Holiday rentals near The Windjammer Gallery

We found 246 holiday rentals — enter your dates for availability

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November 2025

December 2025

Select the perfect holiday rental within close proximity to The Windjammer Gallery. Holiday rentals provide the best amenities for your stay with friends, family or just your pet, such as parking and a pool. You'll be sure to find a property to rent for everyone's needs, including options that are accessible or non-smoking.

Holiday rentals with weekly discounts - The Windjammer Gallery

Showing deals for:30 Jan - 6 Feb

Exceptional

(92 reviews)

Amazing Property Close To Beaches/Golf Course/Railway Trails

Warwick Parish

10% off

for 7 nights, 1 home

AU$421 per night

includes taxes & fees

Exceptional

(64 reviews)

Wild Bird, Paget - Pool, Twizy charger, Kitchenette - non smoking property

Paget Parish, Paget

8% off

for 7 nights, 1 home

AU$342 per night

includes taxes & fees

Exceptional

(37 reviews)

Two Bedroom with Private Dock near Golf and Beach

Southampton Parish

8% off

for 7 nights, 1 home

AU$451 per night

includes taxes & fees

Exceptional

(100 reviews)

Sand Dollar 2 Bedrm Beachfront house on private Marley Beach with beach views.

Warwick Parish, Warwick

8% off

for 7 nights, 1 cottage

AU$797 per night

includes taxes & fees

Exceptional

(84 reviews)

Sea Song 3 Bdrm Beachfront house on Marley Beach with great beach and sea views.

South Shore Road, Warwick

8% off

for 7 nights, 1 cottage

AU$898 per night

includes taxes & fees

Leamington Caves is a stunning, private retreat for families and friends

Exceptional

(14 reviews)

Extraordinary Bermuda retreat w/large cave, panoramic pool and viewing deck.

Hamilton Parish

14% off

for 7 nights, 1 home

AU$7,553 per night

includes taxes & fees

Exceptional

(13 reviews)

“Long Bay” Studio Overlooking Bermuda

Somerset Village, Sandys Parish

8% off

for 7 nights, 1 apartment

AU$382 per night

includes taxes & fees

Exceptional

(14 reviews)

Exquisite 1-bedroom Apartment is centrally located in Devonshire Parish.........

Devonshire Parish

8% off

for 7 nights, 1 apartment

AU$333 per night

includes taxes & fees

Wonderful

(5 reviews)

Blue Horizon Guest House with sofa bed - Studio #9

Warwick Parish, Warwick

9% off

for 7 nights, 1 home

AU$306 per night

includes taxes & fees

View from spring board. Pool and patio deck decor may vary upon arrival.

Exceptional

(6 reviews)

'RIPPLE WATERS' - More for Le$$ Great One Bedroom Pool House

Southampton Parish

8% off

for 7 nights, 1 apartment

AU$336 per night

includes taxes & fees

Exceptional

(15 reviews)

“Cavello Bay” Charming Spacious 2-Bedroom Family Getaway with ocean views.

Somerset Village, Sandys Parish

8% off

for 7 nights, 1 apartment

AU$426 per night

includes taxes & fees

Exceptional

(77 reviews)

Dreamscape Cottage POOLVIEWSMODERN*ELECTRICCARCHARGE

Smith's Parish, Smith's

17% off

for 7 nights, 1 cottage

AU$422 per night

includes taxes & fees

Exceptional

(7 reviews)

Luxurious 4 Bedroom Oceanside house with pool

Sandys Parish

8% off

for 7 nights, 1 home

AU$1,971 per night

includes taxes & fees

Exceptional

(135 reviews)

Spacious Beachfront and Private Resort living

Southampton Parish

8% off

for 7 nights, 1 apartment

AU$501 per night

includes taxes & fees

Exceptional

(46 reviews)

Cozy Studio Apt Devonshire, near Botanical Gardens and Close to town

Devonshire Parish

8% off

for 7 nights, 1 apartment

AU$294 per night

includes taxes & fees

Looking at the beach from the top of the stairs.

Exceptional

(120 reviews)

Sand Pebble 1 Bdrm Apt on Marley Beach w/ ocean views & steps to private beach

Hamilton, Warwick

8% off

for 7 nights, 1 apartment

AU$396 per night

includes taxes & fees

Exceptional

(40 reviews)

CHARMING THREE BEDROOM COTTAGE AT MARLEY BEACH, WARICK

Warwick Parish

22% off

for 7 nights, 1 home

AU$693 per night

includes taxes & fees

There's a gas grill and charcoal bbq for your use

Exceptional

(125 reviews)

Pool House Studio In A Garden Setting + EV chargers

Smith's Parish

8% off

for 7 nights, 1 cottage

AU$252 per night

includes taxes & fees

Exceptional

(25 reviews)

“Oceanfront Paradise Property: access to pool, ocean and Complimentary Kayaks”

Hamilton Parish

7% off

for 7 nights, 1 apartment

AU$471 per night

includes taxes & fees

Leamington Caves main house is 5 bedrooms (to the rear, and right in photo)

Exceptional

(9 reviews)

Unique Bermuda retreat with large cave & panoramic pool nestled into hillside

Hamilton Parish

9% off

for 7 nights, 1 home

AU$5,579 per night

includes taxes & fees

Enjoy the pool only steps from the apartment!

Exceptional

(80 reviews)

Las Brisas apartment with pool and walk to beach + EV chargers

Smith's Parish

8% off

for 7 nights, 1 apartment

AU$237 per night

includes taxes & fees

Find spaces that suit your style

House

Condo/Apartment

Find the best place to stay - The Windjammer Gallery

Multiple family weddings every year. #Cambridgeweddinghouse

Premier Host

Historic 1780’s Beach House with Large Veranda! Nestled on Cambridge Beach!

Sleeps 16 · 8 bedrooms · 5+ bathrooms

Premier Host

Stunning sunsets, turtle watching, longtails wheeling and glow worms ....

Sleeps 4 · 1 bedroom

Relaxing sit down by yourself or with your significant other. Look out to the Atlantic that is just breath taking!

Beautiful Water Front Property - Snorkel, Fish, or RELAX in the BEST LOCATION!

Sleeps 7 · 3 bedrooms · 2 bathrooms

Premier Host

Family Thanksgiving 2025 Bermuda! Private Luxury Villa 3 Bedrooms Pool Beach

Sleeps 6 · 3 bedrooms · 2 bathrooms

Stunning views from the Moongate believed to be good luck for newlyweds!

Premier Host

Luxury Villa with Stunning Views of Horseshoe Bay on the Turtle Hill Golf course

Sleeps 10 · 4 bedrooms · 4+ bathrooms

Premier Host

Location! Location! HALF PRICE SALE @ 100 Daily, November 9th - December 9th ASK

Sleeps 2 · 1 bathroom

Top rated rentals - The Windjammer Gallery

Premier Host

Great place

Spacious home easy walk to Georgetown

steve p.

Stayed July 2024

Snorkeling 50 feet from the property (photo Aug 2, 2019)

Premier Host

Excellent stay at Sandy's

The property was neat and clean and the views were beautiful. There was no need to go anywhere else. The water was like a swimming pool. My hosts were so kind and thoughtful, constantly making suggestions of places I could go and see while I was there. Everything was explained very well upon arrival and I took advantage of the wonderful taxi driver suggested by the hosts which I prebooked prior to arrival in Bermuda. The whole experience was effortless and I cannot wait to return.

Bonny W.

Stayed Jan 2019

Peace of mind
Our Book with Confidence Guarantee gives you 24/7 support
More quality time
From booking to staying, the whole process is simple and enjoyable
All the privacy of home
Enjoy full kitchens, laundry, pools, gardens and more
More for less
More space, more privacy, more amenities — more value

Holiday rentals near The Windjammer Gallery

Holiday rentals with weekly discounts - The Windjammer Gallery

Image gallery for Amazing Property Close To Beaches/Golf Course/Railway Trails

Amazing Property Close To Beaches/Golf Course/Railway Trails

Find spaces that suit your style

Find the best place to stay - The Windjammer Gallery

Historic 1780’s Beach House with Large Veranda! Nestled on Cambridge Beach!

Top rated rentals - The Windjammer Gallery

Great place

Peace of mind

More quality time

All the privacy of home

More for less

Holiday Rental options near The Windjammer Gallery

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