Family-friendly holiday rentals in Chesapeake
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Chesapeake
Guests agree: these family-friendly homes are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Chesapeake family-friendly rentals
Family-friendly home rentals with a hot tub
Cottage in Corolla
4.87 out of 5 average rating, 126 reviewsHorses-Views-Dog Friendly-4WD Area
6–13 Nov
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, 109 reviewsCroatan Beach - Big Kitchen, Hot Tub, 2 Masters
30 Nov – 7 Dec
Serviced apartment in Virginia Beach
4.67 out of 5 average rating, 21 reviewsBeach Quarters Resort- Oceanfront 1 bedroom
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
4–11 Dec
Serviced apartment in Virginia Beach
4.67 out of 5 average rating, 9 reviewsTurtle Cay during Beach Street USA - Huge Pool!
16–23 Apr
Family- and pet-friendly home rentals
Home in Virginia Beach
4.79 out of 5 average rating, 131 reviewsQuaint 2 Bedroom Cottage in Chicks Beach
7–14 Jun
Home in Chic's Beach
4.77 out of 5 average rating, 149 reviewsChic's Beach Retreat
30 Aug – 6 Sep
Home in Virginia Beach
4.95 out of 5 average rating, 106 reviewsWater Oaks at Chic's Beach
25 Dec – 1 Jan
Bungalow in Hampton
4.89 out of 5 average rating, 201 reviewsBungelow by The Beach 2BR 1BA CABLE-Hampton, VA
1–8 Apr
Home in Virginia Beach
4.99 out of 5 average rating, 128 reviewsQuiet family location and close to BEACH!
12–19 Oct
Cottage in Corolla
4.87 out of 5 average rating, 174 reviewsQuaint Beach Cottage in 4WD-OBX
15–22 Mar
Tiny home in Virginia Beach
4.85 out of 5 average rating, 13 reviewsSunset View/Waterfront RV Cottage Sandbridge Beach
10–17 Sep
Home in Hampton
4.55 out of 5 average rating, 117 reviewsBuckroe Beach Affordable for 4 -Walk to the Beach!
4–11 Aug
Family-friendly home rentals with a pool
Home in Virginia Beach
4.83 out of 5 average rating, 106 reviewsStunning Views of Back Bay & Seconds to the Beach
12–19 Sep
Flat in Virginia Beach
4.87 out of 5 average rating, 78 reviewsBeach Nut - Virginia Beach Oceanfront!
11–18 Sep
Home in Cape Charles
4.76 out of 5 average rating, 74 reviewsFamily Retreat, In-Ground Pool, plus Private Beach
2–9 Mar
Home in Virginia Beach
4.9 out of 5 average rating, 119 reviewsBeach Home, Upscale Croatan Resort + Private Pool
16–23 Apr
Flat in Virginia Beach
4.92 out of 5 average rating, 13 reviewsLuxury Studio Beach Front Resort Ocean Beach Club
7–14 Jun
Apartment in Virginia Beach
4.82 out of 5 average rating, 50 reviewsSeas The Day of Virginia Beach
12–19 Jan
Flat in Virginia Beach
4.69 out of 5 average rating, 156 reviewsOceanview, 2 Double Beds, Kitchenette, Balcony-C
28 Aug – 4 Sep
Campervan/Motorhome in Virginia Beach
4.8 out of 5 average rating, 49 reviewsLil' 60's SCOTTY/Best Spot in VIRGINIA BEACH!!!
18–25 Apr
Quick stats about holiday rentals that are family-friendly in Chesapeake
Total rentals
510 properties
Wifi availability
500 properties include access to wifi
Rentals with dedicated workspaces
320 properties have a dedicated workspace
Rentals with a pool
60 properties have a pool
Pet-friendly rentals
200 properties allow pets
Total number of reviews
14K reviews
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
- New York Holiday rentals
- Jersey City Holiday rentals
- Family-friendly rentals United States
- Family-friendly rentals Outer Banks
- Family-friendly rentals Virginia Beach
- Family-friendly rentals Virginia
- Rentals with an EV charger Chesapeake
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