Family-friendly holiday rentals in Chesapeake Beach
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Top-rated family-friendly rentals in Chesapeake Beach
Guests agree: these family-friendly homes are highly rated for location, cleanliness and more.
Holiday rentals for every style
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Popular amenities for Chesapeake Beach family-friendly rentals
Family-friendly home rentals with a hot tub
Apartment in Virginia Beach
4.82 out of 5 average rating, 11 reviews1 BR/Kitchen w/Balcony, Beach Quarters Oceanfront
15–22 Jun
Home in Virginia Beach
4.61 out of 5 average rating, 108 reviewsCroatan Beach - Big Kitchen, Hot Tub, 2 Masters
5–12 Nov
Apartment in Williamsburg
4.71 out of 5 average rating, 14 reviewsTimeshare Resort condo- 1 bdrm
2–9 May
Flat in Virginia Beach
4.79 out of 5 average rating, 19 reviewsTurtle Cay Resort- 1 bedroom
19–24 May
Apartment in Virginia Beach
4.6 out of 5 average rating, 5 reviewsTurtle Cay Va. Beach 1 bdrm
18–25 Jul
Flat in Virginia Beach
Direct Beachfront on Boardwalk facing Ocean
13–20 Jul
Flat in Virginia Beach
Turtle Cay-KeyWest style 2room 1.5ba: July 7-14 Wk
7–14 Jul
Home in Virginia Beach
4.85 out of 5 average rating, 81 reviewsComfortable 3 bedroom house with deck with hot tub
27 Oct – 3 Nov
Family- and pet-friendly home rentals
Bungalow in Hampton
4.89 out of 5 average rating, 201 reviewsBungelow by The Beach 2BR 1BA CABLE-Hampton, VA
12–19 Feb
Home in Virginia Beach
4.89 out of 5 average rating, 292 reviewsLess than one mile to ocean, 3 bedrooms
14–21 Jan
Home in Virginia Beach
4.99 out of 5 average rating, 127 reviewsQuiet family location and close to BEACH!
10–17 Nov
Home in Virginia Beach
4.89 out of 5 average rating, 84 reviewsThe Happy Place-Quiet, North End 1 block to ocean!
8–15 May
Tiny home in Virginia Beach
4.85 out of 5 average rating, 13 reviewsSunset View/Waterfront RV Cottage Sandbridge Beach
2–9 Nov
Home in Virginia Beach
4.99 out of 5 average rating, 68 reviewsBreathtaking Ocean views at Pinch Me, 8bdrm, 6bath
31 Dec – 7 Jan
Home in Hampton
4.55 out of 5 average rating, 117 reviewsBuckroe Beach Affordable for 4 -Walk to the Beach!
27 Oct – 3 Nov
Home in Norfolk
5.0 out of 5 average rating, 5 reviews"Sisters Beach House" On the Chesapeake!
22–29 Sept
Family-friendly home rentals with a pool
Home in Virginia Beach
4.88 out of 5 average rating, 115 reviewsHalf house w/pool & new patio all to yourself
3–10 Aug
Home in Virginia Beach
4.83 out of 5 average rating, 105 reviewsStunning Views of Back Bay & Seconds to the Beach
23–30 Nov
Flat in Virginia Beach
4.87 out of 5 average rating, 78 reviewsBeach Nut - Virginia Beach Oceanfront!
14–21 Sept
Home in Cape Charles
4.76 out of 5 average rating, 74 reviewsFamily Retreat, In-Ground Pool, plus Private Beach
18–25 Jan
Flat in Williamsburg
4.78 out of 5 average rating, 23 reviews★Colonial Wmbg/Busch Gardens 2BR★ ps
24–31 Aug
Home in Virginia Beach
4.9 out of 5 average rating, 119 reviewsBeach Home, Upscale Croatan Resort + Private Pool
4–11 Dec
Apartment in Virginia Beach
4.82 out of 5 average rating, 50 reviewsSeas The Day of Virginia Beach
5–12 Jan
Flat in Virginia Beach
4.69 out of 5 average rating, 154 reviewsOceanview, 2 Double Beds, Kitchenette, Balcony-C
10–17 Jul
Destinations to explore
- Outer Banks Holiday rentals
- Virginia Beach Holiday rentals
- Richmond Holiday rentals
- Norfolk Holiday rentals
- Williamsburg Holiday rentals
- Nags Head Holiday rentals
- Myrtle Beach Holiday rentals
- Washington Holiday rentals
- Deep Creek Lake Holiday rentals
- Philadelphia Holiday rentals
- Jersey City Holiday rentals
- New York Holiday rentals
- Family-friendly rentals United States
- Family-friendly rentals Outer Banks
- Family-friendly rentals Virginia Beach
- Family-friendly rentals Virginia Beach
- Family-friendly rentals Virginia
- Monthly Rentals Chesapeake Beach
- Beachfront rentals Chesapeake Beach
- Rentals with a fireplace Chesapeake Beach
- Rentals with outdoor seating Chesapeake Beach
- Rentals with a patio Chesapeake Beach
- Rentals with a washing machine and dryer Chesapeake Beach
- Rentals with pools Chesapeake Beach
- Hotel rentals Chesapeake Beach
- Rentals with beach access Chesapeake Beach
- Pet-friendly rentals Chesapeake Beach
- Fitness-friendly rentals Chesapeake Beach
- House rentals Chesapeake Beach
- Family-friendly rentals Chesapeake Beach
- Yurt Rentals United States
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- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
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- Farm Houses United States
- Farm Cottages United Kingdom
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- Holiday Chalets United Kingdom
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- Condo Rentals United States
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- Big House Rentals United States
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- House Rentals with a Pool United States
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- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
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- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
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- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom