Vacation rentals with a pool in Pinecrest

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Pinecrest

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

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Guest favourite
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, 169 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 favourite
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
4.98 out of 5 average rating, 219 reviews

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.

Top guest favourite
A tranquil pool area is surrounded by lush greenery and tropical plants, creating a serene atmosphere. The rectangular swimming pool is framed by terracotta tiles and features potted plants on the edges, offering spaces for relaxation in the sun.
Guest suite in Coconut Grove
4.96 out of 5 average rating, 292 reviews

"Casa Mia's" pool & BBQ bungalow

Private entrance offers bungalow experience to the one bedroom space, walk in closet en suite bathroom. Shared structural walls: sounds do travel. Exclusive access to pool (unheated), BBQ, stove top, small outdoor fridge, and “makeshift” sink. Plenty of privacy! 20 minute stroll to Coco Walk; restaurants, lush nature and historic sites. Nestled between Coral Gables ; South Miami and Brickell. Close to University of Miami; quick access to airport and beaches. Merry Christmas Park’s a block away

Top guest favourite
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 Kendall
4.94 out of 5 average rating, 196 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
Home in Miami
4.94 out of 5 average rating, 228 reviews

Miami Getaway - Heated Pool, Hot tub, BBQ

Be our guest and have a wonderful stay in this beautiful Miami home designed to create great memories. 3 bedrooms 2 bathrooms with enough space to sleep 10 guests. Heated pool & seperate HotTub to enjoy even during winter season. Conveniently located within a short distance from all of Miami's main attractions. Restaurants, shopping malls, nightclubs, bar/pubs, art centers, bicycle trails, beautiful parks and bay views between 5 - 10 minutes away. Only 50 minutes away from the Florida keys.

Top guest favourite
A heated pool is surrounded by palm trees, offering a refreshing oasis. Comfortable outdoor seating arrangements include chairs and loungers, alongside a sun umbrella. The patio area is designed for relaxation and leisure, with vibrant greenery adding to the tranquil atmosphere.
Guesthouse in Miami
4.99 out of 5 average rating, 289 reviews

Guesthome w/ Heated Pool 5 mins from Miami Airport

This home is located just 5 minutes from the Miami Airport and is central to many attractions here in Miami. Take a walk down Calle Ocho, swim at Miami Beach, enjoy a game at Marlins baseball stadium or American Airlines Arena (home to the Miami Heat), and dine at one of the many popular restaurants such as Versailles. These are all within 15 minutes of this private comfortable home. Come enjoy a location that provides a rich experience into the vibrant hispanic culture that Miami radiates.

Top guest favourite
A spacious backyard is showcased, featuring a clean saltwater pool surrounded by lounge chairs and tropical landscaping. A covered patio area is visible, with a stone countertop and decorative plants. The bright blue sky complements the serene outdoor setting.
Home in Fountainebleau
5 out of 5 average rating, 439 reviews

Sanctuary Salt water heated pool BBQ Grill Oasis

Come and create unforgettable memories in this modernly designed single-family home with a spacious layout and a range of comfortable bedrooms. It features two king-size beds, one queen-size bed, and a twin fold-up bed, as well as an Italian queen-size sofa bed. The house is bathed in natural light and boasts modern amenities that cater to your convenience. Located in a prime location, this house is close to all the tourist areas!! The pool is salt water with heater, Also a grill area

Superhost
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.
Home in Miami
4.93 out of 5 average rating, 117 reviews

Family Oasis Retreat• 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.

Guest favourite
A bright living area is furnished with a light-colored sofa and a wooden coffee table, enhancing the spacious feel. A large TV sits on a console, and natural light flows in from sliding glass doors that open to a balcony, framed by greenery.
Apartment in South Miami
4.84 out of 5 average rating, 136 reviews

Dharma |15% off Monthly| Perfect 1B | South Miami

Spacious, comfortable, upscale, and ideally located, Dharma Home Suites at Red Road Commons are the furnished accommodations you’ve been looking for. Quality living is at the forefront of this apartment community and we’ve made sure its modern and cozy interior offers the perfect home away from home for all travelers. Immerse yourself in Coral Gables’ vibrant surroundings, enjoy resort-style amenities and beautiful surroundings in the heart of South Miami.

Top guest favourite
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 Kendall
4.97 out of 5 average rating, 408 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.

Guest favourite
A modern exterior of the house showcases a private pool with a surrounding patio featuring loungers. Tall, elegant arches and windows allow for ample natural light, while tropical leaves in the foreground add a vibrant touch to the inviting outdoor space.
Home in Miami
4.99 out of 5 average rating, 116 reviews

Eva | 12 ppl HOT Pool |Top Location | Piano | Golf

Renovated family home with 5 bedrooms and 4 full bathrooms. Heated pool year-round, mini golf, BBQ area and swing. Modern design with piano and Smart TVs. Parking for 5 cars. Prime location near airport, beaches and nightlife. Sleeps up to 16: 1 king, 2 queen, 2 full, 2 twin and 2 sofa beds (full & queen). Please confirm total guests. Add pets to reservation. Notify us if traveling with children for pool fence.

Superhost
Apartment in Dadeland
4.82 out of 5 average rating, 237 reviews

South Miami 2BR/2BA - Steps from Dadeland Mall

Minimum age to book and check in is 21 years old. Valid ID required at check-in. Modern 2-bedroom, 2-bath apartment in a prime Miami location! Enjoy a bright living space, fully equipped kitchen, and access to a beautiful outdoor pool. Just minutes from Dadeland Mall, Coral Gables, and Coconut Grove. Includes free parking, WiFi, and in-unit laundry—ideal for families, professionals, or weekend getaways!

Popular amenities for Pinecrest rentals with a pool

When is the best time to visit Pinecrest?

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Quick stats about vacation rentals with a pool in Pinecrest

  • Total vacation rentals

    Explore 50 vacation rentals in Pinecrest

  • Nightly prices starting at

    Pinecrest vacation rentals start at $55 CAD per night before taxes and fees

  • Verified guest reviews

    Over 1,570 verified reviews to help you choose

  • Family-friendly vacation rentals

    20 properties offer extra space and kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wifi availability

    40 of Pinecrest vacation rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Pinecrest rentals

  • 4.8 Average rating

    Pinecrest stays are highly rated by guests—averaging 4.8 out of 5!