Cutler Bay vacation rentals

We found 446 vacation rentals — enter your dates for availability

Discover a selection of 37 homes and other vacation rentals in Cutler Bay that are perfect for your trip. Whether you're staying in a vacation rental with a group or just with your pet, you'll find the best amenities for hanging out with the people that matter most, such as parking and air conditioning. You're sure to find a rental for everyone's needs, including places that are non-smoking or accessible.

Vacation rentals with weekly discounts - Cutler Bay

Showing deals for:Aug 7 - Aug 14

Image gallery for Experience Homestead charm near Black Point Park and Marina

Exterior
9.0 out of 10, Wonderful, (25 reviews)
Wonderful
(25 reviews)

Experience Homestead charm near Black Point Park and Marina

Princeton

8% off
Price is $268
$1,874 for 7 nights
All fees included
Experience Homestead charm near Black Point Park and Marina

Find spaces that suit your style

  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, yards and more

  • More for less

    More space, more privacy, more amenities — more value

  • A place for everyone

    We stand for diversity, inclusion and families everywhere.
    Learn more

Find out more about Cutler Bay

Why visit Cutler Bay

  • Family-friendly attractions: Cutler Bay offers a variety of outdoor parks and recreational areas perfect for family fun.
  • Scenic beaches: Nearby Haulover Beach provides beautiful views and relaxation options for visitors.
  • Charming neighborhoods: Explore Cutler Ridge, known for its friendly atmosphere and outdoor seating.
  • Outdoor activities: Enjoy sports at local batting cages and snorkel in vibrant coral reefs.
  • Diverse accommodations: Choose from spacious apartments, cozy condos, or private homes to suit your needs.

Popular types of accommodation in Cutler Bay

If you’re planning a getaway to Cutler Bay, you'll find an array of vacation rentals to suit your needs. Our most popular options include spacious apartments, cozy condos, and inviting houses. Whether you’re looking for a one-bedroom apartment in Cutler Bay or a larger rental for the whole family, we have the perfect accommodations to make your stay memorable. Explore our selection of Cutler Bay rentals today.

  • Apartments: The top choice among travelers to Cutler Bay, offering convenient and stylish living spaces for individuals or families.
  • Condos: A favored option for vacationers, providing modern amenities and often stunning views, perfect for short or long stays.
  • Houses: Ideal for larger groups seeking privacy, these homes deliver comfort and a home-like atmosphere.
  • Villas: A luxurious option for those looking for spacious accommodations with upscale features and serene surroundings.
  • Cottages: A delightful choice for a quaint and cozy experience, perfect for couples or solo travelers.**

Top attractions near Cutler Bay

Cutler Bay, Florida, is a fantastic destination for family-friendly vacations, offering a mix of outdoor and urban experiences. Explore local attractions like urban parks, the botanical garden, and recreational areas. Don't miss nearby Haulover Beach and Thalatta Estate for scenic views and relaxation. For some fun activities, consider visiting batting cages to enjoy a day of sports. Cutler Bay has something for everyone, making it an ideal spot for your getaway.

  • Biscayne Bay: This picturesque lagoon offers stunning scenery and a vibrant outdoor atmosphere. Enjoy activities like kayaking and snorkeling in its crystal-clear waters, perfect for nature lovers and adventure seekers.
  • Homestead Air Force Base: A military installation with a rich history, it features friendly people and a tropical environment. Families can explore the base's significance and enjoy community events.
  • Biscayne National Park: This national park is a paradise for adventure enthusiasts, boasting breathtaking scenery and outdoor activities like hiking, boating, and wildlife viewing in a serene natural setting.

Things to do recommended for couples

For a romantic getaway in Cutler Bay, indulge in the luxury of Key Largo Anglers Club or enjoy a round of golf at Card Sound Golf Club. Both offer a serene atmosphere, perfect for couples looking to escape and enjoy each other's company.

Things to do recommended for families

Families can explore the beautiful parks in Cutler Bay, like the serene Cutler Ridge Park, perfect for picnics and playground fun. Additionally, they can visit the nearby Biscayne National Park for kayaking and wildlife watching, offering memorable outdoor adventures for all ages.

Things to do recommended for groups

Explore the beauty of the Biscayne Bay with a group kayaking tour, or enjoy a fun day at the Cutler Ridge Park, featuring picnic areas and sports facilities. Don’t miss the local dining scene with fresh seafood at nearby restaurants for a taste of Florida.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation in Cutler Bay

When traveling with a group, family, pets, or planning an extended stay, it’s important to prioritize your needs while filtering options. Here are some helpful Vrbo booking tips to assist you.

  • Traveling to Cutler Bay with a group: Think about how many bedrooms you'll require, along with features like a full kitchen or outdoor area for group gatherings. Thankfully, you can easily filter for these options and more on Vrbo.
  • Traveling to Cutler Bay with young kids: Traveling with little ones can be quite demanding. It's important to prioritize their comfort and safety, as well as ensure access to suitable amenities like a private pool. Additionally, it's wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Cutler Bay: For many families, a vacation isn’t truly complete without their furry companions. If this resonates with you, explore Vrbo listings that welcome pets. Most of these pet-friendly properties come equipped with feeding bowls and cozy beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Cutler Bay: If you're searching for vacation rentals that offer discounts for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to include options like a parking space, a well-equipped kitchen, or a private pool in your search criteria.

Where to stay in Cutler Bay

Cutler Bay, Florida, offers a delightful vacation experience perfect for families and outdoor enthusiasts. Explore charming neighborhoods like Cutler Ridge, where you can enjoy outdoor seating and a friendly atmosphere. Nearby, discover the vibrant coral reefs ideal for snorkeling and relaxation. With its convenient location, Cutler Bay provides easy access to urban amenities while maintaining a welcoming residential feel, making it a fantastic destination for a memorable getaway.

  • Miami: Miami, a vibrant metropolis, serves as a cultural melting pot, offering an array of experiences for travelers. Located adjacent to Cutler Bay, Miami is renowned for its stunning beaches, lively tourist precincts, and bustling shopping areas. Visitors can enjoy family-friendly activities, from soaking up the sun on the sandy shores to exploring the diverse culinary scene. Popular attractions include the iconic South Beach and the lively shopping malls, making it a perfect destination for both relaxation and adventure.
  • Lakes by the Bay: Nestled around Cutler Bay, Lakes by the Bay is a picturesque neighborhood that offers a serene escape for families and business travelers alike. This community boasts access to beautiful parks and family beaches, ideal for outdoor activities and picnics. The area features shopping centers and resorts, catering to those looking for leisure and entertainment. With its tranquil atmosphere and close proximity to theme parks, Lakes by the Bay is an excellent spot for families seeking fun and relaxation.
  • Perrine: Just a couple of miles from Cutler Bay, Perrine is a charming village that offers a blend of city and family-friendly experiences. This community is perfect for those who enjoy adventure activities and vibrant shopping venues. Visitors can explore local beaches and tourist precincts, making it a convenient home base for exploring the region. Perrine’s welcoming atmosphere and proximity to outdoor activities make it a great option for families and business travelers seeking a local experience.

Best time to go to Cutler Bay

If you're planning a trip to Cutler Bay, it's a good idea to check both the weather and property rates. The warmest month is August. Peak season runs in March, July and September, while off-peak times, like August and October to November tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January68.5°F (20.3°C)No Rain (Dry)Mostly SunnyAverageAverage
February71.1°F (21.7°C)No Rain (Dry)Mostly SunnyAverageAverage
March72.7°F (22.6°C)No Rain (Dry)Mostly SunnySlightly HighSlightly High
April77.0°F (25.0°C)Light RainMostly SunnyAverageSlightly High
May79.7°F (26.5°C)Light RainMostly SunnyAverageAverage
June82.6°F (28.1°C)Moderate RainMostly SunnyAverageAverage
July84.0°F (28.9°C)Moderate RainMostly SunnySlightly HighAverage
August84.4°F (29.1°C)Moderate RainMostly SunnySlightly LowSlightly Low
September82.8°F (28.2°C)Moderate RainMostly SunnySlightly HighSlightly Low
October79.3°F (26.3°C)Light RainMostly SunnySlightly LowSlightly Low
November74.7°F (23.7°C)Light RainMostly SunnySlightly LowAverage
December71.4°F (21.9°C)No Rain (Dry)Mostly SunnyAverageSlightly High

Booking with Vrbo is simple

Are you hoping to get the best deal on your upcoming trip? Being flexible with your travel dates can really help, as prices can vary significantly. Additionally, booking a longer stay often leads to substantial savings. To discover the perfect Vrbo property that fits your budget, take advantage of our filters to narrow down options by price, location, and type of vacation rental.

Vrbo Trips: Planning made easy

Vrbo's Trip Board feature offers you a convenient way to plan your travel. You can start new trips, pick up right where you left off, or easily manage and organize your travel plans. Any properties you’ve saved or booked in the past can now be accessed under Potential, Upcoming, or Current Trips. To explore Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Explore Miami and South Florida from Cutler Bay

Sandwiched between the wonderful city of Miami and the unique natural environment of the Everglades National Park, Cutler Bay is a great base to explore Southern Florida. With fun family attractions like Zoo Miami and Monkey Jungle on your doorstep and thrilling natural adventures to be enjoyed in Biscayne Bay and the Everglades, a Cutler Bay vacation rental is a great choice for a sunny, fun-filled vacation. Choose from smart modern condos on luxurious resorts to traditional houses in the local Florida coral rock or smart family homes with their own private pool.

Family-friendly animal fun near Cutler Bay

If you're staying at your Cutler Bay vacation rental with kids, don't miss a trip to the wonderful 750-acre Zoo Miami, just a 20 minute drive from Cutler Bay. The zoo is home to more than 500 different species, including elephants, rhinos, lions and orangutans. As well as daily shows, feedings and meet the zookeeper talks, the zoo runs a fun-packed program of seasonal events. There's more family-friendly animal-themed fun to be enjoyed nearby at Monkey Jungle. Kids will love taking a walking tour through its 5-acre natural rainforest habitat filled with monkeys

Cutler Bay beach fun

The coastline closest to Cutler Bay is dedicated to Biscayne National Park, a protected coastal environment of coral reefs and mangrove forests. This puts wonderful opportunities for snorkeling and kayaking right on the doorstep of your Cutler Bay vacation rental. However, if you want sandy beaches you'll need to travel around 30 minutes in either direction. To the north, the Matheson Hammock Beach offers silky white sand and emerald waters popular with kite surfers, kayakers and stand-up paddle boarders. Thirty minutes south, Homestead Bayfront Park has a pretty beach with designated fishing areas.

Seasonal events around Cutler Bay

Even in the winter months, average temperatures in this part of Florida are in the mid-60s. By the sunny summer months, you can expect highs pushing into the 80s. This makes Cutler Bay a popular winter sun destination. But there is plenty happening throughout the year in this area – there's always an event or festival happening in Miami, just a 40-minute drive from a Cutler Bay vacation rental – from the Miami Open and the Miami Winter Music Conference in March through to Miami Fashion Week in May and the Miami Carnival in September.

Exploring the natural features in Cutler Bay

Whether you're an active traveler or just want to spend some time taking in the scenery, Cutler Bay is a great place to spend some time outside. Here are some of the area’s noteworthy natural features, all within 30 miles (48.2 km) of the city center:

  • Biscayne Bay (7.2 mi / 11.6 km)
  • Fairchild Tropical Botanic Garden (8.1 mi / 13.1 km)
  • Coral Castle Museum (8.3 mi / 13.3 km)
  • Biscayne National Park (9.6 mi / 15.5 km)
  • Tropical Park (10.2 mi / 16.5 km)
  • Bill Baggs Cape Florida State Park (13.5 mi / 21.8 km)

Transportation options to and around Cutler Bay

Fly into Miami Intl. Airport (MIA), the closest airport, located 15.4 mi (24.8 km) from the city center. If you can't find a flight that works for your travel itinerary, you can also fly into Miami, FL (MPB-Public Seaplane Base), which is 17.5 mi (28.2 km) away.

Frequently asked questions

What is the best area to stay in Cutler Bay, Florida, United States of America when booking a vacation rental?
When considering a vacation rental in Cutler Bay, Florida, a popular area to stay is near the picturesque Cutler Bay Park. This neighborhood offers a blend of tranquility and accessibility, making it a great choice for families and nature enthusiasts alike. The park features walking trails, playgrounds, and beautiful picnic areas, superb for enjoying the Florida sunshine.

Another charming option is the area surrounding the nearby Black Point Park and Marina. This location not only provides stunning waterfront views but also offers easy access to activities like boating and fishing. The marina is a popular spot for locals and visitors, and it serves as a gateway to exploring the beautiful waters of Biscayne Bay.

Overall, Cutler Bay has a variety of vacation rental properties, suiting different tastes and budgets, ensuring visitors can find the superb home base for exploring the area's attractions and enjoying its natural beauty.
How much does it cost to rent a vacation home in Cutler Bay?
Prices for vacation rentals in Cutler Bay vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Cutler Bay to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Cutler Bay vacation house rentals?
You can find great discounts on house rentals in Cutler Bay on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Where are the best areas for renting a beach house in Cutler Bay?
For renting a beach house in Cutler Bay, travelers should explore the neighborhoods near Biscayne Bay, particularly around the popular areas of Cutler Ridge and the scenic waterfront of Old Cutler Road. These locations provide easy access to beautiful beaches and parks, such as the nearby Black Point Park & Marina, where visitors can enjoy water activities and stunning views.

Properties in this area often feature modern amenities like private pools, outdoor patios, and spacious living areas, making them superb for families or groups seeking a relaxing getaway. Many vacation rentals also include fully equipped kitchens for self-catering, as well as barbecue grills for outdoor dining.

Additionally, Cutler Bay is conveniently located near various shopping and dining options, allowing guests to enjoy local cuisine and explore nearby attractions. The area is also close to the serene surroundings of the Cutler Bay Nature Preserve, offering opportunities for hiking and bird watching, which can be a delightful complement to beachside activities.
What is the most popular type of vacation rental accomodation in Cutler Bay?
In Cutler Bay, vacation houses are the most popular type of rental, with around 40 available throughout the area. These homes typically feature multiple bedrooms, spacious living areas, and fully equipped kitchens, making them ideal for families or groups looking for a comfortable stay. Many of these vacation houses also come with outdoor amenities such as private gardens, patios, or decks where guests can relax and enjoy the warm Florida weather. Additionally, there are several apartments, villas, and condos available, offering a variety of options for travelers seeking different experiences.
Are there any family house rentals in Cutler Bay?
In Cutler Bay, Florida, there are numerous family-friendly house rentals available—specifically, around 43 options for visitors to choose from. This suburban area is known for its peaceful neighborhoods and proximity to various attractions, making it an ideal spot for families. Many of these homes come equipped with spacious living areas, full kitchens for preparing family meals, and outdoor spaces superb for children to play and explore.

Some properties may also feature amenities such as private pools, game rooms, and comfortable backyards, adding to the convenience and enjoyment of your stay. Families can easily access nearby parks, shopping areas, and dining options that cater to all tastes.
Can I rent a vacation home with a pool or hot tub in Cutler Bay?
In Cutler Bay, there are plenty of vacation homes available for rent that feature pools and hot tubs, with around 32 options to choose from. This charming suburban area in Florida offers a mix of residential neighborhoods, making it a great spot for travelers seeking a relaxing getaway. Many of these rentals come equipped with private pools, hot tubs, outdoor dining areas, and fully equipped kitchens, great for family gatherings or group vacations. Some properties might also include amenities like barbecue grills and spacious backyards, enhancing the outdoor experience. Visitors can enjoy the tranquility of the area while being close to local parks, shopping, and dining options.
Can I find long-stay vacation rentals in Cutler Bay?
A long-stay vacation rental in Cutler Bay is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Are there pet-friendly house rentals in Cutler Bay?
In Cutler Bay, travelers can find a variety of pet-friendly house rentals that cater to both families and pet owners. With around 23 options available, these rentals often feature spacious layouts, fully equipped kitchens, and outdoor spaces such as private backyards or patios, providing a comfortable environment for guests and their furry companions.

The Cutler Bay area is conveniently located near several parks, such as the expansive Cutler Ridge Park and the scenic Old Cutler Trail, which are great for walking dogs and enjoying the outdoors. Additionally, the neighborhood has pet-friendly cafes and shops, making it easy for travelers to enjoy their stay while keeping their pets in mind.
Are there any remote work vacation rentals in Cutler Bay?
In Cutler Bay, there are numerous vacation rentals suitable for remote work, with around 51 options available. This vibrant area in Florida offers a variety of properties equipped with essential amenities for those looking to work remotely. Most rentals come with high-speed Wi-Fi, dedicated workspaces, and comfortable living areas, ensuring a productive environment.

Travelers can expect amenities such as fully equipped kitchens, air conditioning, and outdoor spaces to relax after a day of work. The neighborhood provides easy access to local parks and recreational areas, superb for taking breaks or enjoying leisure time. Cutler Bay's proximity to shopping centers and dining options also adds convenience for those balancing work and relaxation. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Cutler Bay vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Cutler Bay with parking available—perfect for families or travelers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in Cutler Bay?
In Cutler Bay, popular rental amenities include fully equipped kitchens, allowing guests to prepare their own meals. Many properties also offer onsite parking, making it convenient for travelers with vehicles. Outdoor spaces such as decks or patios are common, providing a nice spot for relaxation and enjoying the pleasant Florida weather. Additionally, amenities like coffee and tea makers, as well as blenders, are frequently available, suiting those who appreciate morning beverages or want to whip up smoothies and snacks during their stay.
When is the best time to visit Cutler Bay for a vacation rental?
The best time to visit Cutler Bay for a vacation rental is in September, when the summer peak season begins to wind down. This month offers a delightful balance of warm weather and fewer crowds, allowing travelers to fully enjoy the natural beauty and outdoor activities that Cutler Bay has to offer.

During the peak season, from July through September, visitors can bask in temperatures typically ranging from the mid-70s to low 90s Fahrenheit. This climate is superb for enjoying the area's stunning parks, like the picturesque Biscayne National Park, where you can partake in kayaking, paddleboarding, or simply relaxing by the water. The lush scenery and vibrant wildlife provide a refreshing escape for outdoor enthusiasts and families alike.

For those seeking a more budget-friendly option, October presents an excellent opportunity to explore Cutler Bay at a lower cost. While the weather remains inviting and warm, you'll find that many vacation rentals offer reduced rates, making it a great time for enjoying local attractions without the hustle and bustle of peak tourist traffic.
How early should I book a Cutler Bay vacation rental?
Book your Cutler Bay vacation rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Cutler Bay, Florida, United States of America?
In Cutler Bay, visitors can explore several attractions that highlight the area's natural beauty and recreational opportunities. The Cutler Ridge Park offers green space for picnics, playgrounds for children, and walking trails, making it a great spot for families. Nearby, the Black Point Park and Marina is popular for boating and fishing, providing access to the waters of Biscayne Bay and beautiful waterfront views.

For those interested in wildlife, the nearby Biscayne National Park offers opportunities for snorkeling, kayaking, and hiking, showcasing the region's diverse ecosystems. Additionally, Cutler Bay is close to the Southland Mall, where visitors can shop, dine, and enjoy various entertainment options.
Can I change or cancel my Cutler Bay home rental booking on Vrbo?
To find Cutler Bay vacation rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travelers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cozy cabin or a beach condo, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Cutler Bay vacation rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.

If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.

Vrbo also offers support via live chat through our Help Center, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organizing group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

More Vacation Ideas