Windermere Island Vacations from $727

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The Latest Windermere Island vacation packages

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

Daddy Joes

$727

per person

Dec 10 - Dec 14

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to North Eleuthera (ELH)

9.6/10 Exceptional! (151 reviews)

Most relaxing trip yet…..

Reviewed on Aug 17, 2026

Pink Sands Resort

$1,846

per person

Oct 26 - Oct 30

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to North Eleuthera (ELH)

8.6/10 Excellent! (125 reviews)

Beautiful. Clean. Quiet

Reviewed on Jul 10, 2026

Runaway Hill Inn

Save 100% on your flight

$1,828

per person

Dec 10 - Dec 14

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to North Eleuthera (ELH)

10/10 Exceptional! (1 review)

I love Runaway Hill - everyone is extremely accommodating & nice! My room was super comfortable and quiet, spotless. I had to leave a day early, unfortunately, but I can’t wait to return. Yummy Thai food in their restaurant!

Reviewed on Jun 24, 2026

Cape Eleuthera Resort & Marina

$2,477

per person

Dec 5 - Dec 12

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to North Eleuthera (ELH)

8.8/10 Excellent! (23 reviews)

Romora Bay Resort & Marina

$1,025

per person

Nov 26 - Nov 29

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to North Eleuthera (ELH)

8.6/10 Excellent! (44 reviews)

The marina is very good the food at the restaurant was expensive but taste great We also have a sour experience at the from desk we asked for a water taxi to eluthera airport and they call fo a private taxi without tell us that was private when we got to the island they ask us to pay $70 for the ride that was 10 minutes and for the same ride before they charge us $10 each other than that the experience was nice the beach was very clean and beautiful 😍

Reviewed on Jul 26, 2026

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Stay near popular Windermere Island attractions

Windermere Island Beach

Why not spend a lazy afternoon at Windermere Island Beach during your trip to Savannah Sound?

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What to do in Windermere Island

Private Pink Sand Beach Tour: Swim With Pigs, Turtles & Stingrays

Private Eleuthera Island: Swim With Pigs, Turtles & Stingrays

$8,500

per traveler

See all activities in Windermere Island

Windermere Island Hotel Deals

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

Windermere Island Eleuthera

10/10 Exceptional! (1 review)

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

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La Bougainvillea Hotel and Villas

Banks Road, Governor's Harbour North Palmetto Point Central Eleuthera

$286 nightly

$318 total

Oct 17 - Oct 18

Total with taxes and fees

Pineapple Fields Boutique Condo Hotel

Banks Road Governor's Harbour Eleuthera

$279 nightly

$308 total

Sep 24 - Sep 25

Total with taxes and fees

9.8/10 Exceptional! (15 reviews)

"A great location across the street from a gorgeous pink sand beach and Tippy’s. Rooms are clean and comfortable with a rustic chic feel to them and a well manicured set of grounds. A great place for a low-key getaway."

Reviewed on Jul 5, 2026

See all 585 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.