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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
Home in Naranja
4.9 out of 5 average rating, 311 reviews

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

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
4.95 out of 5 average rating, 163 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.

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
4.97 out of 5 average rating, 271 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. Enjoy the miles of nearby walking paths stretching from Coconut Grove to Black Point Marina.

Guest favorite
Home in Miami
4.86 out of 5 average rating, 259 reviews

Miami Oasis: Chill | Shop | Relax | Charming Home

A spacious and private retreat designed for families and group stays, our home in Palmetto Estates comfortably hosts up to 10 guests. We offer 3 well-appointed bedrooms, 2 full bathrooms, a bright living space, a fully equipped kitchen, laundry area, garage, and a covered patio with a large grassy yard. Located in a quiet neighborhood close to shopping, dining, Miami Zoo, the Everglades, and just 30 minutes from Downtown Miami, it’s an ideal base to explore South Florida.

Guest favorite
Apartment in Palmetto Bay
4.89 out of 5 average rating, 27 reviews

Palmetto Bay #2 | 2BR • 4 Beds • Free Parking

Unit 2, 2nd Floor Unit 2 Bed / 1 Bath | Fully Furnished | Free Parking for 2 Cars ✨ Bright, comfortable, and thoughtfully designed home ideal for vacationers, traveling professionals, or families. Located in the beautiful Village of Palmetto Bay, Village of Parks! ....next to Pinecrest and south of Coral Gables. Enjoy a peaceful setting with easy access to Downtown Miami, the Florida Keys, beaches, parks, dining, and shopping—South Florida living at its best.

Top guest favorite
Villa in Cutler Bay
4.96 out of 5 average rating, 48 reviews

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.

Guest favorite
A pool area is featured, surrounded by lush greenery and palm trees. Sun loungers are positioned next to the inviting pool, with a shaded seating area under an umbrella visible in the background. The structure has large glass doors that provide access to the interior.
Home in Cutler Bay
4.92 out of 5 average rating, 39 reviews

4BR Home with Pool, Playground & Boat/RV Parking

Beautiful Cutler Bay pool home with large backyard, boat/rv parking, and playground. Whether you're planning a getaway to the Florida Keys, soaking up the sun on the beaches of Miami, or just looking for a cozy staycation, this home is your perfect launchpad for everything South Florida has to offer. • The Florida Keys – 48 minutes • Miami Beach – 37 minutes • Everglades National Park – 33 minutes

Superhost
An outdoor dining area features a large rectangular table surrounded by four upholstered chairs, complemented by potted greenery at each end. A kitchen area with cabinetry and a countertop is visible in the background, set against a backdrop of brick walls and lush foliage.
Home in Princeton
4.79 out of 5 average rating, 111 reviews

To the Keys

Your family will be close to all these places if you stay in this centrally located accommodation to shop in stores with more than 50% discounts on the best brands, around the Southland Mall shopping centers, near Miami Zoo, Monkey Jungle, Pintos Farm, Brothers Farms, etc. As well as restaurants and more entertainment around it, you can contact me for more details if you wish

Top guest favorite
A serene waterfront view is presented, with clear water reflecting the surrounding greenery and buildings. An elegant dining area features a glass table surrounded by stylish chairs. The staircase leads to well-lit hallways, while a comfortable bedroom displays a spacious bed and decorative furnishings.
Home in Cutler Bay
4.96 out of 5 average rating, 25 reviews

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.

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, 241 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.

Guest favorite
A shaded cabana is positioned by the pool, featuring a wooden frame with draped fabric. Surrounding the pool are several lounge chairs arranged under large umbrellas. Lush greenery and flowering plants are visible in the background, enhancing the serene outdoor space.
Home in Cutler Bay
5 out of 5 average rating, 15 reviews

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.

Guest favorite
A modern studio apartment features an open layout with a well-equipped kitchen and seating for two at a sleek countertop. A cozy couch sits across from a queen bed, with a light rug underfoot. Natural light enters through a window framed by horizontal blinds.
Condo in Palmetto Bay
4.92 out of 5 average rating, 320 reviews

Bright Modern Studio Apartment

Find yourself at this slick Studio Apartment professionally designed, top of the art appliances with a unique modern touch. Based in a quiet and peaceful neighborhood. Located close to Downtown Miami and also to The Florida Keys. Nearby shoppings centers, restaurants and supermarkets. All you need to enjoy a charming getaway.

Popular amenities for Cutler Bay vacation rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Other great vacation rentals in Cutler Bay

A modern kitchen features a large granite island with seating for four. Stainless steel appliances are positioned alongside light cabinetry, while natural light enters through sliding glass doors that open to an outdoor space. A comfortable and functional atmosphere is created for cooking and socializing.
Home in Cutler Bay
4.63 out of 5 average rating, 123 reviews

Miami Family Lake House 3BD/2BTH 3Beds 6 Guests

Guest favorite
Guesthouse in Cutler Bay
4.83 out of 5 average rating, 30 reviews

Dulce Hogar

Guest favorite
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, 136 reviews

Heated Pool/Jacuzzi Paradise: Cozy Miami Retreat

A cozy sleeping area features a spacious bed covered with a light quilt. Soft lighting is provided by two bedside lamps on turquoise tables. A large framed artwork of a serene ocean scene hangs above the bed, complemented by a stylish black and white patterned closet door.
Guest suite in Cutler Bay
4.82 out of 5 average rating, 557 reviews

Private 1bd/1bath guest suite.

The private pool area is illuminated at night, showcasing clear blue waters next to a waterfall feature. Two lounge chairs are positioned nearby on a spacious deck, surrounded by greenery and a fenced perimeter for privacy.
Home in Cutler Bay
4.68 out of 5 average rating, 19 reviews

Andy Resort

Guest favorite
Home in Cutler Bay
4.86 out of 5 average rating, 7 reviews

Vacation QJR

Guest favorite
Guesthouse in Cutler Bay
4.93 out of 5 average rating, 14 reviews

Cutler Bay Guest House

Home in Cutler Bay
5 out of 5 average rating, 4 reviews

Roxina's Miami Home

When is the best time to visit Cutler Bay?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$36,827 GYDG$37,664 GYDG$41,431 GYDG$36,618 GYDG$33,479 GYDG$31,387 GYDG$37,036 GYDG$31,387 GYDG$31,387 GYDG$31,387 GYDG$37,664 GYDG$37,664 GYD
Avg. temp20°C22°C23°C25°C27°C28°C29°C29°C28°C27°C24°C22°C

Frequently Asked Questions

  • What are the best places to stay in Cutler Bay?

    Stays around lakeside neighborhoods, near parks, and in residential areas of Cutler Bay are frequently suggested for a peaceful experience. Many guests choose homes with easy access to outdoor spaces.

  • What are the best things to do in Cutler Bay with kids?

    Families often explore playgrounds, splash pads, and nature trails in Cutler Bay. Black Point Park and Marina is frequently suggested for spotting birds, learning about local wildlife, and enjoying waterfront activities.

  • What are some of the best things to do in Cutler Bay?

    Visitors explore local parks, kayak or boat in Biscayne Bay, and visit farmers markets on weekends. Many enjoy discovering neighborhood art and taking guided nature walks.

  • How is the weather in Cutler Bay?

    Cutler Bay has warm, humid weather almost year-round, with temperatures ranging from 61–91°F (16–33°C). Rain is most frequent from late spring through early autumn, so an umbrella or rain jacket can be helpful.

  • When is the best time to visit Cutler Bay?

    Late autumn and winter are often suggested for visiting Cutler Bay, as temperatures are milder and rainfall tends to be lower. Spring draws visitors with blooming gardens and outdoor events.

  • What are the best places to visit in Cutler Bay?

    Cutler Bay has lush parks, community gardens, and access to Biscayne Bay for water activities. Popular spots often include Black Point Park and Marina, winding trails, and spaces for picnics or birdwatching.

  • What are some hiking trails in Cutler Bay?

    Cutler Bay has walking and hiking paths in local parks such as Cutler Ridge Park and Black Point Park and Marina, where visitors wander through mangrove areas and scenic waterfront routes.

  • What are some family activities we can do in Cutler Bay?

    Families explore local parks, playgrounds, and take part in community recreation programs in Cutler Bay. Visiting Black Point Park and Marina is also often recommended for wildlife spotting and waterfront fun.

  • What are some of the best day trip ideas from Cutler Bay?

    Explore nearby nature preserves, take a trip to cultural attractions around Miami, or unwind at area beaches. The region also has gardens, wildlife centers, and local art galleries to discover.

  • Are there any pet friendly accommodations available in Cutler Bay?

    Cutler Bay has pet-friendly accommodations, including homes with fenced yards and rentals near green spaces. Neighborhood parks around the area make visiting with pets convenient.

  • What are some local tips for visiting Cutler Bay?

    Locals suggest exploring parks early to avoid midday heat and bringing sun protection for outdoor adventures. Sampling regional seafood and supporting area markets often adds to the experience.

  • What is Cutler Bay known for?

    Cutler Bay is known for its coastal setting, local parks, and family-friendly neighborhoods. The area frequently draws visitors for boating, fishing, and exploring its green spaces.

  • What are the best hidden gems to explore in Cutler Bay?

    Visitors often enjoy local nature trails, community art installations, and quiet waterfront picnic spots around Cutler Bay. Neighborhood farmers markets are a frequent weekend find.

  • What are the best foods to try in Cutler Bay?

    Regional seafood dishes, Cuban-inspired cuisine, and tropical fruit smoothies are frequently suggested in Cutler Bay. Locally owned cafes and restaurants often serve specialties made with fresh area ingredients.

  • What should I bring for a trip to Cutler Bay?

    Pack lightweight clothing, comfortable shoes for walking, and sun protection such as hats and sunscreen. A reusable water bottle is useful, especially during warmer months.

  • What is the nightlife in Cutler Bay like?

    Cutler Bay has a laid-back nightlife scene with neighborhood bars, locally owned restaurants, and occasional live music. Many venues feature outdoor seating and a casual atmosphere.

  • What are the most popular events or festivals in Cutler Bay?

    Cutler Bay’s calendar regularly features community celebrations, outdoor concerts, and neighborhood art fairs, especially during spring and early summer. Holiday parades and family-oriented festivals are also popular.

  • Are there family friendly vacation rentals in Cutler Bay?

    Cutler Bay has many family-friendly vacation rentals, ranging from houses in quiet neighborhoods to condos near parks and playgrounds. Listings often highlight spacious layouts and amenities for children.

Quick stats about vacation rentals in Cutler Bay

  • Total vacation rentals

    Explore 130 vacation rentals in Cutler Bay

  • Nightly prices starting at

    Cutler Bay vacation rentals start at G$4,185 GYD per night before taxes and fees

  • Verified guest reviews

    Over 5,610 verified reviews to help you choose

  • Family-friendly vacation rentals

    70 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

Destinations to explore

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  5. Cutler Bay