Compare best Airbnb in Cutler Bay, FL from 100+ providers!

171 available vacation rental offers

7 nights
2
1
  • airbnb
  • booking
  • vrbo
  • expedia
  • sonder
  • priceline
  • tripadvisor
  • tripcom
  • homestay
  • hotelscom
  • orbitz
  • vacasa
Cutler Bay, FL vacation rentals
Choose the perfect vacation accommodation
Price per night
Accommodation type
Rating

Best Vacation rentals and Airbnb offers in Cutler Bay, FL

Best Cutler Bay, FL vacation rentals with a balcony

Deluxe Miami House W 5br Mini Golf & Heated Pool L62 - Cutler Bay, FL
9.7 121 reviews
Cutler Bay, FL
07/03 – 07/06
$1234/nighttotal: $3702 (3 )

Deluxe Miami House W 5br Mini Golf & Heated Pool L62

5 12
house , Country Walk
This Country Walk home is located in Miami, Florida, just a short drive from Fruit Spice Park and Homestead Miami Speedway. The property has earned excellent ratings for location, cleanliness, and user experience.
This spacious 5-bedroom house offers 1510 square feet of living space. Enjoy amenities like a private pool and patio, a fully equipped kitchen, a tennis court, and a garden.
Guest Fav | 5br Pool Estate | Sleeps 12 - Cutler Bay, FL
Cutler Bay, FL
08/17 – 08/23
$1268/nighttotal: $7608 (6 )

Guest Fav | 5br Pool Estate | Sleeps 12

5 16
house , Palmetto Bay
This 5-bedroom house in Palmetto Bay is located 7.6 miles from the University of Miami and 9 miles from Cocowalk Shopping Center.
This spacious vacation home accommodates up to 16 guests and features 4 bathrooms, a fully equipped kitchen, air conditioning, a swimming pool, a terrace, a garden, and billiards.
Rosa Bella Comfort Suite - Cutler Bay, FL
Cutler Bay, FL
06/20 – 06/27
$92/nighttotal: $644 (7 )

Rosa Bella Comfort Suite

1 2
house , Princeton
Rosa Bella Comfort Suite in Homestead is located 5.8 miles from Homestead Miami Speedway, 6.1 miles from Fruit Spice Park, and 5.3 miles from Homestead Air Force Base.
This air-conditioned vacation home offers 1 bedroom, 1 bathroom, a fully equipped kitchenette, free WiFi, and a private terrace for 2 guests.
Pinecrest #1 2br 4 Beds Free Parking - Cutler Bay, FL
Cutler Bay, FL
06/20 – 07/06
$399/nighttotal: $6384 (16 )

Pinecrest #1 2br 4 Beds Free Parking

2 2
apartment , Palmetto Bay
Pinecrest #1, a rental home in Rockdale, is located 7.2 miles from the University of Miami and 9.1 miles from Cocowalk Shopping Center.
This 900 square foot residence offers two bedrooms for up to four guests, complimentary WiFi, air conditioning, a full kitchen with a fridge and microwave, a terrace, a garden, and free private parking, with Vizcaya Museum 12 miles away and Marlins Park 13 miles away.

Browse Family-Friendly Vacation Rentals in Cutler Bay, FL

Family beach vacations in Cutler Bay, FL are better in spacious rentals that offer plenty of room to spread out near the shore.

3br Townhouse, Miami And The Keys - Cutler Bay, FL
8.8 4 reviews
Cutler Bay, FL
06/20 – 07/06
$232/nighttotal: $3712 (16 )

3br Townhouse, Miami And The Keys

2 2
apartment , Naranja
This Homestead townhouse, near Homestead Air Force Base (7.1 miles), Florida Keys Factory Shops (8.3 miles), and Fruit & Spice Park (5.7 miles), offers easy access to both Miami and the Florida Keys.
This 1000-square-foot, two-bedroom, three-bathroom rental sleeps thirteen guests and includes a fully equipped kitchen with a dishwasher, free parking, and a flat-screen TV.
Luxury Villa | Spa - Pool |Top Location| Pets |Bbq - Cutler Bay, FL
9.9 131 reviews
Cutler Bay, FL
07/03 – 07/06
$711/nighttotal: $2133 (3 )

Luxury Villa | Spa - Pool |Top Location| Pets |Bbq

1 12
house , South Miami Heights
This South Miami Heights house is conveniently located just five minutes from the Miami Zoo, 20 minutes from Coral Gables and Little Havana, and 25 minutes from the beach. It's nestled in a quiet residential neighborhood, offering a peaceful escape from the bustling city. The house consistently earns excellent ratings for its location, cleanliness, and overall experience.
This spacious home has three bedrooms and two bathrooms, comfortably accommodating up to 12 guests. Enjoy a private outdoor oasis with a heated swim spa, patio furniture, a ping-pong table, and cornhole, perfect for relaxation and entertainment. The house also includes a fully equipped kitchen, a dedicated workspace, washer and dryer, complimentary toiletries, and private parking for up to four vehicles.
•Perfect For Families•the White House Of Miami - Cutler Bay, FL
10 132 reviews
Cutler Bay, FL
07/03 – 07/06
$2617/nighttotal: $7851 (3 )

•Perfect For Families•the White House Of Miami

1 12
house , Princeton
This Miami mega-home, near Homestead Air Reserve Base (5 miles) and Zoo Miami (10 miles), offers easy access to Miami Beach and Downtown Miami (20-35 miles).
This 1.25-acre property boasts 9 bedrooms, 5 bathrooms, sleeps 16, includes two kitchens, a heated pool, jacuzzi, extensive outdoor amenities (outdoor kitchen, fire pit, pool table), and activities like soccer, basketball, and kayaking.
Explore South Florida From This Comfy Family-friendly Home! - Cutler Bay, FL
9.6 10 reviews
Cutler Bay, FL
07/01 – 07/06
$591/nighttotal: $2955 (5 )

Explore South Florida From This Comfy Family-friendly Home!

4 2
apartment , Princeton
This family-friendly Princeton, Florida apartment rental is conveniently located near the Coral Castle Museum and Miami Paper Museum, offering easy access to local attractions.
The 4-bedroom, 2-bathroom unit sleeps 9 guests and features a fully equipped kitchen with a refrigerator, oven, stovetop, dishwasher, and ice maker, plus amenities including air conditioning, a spa, parking, and internet access.

Frequently Asked Questions about vacation rentals in Cutler Bay, FL

  • What should a first-time visitor not miss in Cutler Bay, FL?

    For a first-timer in Cutler Bay, you gotta check out the Cutler Bay Waterfront Park. It's a great place to relax by the water, go for a walk, or have a picnic. You can also visit the Deering Estate, a historic site with beautiful gardens and a museum.
  • What are the best Airbnb and vacation rentals in Cutler Bay, FL?

  • Which neighborhood in Cutler Bay, FL should you consider for a vacation rental?

    If you're looking for a vacation rental in Cutler Bay, the area around the Cutler Bay Waterfront Park is a great option. It's close to the beach, restaurants, and shops. You'll also find plenty of family-friendly activities in the area.
  • What are the most popular Airbnbs in Cutler Bay, FL?

  • What are the top family-friendly attractions in Cutler Bay, FL?

    Cutler Bay has a lot to offer families. The Deering Estate is a great place to learn about history and explore nature. You can also check out the Cutler Bay Aquatic Center for some swimming and water fun.
  • What are the best vacation rentals with a pool in Cutler Bay, FL?

  • When is the best time to book a vacation rental in Cutler Bay, FL?

    The best time to book a vacation rental in Cutler Bay is during the shoulder seasons, which are spring and fall. You'll get the best prices and avoid the crowds.
  • What are the best rentals for families and kids in Cutler Bay, FL?

  • What are the best budget-friendly activities in Cutler Bay, FL?

    For a budget-friendly day out, head to the Cutler Bay Waterfront Park. It's free to enter and offers beautiful views of the bay. You can also go for a walk or bike ride along the Cutler Bay Trail.
  • What are the best rentals or Airbnbs with a jacuzzi in Cutler Bay, FL?

    The best vacation rentals or Airbnb with a jacuzzi in Cutler Bay, FL are Luxe 5br Pool Jacuzzi Basketball L17, Private Villa Pool Spa Games-beach L27 and Stylish Haven Heated Pool Pool Table L28.

  • What are the best restaurants with local dishes in Cutler Bay, FL?

    Cutler Bay has some great restaurants serving up local dishes. 'The Rusty Pelican' has a nice view and is known for its fresh seafood. For a more casual experience, try 'The Local' - they have a great menu and a relaxed atmosphere.
  • What are the best walking or cycling routes in Cutler Bay, FL?

    The Cutler Bay Trail is a great option for both walking and cycling. It's a paved trail that runs along the waterfront and offers beautiful views of the bay. You can also explore the many parks and green spaces in Cutler Bay.
  • Are there pet-friendly attractions in Cutler Bay, FL?

    Cutler Bay Waterfront Park is pet-friendly, so you can bring your furry friend along for a walk or a picnic. The Deering Estate also allows pets in certain areas, so you can check their website for details.
  • What are the benefits of choosing a vacation rental in Cutler Bay, FL?

    Choosing a vacation rental in Cutler Bay can give you more space and privacy than a hotel. You'll also have access to a kitchen and laundry facilities, which can be very convenient. Plus, vacation rentals are often located in more residential areas, giving you a taste of local life.
  • What are the top sports attractions and facilities in Cutler Bay, FL?

    Cutler Bay has a few great sports facilities. The Cutler Bay Aquatic Center has a swimming pool, a diving board, and a water slide. The Cutler Bay Park and Recreation Department also offers a variety of sports programs and activities.

Destinations nearby

Best Cutler Bay, FL vacation rentals with parking

Quiet Zen Tiny House In Japanese Garden - Cutler Bay, FL
8.1 20 reviews
Cutler Bay, FL
06/20 – 07/06
$178/nighttotal: $2848 (16 )

Quiet Zen Tiny House In Japanese Garden

1 2
house , Princeton
This tiny house retreat is located in Homestead, Florida, just a short drive from Fruit Spice Park and Homestead Miami Speedway. The surrounding area offers a peaceful and tranquil atmosphere.
The house has one bedroom and one bathroom, with a floor area of 400 square feet and a guest capacity of 7. Guests can enjoy amenities like air conditioning, a fully equipped kitchen, and a private garden.
Beauty Spacious Miami Pool Lake House 4bed/2bath - Cutler Bay, FL
8.9 41 reviews
Cutler Bay, FL
06/20 – 06/27
$299/nighttotal: $2093 (7 )

Beauty Spacious Miami Pool Lake House 4bed/2bath

3 2
apartment , Cutler Bay
This Cutler Bay home boasts a convenient location, just five minutes from Biscayne Bay National Park and Black Point Marina, and 20 minutes from Miami International Airport and South Beach.
This three-bedroom, two-bathroom house sleeps eight guests comfortably, offering an open-concept layout, a fully equipped kitchen with a kitchen island and washer/dryer, a private backyard, a swimming pool, free Wi-Fi, and access to community amenities including tennis courts and a playground.
Brand New Private 1br/1ba Cutler Bay Studio - Cutler Bay, FL
Cutler Bay, FL
06/20 – 06/27
$128/nighttotal: $896 (7 )

Brand New Private 1br/1ba Cutler Bay Studio

1 2
studio , Cutler Bay
This studio apartment in Cutler Bay is located a 3-minute drive from Southland Mall and offers convenient access to Everglades National Park and Biscayne National Park.
This 200-square-foot accommodation features a kitchenette with a fridge and microwave, air conditioning, Wi-Fi, and parking for up to 2 guests.
Hamilton House Miami - Tropical Oasis / Heated Pool / Tiki / Brazilian Bbq - Cutler Bay, FL
9.8 36 reviews
Cutler Bay, FL
08/17 – 08/23
$930/nighttotal: $5580 (6 )

Hamilton House Miami - Tropical Oasis / Heated Pool / Tiki / Brazilian Bbq

6 16
apartment , Palmetto Bay
This spacious house in Palmetto Bay is located just 20 minutes from South Beach, Little Havana, Coral Gables, Downtown Brickell, and Everglades National Park. The property is rated excellent by previous guests and offers a peaceful retreat in a quiet neighborhood.
This 6-bedroom, 4-bathroom home can accommodate up to 16 guests and features a large kitchen, game room, and outdoor entertainment area with a Brazilian BBQ and smoker grill. You can enjoy a heated swimming pool, waterfall, Jacuzzi, spa, and a lush tropical landscape.

Choose the Right Vacation Rentals with a Pool in Cutler Bay, FL

Complement your beach days with a dip in the pool at these premier vacation rentals in Cutler Bay, FL.

Resort Style Pool House 5 Bed Mini-golf Game-room - Cutler Bay, FL
9.5 149 reviews
Cutler Bay, FL
07/03 – 07/06
$590/nighttotal: $1770 (3 )

Resort Style Pool House 5 Bed Mini-golf Game-room

1 12
apartment , Princeton
This two-story home is located in Princeton, a short distance from the town's downtown area and Princeton University. The apartment has received excellent ratings for its location, cleanliness, and overall user experience. This spacious rental has four bedrooms and three full bathrooms, comfortably accommodating up to 10 guests. Amenities include a fully equipped kitchen, air conditioning, a private swimming pool, a jacuzzi, a garden, and parking.
La Acualina - Cutler Bay, FL
Cutler Bay, FL
07/01 – 07/06
$788/nighttotal: $3940 (5 )

La Acualina

3 2
apartment , Kendall
This 3-bedroom house in Miami's Kendall neighborhood is located 2 miles from Dadeland Mall and Dolphin Mall, and within 5 miles of Zoo Miami and Vizcaya Museum and Gardens.
This accommodation sleeps up to 6 guests and features 2 bathrooms, air conditioning, and internet access, with comfortable sleeping arrangements including two queen beds and one full bed.
Central Miami House Pool 4 Bds/2 Near Attraction - Cutler Bay, FL
8.4 5 reviews
Cutler Bay, FL
06/20 – 07/06
$270/nighttotal: $4320 (16 )

Central Miami House Pool 4 Bds/2 Near Attraction

1 2
apartment , Cutler Bay
This comfortable apartment in Cutler Bay is a 5-minute drive from Black Point Marina and a 20-minute drive from Miami International Airport. It has earned excellent ratings for location, cleanliness, and user experience.
The apartment has three bedrooms and two bathrooms, sleeping up to six guests comfortably. Enjoy amenities like a private backyard, a swimming pool, a tennis court, and a playground, all within the apartment complex.
Modern Retreat  Gameroom, Court, Bbq & Playground - Cutler Bay, FL
8.4 5 reviews
Cutler Bay, FL
07/01 – 07/06
$1119/nighttotal: $5595 (5 )

Modern Retreat Gameroom, Court, Bbq & Playground

5 2
apartment , Cutler Bay
This spacious Cutler Bay vacation home, near the Gold Coast Railroad Museum and Lowe Art Museum, offers a tranquil escape in a peaceful residential setting.
The 15,000-square-foot property boasts 2,500 square feet of interior space, including five bedrooms with 55" smart TVs, three bathrooms, and amenities such as a heated pool, basketball court, and game room, accommodating up to 10 guests.

Discover Vacation Rentals by the Sea in Cutler Bay, FL

Relax near the shore in these coastal Cutler Bay, FL vacation rentals, combining comfortable amenities with beautiful seaside scenery just moments away.

Cutler Bay Guest House - Cutler Bay, FL
9.9 21 reviews
Cutler Bay, FL
07/01 – 07/06
$141/nighttotal: $705 (5 )

Cutler Bay Guest House

1 2
house , Cutler Bay

Traveler-Approved Luxury Vacation Rentals in Cutler Bay, FL

Indulge in a luxury vacation rental in Cutler Bay, FL, where high-end design meets world-class 5-star comfort.

Resort Oasis: Heated Pool, Jacuzzi & Sports Court - Cutler Bay, FL
9.4 13 reviews
Cutler Bay, FL
07/03 – 07/06
$970/nighttotal: $2910 (3 )

Resort Oasis: Heated Pool, Jacuzzi & Sports Court

1 12
apartment , Cutler Bay

Explore Vacation Rentals with Saunas in Cutler Bay, FL

Relax in style with an on-site sauna at these premium Cutler Bay, FL vacation rentals near the water.

El Lindo Paso - Cutler Bay, FL
8.8 3 reviews
Cutler Bay, FL
06/20 – 07/06
$387/nighttotal: $6192 (16 )

El Lindo Paso

4 2
apartment , Princeton
©2026 cozycozy.com