Best Vacation Homes in Cutler Bay
House
10.0(11 Reviews)
2 Bedrooms
1 Bath
6 Guests
800 ft²
Balcony/Terrace
Pet Friendly
Kitchen
Parking
£148/Night
7 Nights - £1,033
House
10.0(8 Reviews)
4 Bedrooms
3 Baths
11 Guests
1646.88 ft²
Oceanfront
Pool
Ocean View- Balcony/Terrace
£343/Night
7 Nights - £2,404
£69/Night
7 Nights - £481
House
10.0(5 Reviews)
2 Bedrooms
2 Baths
4 Guests
1650 ft²
Private Pool
Fireplace/Heating- Pool
- Balcony/Terrace
£150/Night
7 Nights - £1,048
House
10.0(6 Reviews)
3 Bedrooms
2 Baths
6 Guests
2464.94 ft²
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
£283/Night
7 Nights - £1,979
House
10.0(4 Reviews)
2 Bedrooms
2 Baths
4 Guests
1650 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
£184/Night
7 Nights - £1,289
House
10.0(2 Reviews)
2 Bedrooms
1 Bath
4 Guests
360 ft²
- Pool
- Balcony/Terrace
- Pet Friendly
- Kitchen
£154/Night
7 Nights - £1,077
Condo
10.0(1 Review)
2 Bedrooms
2 Baths
4 Guests
1100 ft²
- Kitchen
- Parking
Air Conditioner
Internet
£332/Night
7 Nights - £2,321
Cutler Bay Luxury Rentals
House
7 Bedrooms
4 Baths
12 Guests
1399.31 ft²
- Pool
- Balcony/Terrace
- Parking
- Air Conditioner
£965/Night
7 Nights - £6,754
Villa
10.0(6 Reviews)
6 Bedrooms
4 Baths
16 Guests
3498 ft²
- Private Pool
- Oceanfront
Hot Tub
Spa
£922/Night
7 Nights - £6,455
Villa
9.6(22 Reviews)
4 Bedrooms
3 Baths
12 Guests
- Private Pool
- Fireplace/Heating
- Pool
- Ocean View
£689/Night
7 Nights - £4,826
Villa
10.0(1 Review)
4 Bedrooms
3 Baths
8 Guests
2970 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Fireplace/Heating
£672/Night
7 Nights - £4,702
House
10.0(3 Reviews)
3 Bedrooms
3 Baths
6 Guests
2152.78 ft²
- Fireplace/Heating
- Pool
- Balcony/Terrace
View
£653/Night
7 Nights - £4,571
House
9.8(10 Reviews)
6 Bedrooms
5 Baths
18 Guests
- Hot Tub
- Fireplace/Heating
- Pool
- Ocean View
£643/Night
7 Nights - £4,499
House
9.0(1 Review)
5 Bedrooms
3 Baths
12 Guests
1399.31 ft²
- Pool
- Balcony/Terrace
- View
- Pet Friendly
£638/Night
7 Nights - £4,464
Villa
9.0(8 Reviews)
5 Bedrooms
4 Baths
12 Guests
- Private Pool
- Fireplace/Heating
- Pool
- Ocean View
£620/Night
7 Nights - £4,339
Cutler Bay Pet Friendly Vacation Rentals
Apartment
10.0(1 Review)
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
£94/Night
7 Nights - £659
House
10.0(3 Reviews)
3 Bedrooms
2 Baths
10 Guests
2400.35 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
£191/Night
7 Nights - £1,334
Hotel
7.6(1007 Reviews)
1 Bath
- Pool
Breakfast- Pet Friendly
- Kitchen
£83/Night
7 Nights - £583
House
7.8(21 Reviews)
1 Bedroom
1 Bath
3 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
£121/Night
7 Nights - £846
House
10.0(3 Reviews)
2 Bedrooms
1 Bath
2 Guests
355.21 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
£137/Night
7 Nights - £956
Apartment
1 Bedroom
1 Bath
2 Guests
- Balcony/Terrace
- Pet Friendly
- Kitchen
- Parking
£95/Night
7 Nights - £663
New
House
2 Bedrooms
1 Bath
5 Guests
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- Internet
£77/Night
7 Nights - £539
House
10.0(14 Reviews)
4 Bedrooms
2 Baths
8 Guests
2756 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Ocean View
£266/Night
7 Nights - £1,862
Cutler Bay Large Vacation Homes
House
10.0(15 Reviews)
4 Bedrooms
3 Baths
11 Guests
- Private Pool
- Fireplace/Heating
- Pool
- Ocean View
£391/Night
7 Nights - £2,740
Villa
10.0(2 Reviews)
4 Bedrooms
2 Baths
8 Guests
3498.27 ft²
- Pool
- Balcony/Terrace
- Pet Friendly
- Parking
£231/Night
7 Nights - £1,620
House
10.0(11 Reviews)
4 Bedrooms
3 Baths
12 Guests
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Pet Friendly
£422/Night
7 Nights - £2,957
House
9.9(7 Reviews)
4 Bedrooms
2 Baths
12 Guests
2002.09 ft²
- Fireplace/Heating
- Balcony/Terrace
- View
- Parking
£172/Night
7 Nights - £1,205
Villa
10.0(10 Reviews)
4 Bedrooms
4 Baths
10 Guests
- Private Pool
- Fireplace/Heating
- Pool
- Ocean View
£595/Night
7 Nights - £4,167
House
10.0(1 Review)
4 Bedrooms
3 Baths
10 Guests
- Hot Tub
- Fireplace/Heating
- Pool
- Balcony/Terrace
£603/Night
7 Nights - £4,221
Apartment
10.0(1 Review)
3 Bedrooms
2 Baths
10 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
£263/Night
7 Nights - £1,844
House
9.6(66 Reviews)
4 Bedrooms
2 Baths
10 Guests
2500 ft²
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
£310/Night
7 Nights - £2,170
Why Choose Rent By Owner for your Cutler Bay Vacation Rental Homes?
What makes our Vacation Rentals special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Best Times to Visit Cutler Bay
When should you plan your Vacation Rentals stay?
Choosing the right time to visit this destination ensures you enjoy comfortable weather and avoid peak crowds, making it ideal for securing your perfect vacation rental in the region.
Peak Season Highlights
December to April
This period offers warm weather with less humidity, making it ideal for outdoor activities and exploring the region's natural beauty.
Average Temperature Daytime: 75°F to 85°F - Nighttime: 60°F to 70°F
June to August
During these summer months, you can enjoy longer daylight hours and vibrant local events, perfect for an active getaway or relaxation in the sun.
Average Temperature Daytime: 88°F to 92°F - Nighttime: 75°F to 80°F
Off-Season Highlights
May and November
These shoulder months typically see fewer visitors, offering a quieter experience while still enjoying pleasant weather conditions.
Average Temperature Daytime: 78°F to 85°F - Nighttime: 65°F to 70°F
September and October
This time marks the tail end of hurricane season, leading to lower crowds and more availability for your preferred vacation rentals in the area.
Average Temperature Daytime: 85°F to 88°F - Nighttime: 72°F to 75°F
Weekly Weather Forecast for Cutler Bay
How to Book Your Cutler Bay Vacation Rental Home
What's our booking process?
Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Explore and book the perfect rental in Cutler Bay
Common Vacation Rentals Amenities
What amenities can you expect?
Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Outdoor Amenities
- Enjoy a private outdoor pool to relax and unwind under the Florida sun.
- Take advantage of spacious patios or decks ideal for outdoor dining and entertaining.
- Benefit from lush landscaped gardens that enhance your outdoor experience in the region.
- Make use of outdoor grilling facilities for memorable barbecues with family and friends.
- Relax on sun loungers by the pool area, perfect for soaking up the warm weather.
- Explore well-maintained backyard spaces suitable for outdoor activities and play.
- Utilize shaded seating areas to enjoy the fresh air comfortably at any time of day.
Top Attractions Around Cutler Bay
What attractions are nearby?
While staying here, you can enjoy a variety of activities nearby, including exploring scenic parks and engaging in water-based adventures that highlight the natural beauty of this region.
Family Activities
- Deering Bay Yacht & Country Club: Spend a day enjoying family-friendly boating and water activities at this scenic marina in the region.
- Black Point Park and Marina: Explore the picturesque waterfront park, perfect for picnicking, fishing, and observing local wildlife with your loved ones.
- Lighthouse Park: Discover a relaxing outdoor space where your family can enjoy walking trails, playgrounds, and beautiful views of the coast.
- Everglades Alligator Farm: Experience an educational adventure right here, with guided tours and interactive exhibits about the region’s unique ecosystem.
Adult Activities
- Fishing at Black Point Marina: You can enjoy a relaxing day of fishing and boating just minutes from your vacation rentals in the region.
- Exploring Coral Reef Park: Spend time walking or picnicking in this scenic park that offers beautiful views and outdoor recreation close to your stay.
- Kayaking and Paddleboarding: Experience the calm waters and natural beauty by renting equipment nearby, perfect for an adventurous day here.
- Wildlife Watching in the Everglades: Embark on a guided tour to observe local wildlife and learn about the area's unique ecosystem during your visit.
Other Places to Stay in Cutler Bay, FL
Lakes by the Bay
Cutler Bay Travel Tips
How Can You Make the Most of Your Stay?
- Explore Local Cuisine and Markets: Take the opportunity to sample fresh, regional flavors at nearby markets and eateries to truly immerse yourself in the area's culinary scene.
- Plan Outdoor Activities: Utilize the area's natural landscapes by scheduling outdoor activities such as kayaking, cycling, or walking along scenic trails to enjoy the region’s climate and beauty.
- Visit Nearby Attractions: Discover the attractions surrounding your rental property to make the most of your stay and experience the local culture and history.
- Optimize Your Booking Experience: Choose well-rated vacation rentals that provide all necessary amenities for a comfortable and seamless stay in this destination.
Transportation Options
- Miami-Dade Transit Bus Service: You can rely on this extensive bus network to navigate the area conveniently and affordably during your stay.
- Rental Car Services: Accessible rental agencies provide a flexible way to explore the region at your own pace, ideal for visiting nearby attractions from your vacation rental.
- Ride-Sharing Platforms: Popular ride-sharing options offer quick and reliable transportation, helping you get around without the need for a personal vehicle.
- taxis and Local Shuttles: Local taxi services and shuttle options serve the area efficiently, making short trips and airport transfers straightforward during your visit.
Local Customs Options
- Local Cuisine Etiquette: When dining in the area, it's customary to share dishes that highlight the region's fresh, local flavors and to engage in friendly conversation at the table.
- Respect for Nature: Visitors often observe a strong appreciation for the natural surroundings by participating in outdoor activities responsibly and preserving the environment.
- Community Events: Attending seasonal festivals and local gatherings provides an authentic way to connect with residents and experience regional customs firsthand.
- Greetings and Social Norms: Friendly greetings such as a handshake or a nod are typical when meeting new people, reflecting the area's welcoming atmosphere.
Frequently Asked Questions About Cutler Bay?
1. What are the top vacation rentals in Cutler Bay?
There are a lot of options in Cutler Bay. If you plan on staying in the Cutler Bay area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Cutler Bay:
- Villa Elena - Private Pool
- Family Retreat Sleeps 11, Heated Pool, Mini Golf, Kayak Experience, Waterfront
- Peaceful Exotic Family Home on Cul-de-sac -Minutes from most tourist attractions
- Paradise Miami Home
- Welcome to Casa Luna – Your Private Oasis with Heated Pool!
- Cozy Blue Door Duplex, Central in Cutler Bay
- Private Villa Pool & Waterfall
- Spacious 4BR Waterfront Home with Private Pool, Tiki Hut & Free Parking near Miami & Key Largo
- Charming 3-bedroom house with HEATED pool, Near Stadium ⚽ FIFA World Cup 2026
- 6BR | Heated Pool | Jacuzzi | Sauna | Beach area
2. How many vacation rentals have private pools in Cutler Bay?
There are 27 vacation rentals with private pools near Cutler Bay. Top-rated RBO homes that have access to a swimming pool include:
3. Which vacation homes in Cutler Bay are best for families?
If you are looking for a family-friendly vacation home in Cutler Bay, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Cutler Bay:
4. How many Rentbyowner vacation rentals are available in Cutler Bay?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 151 in the Cutler Bay area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Cutler Bay.
5. What is the cancellation policy for vacation rentals in this area?
Cancellation policies vary by property. You should review the specific listing details or contact the property owner directly to understand the terms and any potential fees associated with canceling your reservation.
6. Are there any house rules I should be aware of before booking?
Yes, each vacation rental will have its own set of house rules outlined in the listing. It’s recommended to read these carefully and reach out to the owner if you have any questions or special requests.
7. How do I know if a property is available for my travel dates?
Availability is shown on the listing page. If your dates are unavailable, you can often contact the owner directly to inquire about flexibility or alternative dates.
8. What amenities can I expect at vacation rentals here?
Amenities vary between properties but commonly include essentials like Wi-Fi, parking, and kitchen facilities. For specific amenities, review the property description and photos or contact the host directly.
9. Is it safe to book vacation rentals in this region?
Trustworthy vacation rentals in the area are verified for quality and safety standards. Always read guest reviews and communicate with the host to ensure your comfort and security during your stay.
Cutler Bay Top Rated Vacation Rentals
House
10.0(15 Reviews)
4 Bedrooms
2 Baths
8 Guests
- Private Pool
- Fireplace/Heating
- Pool
- Ocean View
£471/Night
7 Nights - £3,298
House
10.0(8 Reviews)
3 Bedrooms
2 Baths
6 Guests
2465 ft²
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
£318/Night
7 Nights - £2,228
House
10.0(2 Reviews)
3 Bedrooms
2 Baths
7 Guests
1250 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
£252/Night
7 Nights - £1,766
House
9.6(52 Reviews)
5 Bedrooms
3 Baths
10 Guests
2500 ft²
- Private Pool
- Pool
- Ocean View
- Balcony/Terrace
£520/Night
7 Nights - £3,637
House
9.6(20 Reviews)
7 Bedrooms
4 Baths
19 Guests
3000 ft²
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
£563/Night
7 Nights - £3,939
House
9.5(2 Reviews)
4 Bedrooms
3 Baths
10 Guests
2066.67 ft²
- Hot Tub
- Pool
- Balcony/Terrace
- View
£240/Night
7 Nights - £1,677
House
9.4(8 Reviews)
5 Bedrooms
3 Baths
16 Guests
2497.23 ft²
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
£557/Night
7 Nights - £3,901
House
9.3(20 Reviews)
3 Bedrooms
2 Baths
8 Guests
2497.23 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
£209/Night
7 Nights - £1,465
