Vacation rentals in Cutler Bay

Boutique Style House Hot-Tub Mini-Golf BBQ & Games

Come enjoy this beautiful vacation townhouse with 3 bedrooms, 2.5 bathrooms in Homestead - Miami with a large parking driveway. This is a tropical paradise close to everything needed to live the good life! Great location close to Miami Zoo, Homestead Speedway, and US1 to the Florida Keys The property sleeps up to 8 guests and is ideal for a group of friends or family looking to experience all the sunshine and fun that South Florida has to offer. Property is located in 137 Avenue and 260th Lane

The Pass-Through 2 | Cozy 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.

Beautiful Family Villa. Large Outdoor Space & BBQ

Spacious 4BR, 2BA home in Cutler Bay with 5 comfy beds, full kitchen, washer & dryer, and a massive backyard! Enjoy the oversized outdoor space — perfect for playing sports, barbecues, or relaxing under the sun. Located in a peaceful area near shops, parks, and Black Point Marina. Ideal for families and groups seeking comfort, privacy, and a true South Florida experience. The home offers free parking, fast Wi-Fi, smart TVs, and plenty of room to unwind and make lasting memories together.

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.

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.

Escape to Miami/Heather+Pool/9pl/BBQ/pool table.

🏡 Spacious Home with Heated Pool, BBQ & Game Room 🎉 Enjoy this perfect getaway for families and groups! 🛏 4 bedrooms: King, 2 Queen, and a bunk bed (Full + 2 Twin). 🚿 2.5 bathrooms. 🎱 Game room with pool table. 📺 TVs in all rooms, living room & patio. 👶 Crib & high chair available. 🍽 Fully equipped kitchen. 🏊‍♂️ Private heated pool 🔥. 🍖 BBQ & 🌿 2 hammocks in the patio. 🏠 Spacious, cozy, and perfect for relaxation. Book now for an unforgettable stay! ✨

Heated Pool/Jacuzzi Paradise: Cozy Miami Retreat

Welcome to our spacious 3 bedroom, 2 bathroom home located in the highly desirable Cutler Bay neighborhood! The home is perfect for families, couples, or friends looking for a comfortable getaway. Our home boasts a large pool with an attached Jacuzzi and a screened-in pool area perfect for enjoying the Florida sun. ✔ Fully Equipped Kitchen ✔ Comfortable Bedrooms with King/Queen/Full beds ✔ Open Concept Living Area ✔ Office Desk ✔ Piano ✔ High-Speed Wi-Fi

Waterfront Miami Villa | Pool, Kayaks, Mini Golf

Escape to this stunning waterfront villa, perfect for families and groups up to 11. Set along a peaceful canal, this private retreat blends relaxation and adventure with direct water access and resort-style amenities. Resort-Style Highlights: • Heated private pool • Complimentary kayaks & life jackets • Mini golf & outdoor lounging • Smart TVs, fast WiFi, and modern interiors Minutes from Black Point Marina, Miami, and the Florida Keys.

Hunter 26 Sailboat

A one-of-a-kind experience for those who want to enjoy Miami from a different perspective. Can accommodate up to two people, includes a basic toilet and freshwater. The boat is anchored in Biscayne Bay, which allows you to view the Miami skyline from a distance. You'll be in the famous Coconut Grove area. I will be taking you from the dinghy dock to the boat. Two kayaks are included for guests.

Perfect 3 bedroom Home for Miami Getaway

Relax in this cozy, fully equipped home featuring a spacious living area, modern kitchen, and comfortable bedrooms ideal for families or small groups. Perfectly located just steps from Old Cutler Road, surrounded by unique dining, shopping, and top attractions like Southland Mall, The Falls, Black Point Marina, Deering Estates, Everglades National Park, and Miami Beach.

Chicness-Oasis FIFA World Cup 2026 • Near Stadium

Welcome to your dream escape! A boho chic retreat blending laid-back luxury with natural charm. This haven features an open-plan living area, sunlit pool deck with plush daybeds, and a lush backyard with a whimsical tree swing. Thoughtfully designed for relaxation and style—perfect for families, couples, or creatives seeking a soulful getaway.

Private Villa • Pool & Waterfall

Spacious 4BR/4.5BA villa with 5,000 sq ft of fun. Enjoy a spa-style pool, BBQ with outdoor TV, ping pong, pool table, axe throwing (safe), and more. Every room has a Smart TV. Beaches and marina nearby. Private access, big driveway, and full guest access. Perfect for families or groups looking to relax, play, and enjoy Miami in comfort.