
Family-friendly vacation rentals in Fairfield
Find and book unique family-friendly homes on Airbnb
Quick stats about vacation rentals that are family-friendly in Fairfield

Total vacation rentals
Explore 230 vacation rentals in Fairfield

Nightly prices starting at
Fairfield vacation rentals start at G$16,739 GYD per night before taxes and fees

Verified guest reviews
Over 5,680 verified reviews to help you choose

Pet-friendly vacation rentals
Find 100 rentals that welcome pets

Vacation rentals with a pool
30 properties feature pools

Rentals with dedicated workspaces
130 properties have a dedicated workspace

Wi-Fi availability
220 of Fairfield vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Fairfield rentals

4.9 Average rating
Fairfield stays are highly rated by guests—averaging 4.9 out of 5!
Top-rated family-friendly rentals in Fairfield
Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

Cape on the Water
Welcome to our Cape on the Water! This unique property is located on beautiful Ash Creek, an inlet off Long Island Sound offering views of tidal wetlands, including tons of fish, bird, kayakers, paddle boarders, small sail boats etc. The house is a newly renovated Cape Cod with an open floor plan, updated Kitchen and bath rooms. Refinished oak hardwood floors through out the entire house. Large deck -great view. The house has a very cozy feel and has been also updated with brand new HVAC system.
4.97 out of 5 average rating, 113 reviews
Downtown Fairfield 3 bedroom Colonial
Enjoy a charming, 3 bed/2 full bath Colonial that is only a 4 block walk from the coffee shops, bars, and restaurants on the Post Road and .7 mile from the Fairfield Train Station. The house is over 1500 sq. feet on a quiet street and only a mile to the town beaches. Work has taken me from Fairfield, but it remains home, so the house is fully stocked with everything. If you're into shooting hoops, you'll like the lined and paved court. Small well-trained dogs and longer stays are negotiable.
4.94 out of 5 average rating, 145 reviews
Adorable private apt w/ W/D in lovely neighborhood
Enjoy a lovely experience at this centrally-located studio in-law apartment. It boasts a newly renovated kitchen and bath, king bed with brand new mattress, pull out full size sofa, ample closet space and more. The eat-in kitchen has all you need to feel right at home. The apartment is located adjacent to a nice residential house, but is fully private with your own front and back entrances. There are also no stairs, making it easily accessible. It’s located in a wonderful neighbor in Fairfield.
4.93 out of 5 average rating, 208 reviews
Spacious Westport Apt surrounded by nature!
Spacious mother-in-law basement apartment with private entrance that opens to the backyard. Large windows in every room give view to the creek in the backyard and birds welcoming our guests. Two bedrooms with a queen size bed. Walk-in shower. Plenty of space for up to four people. Very family friendly - little humans and furry friends welcome! Centrally located 8 min drive to downtown Westport, Fairfield, or Southport. Beach, golf course, playgrounds, hikes, wonderful bakeries and restaurants.
4.92 out of 5 average rating, 340 reviews
Cheerful 3 Bedroom Cottage with Fire Place
We are happy to still offer some dates for September. Come enjoy the solitude of the beach as the tide ebbs & flows. Reconnect with loved ones in this family-friendly place. Enjoy strolls on the beach located just out the back door or a sunset meal on the back porch. This wonderful cottage offers everything you will need during your stay. Including, comfortable beds, beach strolls and a bright upgraded kitchen with many amenities. The 3 bedrooms will fit up to 8 people comfortably.
4.88 out of 5 average rating, 109 reviews
Private Studio Apartment Kitchen Fully Furnished
This 625 sqft fully furnished studio apartment has its own private entrance and sleeps 2-3 with a queen bed and Murphy bed. Other than outside, there is no contact with other people (hosts, other guests, etc) possible unless the guest allows such. The unit consists of a living room, dining space (breakfast basics provided), kitchen, full bathroom/laundry. Walk to Fairfield U; an easy train ride to NYC. (Need the Murphy bed? PLEASE do not wait until just before checkin to let us know that!)
4.95 out of 5 average rating, 473 reviews
Designer Beach Retreat on Exclusive Cedar Beach
Welcome to your own slice of heaven! Enjoy dinner in your Chef's kitchen while watching one of the most radiant sunsets you will ever see. Stunning views from the private rear deck or snuggled on the couch inside the living room. Wade into Long Island Sound with semi-private beach access 250 feet away. The property is 5 doors down from the CT Audubon Society, known for its epic views and wildlife watching. The sunrises & sunsets are beautiful! 15 minutes to Yale. We can't wait to host you!
4.97 out of 5 average rating, 270 reviews
Cozy Studio in Bridgeport
Charming and fully equipped studio located in the heart of Bridgeport. Perfect for business travelers, couples, or solo adventurers, this cozy retreat features a comfortable bed, high-speed Wi-Fi, a private entrance, and a fully stocked kitchen for your convenience. Enjoy easy access to local restaurants, cafes, and shops, as well as public transportation and major highways. Whether you’re here for work or leisure, this studio offers everything you need for a relaxing and stress-free stay.
4.95 out of 5 average rating, 121 reviews
Cozy 3-Bed 2-Bath Condo | Parking and Laundry!
Come stay in our clean and cozy condo located close to Fairfield University, great restaurants, local grocery stores, appliance centers, and other essential shops. Also includes: - Free Wi-Fi - Washer and dryer - Keurig with K-cups - Full kitchen with essentials - Smart Roku TVs with apps (Netflix, Hulu, etc.) - Fenced in/gated backyard - Outdoor patio set and grill - Free parking (4 car max) - Central heating and AC Perfect for those that need a temporary space!
4.84 out of 5 average rating, 161 reviews
Beautifully Restored Barn With New England Charm
Set back from the road on one wooded acre with a brook, this renovated 4-bedroom converted barn pairs rustic New England character with modern comfort. Expect 30-foot ceilings, exposed beams, oversized windows, a babbling brook, large yard, eclectic art and furniture, a grand piano, a stocked kitchen, deck, grill, and space to gather. A memorable Fairfield stay for families, couples, small groups, beach weekends, and quiet escapes.
4.96 out of 5 average rating, 355 reviews
5 Minute Walk to Beach & Downtown Fairfield
This Immaculate 3-bedroom cape in the desirable Fairfield Beach Area is only a 5 minute walk to the sand. The home has just been beautifully updated and has all modern amenities. Lovely level fenced in backyard and enjoy an evening cocktail on the deck. Close enough to the train and downtown to walk and take a stroll to the Marina in the evening. The location is just perfect and the house is a wonderful place to relax and recharge.
4.97 out of 5 average rating, 105 reviews
Sunny Fairfield Studio Apartment
Enjoy this sunny, newly-renovated, modern Fairfield studio apartment, located in the carriage building of a historic early 1900's house. Great for an individual, couple, or family. Well situated, a short drive to Sacred Heart & Fairfield Universities, downtown Fairfield and the beach, Silverman's Farm and other Easton farms for apple picking, petting zoos, and the like, and Fairfield Metro Station for a 1 hour train ride to NYC.
4.98 out of 5 average rating, 195 reviewsPopular amenities for Fairfield family-friendly rentals
Family-friendly home rentals with a hot tub

3 Bedroom Beach House with Hot Tub!
4.97 out of 5 average rating, 158 reviews
Oceanfront Beach House w/ Private Hot Tub
4.94 out of 5 average rating, 145 reviews
Cozy Colonial - Private Hot Tub & Entire House
4.96 out of 5 average rating, 242 reviews
The Hilltop Harborview
4.81 out of 5 average rating, 423 reviews
A Spacious 5BR Near Yale|Ideal For Groups&Family
4.99 out of 5 average rating, 182 reviews
Beach Haven - waterfront, near Yale, sunsets
4.96 out of 5 average rating, 146 reviews
Sleeping Giant Stay/Swim Spa w/Tread/Tonal/Peleton
4.88 out of 5 average rating, 130 reviews
OCEAN COAST LUXURY BEACH HOUSE/45 min to NYC
4.94 out of 5 average rating, 120 reviewsFamily- and pet-friendly home rentals

The ARLO - Walk to Brewery & Restaurants
4.99 out of 5 average rating, 194 reviews
Charming Historic Cottage in the Redwoods
4.98 out of 5 average rating, 103 reviews
Fully renovated/Walk to water & shops/fenced yard!
4.98 out of 5 average rating, 161 reviews
Peaceful Light-Filled Guesthouse salt pool/sauna
5.0 out of 5 average rating, 190 reviews
Summer Sale! CozyCottage/Pet-friendly/ WalktoBeach
4.94 out of 5 average rating, 421 reviews
Private Guest Suite | Entrance, Bath & Parking
4.81 out of 5 average rating, 310 reviews
Bright 3-bedroom house with ample parking & patio!
4.84 out of 5 average rating, 128 reviews
The Cozy Little Cottage
4.97 out of 5 average rating, 155 reviewsFamily-friendly home rentals with a pool

The Pond Mill Retreat w/ 2 Bdrms & Pool
4.98 out of 5 average rating, 165 reviews
Escape to a Restored New England Antique Milk Barn
4.98 out of 5 average rating, 267 reviews
Garden Level Suite with Beautiful Pool
4.97 out of 5 average rating, 214 reviews
Port Jefferson Convenient, Cozy and Chic!
4.92 out of 5 average rating, 160 reviews
King 1BR Apt with Cozy Den and Luxury Amenities
4.95 out of 5 average rating, 141 reviews
Midcentury Modern ZenHouse Sculptor Studio
4.96 out of 5 average rating, 270 reviews
The Cottage by the Lake: Hudson Valley Indulgence
4.99 out of 5 average rating, 330 reviews
Private Guest Studio
4.92 out of 5 average rating, 233 reviewsWhen is the best time to visit Fairfield?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$43,940 GYD | G$45,823 GYD | G$47,916 GYD | G$52,937 GYD | G$77,209 GYD | G$89,763 GYD | G$87,880 GYD | G$83,486 GYD | G$61,098 GYD | G$65,910 GYD | G$61,307 GYD | G$61,516 GYD |
| Avg. temp | 0°C | 1°C | 4°C | 10°C | 16°C | 21°C | 24°C | 24°C | 20°C | 14°C | 8°C | 3°C |
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- Family-friendly rentals Connecticut
- Family-friendly rentals United States
- Times Square
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- American Dream
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