Vacation rentals with a pool in Boston

Find and book unique homes with a pool on Airbnb

Quick stats about vacation rentals with a pool in Boston

  • Total vacation rentals

    Explore 10 vacation rentals in Boston

  • Nightly prices starting at

    Boston vacation rentals start at G$2,092 GYD per night before taxes and fees

  • Verified guest reviews

    Over 70 verified reviews to help you choose

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    10 of Boston vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Boston rentals

Top-rated rentals with a pool in Boston

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

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Top guest favorite
An open lounge area features comfortable white sofas and a rustic wooden coffee table. Large windows allow ample natural light, framed by patterned blinds, with a view of the lush garden outside. A chandelier hangs from the ceiling, adding elegance to the space.
Apartment in Bishopscourt

Romantic Cape Town Cottage with Mountain Views

This stand alone cottage on our private property is located in the Bishopscourt area of the Western Cape. The cottage is an open plan lounge,bedroom with two big verandas, a kitchenette and a large bathroom with a shower and bath that opens out to a very private balcony with sun loungers and an outside shower. With magnificent views of the mountain and terrains, one can fully unwind and relax in this more than spacious cottage. This private cottage will be all yours during your stay. There are multiple lounging areas inside and outside the cottage. Our long serving housekeeper, Maks, will be there to look after you and make sure you always have what you need.She cleans and does the washing daily except on a Sunday. Located within walking distance to many stunning hikes, walking routes, mountain biking, and cycling routes. There are many places nearby that you can rent bikes and there is ample storage at the house for bikes to be stored. There is ample and secure parking on our property for the vehicle you bring along for your stay. I am usually here and am very happy to help with advice at all times. This home is in a quiet residential area with beautiful houses and leafy streets. Close to the botanical gardens and near the city. Uber Available.Safe parking on the grounds of the property. No need for Air Conditioning units as the mountain air in the mornings and evenings will be cool and crisp all year long. There is a ceiling fan, if you need additional cooling. Towels,beach towels,picnic basket all available at the cottage. The space is about 60sqm +

5.0 out of 5 average rating, 128 reviews
Top guest favorite
A private plunge pool is set within a landscaped garden, surrounded by greenery. The water sparkles under sunlight, and the ocean can be seen in the background, enhancing the serene atmosphere of the space.
Condo in Camps Bay

Camps Bay The View Villa Gdn apt & Pvt Pool

Renovated July 2026 A calm, neutral-toned, contemporary, exclusive garden apt with a private plunge pool in Upper Camps Bay will blow you away with its awe-inspiring views of Camps Bay Beach, Lions Head and Table Mountain. It occupies the entire garden level of a 2 apt. property. Safe and secure. Nature Reserve walks just 1 min away. V&A w/front- 15 mins drive. 3 en suite bedrooms, Netflix, Wi-Fi. ! Aircon/heating is available in bedrooms. Pse note: min 12-day booking req over xmas/new year.

4.92 out of 5 average rating, 182 reviews
Luxe
Apartment in Camps Bay

Amara 2 -Designer Penthouse with Solar Power

This designer Penthouse offers spectacular views of the ocean and Lion's Head and is situated in one of the most sought after areas Cape Town has to offer. This stunning 236 sqm property flows seamlessly over 2 floors with access via a private lift. The open plan, Italian kitchen is a real show stopper leading to the private pool and terrace with a picturesque background of the ocean and lions head. It comes with a double garage. The penthouse shared an entrance with the villa downstairs.

4.93 out of 5 average rating, 108 reviews
Top guest favorite
A spacious living area features large windows allowing natural light to fill the room. Comfortable seating is arranged around a coffee table, with a television mounted above a fireplace. A chandelier hangs from the ceiling, adding a contemporary touch to the warm environment.
Villa in Table Mountain

Table Mountain Villa

Set on the slopes of Table Mountain bordering the national park, this spectacular property offers panoramic views of the mountain, forest and city. Guests have a private entrance to mountain trails. A short walk from Kirstenbosch Botanical Gardens. 5-10 min drive to Constantia Wine Estates; Newlands Cricket, Rugby Stadiums; 1 traffic light to the city centre ; 15-20 min to the city's iconic beaches. Comprehensive security; unlimited WIFI, basement parking. A perfect base to explore Cape Town.

4.94 out of 5 average rating, 162 reviews
Top guest favorite
A spacious living area is characterized by large glass walls that provide panoramic views of the ocean. Comfortable seating is arranged around a central table, and natural light brightens the space. Elegant outdoor loungers are visible through the glass, inviting relaxation.
Villa in Camps Bay

360° Design Villa with sunset, whirlpool & privacy

With views for almost 360 degrees, there is a perfect blend of the high life together with tranquility as you move through the home. This stylish and spacious villa is situated high on the slopes of the Table Mountain Nature Reserve with its own garden gate leading straight into the reserve. The en-suite bedrooms are spacious and luxurious. The upper deck and lounge adjoin the kitchen have incredible views of the Twelve Apostles and Camp's Bay, the perfect place for sundowners in the jacuzzi !

4.89 out of 5 average rating, 100 reviews
Luxe
Villa in Clifton

Private Villa & Heated Pool, Steps Away from Beach

Part of the YOLO Spaces Collection. Clifton is Cape Town’s jewel, no matter how many sunsets you have seen, it’s simply different here. The Private Villa is located near the promenade, in a wind free pocket, in the heart of energetic Clifton. Less than 2 minutes walking distance to the famous 4 Clifton Beaches. It is +/- 5 min drive from restaurants, shopping, entertainment & nightlife; 10 to 15 min drive to city centre; 25 to 30 min to the airport & is central to nearby tourist attractions.

4.91 out of 5 average rating, 121 reviews
Guest favorite
Apartment in Lagoon Beach

Tideline No. 217, Cape Town

Welcome to this beachfront property. The light and open apartment is an easy 8km from Cape Town's city center. The spacious apartment has direct access to the beach as well as breathtaking table mountain and sea views. Fall asleep to the sound and smell of the ocean and wake up ready to enjoy the pool, Beach and Cape Town's many attractions. Has battery backup for WiFi and TV during load shedding. The following TV streaming services are included: AmazonPrime Video, Disney plus.

4.94 out of 5 average rating, 263 reviews
Guest favorite
Vibrant red and orange aloes frame a view of a white-washed annex and a large tree in the background. The landscape features a gently sloping pathway leading to the annex, with rolling hills visible in the distance under a soft overcast sky.
Farm stay in Stellenbosch

2 Bedroom Annex on a Stellenbosch Farm near town

Escape to a charming 2-bedroom annex on a working Stellenbosch wine farm, attached to our historic 1822 Cape Dutch farmhouse on the scenic Stellenbosch Kloof Road. Private, comfortable and rich in old-world charm, the space includes a lounge, kitchen and bathroom. Enjoy birdlife, hiking, fishing, mountain biking and lazy summer days at the giant pool (Mid Sep–Apr, 8am–4pm). Surrounded by top wine farms and restaurants, with Uber available right to your doorstep.

4.91 out of 5 average rating, 102 reviews
Guest favorite
The outdoor area features a sparkling blue pool surrounded by a spacious deck. Comfortable lounge chairs are positioned near lush greenery, creating a serene atmosphere. A stylish building with large windows offers views of the yard, enhancing the tranquil setting.
Home in Stellenberg

Villa Luisa: Sun-filled hidden gem with Pool.

This Mediterranean inspired home away from home offers great accommodation, marvelous ambiance and breathtaking mountain views. Guests will have exclusive use of the Villa, offering three living areas, open plan kitchen and a separate downstairs entertainment area with a built-in indoor pizza oven and braai (BBQ) next to the pool. The house has a solar system installed ensuring permanent connectivity during power outages for all plugs, lights and the WiFi.

4.85 out of 5 average rating, 116 reviews
Top guest favorite
A modern three-story home is surrounded by lush greenery, featuring large glass windows and a spacious wooden deck. The inviting pool reflects the clear blue sky, enhancing the outdoor space's appeal. Comfortable lounge seating is arranged on the deck, creating a relaxed atmosphere.
Home in Sea Point

Stunning Modern, Spacious, Sea Views in Sea Point!

Our family friendly home is situated on Ocean View Drive in Sea Point and is a beautiful synergy of wood, glass & steel. The views from the top floor to the right of us are exquisite stretching to Robben Island & Tableview. Our location is perfectly located ten minutes drive/Uber ride from almost everywhere - Camps Bay & Clifton beaches, V&A Waterfront & amazing restaurants in the CBD! You can even take a five minute stroll down to the beautiful promenade.

4.99 out of 5 average rating, 116 reviews
Guest favorite
Apartment in Cape Town City Centre

Designer PH with 180° views of City, Mntn & Ocean.

Welcome to this super spacious, luxurious penthouse in the heart of the city centre. Enjoy 180° views of the City, Ocean and Table Mountain & Lions Head from the massive wrap around balconies on both floors. Close to all the best restaurants, art galleries, coffee shops, bars, museums and much more! All amenities are there as well as fast uncapped WiFi. There is lovely games area upstairs with a view for the best quality-time. No visitors allowed.

4.84 out of 5 average rating, 187 reviews
Guest favorite
The exterior of a chic coastal home is illuminated by dusk, showcasing a private pool reflecting the evening sky. The open-plan living area features large doors that connect to a spacious wooden deck, ideal for dining and relaxation, surrounded by tropical vegetation.
Home in Clifton

Bungalow 21 - Clifton 3rd by Steadfast Collection

Bungalow 21 feels like a hidden gem amongst Cape Town’s most prestigious coastline. Nestled above Clifton 3rd beach, the bungalow offers sweeping ocean views while you listen to the waves tumble in the bay. Within easy walking distance or a short drive to nearby shops, restaurants and bars, yet secluded enough to unwind to in peace, with its private swimming pool, which is a rare find within Clifton’s prestigious bungalows.

4.92 out of 5 average rating, 120 reviews

Popular amenities for Boston rentals with a pool