Vacation rentals with a pool in Cutler Bay

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.

4.96 out of 5 average rating, 158 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.

4.98 out of 5 average rating, 212 reviews

The exterior of a private guesthouse is showcased, surrounded by lush greenery and tropical plants. Screened windows provide a view of the outdoors while offering a sense of openness. The building is designed with a light-colored façade, blending harmoniously with the natural setting.

Guesthouse in Miami

Cozy private guest studio

Welcome! This is a private guesthouse located in a quiet neighborhood. Accommodations are with a private entrance and parking space to make you feel at home. We are located near a major expressway. We have a pool; The POOL is a SWIM AT YOUR OWN RISK. It is shared with Owner. Enjoy a smoke free cottage. Ashtrays are provided outside for those guest that do smoke. We provide a queen size bed and a couch/bed. This space is perfect and comfortable for two guest.Please NO children and NO animals.

Apartment in Coconut Grove

A spacious suite featuring a king size bed with crisp white linens. Dark accent walls provide contrast against light wooden flooring. Natural light enters through large windows adorned with sheer curtains, while a small desk and tasteful decorative elements complete the stylish environment.

4.81 out of 5 average rating, 126 reviews

Coconut Grove Stunning City View Suite Free Park

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 bright suite on the 15th floor of a luxurious waterfront property offers breathtaking city views, is fully equipped for 2 w/ a king size bed & full bath. Enjoy all the luxury amenities this property has to offer, pool & hot-tub with incredible bay views, penthouse gym, sauna, business center, 24-hr security, squash

4.94 out of 5 average rating, 190 reviews

The outdoor pool area features a clear blue salt-water pool, surrounded by lounge chairs and shaded by umbrella canopies. A natural rock slide is integrated into the design, set against lush green foliage and palm trees in the background.

Apartment in Miami

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!

4.94 out of 5 average rating, 102 reviews

A modern two-story house is showcased, featuring a light-colored exterior with stone accents. The garage door is closed, and decorative shutters frame the windows. A welcoming front entry is highlighted by a small archway and a stylish light fixture.

Home in Goulds

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.

4.9 out of 5 average rating, 389 reviews

A spacious driveway curves past vibrant tropical plants and palm trees leading to a welcoming entrance of the property. The house features a warm orange exterior with decorative elements and a large garage door, complementing the lush landscaping.

Guest suite in Miami

Guest Suite-Exterior Entrance, SelfCheckin.

If you like Clean, New, Quiet and Great Hospitality, then this is the Perfect Place 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 -Swimming Pool -Central A/C -Ceiling fan -Kitchenette -Refrigerator -Microwave -Coffee maker -Netflix-HBO TV -Ceramic Tile Floors -Full Closet -Towels/Bath essentials -Iron & Board

The outdoor area features a heated pool surrounded by colorful murals, with a jacuzzi nearby. Poolside loungers and a basketball hoop are visible, offering a vibrant space for relaxation and fun under a clear blue sky.

4.97 out of 5 average rating, 102 reviews

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.

Hotel room in Atlantic Heights

The beach scene displays numerous lounge chairs arranged under white umbrellas on soft, sandy shores. Gentle waves create a serene backdrop, while a beach hut is positioned centrally, providing some shelter. People can be seen enjoying the ocean, enhancing the active beach atmosphere.

4.94 out of 5 average rating, 177 reviews

1208 Ocean Front View 1BD Free park Monte Carlo

APART HOTEL. 24/7 FRONT DESK. FREE VALET PARKING. OCEAN FRONT VIEW WITH BALCONY, 1 BEDROOM, 1 BATH LOCATED AT A LUXURY OCEAN-FRONT CONDO "MONTE CARLO" ON COLLINS AVE, MIAMI BEACH. UNIT HAS: WI-FI, KING SIZE BED, SLEEPER SOFA, SINGLE SOFA BED, CRIB, 2 TV'S, LAUNDRY, DISHWASHER, FULL KITCHEN AND FREE PARKING! 2 SWIMMING POOLS, JACUZZI, GYM, STEAM ROOM, LOUNGE ROOM DIRECT BEACH ACCESS, LOUNGE CHAIRS AND UMBRELLAS AVAILABLE AT THE BEACH. WI-FI THROUGHOUT THE BUILDING. NETFLIX, HULU.

Guest suite in Cutler Bay

A spacious lawn features a large shade tree with swings hanging from its branches. Nearby are colorful chairs arranged on the grass, along with a hammock tied between tree trunks. Water is visible in the background, surrounded by lush greenery.

4.78 out of 5 average rating, 305 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.

4.98 out of 5 average rating, 261 reviews

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 homes in Cutler Bay

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.

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.

4.97 out of 5 average rating, 398 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.

4.99 out of 5 average rating, 176 reviews

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

“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.

Popular amenities for Cutler Bay rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

Home in North Miami Beach

A modern living space features a sectional couch facing a large flat-screen TV mounted on a sleek white console. Natural light floods in through glass doors, revealing a view of the outdoor area. A round coffee table sits in front, complemented by a modern floor lamp.

4.99 out of 5 average rating, 119 reviews

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

4.96 out of 5 average rating, 194 reviews

A shaded outdoor seating area features a hanging chair, a small table, and decorative lanterns. The pool is visible in the background, surrounded by a well-maintained garden and sun loungers. The space is designed for relaxation, with ample natural light filtering through.

Home in Miami Springs

Spanish House 3 Bedroom Pool House

A spacious backyard is showcased with a clear pool reflecting the sky. Sun loungers are arranged nearby, accompanied by a large umbrella for shade. Paths of stepping stones lead through a pebble area, enhancing the serene outdoor setting.

4.92 out of 5 average rating, 386 reviews

Charming house with private pool & large patio

A tranquil salt-water pool is illuminated in soft hues of blue, surrounded by lush greenery and palm trees. Soft lighting enhances the outdoor space, with seating visible and a scenic lake view in the background, providing a peaceful atmosphere for relaxation.

4.97 out of 5 average rating, 115 reviews

3B/2B Tropical Oasis w Salt-Water Pool! Lake views

Superhost

A spacious living area is presented with modern furnishings, including a large gray sofa facing a sleek television mounted on the wall. Light-colored cabinetry and a dining table are visible in the background, while a fireplace adds warmth to the ambiance. Potted plants offer a touch of greenery.

4.88 out of 5 average rating, 129 reviews

The Lux Paradise Miami

4.9 out of 5 average rating, 301 reviews

A sparkling pool is framed by a spacious patio with tiled flooring and surrounded by lush greenery. A tall plant stands in a black pot nearby, while a screened enclosure allows natural light to fill the area, creating a serene atmosphere.

Home in Miami Springs

Centrally Located Resort Style Miami home

4.93 out of 5 average rating, 166 reviews

Heated Pool/Basketball Court/Ping Pong Table/Golf

A serene outdoor space is highlighted by a saltwater pool, surrounded by lush greenery. String lights create a warm ambiance above a covered dining area with a table and chairs, while a fire pit invites gatherings in the evening.

4.96 out of 5 average rating, 139 reviews

Luxe Pool & Fire Pit | 5 min to Dolphin Mall

Condo rentals with a pool

4.94 out of 5 average rating, 125 reviews

Condo in Coconut Grove

*Coconut Grove Retreat: Balcony Pool, Free Parking

4.84 out of 5 average rating, 147 reviews

A modern high-rise building is surrounded by lush green lawns and palm trees. People are seen enjoying outdoor activities in the park, with a clear blue sky in the background showcasing a vibrant urban atmosphere.

Condo in Doral

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

4.9 out of 5 average rating, 181 reviews

A bright studio space features a plush bed with decorative cushions, a smart TV, and a cozy sofa. A dining table for four is positioned near large windows, offering views of the surrounding cityscape. Light-colored walls and tiles enhance the airy atmosphere.

Condo in Brickell

Stylish Studio Icon, Waterfront Building

Superhost

A modern studio suite presents a spacious layout featuring a king bed and a pull-out sofa. Natural light floods through floor-to-ceiling windows adorned with sheer curtains. A contemporary desk and chair are positioned near a sleek dresser, while a comfortable seating area invites relaxation.

Condo in Ocean Front

4.94 out of 5 average rating, 220 reviews

Fontainebleau Jr. Suite King Bed with Ocean Views.

4.95 out of 5 average rating, 116 reviews

A private patio area features a round table surrounded by four decorative chairs, set under a large blue umbrella. The space is framed by wooden fencing and white stones, offering a tranquil outdoor dining option.

Condo in Key Biscayne

Gorgeous Beachy Chic Condo in Key Biscayne

4.77 out of 5 average rating, 104 reviews

The living area features a spacious sectional sofa arranged around a television. Decorative wall art in vibrant colors adds interest to the surroundings. Large doors provide access to an outdoor space, while a few potted plants complement the room's layout.

Condo in Miami

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

Superhost

The sleeping area is furnished with a spacious bed adorned with a decorative blanket featuring intricate patterns. Grey plush pillows are placed against the headboard, and a modern light fixture illuminates the room. A large window offers views of the surrounding cityscape.

Condo in Doral

4.87 out of 5 average rating, 171 reviews

Modern and comfortable Studio In Downtown Doral

4.95 out of 5 average rating, 116 reviews

A private wrap-around balcony features two white lounge chairs overlooking the expansive blue ocean. City skyline and distant landmasses are visible under a bright sky with scattered clouds. The green carpet adds a touch of color to this outdoor space.

Condo in Brickell

Front Facing Top Floor Penthouse with Ocean Views

Other vacation rentals with a pool

Hotel room in Atlantic Heights

The sandy beach is dotted with numerous lounge chairs and white umbrellas, providing shaded areas for relaxation. The calm turquoise water gently laps the shore, while visitors can be seen enjoying various activities along the beach.

4.88 out of 5 average rating, 214 reviews

1BR Corner Ocean Front VW 808 Collins Monte Carlo

5 out of 5 average rating, 9 reviews

Apartment in Cutler Bay

Hidden Gem. Luxe 1BR w/Patio

An open living area features a spacious, modern sofa in warm tones, complemented by a stylish coffee table. Natural light fills the space, highlighting the glossy tiled floor. A dining table is positioned nearby, with glass doors offering views of the outdoor area.

5 out of 5 average rating, 22 reviews

South Miami Gem!

5 out of 5 average rating, 8 reviews

Home in Homestead

Ultimate Heated Pool Escape:Midway to Keys & Miami

A private backyard features a sparkling pool surrounded by five lounge chairs in blue. A gazebo with draped curtains offers a shaded seating area, complemented by vibrant green trees and a white fence in the background. The scene is set against a colorful sky.

5 out of 5 average rating, 39 reviews

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

4.95 out of 5 average rating, 242 reviews

An open living area features a white leather sofa, a coffee table with magazines, and two ottomans in teal. A mounted TV is positioned on a white console, while a dining area is visible in the background, showcasing a modern kitchen design.

Apartment in Brickell

Condo in Brickell Business District

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.

5 out of 5 average rating, 12 reviews

Chic-ness Oasis