10 Best Vacation Rentals With Private Pool In Bermuda - Updated 2024

Nicole
Nicole 
Updated
| 5 min read

Set in North Atlantic Ocean, Bermuda is a British territory and a paradise for beach lovers. Here, you can fall in love with breathtaking pink sand shorelines. Some of the most magical of them are Horseshoe Bay, Elbow Beach, Tobacco Bay, and Warwick Long Bay. Adventure seekers should not miss the chance to see the enchanting Crystal and Fantasy Caves in Hamilton Parish. For tourists who are into sightseeing and city walks, the UNESCO World Heritage Site of the historic town of Saint George is a great place. Instagram-savvy vacationers will also love breezing through the picture-perfect streets of Hamilton that are lined with colorful colonial architecture. To find the perfect home away from home for your holiday, browse through this list of the best vacation rentals with private pool in Bermuda.

We handpicked these listings carefully, considering (wherever possible) host status, recent guest reviews, location, accommodation type, prices, availability of dates, decor, and access to private pool. The image galleries get refreshed with the latest updates regularly. They were last updated on April 12, 2024.

1. Fantastic villa with sea views, Southampton Parish (from USD 950)

This villa is suitable for big groups looking for accommodations with the comforts of a home and the amenities of a resort. From the stunning sea views to the stylish interior design, exciting features are in store for travelers. One of the most sought-after amenities of this accommodation is the outdoor pool that overlooks the ocean. The poolside is accentuated by Acapulco chairs and sun beds where you can relax after a soak.

Vacationers who smoke should note that smoking is allowed only in the pool area and the outdoor fireplace.

Stayed at this property?

15.06 km (9.4 mi) from Crystal and Fantasy Caves
20 reviews   Wifi Available
House 12 Guests 4 Bedrooms 3 Bathrooms

Accommodates: 12
Minimum Nights: 2
Refund Policy : 100% refund if you cancel at least 30 days before check-in.

Top guest reviews
Amenities & Room:
air conditioner instructions would be helpful
pool was super and views gorgeous
our family of 6 adults were very comfortable and there was even room for more people
Cleanliness:
also drain basket and filters were clogged and needed to be cleaned as dishes weren’t coming clean
the house was a nice size for a large group and is very clean and comfortable
this home was spectacular clean spacious and perfect location
clean and spacious location pictures don’t do it justice
this home was better that we expected it had everything we needed and was very clean
Host:
it is a wonderful spot and the host was extremely accommodating
Location:
the house was walking distance to the lighthouse grocery store take out restaurant and many other attractions
large supermarket in walking distance and take out food around the corner would love to stay again
bermuda is easy to get around and the villa is an easy walk to beaches and golf
it was spacious clean and in a great location on the island
Read more reviews

2. Gorgeous villa near Horseshoe Bay, Southampton Parish (from USD 1800)

If you wish to experience the lifestyle of the rich and famous on your holiday, you can start by booking this luxurious lemon-colored villa with million-dollar views of Horseshoe Bay. Besides being a few paces away from the sandy shores, you will also have access to an on-site outdoor pool. The Instagram-worthy pool area is nestled in a beautiful garden with palm trees, colorful blooms, rustic seating, and chic sun beds.

The accommodation also has a hot tub in case you’re in the mood for a bubbly bath.

Stayed at this property?

14.94 km (9.3 mi) from Crystal and Fantasy Caves
76 reviews   Wifi Available
House 10 Guests 4 Bedrooms 5 Bathrooms

Accommodates: 10
Minimum Nights: 1
Refund Policy : 100% refund if you cancel at least 30 days before check-in.

Top guest reviews
Amenities & Room:
unbeatable views very comfortable accommodations
the furniture is comfortable with plenty of seating
the pool patio and terrace areas were perfect for relaxing and taking in the views
our family thoroughly enjoyed the spaciousness the pool the view the location
kitchen has plenty of seasoning we purchase a redundant supply so don't worry about bringing too much
Cleanliness:
the property was as expected very nice clean and spacious
the house was clean and very comfortable for our group of 8
Host:
the host kim was very nice accommodating and extremely responsive
kim the owner was super responsive if we needed anything
i highly recommend this property and the owners
kim the owner was a pleasure to deal with
and finally the owner kim was incredibly gracious and helpful
Location:
location is great- very close to horseshoe bay spectacular view
Read more reviews

3. Fabulous retreat near the ocean, Sandys Parish (from USD 459)

If a swimming pool is a must-have feature in your ideal vacation home in Bermuda, check out this upscale guesthouse. While it boasts proximity to the sea, the swimming pool offers guests easy access to a refreshing soak within the premises itself. The pool nestles in a private garden, providing vacationers seclusion and exclusivity. For safety issues, kids under the age of eight and pets are not allowed here.

You’ll have WiFi to help you document all your holiday activities on your socials.

Stayed at this property?
Sandys, BM
6 Guests 3 Bedrooms 2 Bathrooms

4. Seaside villa with a hot tub, Southampton Parish (from USD 1450)

Make the most of your holiday by staying in this chic getaway right on the sea. The bright interiors with floor-to-ceiling glass windows and tropical touches are just as easy on the eyes. Apart from the aesthetics, the amenities that this three-bedroom abode provides are worth appreciating as well.

The property boasts an outdoor pool overlooking the ocean, inviting guests to enjoy a swim under the starry skies. The hot tub provides additional options for relaxing soaks.

Stayed at this property?
SOUTHAMPTON, SOUTHAMPTON, Bermuda
16.73 km (10.4 mi) from Crystal and Fantasy Caves
PRIVATE VACATION HOME 10 Guests 4 Bedrooms 4 Bathrooms

Top guest reviews
Amenities & Room:
everything in the house worked perfectly - tv's washer/dryer a/c etc
the pool is good size surrounded by a fully furnished patio area
and the grill was perfect for breakfast links & bacon
we ate many meals at home taking advantage of the well appointed kitchen and enjoying the breathtaking views
my children loved the pool and the hot tub
Cleanliness:
it was very clean we ordered groceries which was a huge time-saver
the cliff was the perfect place to be-the comfort and cleanliness the great pool and well equipped kitchen
the interior is spotless and equipped with everything a family needs to have a successful vacation
we thoroughly enjoyed the home and the spotless condition it was in
the property is spotless and each of the 4 bedrooms was very comfortable and had its own bathroom
Host:
the owner is very responsive and helpful
she was extraordinarily helpful and informative
our host sally was extremely gracious
her home and vicinity guide was very helpful
i can say that sally was the absolute best host i've ever encountered
Location:
the location is great
the location near restaurants and the best beach horseshoe bay was perfect
the master bedroom is well equipped with a large walk in closet and huge master bathroom
Read more reviews

5. Bungalow 41, Paget (from USD 210)

How would you like to spend your holiday in a beautiful home surrounded by lush greens, making you feel like you’re secluded in a tropical jungle? If you would, Bungalow 41 is the perfect fit for you. This tranquil studio-style accommodation can fit two, making it suitable for couples on a romantic holiday. Apart from standard facilities that include a kitchenette, it features a fantastic outdoor pool with floaters for that perfect lovers-on-vacation selfie. There are alfresco dining facilities, sun beds, and hammocks you can use whenever you need a break from floating in the water.

This property has an outdoor hose that comes in handy for rinsing off sand or showering before plunging into the pool or entering the bungalow.

Stayed at this property?
Paget, Paget Parish, Bermuda
8.52 km (5.3 mi) from Crystal and Fantasy Caves
117 reviews   Wifi Available
Entire guesthouse 1 Bed 2 Guests 1 Bathroom

Accommodates: 2

Top guest reviews
Amenities & Room:
bungalow 41 is a fantastic secluded oasis complete with a wonderful private pool
the bungalow with its private pool and outstanding bed and bath were incredible
beautiful private cabin with exclusive pool access
we enjoyed the beautiful bungalow that opened up to the well manicured pool and outdoor space
bungalow 41 was fabulous several nice little touches a fabulous patio with private pool and extremely comfortable
Cleanliness:
bungalow 41 was spotless and nicely furnished
the bungalow was very clean and private
the bungalow is clean and very comfortable
her place was clean and perfect for what we needed
tina's home is clean comfortable and on a beautiful property
Host:
tina was a wonderful host
tina was an amazing host
tina is a great host
tina was truly an amazing host
tina is an absolutely fantastic host
Location:
tina's place is great perfect location in the center of the island close to everything
perfect location for walking exploring catching the bus to beaches and more
the bungalow is absolutely adorable and the location is just a short walk from town
so relaxing and perfectly central to get around the island
beautiful property in an excellent location
Read more reviews

6. Frognal Apartment, Devonshire (from USD 195)

If you are planning to base yourself on the north shore of Devonshire, you might want to consider booking this homey apartment close to the shore. In fact, you can enjoy breathtaking ocean views from the property itself. The private swimming pool is one of the top-selling factors of this rental. You’ll find cozy seats on the poolside where you can cool down while relishing some fruity refreshments.

You can easily explore the capital of Bermuda as Hamilton is only 2 mi (3.2 km) away.

Stayed at this property?
Devonshire, Devonshire Parish, Bermuda
7.2 km (4.5 mi) from Crystal and Fantasy Caves
32 reviews   Wifi Available
ENTIRE RENTAL UNIT 2 Beds 5 Guests 2 Bedrooms 1 Bathroom

Accommodates: 5

Top guest reviews
Amenities & Room:
with an operational wifi would definitely come back
Cleanliness:
very clean comfortable beds and just a short bus ride to hamilton
Host:
bryony and llew were exceptional hosts and the apartment was just the best
both bryony and llew are great hosts and very helpful dan bermuda
the hosts are really really nice and arranged for shopping groceries etc
you'll get the whole pool area to yourself very friendly and helpful hosts
Location:
good location close to bus stops shops not from from city
it was great that a grocery store and bus stops were close by
i love that there is a bus stop super close by made getting around super easy
two bus routes make it easy to get around the island
lovely roomy airy place to stay
Read more reviews

7. Contemporary villa with a lovely deck, Southampton (from USD 1295)

Do you like spending your vacations in luxury and comfort? Then book this rental for a fabulous getaway. Featuring a seaside location, it treats guests to unforgettable views of the ocean. The contemporary all-white design is just as remarkable, making you feel like holidaying in Santorini.

A luxurious vacation home will not be complete without a swimming pool for exclusive use by guests. Thus, this upscale property also has one set on a large deck facing the ocean. The pool is sleek and sits parallel to the alfresco dining and lounge area.

Stayed at this property?
Southampton, Southampton Parish, Bermuda
16.32 km (10.2 mi) from Crystal and Fantasy Caves
135 reviews   Superhost Wifi Available
ENTIRE HOME 3 Beds 6 Guests 3 Bedrooms 3 Bathrooms

Accommodates: 6

Top guest reviews
Amenities & Room:
views of the turquoise sea orange sunsets comfortable crisp white bedding
loved the views great kitchen for cooking easy taxi access
the kitchen is well furnished and the sound system tv and amenities are really well done
the decor is perfect for the setting the beds and bedding is comfy
(vincent was great) backyard very privategreat tv and sound system
Cleanliness:
very clean & comfortable
beds were very comfortable kitchen spotlessly clean and well-equipped
the house was super clean with everything you could possibly need
comfortable clean nicely appointed and spacious for three girlfriends traveling together
tranquil well-appointed immaculately clean and amazing location
Host:
we truly enjoyed the home and the hosts’ attention to detail and service
karen and richard are amazing host and made sure we where comfortable in their home
your hosts richard and karen are very responsive to questions/requests
the hosts were very helpful and responsive prior to and during our visit
great hosts - highly recommend this property
Location:
perfect accessible location
the location is wonderful and convenient to restaurants and beaches and transportation
the location was perfect for us
the most beautiful location on the island
amazing location and stylish immaculate home
Read more reviews

8. Cozy love nest with a courtyard, Pembroke (from USD 179)

Daydreaming of a romantic holiday with the love of your life? Set the plans in motion by booking this one-bedroom rental. It is dressed in simple furnishings with bright walls and standard home facilities, including kitchen appliances and WiFi.

The star of the show is the lovely pool area that is beautified by the surrounding lush vegetation. When not soaking in the water, you can chill poolside on a lounger while reading a book, browsing the web, or savoring a glass of margarita.

Stayed at this property?
Pembroke, Bermuda
9.78 km (6.1 mi) from Crystal and Fantasy Caves
35 reviews   Wifi Available
Entire guesthouse 1 Bed 2 Guests 1 Bedroom 1 Bathroom

Accommodates: 2

Top guest reviews
Amenities & Room:
the edgehill suites are nice replete with small kitchen amenities wifi and a nice big comfy bed
great spot good room and lovely pool
Cleanliness:
it was very clean
the pool is clean and a nice perk
Host:
owner is very message friendly
lana was an excellent host
lana was very helpful and a great host
lana is super nice and a great host
lana was very accommodating and a helpful guide
Location:
nice place right near hamilton
great location and very quiet
this airbnb is in a great location and shops and stores are all in walking distance
location is perfect to downtown and a 25-30 min walk to the beach
this is a fantastic location for exploring hamilton bermuda
Read more reviews

9. Beach Walk, Paget (from USD 1035)

Suitable for big groups, this property can accommodate families, friends, or colleagues on a team-building getaway. There are no dull days for vacationers staying here as it is a short walk away from a private beach. It also has an on-site pool for those who wish to stay within the premises. The pool area is nestled in a landscaped garden with lovely blooms, sun beds, and alfresco dining facilities.

A diving board and a slide are built into the pool for added fun.

Stayed at this property?
Paget, Paget Parish, Bermuda
9.48 km (5.9 mi) from Crystal and Fantasy Caves
10 reviews   Superhost Wifi Available
Entire cottage 4 Beds 11 Guests 4 Bedrooms 4 Bathrooms

Accommodates: 11

Top guest reviews
Host:
susan and graham were fantastic hosts and their property is beautiful
from the time we first considered renting until our last day there they were responsive and helpful
Read more reviews

10. Finesse-Lucky 7, Warwick Parish (from USD 793)

This freshly revamped guesthouse boasts a tourist-friendly location as it’s a stroll away from Marley Beach, Astwood Cove, and Southlands Beach. Here, you can enjoy convenient facilities, including a well-equipped kitchen and a balcony perfect for alfresco dining with a view. The French doors in the living space open out to a lovely pool area with a lounge and barbecue equipment. Featuring underwater lighting, the pool illuminates at night, looking fantastic under the starry skies.

The management requires that guests keep the pool gates closed. Diving into the pool from the upper floor is prohibited for safety purposes.

Stayed at this property?
Warwick Parish, Bermuda
12.5 km (7.8 mi) from Crystal and Fantasy Caves
29 reviews   Wifi Available
ENTIRE HOME 4 Beds 5 Guests 3 Bedrooms 2 Bathrooms

Accommodates: 5

Top guest reviews
Amenities & Room:
the house was beautiful and the upstairs beds were super comfortable
we enjoyed the pool and grill
the pool was a great way to wind down after a day of site seeing
Cleanliness:
the house was amazingly clean
the pool was clean and the perfect temperature
the house was completely spotless and very nice
the place is sparkling clean
the house is beautiful spacious and clean and had everything we needed
Host:
roxana was an amazing host
roxana was a great host very responsive to all our questions and requests
the hosts were very thoughtful in providing everything guests may need during their stay
they’re wonderful hosts we can’t wait to return
the integrated twizy chargers were super helpful
Location:
the location is central to the best beaches
great location in the centre of the island highly recommend
we had a wonderful vacation at roxi's place
across the street is a huge park and the beaches are minutes away
the home was in a nice central location close to hamilton as well as all the beautiful beaches
Read more reviews

Indulge in some luxury in Bermuda

Bermuda is a mecca for tourists and is packed with breathtaking beaches, Instagram-worthy streets, and fantastic cuisine. Moreover, vacationers can enjoy excellent accommodations that will help make their stay even more memorable. This list of the best vacation rentals with private pools will come in handy for your upcoming visit.

Any must-sees we missed? Tell us about them in the comments section or write a post here to help out fellow travelers!
Disclosure: Trip101 selects the listings in our articles independently. Some of the listings in this article contain affiliate links.

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Nicole, a writer and traveler, also identifies herself as a free spirit with a wild heart. She is dedicated to telling authentic stories in a relatable manner. Nicole also enjoys exploring new,...Read more

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