Vacation rentals in Cutler Bay

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Top-rated vacation rentals in Cutler Bay

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Guest favorite
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
4.96 out of 5 average rating, 148 reviews

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.

Guest favorite
The treehouse stands surrounded by lush greenery and vibrant flowers. A set of stairs leads up to the entrance, which is framed by tropical plants. Decorative stones and a pathway enhance the serene garden setting, creating a tranquil environment.
Tiny home in Cutler Bay
4.93 out of 5 average rating, 131 reviews

Cozy Treehouse in Private Garden, Pool

Read entire listing for FAQ Contact AIRBNB for changes to your reservation We welcome all! Come reconnect with yourself and nature in this Zen garden. Surrounded by love, peace, nature in peaceful surroundings Located between Miami Beach & The Keys Beautiful & Quiet Residential Area South of Miami Close to all major roads. *this is a treehouse, so it is a small space, FULL SIZE bed (54 x 75 inches). Private bathroom adjacent to treehouse. Look at our other listings in main house.

Top guest favorite
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
4.98 out of 5 average rating, 250 reviews

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. We have bikes available to cruise the miles of nearby paths stretching from Coconut Grove to Black Point Marina.

Top guest favorite
A spacious studio features a wooden sleigh bed complemented by two ceiling fans above. A small dining table is visible nearby, along with a wooden nightstand next to the bed. The elegant granite floor reflects the soft lighting from the simple wall fixtures.
Guest suite in Homestead
4.99 out of 5 average rating, 323 reviews

GATED king studio on 5 acres/22OV TESLA charging

Close to Everglades National Park, Biscayne National Park, FL Keys, located in the Redland tropical agricultural area. This is a gated property with secure parking for campers, boats, trailers, etc. The studio is totally renovated with the highest quality of materials. Fruit is available to guests when in season and there is usually something in season during the year. TESLA charging is available at parking area (guest must bring their TESLA charging cable). No children under 12 yrs. old.

Top guest favorite
The entrance of the property is framed by mature palm trees and lush landscaping, showcasing vibrant greenery. A large half-circle driveway leads up to the house, highlighted by a smooth, paved surface. The warm-toned exterior of the home is visible, inviting guests into a tranquil setting.
Guest suite in Miami
4.91 out of 5 average rating, 418 reviews

Cozy Suite -Exterior Entrance, SelfCheckin

If you like Clean, New, Quiet and Great Hospitality, then this is the Perfect Room 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 -Bathroom with 2 sinks -SWIMMING POOL -Central A/C -HBO TV -Refrigerator -Ceiling Fan -Closet Space -Ceramic Tile Floors -Iron & Board -Towels & Bath essentials -Hair dryer

Superhost
A screened-in pool area showcases a large pool and an attached hot tub. Lounge chairs are positioned around the pool, while a dining table with chairs is visible nearby. Lush greenery surrounds the space, creating a tranquil outdoor atmosphere.
Home in Cutler Bay
4.77 out of 5 average rating, 114 reviews

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

Top guest favorite
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.
Home in Miami
4.97 out of 5 average rating, 391 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.

Top guest favorite
A colorful hammock is suspended between two palm trees, inviting relaxation beside a sparkling pool. Lush tropical plants surround the outdoor area, creating a peaceful ambience. The inviting pool area is visible in the background, enhancing the serene outdoor setting.
Guest suite in Homestead
5 out of 5 average rating, 150 reviews

“Have Fun at Hacienda Paraíso” Suite 1 | pool |

Welcome to Room 1, the first addition at Hacienda Paraíso. This suite is conveniently located next to another Airbnb suite, providing flexibility for your stay. It features a private entrance, bathroom, kitchenette, and dining table, ensuring a comfortable and self-contained experience. Enjoy the convenience of hotel-like amenities paired with the added bonus of access to our stunning pool and lush yard, creating a truly relaxing retreat.

Superhost
A private patio area features a large hot tub surrounded by white fencing and small plants. Soft lighting enhances the ambiance, while a decorative rug adds a touch of comfort beneath a wooden step. The space invites relaxation in a serene outdoor setting.
Guest suite in Miami
4.86 out of 5 average rating, 258 reviews

Miami Vibes -Large HOT TUB, Privacy, Clean

Comfortable 1 bedroom guest suite. Full bathroom with toiletries, full kitchen with amenities, walk-in closet. Perfect for up to 3 guests. Private entrance, private patio with large hot tub. Short distance from all of Miami's best attractions. Shopping malls, restaurants, nightclubs, bars/pubs, art centers, bicycle trails, beautiful parks, and bay views under 5-10 minutes away. Midpoint between Miami Beach and the Florida Keys.

Top guest favorite
Guesthouse in Homestead
4.96 out of 5 average rating, 158 reviews

Villa Samsara - on a beautiful 5 acre farm

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

Guest favorite
Guest suite in Homestead
4.9 out of 5 average rating, 445 reviews

Tranquil Retreat with Vintage Charm

🌴 Retreat to a private guest suite in one of the area’s safest communities, just north of Key Largo. With a plush bed, upscale amenities, and a Smart TV, you’ll enjoy boutique comfort in a prime location—minutes from Everglades and Biscayne National Parks, and a short drive to Miami or the Florida Keys. Perfect for travelers who want both style and convenience. ✨ 💝

Guest favorite
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
4.96 out of 5 average rating, 227 reviews

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 vacation rentals

When is the best time to visit Cutler Bay?

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Frequently Asked Questions

  • Do house rentals in Cutler Bay have air conditioning?

    Absolutely! We offer over 90 house rentals with air conditioning in Cutler Bay. Enjoy a tailored experience with all the comforts you desire.

  • Are there Cutler Bay vacation rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 60 vacation homes with pools in Cutler Bay, available on Airbnb. Make a splash and soak up the sun in style!

  • Do house rentals in Cutler Bay have a kitchen?

    Absolutely! We offer over 70 house rentals with a kitchen in Cutler Bay. Enjoy a tailored experience with all the comforts you desire.

  • Are there pet-friendly vacation rentals in Cutler Bay?

    Four-legged friends are welcome in Cutler Bay. Choose from more than 60 vacation rentals for guests traveling with pets.

  • What are the most popular amenities for House Rentals in Cutler Bay?

    Enhance your stay in our House Rentals with the most popular amenities: over 90 homes with wifi, over 90 homes with air conditioning, over 90 homes with free parking, over 70 homes with a kitchen, and more. Indulge in the ultimate retreat, tailored to your preferences.

  • Are there family-friendly vacation rentals in Cutler Bay?

    Cutler Bay has more than 70 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • Are there vacation rentals with a dedicated workspace in Cutler Bay?

    Yes! Work meets play with ease at over 60 vacation rentals in Cutler Bay featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Do house rentals in Cutler Bay have wifi?

    Absolutely! We offer over 90 house rentals with wifi in Cutler Bay. Enjoy a tailored experience with all the comforts you desire.

Quick stats about vacation rentals in Cutler Bay

  • Total vacation rentals

    Explore 140 vacation rentals in Cutler Bay

  • Nightly prices starting at

    Cutler Bay vacation rentals start at ﺩ.ﺇ73 per night before taxes and fees

  • Verified guest reviews

    Over 5,910 verified reviews to help you choose

  • Family-friendly vacation rentals

    80 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 60 rentals that welcome pets

  • Vacation rentals with a pool

    60 properties feature pools

  • Rentals with dedicated workspaces

    70 properties have a dedicated workspace

  • Wi-Fi availability

    130 of Cutler Bay vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Cutler Bay rentals

  • 4.7 Average rating

    Cutler Bay stays receive an average rating of 4.7 out of 5 from guests

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  5. Cutler Bay