Vacation rentals with a pool in Hollywood

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Hollywood

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

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Guest favorite

A private pool area is framed by lush palm trees, creating a serene outdoor oasis. The tranquil water reflects the surrounding greenery, while comfortable loungers invite relaxation. A dining set is visible on the patio, enhancing the inviting ambiance of the space along the New River.

Guesthouse in Fort Lauderdale

4.92 out of 5 average rating, 114 reviews

Guest Suite - Private Pool! 15 Minutes to Beaches

Picture yourself relaxing at a PRIVATE pool not shared with other guests! Casita Del Rio, a stunning vacation rental on the New River in Ft. Lauderdale, FL! This private guest suite offers exclusive comfort with an upscale bathroom, refrigerator, microwave, and Keurig. The pool area is, exclusively yours, with loungers for basking in the sun. Book your unforgettable escape less than 20 minutes away from Ft. Lauderdale's stunning beaches, restaurants, and so much more. Questions? Message us :)

Top guest favorite

A clear swimming pool is surrounded by lush tropical vegetation, including palm trees and large green plants. Two lounge chairs are positioned beside the pool, offering a serene setting for relaxation. The pool deck is made of brick, enhancing the natural ambiance.

Guesthouse in Biscayne Park

4.95 out of 5 average rating, 509 reviews

Cozy and charming cottage

Our cottage is located in a very quiet residential area, 15mn to the beach (Bal Harbor area).20mn from both Miami and Fort Lauderdale Airports, Located in the backyard of the main house but separate and with an independent entry. Enjoy our tropical garden and beautiful pool, in the back of our house. Share with owner only, we give priority to our guests to enjoy it! Parking available in our front yard. No kitchen but microwave and fridge. TV, cable and WIFI. It is suggested to have a car.

Top guest favorite

A modern villa exterior features clean lines and large glass windows, allowing natural light to brighten the facade. The driveway leads to a spacious garage, while lush greenery and tropical plants enhance the landscape. The vibrant blue sky provides a clear contrast to the home's contemporary design.

Home in Fort Lauderdale

4.98 out of 5 average rating, 117 reviews

Topo Encanto-Modern Villa in Sundrenched Paradise!

Topo Encanto is a brand new luxury villa in an upscale neighborhood. This stunning home comes with a free heated pool, cutting edge furnishings, fully stocked kitchen and super fast fiber wi-fi. We care for the home ourselves and deal directly with guests--no management companies or surrogates here! When booking, please confirm you've reviewed our House Rules (link is at the bottom of this page) and note we do not allow extra people beyond the number in your reservation. See you soon!

Top guest favorite

A private, gated pool area features a turquoise pool surrounded by a spacious deck. Poolside lounge chairs offer comfortable seating, while a water slide and colorful pool toys are visible. The backyard includes shaded lounging areas and greenery, providing a relaxing outdoor space.

Home in Hollywood

4.96 out of 5 average rating, 110 reviews

Family Oasis | Heated Pool | Hollywood

The Ultimate Hollywood Family Getaway! This spacious, modern 3-bed, 2-bath home is your private oasis. Fully equipped chefs kitchen and onsite laundry. Relax in your private and gated pool area, equipped with a BBQ grill, pool toys, outdoor dining, and a cozy lounge. Enjoy extra perks like our WATERSLIDE (May-Aug) & HEATED POOL (Nov-May). Prime Location! 3 minute drive to Hard Rock Hotel & Casino | Short drive to Hollywood Beach & FLL Airport | Walking distance to houses of worship.

Guest favorite

An inviting pool area is highlighted under a twilight sky, featuring a shimmering blue pool surrounded by lush greenery. Comfortable seating areas and a shaded patio are visible, providing ample space for relaxation and outdoor gatherings.

Home in Coral Way

4.97 out of 5 average rating, 102 reviews

MIA Oasis: Best Location, Pool, Spacious!

-Less than 5 minutes to the heart of Brickell (closest you can get with a house) -Easy access to South Beach, Wynwood, Midtown, Coral Gables (all within 10-15 minutes) -Newly renovated with stylish, high-end finishes. Notably two rooms have their own bathrooms, so its a comfortable setup for large groups. -Backyard pool and patio area feels like an oasis. Great place to hangout with friends, grill, or just relax and enjoy the greenery, the sun during the day, and the stars at night.

Superhost

A serene backyard features a refreshing pool surrounded by palm trees and neatly manicured grass. Overhead, a clear blue sky enhances the tranquil waters of the canal visible beyond. Lounge chairs are positioned by the pool, inviting relaxation.

Home in Dania Beach

4.81 out of 5 average rating, 140 reviews

Sunshine Oasis, Pool, Canal, b.b.q, Close to beach

Welcome to your waterfront oasis. Fully remodeled (2 BE/2 BA) with a pool at the backyard and in front of a Canal. Everything you need to complete your South Florida retreat. Enjoy all the amenities offered in the comfort of the pool. Sit at the deck to spend a quiet afternoon fishing, enjoying the sun under the tropical breeze or practicing yoga. 7 minute drive to the beach. Close to restaurants & shops Enjoy the backyard then have a relaxing therapy at the master bedroom sauna!

Guest favorite

A spacious outdoor area highlights a custom-designed heated pool surrounded by chaise lounges. A Tiki lounge with thatched roof is complemented by a bar area and a swing chair. Clear blue skies create a vibrant backdrop for relaxing under the sun.

Villa in Hollywood Hills

4.96 out of 5 average rating, 159 reviews

Spacious 5.5 BR Renovated Villa | Heated Pool Tiki

Upgraded in 2025! Your private, stunning, recently renovated villa! The sleek design offers the feel of a modern home. Enjoy 5.5 bedrooms and 3.5 baths, each designed to satisfy any travel connoisseur: open-concept living space and top-of-the-line kitchen with plenty of natural light. A custom-lit heated pool, a Tiki Space, and a beautiful outdoor dining area are perfect if skipping a beach day in style. We created this space to allow you to enjoy a lovely vacation away from home.

Guest favorite

A serene pool area is lined with palm trees and lounge chairs, reflecting the clear sky above. The building’s modern architecture complements the inviting atmosphere, with shaded seating options nearby, providing a relaxed environment for guests to enjoy the outdoor space.

Condo in Hollywood Beach

4.83 out of 5 average rating, 213 reviews

Sea, City, Sun, views and wonderful surroundings

Very exclusive accommodation, located within a 5-star building, at the foot of the sea, on the famous Ocean Drive Avenue, 5 min from "Aventura Mall", banks, pharmacies, restaurants, entertainment, adventure sites. On the 38th floor with wonderful views of the sea, the canal and the City. Elegance and services, return to stay in a wonderful experience. Porcelain floor with individual carpets which greatly facilitates cleaning and its cost. It has seats and beach umbrella.

Top guest favorite

A private pool is centered in a spacious outdoor area, surrounded by paver stones. Lush palm trees provide shade, while a basketball hoop is visible in the background. A blue kayak rests along the wooden fence, complementing the tranquil setting.

Guest suite in Hollywood Hills

4.97 out of 5 average rating, 157 reviews

Best Suite in town - Hollywood Hills w/Pool&Patio

It's a cozy, modern, newly remodeled suite, completely independent, with private entrance, patio area, and pool access. Located in a quite, residential neighborhood just minutes away from: - Hollywood Beach (4 miles) - Hard Rock “The guitar” Hotel Casino (2.4 miles) - Ft. Lauderdale-Hollywood International Airport (4.5 miles) - Súper Walmart (1.3 miles) - Aventura Mall (5 miles) - Sawgrass Mills Mall (12 miles) - Tri Rail / Amtrak Station (1.4 miles) Come and relax!

Top guest favorite

A private patio features a heated saltwater pool surrounded by lush tropical greenery. A gazebo with comfortable seating and a gas BBQ area is showcased, alongside cozy loungers positioned for relaxation. An umbrella stands ready, providing shade over a dining area nearby.

Home in Poinsettia Heights

5 out of 5 average rating, 104 reviews

Casa Déjàvu 5*spot Heated pool /HotTub /8min Beach

Welcome to CASA DÉJÀ VU A high-end space thoughtfully created just for you, in the heart of Fort Lauderdale. ✔️ 8 min to the beach | 10 min to Las Olas ✔️ Heated saltwater pool + outdoor hot tub ✔️ Garden with gazebo, BBQ & loungers ✔️ 2 beds (King + Queen), fast Wi-Fi ✔️ Fully equipped kitchen + Smart TVs ✔️ Free bikes & beach gear ✔️ Quiet and safe neighborhood ✔️ Free parking + 24/7 hosts

Guest favorite

A sunny outdoor area features a heated pool surrounded by lounge chairs and lush greenery. A top-of-the-line ping pong table is positioned prominently, alongside shaded seating under umbrellas. The space is complemented by vibrant plants and an inviting gazebo in the background.

Guesthouse in Fort Lauderdale

4.92 out of 5 average rating, 206 reviews

Villa with Heated Pool, Laundry, Ping Pong & More

Romantic, clean, private and quiet: perfect to relax after a day at the beach or work. Modern décor, high end appliances and furniture, 82inch Samsung smart TV with Bose soundbar, private gazebo with grill. Just 3 miles from the beach and 1 mile from main highway i95 and 1 mile from Wilton Manors. Walking distance to grocery stores, bars and restaurants.

Guest favorite

Condo in Hollywood Beach

4.89 out of 5 average rating, 114 reviews

★★★★★HYDE MANSION 2BD/2BA WITH DIRECT OCEAN VIEW

🎁 LIMITED TIME OFFER Valid from August 1, 2025 to January 1, 2026 Guests who book this listing during the promotion period will receive an exemption from the daily resort fee and complimentary valet parking - a total value of $80+tax per day! 💸 To claim this offer, simply text us “FLEX_ME_25” after your booking!