Windermere Island Vacations from $909

Name: Pineapple Fields Boutique Condo Hotel
Price range: $319 total

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The Latest Windermere Island vacation packages

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

Daddy Joes

$909

per person

Dec 14 - Dec 21

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to North Eleuthera (ELH)

9.6/10 Exceptional! (151 reviews)

If you are looking for your home away from home you have found it. Everyone here is like family.

Reviewed on Nov 8, 2026

Pink Sands Resort

$4,145

per person

Dec 14 - Dec 21

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to North Eleuthera (ELH)

8.6/10 Excellent! (125 reviews)

Runaway Hill Inn

$2,450

per person

Jan 28 - Feb 2

found 24 hours 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

Romora Bay Resort & Marina

$4,339

per person

Dec 11 - Dec 17

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

Cape Eleuthera Resort & Marina

$1,972

per person

Jan 29 - Feb 3

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to North Eleuthera (ELH)

8.8/10 Excellent! (23 reviews)

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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 Eleuthera Island: Swim With Pigs, Turtles & Stingrays

$8,500

per traveler

See all activities in Windermere Island

Windermere Island Hotel Deals

Historic Home on Windermere Beach w/Club

Windermere Governor's Harbour

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La Bougainvillea Hotel and Villas

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

$302 nightly

$335 total

Nov 10 - Nov 11

Total with taxes and fees

9.4/10 Exceptional! (125 reviews)

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Reviewed on Sep 22, 2026

Pineapple Fields Boutique Condo Hotel

Banks Road Governor's Harbour Eleuthera

$287 nightly

$319 total

Nov 18 - Nov 19

Total with taxes and fees

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.