House
10.0(27 Reviews)
2 Bedrooms
6 Guests
Parking
Pool
Ocean View
Balcony/Terrace
R5,226/Night
7 Nights - R36,588
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
R3,097/Night
7 Nights - R21,672
House
4 Bedrooms
8 Guests
Oceanfront
Hot Tub- Parking
- Ocean View
R11,245/Night
7 Nights - R78,711
New
House
10.0(8 Reviews)
3 Bedrooms
6 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
R4,321/Night
7 Nights - R30,245
Bed & Breakfast
10.0(8 Reviews)
1 Bedroom
6 Guests
- EV Charge Station
- Parking
- View
- Air Conditioner
R4,547/Night
7 Nights - R31,831
Condo
10.0(5 Reviews)
2 Bedrooms
6 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
R7,524/Night
7 Nights - R52,677
New
Apartment
10.0(5 Reviews)
2 Bedrooms
4 Guests
- Parking
Kitchen- Air Conditioner
Internet
R5,089/Night
7 Nights - R35,630
New
House
10.0(2 Reviews)
4 Bedrooms
8 Guests
- Parking
- Balcony/Terrace
- View
- Kitchen
R6,542/Night
7 Nights - R45,789
Condo
10.0(2 Reviews)
3 Bedrooms
10 Guests
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
R2,056/Night
7 Nights - R14,388
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
Condo
10.0(271 Reviews)
4 Bedrooms
8 Guests
- Oceanfront
- Hot Tub
- Parking
- Pool
R6,469/Night
7 Nights - R45,277
House
10.0(266 Reviews)
3 Bedrooms
8 Guests
Private Pool- Hot Tub
- Parking
- Pool
R7,157/Night
7 Nights - R50,101
House
10.0(200 Reviews)
6 Bedrooms
14 Guests
- Private Pool
- Hot Tub
- Parking
- Pool
R6,098/Night
7 Nights - R42,684
Condo
10.0(193 Reviews)
2 Bedrooms
6 Guests
- Private Pool
- Oceanfront
- Parking
- Pool
R6,388/Night
7 Nights - R44,715
Condo
10.0(192 Reviews)
3 Bedrooms
8 Guests
- Parking
- Pool
- Balcony/Terrace
- View
R3,771/Night
7 Nights - R26,397
Condo
10.0(188 Reviews)
2 Bedrooms
6 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
R2,769/Night
7 Nights - R19,376
House
10.0(185 Reviews)
2 Bedrooms
5 Guests
- Parking
- Pool
- Balcony/Terrace
- Kitchen
R3,188/Night
7 Nights - R22,316
Condo
10.0(184 Reviews)
1 Bedroom
2 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
R3,208/Night
7 Nights - R22,449
Condo
10.0(181 Reviews)
1 Bedroom
4 Guests
- Private Pool
- Oceanfront
- Parking
- Pool
R2,663/Night
7 Nights - R18,649
Pet-Friendly Holiday Rentals in Hampton Roads
Over 8618+ Pet-Friendly Holiday Rentals in or Near Hampton Roads
House
10.0(1 Review)
3 Bedrooms
6 Guests
- Parking
- Balcony/Terrace
- View
- Kitchen
R2,382/Night
7 Nights - R16,684
House
10.0(7 Reviews)
3 Bedrooms
6 Guests
- Parking
- View
- Internet
Pet Friendly
R10,225/Night
7 Nights - R71,575
House
10.0(1 Review)
1 Bedroom
- Oceanfront
- Ocean View
- View
- Kitchen
R10,320/Night
7 Nights - R72,235
House
8.0(4 Reviews)
2 Bedrooms
4 Guests
- Pool
- Internet
- Pet Friendly
Child Friendly
R4,254/Night
7 Nights - R29,783
R9,859/Night
7 Nights - R69,014
New
House
7.8(14 Reviews)
4 Bedrooms
8 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
R4,190/Night
7 Nights - R29,337
New
House
7.8(10 Reviews)
2 Bedrooms
5 Guests
- Kitchen
- Air Conditioner
- Internet
- Pet Friendly
R7,500/Night
7 Nights - R52,496
House
2.0(1 Review)
6 Bedrooms
16 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
R20,073/Night
7 Nights - R140,506
New
House
7 Bedrooms
16 Guests
- Private Pool
- Hot Tub
- Parking
- Pool
R22,629/Night
7 Nights - R158,396
Large Holiday Rentals and Private Villas in Hampton Roads
Over 9063+ Large Holiday Rentals and Private Villas in or Near Hampton Roads
Condo
10.0(1 Review)
4 Bedrooms
16 Guests
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
R3,471/Night
7 Nights - R24,299
House
10.0(7 Reviews)
4 Bedrooms
10 Guests
- Hot Tub
- Parking
- Internet
- Child Friendly
R6,062/Night
7 Nights - R42,436
R9,716/Night
7 Nights - R68,007
New
Condo
10.0(1 Review)
4 Bedrooms
16 Guests
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
R3,313/Night
7 Nights - R23,192
House
10.0(3 Reviews)
4 Bedrooms
10 Guests
- Parking
- Balcony/Terrace
- Internet
Sports/Activities
R9,283/Night
7 Nights - R64,984
Condo
8.8(16 Reviews)
3 Bedrooms
10 Guests
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
R1,947/Night
7 Nights - R13,628
New
Condo
7.4(3 Reviews)
4 Bedrooms
16 Guests
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
R4,854/Night
7 Nights - R33,978
House
10 Bedrooms
32 Guests
- Private Pool
- Hot Tub
- Parking
- Pool
R30,525/Night
7 Nights - R213,683
New
Apartment
3 Bedrooms
10 Guests
- Pool
Spa- Kitchen
- Air Conditioner
R16,384/Night
7 Nights - R114,688
Wheelchair Accessible Holiday Homes in Hampton Roads
Over 4432+ Wheelchair Accessible Holiday Homes in or Near Hampton Roads
Condo
10.0(2 Reviews)
2 Bedrooms
8 Guests
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
R1,325/Night
7 Nights - R9,267
R16,320/Night
7 Nights - R114,242
Hotel
10.0(1 Review)
Breakfast- Parking
- Internet
- Child Friendly
R3,070/Night
7 Nights - R21,491
New
House
5 Bedrooms
14 Guests
- Hot Tub
- Parking
- Pool
- Ocean View
R8,044/Night
7 Nights - R56,311
House
9.5(2 Reviews)
3 Bedrooms
6 Guests
- Parking
- Pool
- View
- Air Conditioner
R6,699/Night
7 Nights - R46,896
New
Condo
3 Bedrooms
9 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
R5,159/Night
7 Nights - R36,109
New
Condo
3 Bedrooms
10 Guests
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
R5,093/Night
7 Nights - R35,647
New
Condo
2 Bedrooms
6 Guests
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
R4,325/Night
7 Nights - R30,278
New
Condo
3 Bedrooms
6 Guests
- Parking
- Pool
- Ocean View
- View
R4,285/Night
7 Nights - R29,998
Hampton Roads Private Villas and Holiday Homes Under $200
Over 5550+ Hampton Roads Private Villas and Holiday Homes Under $200
Condo
10.0(1 Review)
1 Bedroom
4 Guests
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
R975/Night
7 Nights - R6,822
House
10.0(6 Reviews)
2 Bedrooms
4 Guests
- Parking
- Internet
- Sports/Activities
Security/Safety
R3,144/Night
7 Nights - R22,003
House
10.0(232 Reviews)
1 Bedroom
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
R3,053/Night
7 Nights - R21,375
New
Condo
9.4(13 Reviews)
2 Bedrooms
6 Guests
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
R1,424/Night
7 Nights - R9,961
House
10.0(4 Reviews)
2 Bedrooms
4 Guests
- Oceanfront
- Parking
- Spa
- Ocean View
R1,668/Night
7 Nights - R11,679
Condo
8.6(7 Reviews)
2 Bedrooms
6 Guests
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
R1,424/Night
7 Nights - R9,961
New
Condo
8.0(1 Review)
2 Bedrooms
6 Guests
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
R1,135/Night
7 Nights - R7,945
New
House
1 Bedroom
3 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
R2,822/Night
7 Nights - R19,756
New
Apartment
1 Bedroom
4 Guests
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
R2,327/Night
7 Nights - R16,287
Instantly Bookable Holiday Homes in Hampton Roads
Over 16250+ Instantly Bookable Holiday Homes in or Near Hampton Roads
Apartment
9.0(20 Reviews)
2 Bedrooms
4 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
R4,002/Night
7 Nights - R28,015
R3,817/Night
7 Nights - R26,727
New
House
8 Bedrooms
18 Guests
- Private Pool
- Hot Tub
- Parking
- Pool
R15,384/Night
7 Nights - R107,684
R14,063/Night
7 Nights - R98,450
New
House
8 Bedrooms
22 Guests
- Private Pool
- Hot Tub
- Parking
- Pool
R12,355/Night
7 Nights - R86,491
New
House
3 Bedrooms
6 Guests
- Parking
- Pool
- Balcony/Terrace
- Kitchen
R12,336/Night
7 Nights - R86,359
New
House
4 Bedrooms
10 Guests
- Private Pool
- Parking
- Pool
- Ocean View
R11,802/Night
7 Nights - R82,609
New
House
5 Bedrooms
10 Guests
- Private Pool
- Hot Tub
- Parking
- Pool
R11,773/Night
7 Nights - R82,411
New
Condo
3 Bedrooms
8 Guests
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
R11,386/Night
7 Nights - R79,702
Book a Last Minute Place to Stay in Hampton Roads
About Casai's Private Villas and Holiday Rentals in Hampton Roads
Discover more than 24701 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 1210.69 ft², with nightly prices averaging R8,070.
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 24701 Hampton Roads, US Holiday Rentals
- Prices for a holiday home in Hampton Roads start at R496
- 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.co.za holiday rentals are available in Hampton Roads?
As of 2026, Casai boasts over 24701 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 | 1053 |
| Sandbridge Vacation Rentals in Hampton Roads, US | 642 |
| South Nags Head Vacation Rentals in Hampton Roads, US | 587 |
| Whalehead Beach Vacation Rentals in Hampton Roads, US | 464 |
| Corolla Light Vacation Rentals in Hampton Roads, US | 332 |
| East Ocean View Vacation Rentals in Hampton Roads, US | 183 |
| Willoughby Spit Vacation Rentals in Hampton Roads, US | 181 |
| Downtown Vacation Rentals in Hampton Roads, US | 135 |
| Sea Scape Vacation Rentals in Hampton Roads, US | 108 |
| Monteray Shores 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 |
