
Vacation rentals with a pool in Cutler Bay
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Top-rated rentals with a pool in Cutler Bay
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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.

Stunning Studio w/Bay & City View Free Park/Pool
INCREDIBLE VALUE! First, a $30 gift card to our restaurant GreenStreet and a bottle of champagne will be awaiting you in your room! in Coconut Grove, this privately owned & renovated deluxe bright studio on the 15th floor of a luxurious waterfront property offers breathtaking bay & city views, is equipped for 2 guests w/king size bed, full kitchen, full bath & balcony. Enjoy all the luxury amenities we offer, pool & hot-tub w/ incredible bay views, penthouse gym, sauna, business center, squash.

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!

Cozy house
Welcome to Your Tranquil Getaway! Discover a serene escape at our unique and tranquil retreat, perfect for families and friends seeking relaxation and adventure. This beautifully designed property features a sparkling private pool, ideal for enjoying sunny days and creating lasting memories. Nestled in a prime location, you’re just minutes away from top attractions such as Monkey Jungle, the Miami Metro Zoo, Black Point Marina, and the Florida Keys. Explore nearby gems like Gilbert’s Resort.

Family retreat oasis, heated pool, jacuzzi & grill
Welcome to Forget-me-not Villa, a sanctuary for your family and friends to let loose barefoot and unwind in the private backyard fully fenced, feel the breeze, stargaze at night, and savor the comfort of our exquisite vacation home. The villa features a heated pool and jacuzzi, a grill station, a love seat for romantic moments, a playground for children, an Xbox S for gamers, board games, mini golf, pool volleyball and basketball hoop, Smart TVs& high-speed Wi-Fi & electric car connection.

NEW! "Villa Paradise" ~ Luxury 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. ✔ 3 Comfortable BRs ✔ Open Design Living ✔ Fully Equipped Kitchen ✔ Heated Pool ✔ Game Room ✔ Smart TVs ✔ Smart House ✔ High-Speed Wi-Fi ✔ Free Parking

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

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.

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.

Your Bay View Escape in Coconut Grove, Pool & Gym
- Enjoy breathtaking bay views & sunsets in this fully remodeled Coconut Grove condo - Private balcony perfect for relaxing and taking in the scenic surroundings - Full access to building amenities, including a gym, pool, sauna/steam room and jacuzzi -Onsite restaurant, valet/parking and 24/7 security. - Located just steps from Coconut Grove’s best restaurants, shops, and marinas -Fully equipped kitchen, luxurious oversized shower and cozy bedroom with work desk.

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.

Marriott Villas and Doral 2BD sleeps 8
Located in one of the most prestigious areas of Miami, Marriott's Villas at Doral are a tranquil hideaway; only 13 miles from the sizzling excitement of Miami Beach, yet a world away. Sharing the 650-acre lush landscape is the celebrated Trump National Doral Miami, a Trump-managed resort. There, you have access to four championship courses, a classic European spa, a water recreation playground and several restaurants.
Popular amenities for Cutler Bay rentals with a pool
House rentals with a pool

4BR Miami Villa | Heated Pool | BBQ | Near Beach

Private Pool and Tropical Garden Oasis

Spanish House 3 Bedroom Pool House

MiMo Luxe Heated Pool/Hot Tub/Private Parking

South Miami Gem!

The Lux Paradise Miami

Centrally Located Resort Style Miami home

Miami Modern Luxury with Pool & Spa
Condo rentals with a pool

*Coconut Grove Retreat: Balcony Pool, Free Parking

Beautiful and Modern Apartment in Doral. 1B/1B

Gorgeous Beachy Chic Condo in Key Biscayne

Beautiful apt. 1st floor 2/2. wifi and parking

Front Facing Top Floor Penthouse with Ocean Views

Key Biscayne little beach place

SF Beautiful Blue & Gold Studio with Ocean View

High Rise Condo w/Gym, Rooftop Pool & Bay View
Other vacation rentals with a pool

Family Villa w/ Heated Salt Pool • Near Key Largo

Hidden Gem. Luxe 1BR w/Patio

Everglades-Homestead. Tropical Retreat. Miami-Keys

Escape to Miami/Heather+Pool/9pl/BBQ/pool table.

Ultimate Heated Pool Escape:Midway to Keys & Miami

Waterfront Miami Villa | Pool, Kayaks, Mini Golf

Casa Luna | Heated Pool |Private Retreat | 4BR

Chic-ness Oasis
When is the best time to visit Cutler Bay?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ841 | ﺩ.ﺇ823 | ﺩ.ﺇ977 | ﺩ.ﺇ867 | ﺩ.ﺇ881 | ﺩ.ﺇ944 | ﺩ.ﺇ981 | ﺩ.ﺇ951 | ﺩ.ﺇ874 | ﺩ.ﺇ892 | ﺩ.ﺇ977 | ﺩ.ﺇ1,149 |
| Avg. temp | 20°C | 22°C | 23°C | 25°C | 27°C | 28°C | 29°C | 29°C | 28°C | 27°C | 24°C | 22°C |
Quick stats about vacation rentals with a pool in Cutler Bay

Total vacation rentals
Explore 60 vacation rentals in Cutler Bay

Nightly prices starting at
Cutler Bay vacation rentals start at ﺩ.ﺇ184 per night before taxes and fees

Verified guest reviews
Over 3,120 verified reviews to help you choose

Family-friendly vacation rentals
40 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 30 rentals that welcome pets

Rentals with dedicated workspaces
40 properties have a dedicated workspace

Wi-Fi availability
60 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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- Miami Beach - South Beach
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- Miami Design District
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