Family-friendly holiday rentals in Cutler Bay

4.96 out of 5 average rating, 156 reviews

A refreshing outdoor pool is framed by palm trees and a surrounding patio of laid stones. Two loungers are positioned partially submerged in the water, complemented by a large umbrella for shade. The clear sky is visible above.

Home in Cutler Bay

King Bed Home by the Bay FAST WI-FI & Coffee

Whether you are visiting the Florida Keys, the beaches of Miami, or looking for a comfortable staycation, discover what South Florida has to offer while feeling at home. You'll be located near Southland Mall, The Falls Shopping Center, Black Point Marina, Miami Metro Zoo, Deering Estates, the Dennis C. Moss Arts Center and more! ❧ 48 minutes from the Florida Keys. ❧ 37 minutes from Miami Beach. ❧ 33 minutes from the Everglades. Message us about long stay, military, & first responder discounts.

4.99 out of 5 average rating, 163 reviews

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

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.

4.98 out of 5 average rating, 459 reviews

A contemporary living space is depicted, featuring a red chair next to a beige couch. A flat-screen TV is mounted on the wall across from the seating area. Light green curtains frame the windows, and a sleek kitchen island with white cabinetry is visible in the foreground.

Apartment in Miami

Serenity Oasis, Garden Retreat with Koi pond

Come and create unforgettable memories at our newly renovated luxury guest house. It boasts a private entrance, separate from the main house, which shares a wall with it. Nestled in a safe neighborhood, it’s conveniently located near everything, including the expressway. Miami Beach is just a 25-minute drive away, the Dolphin Mall is a 10-minute drive, and the Florida Keys are a 45-minute drive. Fiu University is just a 5-minute drive away.Our backyard is shared with us,and a beautiful koi pond!

4.89 out of 5 average rating, 228 reviews

A spacious bedroom features a comfortable bed with a light-colored quilt, complemented by wooden accents. Natural light filters through, illuminating the room's earthy tones. A small nightstand and artwork depicting a bird add character, while a private bathroom entrance is visible in the background.

Guest suite in Coral Way

Guest Studio apt, Private entrance, Patio, Parking

Take it easy at this unique and tranquil getaway in our 1930's Spanish Villa in the center of Little Havana and Coral Gables in the heart of Shenandoah. Your Guest Suite is equipped with a private entrance, private garden, and parking. Casita Amorcita is designed to give you the feeling of 'home' and 'love,' with the guest experience in mind. All linens are 100% cotton. Here you will have all that you need to rest, recover, recharge, and enjoy. We look forward to welcoming you home.

4.9 out of 5 average rating, 384 reviews

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

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

Guest suite in Cutler Bay

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.

4.78 out of 5 average rating, 303 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.

4.98 out of 5 average rating, 257 reviews

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

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.

A light-filled living area features a comfortable sectional sofa in white, complemented by a circular coffee table. A flat-screen TV is mounted on the wall, and a ceiling fan adds to the airy feel. A large window provides views of the greenery outside.

4.89 out of 5 average rating, 236 reviews

Miami Oasis: Chill | Shop | Relax | Charming Home

A spacious and private retreat designed for families and group stays, our home in Palmetto Estates comfortably hosts up to 10 guests. We offer 3 well-appointed bedrooms, 2 full bathrooms, a bright living space, a fully equipped kitchen, laundry area, garage, and a covered patio with a large grassy yard. Located in a quiet neighborhood close to shopping, dining, Miami Zoo, the Everglades, and just 30 minutes from Downtown Miami, it’s an ideal base to explore South Florida.

4.85 out of 5 average rating, 312 reviews

A spacious studio is presented, featuring a king-size bed with soft linens and decorative pillows. Two windows allow natural light to illuminate the room, complemented by a yellow accent chair and various indoor plants. A small table with a bottle of wine and glasses enhances the setting.

Apartment in Allapattah

King Bed Comfort – 5 Mins to Miami Hotspots

- TOTALLY PRIVATE BEAUTIFUL STUDIO Beautiful studio near everything!!! 5 minutes from the Airpot, Wynwood, Design District, South Beach, Port, Brickell, AAA, - King Size Bed - Private parking -Fully stocked kitchen also wifi, Smart Tv - 6 star hospitality - Washer and Dryer on premises to use for free - Property is 1 of 4 Airbnb on the property -$100 Pet fee -per stay. -NOTE: two pets, would be $150 per stay ( not apply for long-term stays)

A spacious pool area is surrounded by vibrant greenery and palm trees. Seating arrangements with cushions are positioned near the water, complemented by a shaded area under an umbrella. The pool features a rock formation and is accented by colorful lounge chairs.

4.97 out of 5 average rating, 396 reviews

The Miracle Cottage & Pool on Acre Miami Florida

Beautiful, brand new PRIVATE cottage on an acre property situated in million dollar neighborhood. Perfect place to relax and enjoy the Miami sun. This is a little piece of heaven in the heart of a magical city. Come & enjoy your best vacation. Charming , peaceful & comfortable . Cottage is a completely separate building from the main house. It’s 900 sf of living area. Cleaning & Decontamination as per CDC guidelines before every check in.

4.9 out of 5 average rating, 218 reviews

A group of horses stands near a white fence under a colorful sunset. The scene captures a brown foal in the foreground, while three other horses, including a white one, are seen closer to the fence. The sky is painted with shades of orange and pink.

Barn in Homestead

The Glamping Barn - on a beautiful 5 acre farm!

When you come and stay with us, it’s a deeply immersive experience with our horses and chickens. 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.

4.96 out of 5 average rating, 231 reviews

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

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

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

The exterior of a renovated house is shown at sunset, featuring a clean white façade and a welcoming entrance. A curved driveway leads to the front door, complemented by well-maintained grass and landscaping along the pathway.

4.93 out of 5 average rating, 99 reviews

10 ppl |Top Location | 20 Min Beach | Bar | Patio

4.87 out of 5 average rating, 307 reviews

A balcony offers a view of the ocean, with boats visible on the water. A small round table and two chairs are positioned for outdoor dining. The clear blue sky provides a bright backdrop, while lush greenery is seen below, blending the natural environment with urban elements.

Condo in Coconut Grove

Ocean View Balcony. Pool & Hot tub. Fast Wi-Fi

4.99 out of 5 average rating, 115 reviews

Villa in Princeton

Perfect for Families - The White House of Miami

4.93 out of 5 average rating, 426 reviews

The outdoor space features a tropical-inspired saltwater pool with a unique shape, surrounded by natural stone decking. A thatched-roof tiki hut is visible nearby, along with a dining table and lounge chairs, creating an inviting area for relaxation and leisure.

Home in Homestead

Private Paradise between Miami & the Keys

4.94 out of 5 average rating, 213 reviews

Miami Getaway - Heated Pool, BBQ, Washer & Dryer

4.94 out of 5 average rating, 188 reviews

The outdoor pool area features a clear blue salt-water pool, surrounded by lounge chairs and shaded by umbrella canopies. A natural rock slide is integrated into the design, set against lush green foliage and palm trees in the background.

Apartment in Miami

Very Private 1/1 Apt w/Oasis Pool Patio Setting

4.84 out of 5 average rating, 405 reviews

A spacious studio features a comfortable king-size bed and a queen pull-out sofa. Natural light floods the area through the large balcony door, which offers views of the city. A stylish dining area with a table is visible, complemented by decorative artworks on the walls.

Condo in Coconut Grove

SF Beautiful Blue & Gold Studio with Ocean View

4.94 out of 5 average rating, 186 reviews

The exterior of the one-story house features a spacious driveway with a paved surface and lush greenery lining the front. Large windows reflect the sunlight, while palm trees provide a tropical touch. A welcoming entryway leads to the interior of the home.

Villa in Homestead

One Story Luxury Villa with Hot Tub

Family- and pet-friendly home rentals

4.88 out of 5 average rating, 197 reviews

A spacious sleeping area features a large king bed with white linens and several pillows. A minimalist kitchenette is visible in the background, equipped with a microwave and storage. Natural light enters through the windows, enhancing the room's serene atmosphere.

Apartment in South Beach

South Beach South of Fifth Miami's Best Beach

4.87 out of 5 average rating, 200 reviews

Home in Homestead

Sukyia Charming House! Japanese Garden in SW Miami

4.89 out of 5 average rating, 133 reviews

A small outdoor seating area is presented, featuring two woven chairs with cushions arranged around a round table. Soft lighting from wall sconces enhances the ambiance, while the large window with horizontal slats provides views of the surroundings.

Home in Florida City

Private Cozy Studio Close to the Keys

4.94 out of 5 average rating, 655 reviews

A cozy studio space features a comfortable queen bed with a twin trundle underneath. A rustic wooden dining table is positioned nearby, complemented by black metal chairs. Large windows invite natural light and offer views of a lush outdoor area, framed by green drapes.

Guesthouse in Coral Way

Brand NEW Cottage with Gorgeous Patio! 5 mi Beach!

Guesthouse in Buena Vista

4.93 out of 5 average rating, 183 reviews

Cozy Studio Retreat • King Bed

Guesthouse in South Miami

A bright sleeping area features a king bed with a wooden headboard, complemented by two bedside lamps on matching nightstands. Soft lighting illuminates the walls, creating a comfortable ambiance. A nearby door leads to a separate bathroom, enhancing the privacy of the space.

4.96 out of 5 average rating, 264 reviews

Cozy Cane Cottage close to UM

4.87 out of 5 average rating, 103 reviews

A bright living room features a large beige sectional sofa facing a glass coffee table. A decorative piece rests on the table, while a tall indoor plant adds greenery. Sunlight streams through expansive windows draped with sheer white curtains, illuminating the white walls and marble flooring.

Home in Homestead

Tropical Paradise Between Miami and the FL Keys

Guest suite in Coconut Grove

A tranquil pool area is surrounded by lush greenery and tropical plants, creating a serene atmosphere. The rectangular swimming pool is framed by terracotta tiles and features potted plants on the edges, offering spaces for relaxation in the sun.

4.96 out of 5 average rating, 287 reviews

"Casa Mia's" pool & BBQ bungalow

Family-friendly home rentals with a pool

4.86 out of 5 average rating, 181 reviews

The outdoor area features a spacious swimming pool surrounded by a tiled patio. Lounge chairs are positioned for relaxation. Lush palm trees provide shade, while a covered seating area is visible in the background. Bright blue skies enhance the inviting ambiance of the space.

Home in Cutler Bay

Tropical House Miami

Guesthouse in Biscayne Park

A tropical tiki hut features natural thatched roofing and wooden flooring, offering a relaxed seating area with a central coffee table. Surrounding greenery enhances the peaceful ambiance, while a scooter is visible in the background, suggesting a convenient way to explore the area.

4.95 out of 5 average rating, 518 reviews

Cozy and charming cottage

4.93 out of 5 average rating, 195 reviews

Guest suite in Miami

Sparkling Clean🌟Brand New Luxury Studio with Pool🏊🏼‍♂️

4.93 out of 5 average rating, 151 reviews

Poolside Haven 4/2, Htd pool, oudr ktch by freeway

Apartment in Key Biscayne

A bright living area is showcased, featuring a dark gray sofa with geometric pillows and a coffee table. The wall-mounted TV displays an image of a tropical beach. Natural light floods the space through large windows, enhancing the clean, modern aesthetic.

4.81 out of 5 average rating, 160 reviews

1 Bedroom King Size Apartment. Walk to the beach

4.93 out of 5 average rating, 165 reviews

Heated Pool/Basketball Court/Ping Pong Table/Golf

4.97 out of 5 average rating, 182 reviews

A clear blue pool is framed by a protective screen enclosure, creating a serene swimming environment. Lush greenery surrounds the pool area, and a guesthouse is visible in the background, featuring a simple facade with a centrally located door.

Guesthouse in Homestead

Charming Private Pool house for two.

The image features a clear pool surrounded by a spacious patio, with two lounge chairs positioned nearby. Lush tropical plants and colorful potted flowers add to the serene environment. Soft string lights are hung above, enhancing the outdoor space during the evening.