Condo
10.0(362 Reviews)
2 Bedrooms
6 Guests
Parking
Ocean View
Balcony/Terrace
View
R4,493/Night
7 Nights - R31,441
Hampton Roads 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
R3,076/Night
7 Nights - R21,529
House
10.0(232 Reviews)
1 Bedroom
- Parking
- Balcony/Terrace
Kitchen- Air Conditioner
R3,033/Night
7 Nights - R21,234
Condo
10.0(285 Reviews)
2 Bedrooms
6 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
R4,314/Night
7 Nights - R30,194
Bed & Breakfast
10.0(8 Reviews)
1 Bedroom
6 Guests
- EV Charge Station
- Parking
- View
- Air Conditioner
R5,213/Night
7 Nights - R36,495
Condo
10.0(278 Reviews)
2 Bedrooms
6 Guests
Private Pool
Oceanfront- Parking
Pool
R6,550/Night
7 Nights - R45,849
Cottage
10.0(213 Reviews)
2 Bedrooms
4 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
R7,281/Night
7 Nights - R50,968
R5,218/Night
7 Nights - R36,528
Cottage
10.0(207 Reviews)
2 Bedrooms
3 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
R2,331/Night
7 Nights - R16,311
Luxury Holiday Rentals in Hampton Roads
Over 10000+ Luxury Holiday Rentals in or Near Hampton Roads
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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(269 Reviews)
4 Bedrooms
8 Guests
- Oceanfront
Hot Tub- Parking
- Pool
R6,426/Night
7 Nights - R44,979
House
10.0(263 Reviews)
3 Bedrooms
8 Guests
- Private Pool
- Hot Tub
- Parking
- Pool
R7,445/Night
7 Nights - R52,117
House
10.0(261 Reviews)
4 Bedrooms
10 Guests
- Private Pool
- Oceanfront
- Hot Tub
- Parking
R3,781/Night
7 Nights - R26,469
House
10.0(200 Reviews)
6 Bedrooms
14 Guests
- Private Pool
- Hot Tub
- Parking
- Pool
R6,057/Night
7 Nights - R42,403
Condo
10.0(192 Reviews)
2 Bedrooms
6 Guests
- Private Pool
- Oceanfront
- Parking
- Pool
R7,086/Night
7 Nights - R49,606
Condo
10.0(192 Reviews)
3 Bedrooms
8 Guests
- Parking
- Pool
- Balcony/Terrace
- View
R3,747/Night
7 Nights - R26,223
House
10.0(191 Reviews)
3 Bedrooms
6 Guests
- Parking
- Pool
- Balcony/Terrace
- View
R5,033/Night
7 Nights - R35,232
Condo
10.0(188 Reviews)
2 Bedrooms
6 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
R2,751/Night
7 Nights - R19,249
House
10.0(185 Reviews)
2 Bedrooms
5 Guests
- Parking
- Pool
- Balcony/Terrace
- Kitchen
R3,167/Night
7 Nights - R22,169
Pet-Friendly Holiday Rentals in Hampton Roads
Over 8817+ Pet-Friendly Holiday Rentals in or Near Hampton Roads
House
10.0(145 Reviews)
1 Bedroom
2 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
R4,052/Night
7 Nights - R28,372
House
10.0(7 Reviews)
3 Bedrooms
6 Guests
- Oceanfront
- Parking
- Ocean View
- View
R10,158/Night
7 Nights - R71,103
House
10.0(1 Review)
1 Bedroom
- Oceanfront
- Ocean View
- View
- Kitchen
R10,252/Night
7 Nights - R71,759
House
10.0(138 Reviews)
2 Bedrooms
6 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
R2,696/Night
7 Nights - R18,871
R9,794/Night
7 Nights - R68,560
Cottage
10.0(124 Reviews)
2 Bedrooms
6 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
R4,491/Night
7 Nights - R31,441
Cottage
10.0(119 Reviews)
2 Bedrooms
6 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
R5,356/Night
7 Nights - R37,496
Condo
10.0(107 Reviews)
1 Bedroom
3 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
R4,484/Night
7 Nights - R31,392
Condo
10.0(97 Reviews)
2 Bedrooms
6 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
R4,172/Night
7 Nights - R29,209
Large Holiday Rentals and Private Villas in Hampton Roads
Over 9277+ Large Holiday Rentals and Private Villas in or Near Hampton Roads
Apartment
10.0(33 Reviews)
1 Bedroom
100 Guests
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
R5,109/Night
7 Nights - R35,757
House
10.0(7 Reviews)
4 Bedrooms
10 Guests
- Hot Tub
- Parking
Spa
Internet
R10,781/Night
7 Nights - R75,468
R53,055/Night
7 Nights - R371,383
House
10.0(23 Reviews)
2 Bedrooms
12 Guests
- Private Pool
- Parking
- Pool
- Balcony/Terrace
R8,645/Night
7 Nights - R60,519
House
10.0(4 Reviews)
10 Bedrooms
4 Guests
- Private Pool
- Hot Tub
- Parking
- Pool
R3,452/Night
7 Nights - R24,171
Villa
10.0(4 Reviews)
2 Bedrooms
6 Guests
- Hot Tub
- Parking
- Pool
- Kitchen
R7,651/Night
7 Nights - R53,561
Villa
10.0(4 Reviews)
2 Bedrooms
5 Guests
- Hot Tub
- Parking
- Ocean View
- Balcony/Terrace
R5,390/Night
7 Nights - R37,726
Villa
10.0(1 Review)
1 Bedroom
4 Guests
- Pool
- Spa
- Ocean View
- Balcony/Terrace
R4,001/Night
7 Nights - R28,011
Villa
10.0(1 Review)
1 Bedroom
4 Guests
- Pool
- Spa
- Ocean View
- Balcony/Terrace
R3,625/Night
7 Nights - R25,369
Wheelchair Accessible Holiday Homes in Hampton Roads
Over 4475+ Wheelchair Accessible Holiday Homes in or Near Hampton Roads
Condo
10.0(127 Reviews)
2 Bedrooms
4 Guests
- Private Pool
- Oceanfront
- Hot Tub
- Parking
R5,791/Night
7 Nights - R40,532
House
10.0(1 Review)
9 Bedrooms
18 Guests
- Oceanfront
- Hot Tub
- Parking
- Pool
R16,738/Night
7 Nights - R117,165
Hotel
9.8(415 Reviews)
- Hot Tub
Breakfast- Pool
- Spa
R9,557/Night
7 Nights - R66,902
Condo
10.0(96 Reviews)
2 Bedrooms
6 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
R6,937/Night
7 Nights - R48,556
R16,213/Night
7 Nights - R113,489
Condo
10.0(72 Reviews)
2 Bedrooms
5 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
R4,902/Night
7 Nights - R34,313
R4,169/Night
7 Nights - R29,193
Condo
10.0(55 Reviews)
2 Bedrooms
4 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
R6,544/Night
7 Nights - R45,816
Condo
10.0(54 Reviews)
2 Bedrooms
6 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
R8,902/Night
7 Nights - R62,324
Hampton Roads Private Villas and Holiday Homes Under $200
Over 5465+ Hampton Roads Private Villas and Holiday Homes Under $200
Condo
10.0(183 Reviews)
1 Bedroom
2 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
R2,918/Night
7 Nights - R20,430
House
10.0(6 Reviews)
2 Bedrooms
4 Guests
- Parking
- Internet
Sports/Activities
Security/Safety
R3,123/Night
7 Nights - R21,858
Cottage
10.0(1 Review)
1 Bedroom
- Oceanfront
- Parking
- Ocean View
- View
R3,183/Night
7 Nights - R22,284
Condo
10.0(181 Reviews)
1 Bedroom
4 Guests
- Private Pool
- Oceanfront
- Parking
- Pool
R2,581/Night
7 Nights - R18,067
House
10.0(4 Reviews)
2 Bedrooms
4 Guests
- Oceanfront
- Parking
- Spa
- Ocean View
R1,657/Night
7 Nights - R11,602
Condo
10.0(138 Reviews)
1 Bedroom
4 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
R3,155/Night
7 Nights - R22,087
Cottage
10.0(129 Reviews)
2 Bedrooms
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
R3,069/Night
7 Nights - R21,480
House
10.0(105 Reviews)
1 Bedroom
2 Guests
- Parking
- Pool
- Balcony/Terrace
- Kitchen
R3,047/Night
7 Nights - R21,333
Apartment
10.0(101 Reviews)
1 Bedroom
2 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
R2,683/Night
7 Nights - R18,773
Instantly Bookable Holiday Homes in Hampton Roads
Over 16489+ Instantly Bookable Holiday Homes in or Near Hampton Roads
Apartment
10.0(130 Reviews)
2 Bedrooms
2 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
R4,185/Night
7 Nights - R29,291
R25,256/Night
7 Nights - R176,798
Condo
10.0(129 Reviews)
1 Bedroom
5 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
R4,320/Night
7 Nights - R30,243
Condo
10.0(120 Reviews)
2 Bedrooms
4 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
R6,958/Night
7 Nights - R48,704
House
10.0(103 Reviews)
2 Bedrooms
4 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
R7,678/Night
7 Nights - R53,742
House
10.0(99 Reviews)
1 Bedroom
2 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
R3,811/Night
7 Nights - R26,682
House
10.0(96 Reviews)
2 Bedrooms
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
R8,175/Night
7 Nights - R57,220
House
10.0(94 Reviews)
1 Bedroom
2 Guests
- Parking
- Pool
- Balcony/Terrace
- Kitchen
R5,477/Night
7 Nights - R38,333
Condo
10.0(87 Reviews)
2 Bedrooms
6 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
R6,383/Night
7 Nights - R44,684
Book a Last Minute Place to Stay in Hampton Roads
About Casai's Private Villas and Holiday Rentals in Hampton Roads
Discover more than 25104 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 1209.41 ft², with nightly prices averaging R7,843.
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 25104 Hampton Roads, US Holiday Rentals
- Prices for a holiday home in Hampton Roads start at R492
- 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 King Suite on the Outer Banks + Restaurants & Spa
Recently Booked Holiday Rentals in Hampton Roads
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.
- OCEANFRONT! BOARDWALK TO THE BEACH. COMPLIMENTARY AMENITIES! GUEST FAVORITE!
- Sandbridge Beach,Virginia Beach Penthouse Condominum
- Riverfront House, Dock, Hot Tub, Salt Pool, near beach, Free WiFi
- -GEZELLIG- FALL SPECIALS! SEMI H2oFRONT VIEWS/HOT TUB/BEACH ACCESS 2min
- Completely Renovated Beach Box with Ocean Views & Easy Beach Access
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 25104 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 | 980 |
| Sandbridge Vacation Rentals in Hampton Roads, US | 619 |
| South Nags Head Vacation Rentals in Hampton Roads, US | 561 |
| Whalehead Beach Vacation Rentals in Hampton Roads, US | 450 |
| Corolla Light Vacation Rentals in Hampton Roads, US | 321 |
| East Ocean View Vacation Rentals in Hampton Roads, US | 182 |
| Willoughby Spit Vacation Rentals in Hampton Roads, US | 171 |
| Downtown Vacation Rentals in Hampton Roads, US | 135 |
| Monteray Shores Vacation Rentals in Hampton Roads, US | 106 |
| Sea Scape Vacation Rentals in Hampton Roads, US | 102 |
| Northwest Vacation Rentals in Hampton Roads, US | 100 |
| North Newport News Vacation Rentals in Hampton Roads, US | 95 |
| Bermuda Bay Vacation Rentals in Hampton Roads, US | 87 |
| Dam Neck Vacation Rentals in Hampton Roads, US | 34 |
| Chic's Beach Vacation Rentals in Hampton Roads, US | 31 |
| Kingsmill Vacation Rentals in Hampton Roads, US | 29 |
