Holiday 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, 161 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.

Guest favourite
A rooftop pool area is shown with two lounge chairs positioned beside the water. The bright blue pool reflects the sky, while a view of the marina and ocean can be seen in the background, with sailboats dotting the horizon.
Flat in Coconut Grove
4.87 out of 5 average rating, 274 reviews

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

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, 420 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

Guest favourite
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.
Home in Tamiami
4.96 out of 5 average rating, 145 reviews

Luxe Pool & Fire Pit | 5 min to Dolphin Mall

Experience sun-soaked luxury in Miami! Dive into the refreshing saltwater pool or unwind on one of the poolside lounge chairs. Newly renovated in 2022, this 4 bed/3.5 bath home comfortably accommodates 10 guests. For endless entertainment, compete in games of ping pong, sing your heart out with the karaoke machine, enjoy board games, or shoot some hoops. Presented by SuCasa Vacay, every detail has been thoughtfully chosen for an unforgettable Miami stay. Property Name: SuCasa Palmas

Guest favourite
A bright living area features large glass doors showcasing a stunning view of the bay. A stylish sofa, accent chairs, and a modern pendant light create a welcoming atmosphere. A kitchen island stands in the foreground, enhancing the open layout.
Apartment in Coconut Grove
4.92 out of 5 average rating, 124 reviews

SF Sight of SAIL Boats Tranquil Coconut Grove

WOW, what a view! The moment you step into this apartment you will be mesmerized by the sight of the bay. Literally wake up in the morning with sailboats and the sunrise, but the cherry on top must be the view at night. Recently renovated, this 1 bedroom 1.5 bath Condo Hotel is one of the most requested places in Coconut grove. Amenities included: 1 Free Parking, Pool, Jacuzzi, Gym, 24-hour security, high-speed wifi, etc. COCONUT GROVE IS KNOWN AS THE GEM OF MIAMI!

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.
Flat in Coral Gables
4.85 out of 5 average rating, 127 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.

Guest favourite
The image features a clear pool surrounded by a spacious patio, with two lounge chairs positioned nearby. Lush tropical plants and colorful potted flowers add to the serene environment. Soft string lights are hung above, enhancing the outdoor space during the evening.
Home in Miami
4.78 out of 5 average rating, 127 reviews

Cozy Oasis Pool Home-1 Min from Baptist Hospital

** No parties allowed. ZERO tolerance for loud music, parties, and drugs including marijuana—even if you smoke outside. No over consumption of alcohol in the property. A $250 fee will be charged if there are noise complaints. ** Welcome to our Cozy Oasis with a spectacular pool! Have fun with the whole family at our stylish place. Our home is completely remodeled with 3 bedrooms, 2 full bathrooms, and a half bathroom downstairs.

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
5 out of 5 average rating, 111 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
An open-concept living area reveals modern furnishings, including a light-colored sofa and two blue chairs. A wooden coffee table with geometric design sits at the center. Natural light floods from large windows, showcasing a clean and contemporary atmosphere, with a kitchen visible in the background.
Home in Brickell
4.94 out of 5 average rating, 188 reviews

Luxury Oasis in Brickell - Only 3 min to Ocean

Relax and tan by the pool and hot tub, grill with your family and friends. This centrally located, luxurious 3 bed/3 bath house comfortably sleeps 10 people. It was completely remodeled, comes with a fully equipped kitchen, living room and indoor/outdoor dining area. Within 3-15min Drive: Brickell, Downtown, Key Biscayne, South Beach, Airport (MIA), Little Havana, Wynwood, Design District, Coconut Grove.

Guest favourite
Flat in Dadeland
4.84 out of 5 average rating, 213 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!

Top guest favourite
Flat in Miami
4.91 out of 5 average rating, 159 reviews

Early Bird Deal:Miami Studio w/Marriot Club Access

Welcome to your NEW studio at The Elser — a modern, resort-style tower in the heart of Downtown Miami. Stay steps from Kaseya Center, Bayside, Bayfront Park, and the waterfront. Enjoy the energy of the city outside and a calm, private space inside. ✨ 11+ years hosting · 10K+ 5-star reviews · 50K+ guests — we focus on clean spaces, smooth check-ins, and stays that simply work.

Superhost
Home in Cutler Bay
4.87 out of 5 average rating, 216 reviews

Miami Relax Oasis: w/ Heated Pool_Spa & Basketball

Heated pool/Jacuzzi/Basketball court/5B Indulge in luxury for a relaxing vacation, basking in Miami's warm weather. Revel in our spacious heated pool and Jacuzzi adorned with umbrellas, loungers, and snack tables. Each room is tastefully decorated with meticulous care. Sports enthusiasts will adore our basketball court. Perfect for your family and friends, our space awaits.

Popular amenities for Pinecrest rentals with a pool

When is the best time to visit Pinecrest?

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Quick stats about holiday rentals with a pool in Pinecrest

  • Total holiday rentals

    Explore 50 holiday rentals in Pinecrest

  • Nightly prices starting at

    Pinecrest holiday rentals start at € 26 per night before taxes and fees

  • Verified guest reviews

    Over 1,690 verified reviews to help you choose

  • Family-friendly holiday rentals

    30 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 20 rentals that welcome pets

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wifi availability

    50 of Pinecrest holiday 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!