Vacation rentals with a pool in Pembroke

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Pembroke

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

0 of 0 items showing

1 of 3 pages

Guest favorite

A crystal-clear swimming pool is surrounded by lush greenery, with tall palm trees lining the background. Several lounge chairs are positioned nearby, inviting relaxation, while the vibrant blue water glistens in the sunlight.

Apartment in Pembroke

4.92 out of 5 average rating, 149 reviews

Chequers Garden- Paradise at the edge of Hamilton

Come & stay where tree frogs sing you to sleep & the birds serenade you awake. A 15min walk to the heart of Hamilton; situated in a private garden & pool setting. A ground floor, south facing, open plan unit; separate foyer & sitting area- converts to 3rd person sleep area. The kitchen: full fridge, microwave, toaster oven & kettle. If you have children, we can add a single bed or pack'n'play, high chair, some toys, books & accessories. We look forward to welcoming you to our little paradise.

Guest favorite

A private patio features a swimming pool surrounded by tile flooring. Lounge chairs are placed beside the pool, accompanied by a pink umbrella for shade. A dining area with a table and chairs sits nearby, with greenery and a palm tree visible in the background under a clear blue sky.

Apartment in Paget

4.93 out of 5 average rating, 15 reviews

Sun kissed Suite - Studio in Paget

Escape to paradise in this charming studio, nestled in the heart of Bermuda. Perfect for couples seeking a romantic retreat or professionals needing a serene workspace, our cozy abode offers the ideal blend of comfort and convenience. Features: * Prime Location: Within walking distance of stunning beaches, supermarkets, and restaurants. * Serene Ambiance: Relax on your lovely patio, soak up the sun, and enjoy the pool. * Modern Amenities: Fully equipped kitchen, high-speed Wi-Fi, TV, and a/c

Guest favorite

A well-appointed bedroom features a spacious bed with neatly arranged pillows in soft blue and white tones. Two bedside tables hold elegant lamps, casting a warm glow. A modern kitchenette is visible in the background, complemented by clean lines and light cabinetry.

Apartment in Smiths

5 out of 5 average rating, 13 reviews

Aqua Mellow - Luxury Apt I

Brand new, luxury apartment, conveniently located in beautiful Smiths parish. You’ll enjoy peaceful surroundings and a high end finish. There’s also lots of amenities including a 55” TV with surround sound, an electric fireplace, a shared swimming pool and laundry onsite. The property is a 10 min drive from the airport and the City of Hamilton. It’s a 2 min drive to the beach (overlooking stunning Gibbets Island) and beautiful Flatts Village with lots of restaurants, sightseeing and the aquarium

Top guest favorite

A serene pool area is surrounded by well-maintained greenery and shrubs, offering partial views of the sky. Two lounge chairs are arranged beside the water, with a pool ladder leading into the inviting turquoise water. Fencing provides a sense of privacy.

Cottage in Smiths

4.98 out of 5 average rating, 40 reviews

Quaint and charming Cottage

A charming stand alone cottage set in 1.5 acres of mature gardens. Beautiful views over the North Shore with picturesque sunsets. There is direct access from the property to Bermuda’s unique Railway Trail. It is a 15 minute walk to Flatt’s Village on the Trail where there are several excellent restaurants (Village Pantry, Tribe and Rustico’s) and the Bermuda Aquarium, Museum and Zoo. Three bus routes are less than a 5 min walk. Hamilton is 10-15 mins by bus and less than 10 mins by taxi.

Top guest favorite

A warm orange exterior of the house is complemented by a spacious back patio featuring a heated pool. Comfortable seating arrangements, including lounge chairs and tables, provide inviting spaces for relaxation. An umbrella offers shade, while steps lead to the upper level of the property.

Home in Hamilton

4.9 out of 5 average rating, 283 reviews

Studio Apt w/ pool - quick walk to town

The perfect edge of town apartment for two. For those who prefer to walk, this is the perfect spot with restaurants and shops within close proximity. We are a very short walk to all the shops, restaurants and bars along Front Street in Hamilton. This unit is a self-contained apartment within our house. We have 3 apartment like this within our home. This means with a total of 3 studios, we have accommodation for up to 6 guests. Head to the back patio and enjoy the heated pool year round.

Top guest favorite

The shared pool area features clear blue water bordered by a spacious patio. Surrounding foliage includes tropical plants and trees, enhancing the inviting ambiance. Two sets of lounge chairs are situated near the pool, providing a relaxing spot for guests to enjoy the outdoors.

Townhouse in Pembroke Parish

5 out of 5 average rating, 201 reviews

Smuggler's Cove - Walk to City of Hamilton

** Early check-in is guaranteed on flight arrival with Bermuda Covid entry requirements. ** Fully furnished, newly renovated, Bermuda themed, one bedroom, one bathroom, two story townhouse located on Rosemont Avenue. Interior Queen bed Bath with shower Split unit air-conditioning and heating Full kitchen with Nespresso machine All dining and cookware Laundry Desk 2 Flat screen TV’s Cable, Wifi and local phone Exterior Private patio/BBQ/outdoor dining Shared pool

Superhost

A private pool is framed by a lush garden, featuring three lounge chairs positioned under blue umbrellas. Shadows from surrounding palm trees dance across the water, creating a serene ambiance. The pool area is paved with light-colored tiles, enhancing the tranquil setting.

Apartment in Paget Parish

4.97 out of 5 average rating, 143 reviews

The Shire

A stand alone pool house in a lovely garden setting with your own private pool. We are located in Paget on a secluded piece of mature property. Sit and relax around the pool and enjoy the Kiskadees and Red birds. A 10 minute walk will bring you to our city center, Hamilton. Rent a motor cycle or Twizzy car and get unlimited access to the Island and the beaches. An 5 minute drive will bring you to Elbow Beach the nearest, stunning, pink sands, public beach.

Top guest favorite

A spacious outdoor pool area is surrounded by tropical greenery, with sun loungers placed around the water. A red umbrella and two red umbrellas provide shaded seating options. The clear blue ocean is visible in the background beneath a bright sky with scattered clouds.

Condo in Paget

4.97 out of 5 average rating, 77 reviews

Private Beach Access, Amazing Location

This home, which has private access to beautiful Grape Bay Beach, is within walking distance to Elbow Beach, the Bermuda Railway Walking Trails, and several of Bermuda's top restaurants. The spacious apartment has a huge balcony with ocean views. It has all necessities and amenities for a short or long-term stay and is accessible to everything you want to do in Bermuda. One special feature is our extensive, triple-filter water filtration system.

Top guest favorite

A private pool area is surrounded by a spacious stone patio, featuring lounge chairs and a steps for easy access. Lush greenery and palm trees provide a natural backdrop, while a nearby pink cottage adds a charming touch to the serene setting.

Cottage in Paget

4.98 out of 5 average rating, 153 reviews

Cottage Priv. Pool & Tennis Beach 5 min Central

Consistently rated 5★★★★ and located in Bermuda's prime location (near Hamilton and Beaches) the cottage features: • Your OWN Refreshing Private Pool and Tennis/Pickleball court... • Centrally located • Short walk to Hamilton • 5 min.ride to Elbow Beach • High speed Internet • Fully equipped kitchen • King-size bed with pillow top mattress • Near bus stops to both ends of the island • 42" Smart TV • Twizy Charger • Extremely safe neighbourhood

Guest favorite

A clear swimming pool is surrounded by well-maintained gardens, with lounge chairs positioned nearby. A two-story building is visible in the background, featuring a balcony that overlooks the pool area. Palm trees add a tropical touch to this serene outdoor space.

Apartment in Smith's

4.96 out of 5 average rating, 148 reviews

Pool, Private Gym, Serenity,Tranquility it's here!

Embrace the tranquility & privacy as you relax in our garden snuggled with your favorite book. Cook outdoors on our BBQ & dine el-fresco, then take a dip in our swimming pool. Fully equipped recreation room. Our property is conveniently located to beaches, restaurants, Flatts Village & other tourist spots. If shopping is on your list visit the city of Hamilton, The Ole' towne of St. George's or venture west to The Royal Naval Dockyard.

Top guest favorite

A refreshing pool is framed by lush greenery and vibrant pink flowers. Beyond the pool, a cottage features glass doors and a shaded sitting area. Sun loungers are positioned beside the pool, inviting relaxation amidst the natural surroundings.

Guesthouse in Paget

5 out of 5 average rating, 158 reviews

Bungalow 41

Visiting Bermuda for the first time? Look no further. Bungalow 41 is a private studio pool cottage located in the heart of Paget and within walking distance of the city of Hamilton, Bermuda Botanical Gardens, Bermuda National Trust headquarters, Pomander Gate Tennis Club and Royal Hamilton Amateur Dinghy Club. Easy access to all bus routes and the main ferry terminal for those not wanting to rent a scooter or small electric car.

A shared pool with a clear blue surface is surrounded by a patio area. Lush greenery and tropical plants are positioned around the pool, enhancing the outdoor space. A light blue building is visible in the background, contributing to the property's inviting atmosphere.

Condo in Bermuda

4.78 out of 5 average rating, 46 reviews

Smuggler's Cove Skyesil Unit

Private one bedroom in a central location within minutes of the town of Hamilton. The fantastic restaurant, Ascots, is immediately next door. Unit has a spacious living room, dining area, and fully equipped kitchen. There is a small garden as well as use of a shared pool with only 5 other units on the property. Ideal for business guests, printer available for use in the unit with fast internet.