New
House
10.0(2 Reviews)
4 Bedrooms
8 Guests
Parking
Balcony/Terrace
View
Kitchen
CA $565/Night
7 Nights - CA $3,952
Hampton Roads, VA Holiday Rentals
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Compare Holiday Rentals, Villas & Resorts in Hampton Roads
10.0
House
10.0(8 Reviews)
3 Bedrooms
8 Guests
- Parking
Spa- Balcony/Terrace
- View
CA $306/Night
7 Nights - CA $2,140
House
4 Bedrooms
8 Guests
Oceanfront
Hot Tub- Parking
Ocean View
CA $970/Night
7 Nights - CA $6,793
Condo
10.0(1 Review)
4 Bedrooms
16 Guests
- Hot Tub
- Parking
Pool- Balcony/Terrace
CA $286/Night
7 Nights - CA $2,001
House
10.0(7 Reviews)
3 Bedrooms
6 Guests
- Parking
- View
Internet
Pet Friendly
CA $882/Night
7 Nights - CA $6,177
Condo
10.0(365 Reviews)
2 Bedrooms
6 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
CA $359/Night
7 Nights - CA $2,516
House
10.0(300 Reviews)
3 Bedrooms
9 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
CA $611/Night
7 Nights - CA $4,278
Condo
10.0(285 Reviews)
2 Bedrooms
6 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
CA $375/Night
7 Nights - CA $2,623
Condo
10.0(271 Reviews)
4 Bedrooms
8 Guests
- Oceanfront
- Hot Tub
- Parking
- Pool
CA $558/Night
7 Nights - CA $3,907
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
Unlock the Best Price
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
Unlock the Best Price
Unlock the Best Price
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
House
10.0(266 Reviews)
3 Bedrooms
8 Guests
Private Pool- Hot Tub
- Parking
- Pool
CA $618/Night
7 Nights - CA $4,324
House
10.0(200 Reviews)
6 Bedrooms
14 Guests
- Private Pool
- Hot Tub
- Parking
- Pool
CA $526/Night
7 Nights - CA $3,684
Condo
10.0(193 Reviews)
2 Bedrooms
6 Guests
- Private Pool
- Oceanfront
- Parking
- Pool
CA $551/Night
7 Nights - CA $3,859
Condo
10.0(192 Reviews)
3 Bedrooms
8 Guests
- Parking
- Pool
- Balcony/Terrace
- View
CA $325/Night
7 Nights - CA $2,278
Condo
10.0(188 Reviews)
2 Bedrooms
6 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
CA $239/Night
7 Nights - CA $1,672
House
10.0(185 Reviews)
2 Bedrooms
5 Guests
- Parking
- Pool
- Balcony/Terrace
- Kitchen
CA $275/Night
7 Nights - CA $1,926
Condo
10.0(184 Reviews)
1 Bedroom
2 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
CA $277/Night
7 Nights - CA $1,937
Condo
10.0(181 Reviews)
1 Bedroom
4 Guests
- Private Pool
- Oceanfront
- Parking
- Pool
CA $230/Night
7 Nights - CA $1,609
House
10.0(178 Reviews)
6 Bedrooms
14 Guests
- Private Pool
- Hot Tub
- Parking
- Pool
CA $960/Night
7 Nights - CA $6,717
Pet-Friendly Holiday Rentals in Hampton Roads
Over 8629+ Pet-Friendly Holiday Rentals in or Near Hampton Roads
House
10.0(169 Reviews)
8 Bedrooms
23 Guests
- Private Pool
- Hot Tub
- Parking
- Pool
CA $1,591/Night
7 Nights - CA $11,134
CA $851/Night
7 Nights - CA $5,956
House
10.0(1 Review)
1 Bedroom
- Oceanfront
- Ocean View
- View
- Kitchen
CA $891/Night
7 Nights - CA $6,234
House
10.0(147 Reviews)
1 Bedroom
2 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
CA $312/Night
7 Nights - CA $2,184
House
10.0(5 Reviews)
4 Bedrooms
8 Guests
- Balcony/Terrace
- View
- Pet Friendly
Child Friendly
CA $866/Night
7 Nights - CA $6,064
House
10.0(95 Reviews)
5 Bedrooms
12 Guests
- Private Pool
- Oceanfront
- Hot Tub
- Parking
CA $3,291/Night
7 Nights - CA $23,034
House
10.0(71 Reviews)
3 Bedrooms
6 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
CA $565/Night
7 Nights - CA $3,956
Cottage
10.0(59 Reviews)
1 Bedroom
4 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
CA $523/Night
7 Nights - CA $3,659
Condo
10.0(56 Reviews)
2 Bedrooms
6 Guests
- Parking
- Pool
- Balcony/Terrace
- Kitchen
CA $416/Night
7 Nights - CA $2,911
Large Holiday Rentals and Private Villas in Hampton Roads
Over 9083+ Large Holiday Rentals and Private Villas in or Near Hampton Roads
House
10.0(175 Reviews)
6 Bedrooms
16 Guests
- Private Pool
- Oceanfront
- Hot Tub
- Parking
CA $941/Night
7 Nights - CA $6,586
House
10.0(7 Reviews)
4 Bedrooms
10 Guests
- Hot Tub
- Parking
- Internet
- Child Friendly
CA $523/Night
7 Nights - CA $3,662
CA $839/Night
7 Nights - CA $5,869
New
House
10.0(127 Reviews)
5 Bedrooms
14 Guests
- Private Pool
- Parking
- Pool
- Balcony/Terrace
CA $1,264/Night
7 Nights - CA $8,850
House
10.0(3 Reviews)
4 Bedrooms
10 Guests
- Parking
- Balcony/Terrace
- Internet
Sports/Activities
CA $801/Night
7 Nights - CA $5,608
House
10.0(100 Reviews)
5 Bedrooms
12 Guests
- Private Pool
- Oceanfront
- Parking
- Pool
CA $1,206/Night
7 Nights - CA $8,441
Villa
10.0(79 Reviews)
3 Bedrooms
6 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
CA $384/Night
7 Nights - CA $2,690
House
10.0(78 Reviews)
4 Bedrooms
12 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
CA $1,178/Night
7 Nights - CA $8,243
House
10.0(52 Reviews)
7 Bedrooms
17 Guests
- Private Pool
- Parking
- Pool
- Ocean View
CA $1,906/Night
7 Nights - CA $13,345
Wheelchair Accessible Holiday Homes in Hampton Roads
Over 4455+ Wheelchair Accessible Holiday Homes in or Near Hampton Roads
Condo
10.0(156 Reviews)
3 Bedrooms
6 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
CA $558/Night
7 Nights - CA $3,906
CA $1,408/Night
7 Nights - CA $9,859
Hotel
10.0(1 Review)
Breakfast- Parking
- Internet
- Child Friendly
CA $265/Night
7 Nights - CA $1,855
Condo
10.0(118 Reviews)
3 Bedrooms
8 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
CA $638/Night
7 Nights - CA $4,465
House
9.5(2 Reviews)
3 Bedrooms
6 Guests
- Parking
- Pool
- View
Air Conditioner
CA $578/Night
7 Nights - CA $4,047
Condo
10.0(96 Reviews)
2 Bedrooms
6 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
CA $603/Night
7 Nights - CA $4,218
House
10.0(90 Reviews)
3 Bedrooms
9 Guests
- Oceanfront
- Hot Tub
- Parking
- Ocean View
CA $877/Night
7 Nights - CA $6,137
New
Condo
10.0(83 Reviews)
2 Bedrooms
5 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
CA $285/Night
7 Nights - CA $1,997
Condo
10.0(76 Reviews)
2 Bedrooms
5 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
CA $356/Night
7 Nights - CA $2,493
Hampton Roads Private Villas and Holiday Homes Under $200
Over 5565+ Hampton Roads Private Villas and Holiday Homes Under $200
House
10.0(77 Reviews)
1 Bedroom
4 Guests
- Parking
- Pool
- Balcony/Terrace
- Kitchen
CA $217/Night
7 Nights - CA $1,517
House
10.0(6 Reviews)
2 Bedrooms
4 Guests
- Parking
- Internet
- Sports/Activities
Security/Safety
CA $271/Night
7 Nights - CA $1,899
House
10.0(232 Reviews)
1 Bedroom
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
CA $263/Night
7 Nights - CA $1,845
House
10.0(15 Reviews)
3 Bedrooms
8 Guests
- Hot Tub
- Parking
- Ocean View
- Balcony/Terrace
CA $272/Night
7 Nights - CA $1,905
House
10.0(4 Reviews)
2 Bedrooms
4 Guests
- Oceanfront
- Parking
- Spa
- Ocean View
CA $144/Night
7 Nights - CA $1,008
Condo
10.0(13 Reviews)
1 Bedroom
2 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
CA $205/Night
7 Nights - CA $1,438
House
10.0(13 Reviews)
2 Bedrooms
6 Guests
- Parking
- Ocean View
- View
- Kitchen
CA $144/Night
7 Nights - CA $1,009
House
10.0(11 Reviews)
3 Bedrooms
9 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
CA $260/Night
7 Nights - CA $1,819
House
10.0(8 Reviews)
3 Bedrooms
9 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
CA $223/Night
7 Nights - CA $1,560
Instantly Bookable Holiday Homes in Hampton Roads
Over 16266+ Instantly Bookable Holiday Homes in or Near Hampton Roads
House
10.0(104 Reviews)
3 Bedrooms
8 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
CA $1,012/Night
7 Nights - CA $7,087
CA $329/Night
7 Nights - CA $2,307
Condo
10.0(73 Reviews)
2 Bedrooms
4 Guests
- Parking
- Pool
- Balcony/Terrace
- Kitchen
CA $500/Night
7 Nights - CA $3,497
Condo
10.0(72 Reviews)
2 Bedrooms
6 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
CA $546/Night
7 Nights - CA $3,821
Condo
10.0(69 Reviews)
2 Bedrooms
6 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
CA $507/Night
7 Nights - CA $3,551
House
10.0(69 Reviews)
2 Bedrooms
4 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
CA $374/Night
7 Nights - CA $2,616
House
10.0(67 Reviews)
3 Bedrooms
8 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
CA $1,104/Night
7 Nights - CA $7,727
House
10.0(64 Reviews)
2 Bedrooms
6 Guests
- Private Pool
- Breakfast
- Parking
- Pool
CA $913/Night
7 Nights - CA $6,389
Condo
10.0(64 Reviews)
2 Bedrooms
6 Guests
- Pool
- Ocean View
- Balcony/Terrace
- View
CA $468/Night
7 Nights - CA $3,273
Book a Last Minute Place to Stay in Hampton Roads
About Casai's Private Villas and Holiday Rentals in Hampton Roads
Discover more than 24726 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 1215 ft², with nightly prices averaging CA $696.
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 24726 Hampton Roads, US Holiday Rentals
- Prices for a holiday home in Hampton Roads start at CA $43
- Top rated vacation home in Hampton Roads is Cozy, Dog-friendly Duplex At The North End Short Walk To The Beach!
- 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:
- 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
- CLASSIC 1935 OCEANFRONT BEACH COTTAGE
- Don't miss out on fall dates and amazing rates. Great Location & Fido-friendly.
- Nags Head OCEANSIDE! 3 Bedroom 4 Bath Home! 5 Star Property! 2 Night Minimum!
- Cypress House Inn
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.ca holiday rentals are available in Hampton Roads?
As of 2026, Casai boasts over 24726 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 | 1055 |
| Sandbridge Vacation Rentals in Hampton Roads, US | 644 |
| South Nags Head Vacation Rentals in Hampton Roads, US | 589 |
| Whalehead Beach Vacation Rentals in Hampton Roads, US | 463 |
| Corolla Light Vacation Rentals in Hampton Roads, US | 333 |
| East Ocean View Vacation Rentals in Hampton Roads, US | 185 |
| Willoughby Spit Vacation Rentals in Hampton Roads, US | 182 |
| Downtown Vacation Rentals in Hampton Roads, US | 133 |
| Monteray Shores Vacation Rentals in Hampton Roads, US | 107 |
| Sea Scape Vacation Rentals in Hampton Roads, US | 107 |
| Northwest Vacation Rentals in Hampton Roads, US | 106 |
| Bermuda Bay Vacation Rentals in Hampton Roads, US | 88 |
| North Newport News Vacation Rentals in Hampton Roads, US | 87 |
| Dam Neck Vacation Rentals in Hampton Roads, US | 36 |
| Chic's Beach Vacation Rentals in Hampton Roads, US | 36 |
| Kingsmill Vacation Rentals in Hampton Roads, US | 30 |
