Holiday rentals with a pool in Pinecrest

Find and book unique homes with a pool on Airbnb

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 $52 SGD per night before taxes and fees

  • Verified guest reviews

    Over 1,570 verified reviews to help you choose

  • Family-friendly holiday rentals

    20 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wifi availability

    40 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!

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, 171 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.
Guest house in Miami
4.98 out of 5 average rating, 223 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
4.95 out of 5 average rating, 296 reviews

"Casa Mia's" World Cup Fifa 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
Home in Miami
4.95 out of 5 average rating, 237 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.

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.
Home in Miami
4.88 out of 5 average rating, 145 reviews

The Lux Paradise Miami

Enjoy a stylish experience at this centrally-located place. Located in the heart of Miami, our property is close to all the main attractions the city has to offer. Whether you’re looking to explore vibrant neighborhoods like Little Havana and Coconut Grove, enjoy the stunning beaches of Miami Beach, or visit popular spots like the Miami Zoo, Vizcaya Museum, and the bustling Brickell area, you’ll find everything within easy reach. Perfect for those who want to experience the best of Miami!

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, 462 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
Home in Cutler Bay
4.86 out of 5 average rating, 159 reviews

South Miami Gem • Pool_BBQ, Mini Golf & Pool table

Discover the pinnacle of modern living in this newly remodeled 7-bedroom, 4-bath masterpiece. With sleek architecture and designer touches, this South Miami retreat offers a private heated pool and resort-style amenities for a truly unforgettable stay. Perfectly situated near stunning beaches, the Miami Zoo, Southland Mall, and top attractions, it’s your gateway to the best of South Florida. Experience unmatched comfort and sophistication—this one-of-a-kind home awaits you!

Superhost
A screened-in pool area showcases a large pool and an attached hot tub. Lounge chairs are positioned around the pool, while a dining table with chairs is visible nearby. Lush greenery surrounds the space, creating a tranquil outdoor atmosphere.
Home in Cutler Bay
4.77 out of 5 average rating, 146 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. ✔ Fully Equipped Kitchen ✔ Comfortable Bedrooms with King/Queen/Full beds ✔ Open Concept Living Area ✔ Office Desk ✔ Piano ✔ High-Speed Wi-Fi

Guest favourite
A modern living area features a comfortable gray sofa with patterned black and white cushions. A wooden coffee table is positioned in front, holding a small decorative arrangement. Art pieces adorn the walls, while a dining area with a wooden table and chairs is visible in the background.
Flat in South Miami
4.89 out of 5 average rating, 153 reviews

Dharma | 20% off Monthly Charming 2B | 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, 423 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
Two lightly dusted croissants are placed on white plates, resting on a weathered wooden table. The serene pool in the background sparkles under sunlight, surrounded by lush greenery and vibrant tropical plants.
Home in South Miami
4.98 out of 5 average rating, 100 reviews

South Miami/Coral Gables House with Exclusive Pool

Artistic, spacious, and beautifully furnished 1500 square foot South Miami house in a quiet family neighborhood. Close to the University of Miami and Coral Gables. Great restaurants and parks nearby. There is another house on the property with a separate entrance and yard, however the pool and cabana areas would be for your exclusive use. We do not allow large parties, film or photo shoots at this listing.

Superhost
Flat in Dadeland
4.82 out of 5 average rating, 252 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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