holiday Rentals
- Prices for a holiday home in Hampton Roads start at US $30
- Top rated vacation home in Hampton Roads is Cottage on a Private Island in the York River
- Most popular short term in Hampton Roads is John Yancey Oceanfront Inn
- Cheapest place to stay in Hampton Roads is Private suite, beautiful old house, quiet location
- Most expensive holiday rental in Hampton Roads is OBX Beach Gem | Pools. Beach & Sunset Porches
Frequently Asked Questions About Hampton Roads?
What are the top holiday rentals in Hampton Roads?
With numerous options available in Hampton Roads, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in Hampton Roads:
- Cottage on a Private Island in the York River
- Cozy, Dog-friendly Duplex At The North End Short Walk To The Beach!
- Fantastic home in the heart of the VB Resort Area Walk to Beach, Boardwalk.
- Historic Cottage on Ware River Estate
- Breezy, Quaint, and Dog- Friendly North End duplex.
- Sandbridge Beach,Virginia Beach Penthouse Condominum
- Riverfront House, Dock, Hot Tub, Salt Pool, near beach, Free WiFi
- Completely Renovated Beach Box with Ocean Views & Easy Beach Access
- CLASSIC 1935 OCEANFRONT BEACH COTTAGE
- Nags Head OCEANSIDE! 3 Bedroom 4 Bath Home! 5 Star Property! 2 Night Minimum!
How many holiday rentals have private pools in Hampton Roads?
Discover a selection of holiday rentals with private pools near Hampton Roads with Casai. Experience the epitome of luxury and relaxation in our top-rated villas and holiday homes, where you can enjoy exclusive access to refreshing swimming pools.
Which holiday homes in Hampton Roads are best for families?
If you're searching for a family-friendly holiday home in Hampton Roads, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in Hampton Roads:
How many Casai.nz holiday rentals are available in Hampton Roads?
As of 2026, Casai boasts over 24955 properties listed in the Hampton Roads area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Hampton Roads.
Nearby Neighborhood (16)
| Neighborhood | Property Count |
|---|---|
| Northeast Virginia Beach Vacation Rentals in Hampton Roads, US | 1029 |
| Sandbridge Vacation Rentals in Hampton Roads, US | 632 |
| South Nags Head Vacation Rentals in Hampton Roads, US | 588 |
| Whalehead Beach Vacation Rentals in Hampton Roads, US | 464 |
| Corolla Light Vacation Rentals in Hampton Roads, US | 329 |
| East Ocean View Vacation Rentals in Hampton Roads, US | 184 |
| Willoughby Spit Vacation Rentals in Hampton Roads, US | 177 |
| Downtown Vacation Rentals in Hampton Roads, US | 134 |
| Monteray Shores Vacation Rentals in Hampton Roads, US | 107 |
| Northwest Vacation Rentals in Hampton Roads, US | 105 |
| Sea Scape Vacation Rentals in Hampton Roads, US | 103 |
| North Newport News Vacation Rentals in Hampton Roads, US | 93 |
| Bermuda Bay Vacation Rentals in Hampton Roads, US | 88 |
| Dam Neck Vacation Rentals in Hampton Roads, US | 36 |
| Chic's Beach Vacation Rentals in Hampton Roads, US | 35 |
| Kingsmill Vacation Rentals in Hampton Roads, US | 30 |
