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Holiday rentals with a pool in Cutler Bay

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Cutler Bay

Guests agree: These homes with a pool are highly rated for location, cleanliness and more.

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Guest favourite
Home in Cutler Bay
4.96 out of 5 average rating, 147 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! âť§ 48 minutes from the Florida Keys. âť§ 37 minutes from Miami Beach. âť§ 33 minutes from the Everglades. Message us about long stay, military, & first responder discounts.

Guest favourite
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.

Guest favourite
Tiny home in Cutler Bay
4.98 out of 5 average rating, 246 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 favourite
Apartment in Miami
4.94 out of 5 average rating, 182 reviews

Very Private 1/1 Apt w/Oasis Pool Patio Setting

Private apartment-1 bedroom w/king size bed, 1 full size bathroom, separate living and dining area. Fully equipped kitchen. Free parking, beautiful oasis setting with salt water pool, hot tub & patio. Gazebo w/fire pit, Bar-be-cue, 2 TV’s, free WiFi. This is NOT a party spot but a place to relax in the pool, hot tub or relaxing dinners at home after visiting Miami venues. Set in a quiet neighborhood, 2 miles from shopping & restaurants. This is your home away from home vacation spot!

Guest favourite
Villa in Miami
4.9 out of 5 average rating, 169 reviews

NEW! "Villa Paradise" ~ Lux Gem ~ Pool ~ Game Room

Bring your family to the luxurious 3BR 2Bath Villa Paradise in the tranquil and friendly neighborhood in southern Miami, FL. Visit the exciting attractions, natural landmarks, restaurants, shops, and much more, and then retreat to the lavish oasis that will leave you in awe with its stylish design, private backyard, and rich amenity list. âś” 3 Comfortable BRs âś” Open Design Living âś” Fully Equipped Kitchen âś” Heated Pool âś” Game Room âś” Smart TVs âś” Smart House âś” High-Speed Wi-Fi âś” Free Parking

Top Guest favourite
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

Guest suite in Cutler Bay
4.77 out of 5 average rating, 302 reviews

Private Waterfront Studio Paradise

Casa Cocos is a private studio, with a private entrance, bathroom and kitchenette, and free and secure parking. It is nestled in Florida's tropical waterfront paradise. Come enjoy the views of the garden, go for a swim, paddle board, canoe, kayak, grill, take a nap in a hammock, and just relax. Casa Cocos is surrounded by nearby restaurants, bars, retail stores, malls all within walking distance or a short drive. 30 minutes to airport, downtown, South Beach, Keys, and Everglades.

Guest favourite
Home in Miami
4.9 out of 5 average rating, 178 reviews

The Finest Pool Jacuzzi Amenities BBQ

Vibrant style and captivating design define every corner of this elegant home. White floors and walls, glass doors, and wooden tables contrast beautifully with colorful seating in the living and dining spaces. In the fully equipped chef-style kitchen, a complimentary bottle of wine elevates hospitality to an art form. This exceptional rental is truly unique, ideal for an inspiring getaway or corporate retreat. The neighborhood offers both safety and serenity.

Superhost
Home in Cutler Bay
4.77 out of 5 average rating, 111 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. âś” Fully Equipped Kitchen âś” Comfortable Bedrooms with King/Queen/Full beds âś” Open Concept Living Area âś” Office Desk âś” Piano âś” High-Speed Wi-Fi

Top Guest favourite
Home in Miami
4.97 out of 5 average rating, 388 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 favourite
Guesthouse in Homestead
4.97 out of 5 average rating, 179 reviews

Charming Private Pool house for two.

Charming private back pool house on a fenced property in a quiet neighborhood close to US 1, the Turnpike, the Keys, Nascar and the Homestead Speedway, and the Everglades. You are 15-20 minutes from the Speedway, 20 minutes from the Everglades, and 30 minutes from Key Largo. For guests wishing to stay a month or more, I would require you to provide a copy of your photo ID.

Home in Cutler Bay
4.93 out of 5 average rating, 183 reviews

Modern Home Gazebo Pool & Spa Games Playground

Luxury Retreat: Modern, Stylish Oasis with Salted Heated Pool, Sunbeds, Cabanas, Basketball Court, Playground, & More! Experience resort-style living in this beautifully designed home, featuring 5 bedrooms, gourmet kitchen, and high-end furnishings for a unique stay. Amazing designed and decorated home with top High end Furnitures that will Provide you a unique Stay. #miami

Popular amenities for Cutler Bay rentals with a pool

Quick stats about holiday rentals with a pool in Cutler Bay

  • Total rentals

    50 properties

  • Nightly prices starting at

    $70 NZD before taxes and fees

  • Total number of reviews

    3.3K reviews

  • Family-friendly rentals

    30 properties are a good fit for families

  • Pet-friendly rentals

    20 properties allow pets

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

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  2. United States
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  6. Rentals with pools