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Family-friendly vacation rentals in Cutler Bay

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Cutler Bay

Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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Top guest favorite
An outdoor space is highlighted by a wooden picnic table and a cozy sofa underneath a large umbrella. String lights are illuminated above, creating a warm ambiance. Stepping stones set in dark rocks lead through the greenery, providing a tranquil setting for relaxation.
Villa in Homestead
4.99 out of 5 average rating, 170 reviews

The Pass Through - Brand New 2 | 1 Modern Villa

The Pass-Through is a cozy home located off of Florida’s Turnpike. Perfect if you’re looking for a pit stop when headed down to the Florida Keys or if you want to stay for a few days to explore Miami. Only a few minutes from Black Point Marina, where you can enjoy waterfront ambiance with outdoor seating, food, drinks, live band, and take your boat out for a ride to Biscayne Nat'l Park or Everglades Nat'l Park.Close to Florida’s Outlet Mall, authentic restaurants, wineries, freshfarms, and more.

Guest favorite
A spacious suite featuring a king size bed with crisp white linens. Dark accent walls provide contrast against light wooden flooring. Natural light enters through large windows adorned with sheer curtains, while a small desk and tasteful decorative elements complete the stylish environment.
Apartment in Coconut Grove
4.81 out of 5 average rating, 126 reviews

Coconut Grove Stunning City View Suite Free Park

INCREDIBLE VALUE! First, a $30 gift card to our restaurant GreenStreet and a bottle of champagne will be awaiting you in your room! In Coconut Grove, this privately owned & renovated bright suite on the 15th floor of a luxurious waterfront property offers breathtaking city views, is fully equipped for 2 w/ a king size bed & full bath. Enjoy all the luxury amenities this property has to offer, pool & hot-tub with incredible bay views, penthouse gym, sauna, business center, 24-hr security, squash

Top guest favorite
A spacious driveway curves past vibrant tropical plants and palm trees leading to a welcoming entrance of the property. The house features a warm orange exterior with decorative elements and a large garage door, complementing the lush landscaping.
Guest suite in Miami
4.9 out of 5 average rating, 389 reviews

Guest Suite-Exterior Entrance, SelfCheckin.

If you like Clean, New, Quiet and Great Hospitality, then this is the Perfect Place for you. We are conveniently located between Key Largo and Downtown Miami, in an upscale community. You’ll feel safe and welcome here! -GATEWAY to the Keys and Everglades -Private entrance -Self Check-in -Free Parking -Fast WIFI -Swimming Pool -Central A/C -Ceiling fan -Kitchenette -Refrigerator -Microwave -Coffee maker -Netflix-HBO TV -Ceramic Tile Floors -Full Closet -Towels/Bath essentials -Iron & Board

Top guest favorite
The outdoor area features a heated pool surrounded by colorful murals, with a jacuzzi nearby. Poolside loungers and a basketball hoop are visible, offering a vibrant space for relaxation and fun under a clear blue sky.
Home in Miami
4.97 out of 5 average rating, 103 reviews

Family retreat oasis, heated pool, jacuzzi & grill

Welcome to Forget-me-not Villa, a sanctuary for your family and friends to let loose barefoot and unwind in the private backyard fully fenced, feel the breeze, stargaze at night, and savor the comfort of our exquisite vacation home. The villa features a heated pool and jacuzzi, a grill station, a love seat for romantic moments, a playground for children, an Xbox S for gamers, board games, mini golf, pool volleyball and basketball hoop, Smart TVs& high-speed Wi-Fi & electric car connection.

Guest favorite
A spacious lawn features a large shade tree with swings hanging from its branches. Nearby are colorful chairs arranged on the grass, along with a hammock tied between tree trunks. Water is visible in the background, surrounded by lush greenery.
Guest suite in Cutler Bay
4.78 out of 5 average rating, 307 reviews

Private Waterfront Studio Paradise

Casa Cocos is a private studio, with a private entrance, bathroom and kitchenette, and free and secure parking. It is nestled in Florida's tropical waterfront paradise. Come enjoy the views of the garden, go for a swim, paddle board, canoe, kayak, grill, take a nap in a hammock, and just relax. Casa Cocos is surrounded by nearby restaurants, bars, retail stores, malls all within walking distance or a short drive. 30 minutes to airport, downtown, South Beach, Keys, and Everglades.

Guest favorite
An open kitchen area features gray cabinetry and a stylish marble countertop. A dining table is set for four, complete with white dishes and black placemats. Stainless steel appliances, including a refrigerator and oven, provide modern convenience, while a cozy living room is visible in the background.
Home in Cutler Bay
4.93 out of 5 average rating, 133 reviews

Spacious Home by the Bay FAST Wi-Fi & Coffee

You will be steps away from Old Cutler Road and an abundance of unique dining and recreational options. Pay a visit to nearby attractions such as Southland Mall, The Falls Shopping Center, Black Point Marina, Deering Estates, Dennis C. Moss Cultural Center, Miami Metro Zoo, and more! ❧ 48 minutes away from the Florida Keys. ❧ 37 minutes away from Miami Beach. ❧ 33 minutes away from the Everglades National Park. Message us about long stay, military, & first responder discounts.

Top guest favorite
A serene outdoor space includes a swimming pool surrounded by terracotta tiles and lush tropical vegetation. A tiki hut is positioned in the background, with an evening sky showcasing warm tones of orange and yellow. Soft furnishings and a relaxed seating area are visible nearby.
Tiny home in Cutler Bay
4.97 out of 5 average rating, 264 reviews

Quiet tropical Oasis setting with 1 bed and 1 bath

Tropical oasis centrally located between Miami Beach and Key Largo. Although you may never want to leave. The cozy casita with private bath and balcony is tucked away, surrounded by lush vegetation and sounds of the waterfall. Take a dip in the pool or grotto, relax with an afternoon cocktail under the tiki hut, or snooze in the hammock. During those cooler months soak in the hot tub. Enjoy the miles of nearby walking paths stretching from Coconut Grove to Black Point Marina.

Top guest favorite
A colorful hammock is suspended between two palm trees, inviting relaxation beside a sparkling pool. Lush tropical plants surround the outdoor area, creating a peaceful ambience. The inviting pool area is visible in the background, enhancing the serene outdoor setting.
Guest suite in Homestead
4.99 out of 5 average rating, 178 reviews

“Have Fun at Hacienda Paraíso” Suite 1 | pool |

Welcome to Room 1, the first addition at Hacienda Paraíso. This suite is conveniently located next to another Airbnb suite, providing flexibility for your stay. It features a private entrance, bathroom, kitchenette, and dining table, ensuring a comfortable and self-contained experience. Enjoy the convenience of hotel-like amenities paired with the added bonus of access to our stunning pool and lush yard, creating a truly relaxing retreat.

Guest favorite
Guesthouse in Homestead
4.96 out of 5 average rating, 187 reviews

Villa Samsara - on a beautiful 5 acre farm

When you come and stay with us, it’s a deeply immersive experience with our horses. Often you will find them in your front door or window. There is something profoundly impactful about being around horses and sharing close-quarters with them. You are in their energy field, receiving all that they have to offer. Without even realizing it, your energies are being grounded and regulated through their presence.

Guest favorite
An outdoor dining area features a large rectangular table surrounded by four upholstered chairs, complemented by potted greenery at each end. A kitchen area with cabinetry and a countertop is visible in the background, set against a backdrop of brick walls and lush foliage.
Home in Miami
4.83 out of 5 average rating, 104 reviews

To the Keys

Your family will be close to all these places if you stay in this centrally located accommodation to shop in stores with more than 50% discounts on the best brands, around the Southland Mall shopping centers, near Miami Zoo, Monkey Jungle, Pintos Farm, Brothers Farms, etc. As well as restaurants and more entertainment around it, you can contact me for more details if you wish

Guest favorite
Guest suite in Homestead
4.9 out of 5 average rating, 468 reviews

Tranquil Retreat with Vintage Charm

🌴 Retreat to a private guest suite in one of the area’s safest communities, just north of Key Largo. With a plush bed, upscale amenities, and a Smart TV, you’ll enjoy boutique comfort in a prime location—minutes from Everglades and Biscayne National Parks, and a short drive to Miami or the Florida Keys. Perfect for travelers who want both style and convenience. ✨ 💝

Guest favorite
A well-lit studio room features a full-size bed with light bedding topped by two pillows. A small dining area with two chairs and a round table is positioned near the window, which is covered by bright, modern shades. Storage is provided by a closet.
Guesthouse in Miami
4.96 out of 5 average rating, 237 reviews

Alma

This completely new studio has a private entrance and private outdoor space to enjoy your stay in Miami. Located at Palmetto Bay, in a very quiet area between Key Largo and Downtown Miami, perfect for travelers that planning visiting Miami, Everglades, the Keys, and our great Beaches. This cozy space is perfect for couples, solo adventures, and business travelers.

Popular amenities for Cutler Bay family-friendly rentals

When is the best time to visit Cutler Bay?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$41,821 GYDG$46,839 GYDG$49,557 GYDG$45,794 GYDG$41,193 GYDG$46,003 GYDG$46,003 GYDG$47,466 GYDG$42,866 GYDG$50,185 GYDG$50,394 GYDG$52,276 GYD
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Quick stats about vacation rentals that are family-friendly in Cutler Bay

  • Total vacation rentals

    Explore 70 vacation rentals in Cutler Bay

  • Nightly prices starting at

    Cutler Bay vacation rentals start at G$14,637 GYD per night before taxes and fees

  • Verified guest reviews

    Over 3,570 verified reviews to help you choose

  • Pet-friendly vacation rentals

    Find 40 rentals that welcome pets

  • Vacation rentals with a pool

    40 properties feature pools

  • Rentals with dedicated workspaces

    40 properties have a dedicated workspace

  • Wi-Fi availability

    70 of Cutler Bay vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Cutler Bay rentals

  • 4.7 Average rating

    Cutler Bay stays receive an average rating of 4.7 out of 5 from guests