Name: Historic Home Directly on Windermere Beach w/Club
Rating: 8.6

Top Beach vacation packages in Windermere Island

Price found within the past 48 hours. Click for updated prices.

Cape Eleuthera Resort & Marina

$2,420

per person

Feb 21 - Feb 28

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to North Eleuthera (ELH)

8.8/10 Excellent! (23 reviews)

Pink Sands Resort

Save 100% on your flight

$3,091

per person

Feb 22 - Feb 27

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to North Eleuthera (ELH)

8.6/10 Excellent! (121 reviews)

Very private and stunning beach!

Reviewed on Mar 16, 2025

The Cove Eleuthera

Save 100% on your flight

$3,715

per person

Feb 22 - Feb 27

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to North Eleuthera (ELH)

9.2/10 Wonderful! (250 reviews)

The Cove feels like your own tropical island. Very quiet and the food at the restaurant was fresh and delicious. If you’re looking to get away and truly relax in the peaceful Caribbean, The Cove is your place!

Reviewed on Jul 23, 2025

Valentines Resort & Marina

Save 100% on your flight

$2,564

per person

Feb 22 - Feb 27

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to North Eleuthera (ELH)

8.8/10 Excellent! (224 reviews)

I had the most wonderful stay! The staff were so wonderful and friendly and accommodating. They set up a golf cart rental for me on arrival and took care of all the arrangements. The food & drinks at their bar was excellent. The location is conveniently just footsteps from the water taxi. The room was enormous, clean, and had everything you could ever need for your trip. A great coffee shop right next door. And that pink sand beach was far better than I imagined it would be. My only regret is that I couldn’t stay longer … but I will most definitely be back and I will be staying at this hotel again. Thanks for an unforgettable experience

Reviewed on Nov 10, 2025

Coral Sands Inn & Cottages

Save 100% on your flight

$4,276

per person

Feb 21 - Feb 26

found 20 hours ago

Roundtrip flight included

New York (NYC) to North Eleuthera (ELH)

9.2/10 Wonderful! (349 reviews)

The pink sand beach and sunrise is breathtaking. The staff is thoughtful and very accommodating.

Reviewed on Jul 24, 2025

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3 Night Beach vacations in Windermere Island

Price found within the past 48 hours. Click for updated prices.

Valentines Resort & Marina

Save 100% on your flight

$1,921

per person

Feb 25 - Feb 28

found 18 hours ago

Roundtrip non-stop flight included

Newark Liberty Intl. Airport (EWR) to North Eleuthera (ELH)

8.8/10 Excellent! (224 reviews)

I had the most wonderful stay! The staff were so wonderful and friendly and accommodating. They set up a golf cart rental for me on arrival and took care of all the arrangements. The food & drinks at their bar was excellent. The location is conveniently just footsteps from the water taxi. The room was enormous, clean, and had everything you could ever need for your trip. A great coffee shop right next door. And that pink sand beach was far better than I imagined it would be. My only regret is that I couldn’t stay longer … but I will most definitely be back and I will be staying at this hotel again. Thanks for an unforgettable experience

Reviewed on Nov 10, 2025

Pink Sands Resort

Save 100% on your flight

$2,422

per person

Feb 25 - Feb 28

found 18 hours ago

Roundtrip non-stop flight included

Newark Liberty Intl. Airport (EWR) to North Eleuthera (ELH)

8.6/10 Excellent! (121 reviews)

Very private and stunning beach!

Reviewed on Mar 16, 2025

The Cove Eleuthera

Save 100% on your flight

$2,471

per person

Feb 25 - Feb 28

found 18 hours ago

Roundtrip non-stop flight included

Newark Liberty Intl. Airport (EWR) to North Eleuthera (ELH)

9.2/10 Wonderful! (250 reviews)

The Cove feels like your own tropical island. Very quiet and the food at the restaurant was fresh and delicious. If you’re looking to get away and truly relax in the peaceful Caribbean, The Cove is your place!

Reviewed on Jul 23, 2025

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See all available trips from Columbus to Windermere Island

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4 Night Beach vacations in Windermere Island

Price found within the past 48 hours. Click for updated prices.

Daddy Joes

$703

per person

Jan 2 - Jan 6

found 1 day ago

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) to North Eleuthera (ELH)

9.6/10 Exceptional! (126 reviews)

Property is across the street from mind-blowingly beautiful beach. Owners were welcoming and communicative about car rental, etc and food at the restaurant is great

Reviewed on Aug 3, 2025

Tingum Village Hotel

$706

per person

Jan 2 - Jan 6

found 1 day ago

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) to North Eleuthera (ELH)

8.4/10 Very Good! (341 reviews)

Review for Tingum Village, Harbour Island My wife and I had a smooth and pleasant check-in at Tingum Village. We were given a wonderful room with a comfortable king-size bed, and it set the tone for a fantastic stay. The staff were exceptional—helpful, friendly, and always willing to go the extra mile. This isn’t a 5-star hotel, but it delivered exactly what we were looking for: comfort, charm, and genuine hospitality. It felt like a true home away from home. Thank you to all the staff for the warm welcome and for making our stay memorable. Rory & Rehana Armstrong

Reviewed on Nov 24, 2025

Pink Sands Resort

Save 100% on your flight

$3,112

per person

Feb 12 - Feb 16

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to North Eleuthera (ELH)

8.6/10 Excellent! (121 reviews)

Very private and stunning beach!

Reviewed on Mar 16, 2025

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How do I book the best Windermere Island beach vacation packages?

Life’s a beach when you dive into our brilliant Windermere Island beach vacation deals. Chuck a check in the filter boxes to find ocean views, pools, and resorts just a short saunter from the sizzling sands.

How can I find cheap beach vacations in Windermere Island?

A rental steps from the shore creates an amazingly affordable Windermere Island beach vacation. Seaside sojourns during low season start from $703. Prices and availability are subject to change. Additional terms may apply.

When should I book a Windermere Island beach holiday?

For a bustling beach break, book in . For a less crowded coast, is the time to turn up.

How can I book the best family beach vacations in Windermere Island?

With a flick of a finger, the family-friendly filter brings you the best breaks on offer for the whole brood. Look out for kids’ clubs, waterparks, and other incredible extras for a vacay the little ones will love.

How do I find a Windermere Island beachfront vacation?

Check the beachfront filter and, bam, the best available oceanside resorts will appear before your eyes. Along with the incredible view, when you book a beachfront resort, you can get from the lapping waves to your patio lounger in a matter of moments.

Can I book a package including a Windermere Island vacation beach house rental?

Hit up the vacation rental filter to book your dream beach house. Once you’ve selected the most alluring abode, add your flights and car rental for the perfect package deal.

Can I find Windermere Island beach vacation deals?

Sort your search results by deals to delight in amazing Windermere Island beach vacation offers. If you want more pizzazz for your pennies, travel outside the high season or stay a little further from the shoreline.

Can I book a Windermere Island beach trip with free cancellation and/or flexible dates?

Just like the Windermere Island tides, plans change. Filter by payment option to find trips with free cancellation. Buy now, pay later options are also available for full-on flexibility.

Why should I book my Windermere Island beach vacation with Expedia?

Relax long before you see the shore with simple search, fantastic filters, and more great deals than there are grains of sand in Windermere Island. (OK, maybe not that last part.)

Top Beach Windermere Island Hotels

Stunning, Private, Pink Sand, Beachfront Estate with 70ft dock on Bonefish Flats

Windermere Island Eleuthera

4 min drive from Windermere Island Beach

Stroll along the shore in Savannah Sound, as you'll be within walking distance of Windermere Island Beach with a holiday at this vacation home. Amenities at ...

Travelers like: on the beach, sun loungers, beach towels, private pool

Paradise Found

Gorgeous home in a spectacular location. Truly far from the ordinary world. Miranda was exceptionally helpful. We will be back.

Reviewed on Jan 2, 2022

Private Home With Ocean Views, Short Walk to Beach & Club w/Pool, Tennis, Gym

Windermere Eleuthera

15 min walk from Windermere Island Beach

Enjoy sunsets on the beach in Savannah Sound, as you'll be a short walk from Windermere Island Beach when booking a getaway at this villa.

10/10 Exceptional! (5 reviews)

Magical place

We enjoyed our stay at Sundowner Villa. The house was clean and very well appointed. The host’s description was accurate, we only needed the air conditioning on very calm days. We enjoyed using the kayaks on Savannah Sound. There are several bonefish flats adjacent to the island, and the Bonefishing ...

Reviewed on May 17, 2025

Historic Home Directly on Windermere Beach w/Club

Windermere Governor's Harbour

8 min walk from Windermere Island Beach

Make the most of this fantastic location, as you'll be a short walk from Windermere Island Beach with a vacation at this vacation home.

8.6/10 Excellent! (12 reviews)

Travelers like: on the beach, pool

Provender

This is the second time we have stayed at this property and once again it was wonderful. Right on the beach and plenty large enough for our large group. The property manager and

Reviewed on Aug 2, 2025

See all 583 properties in Windermere Island

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.