Windermere Island Vacation Rentals from $271: Search Short-Term Rentals

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Our top choices for Windermere Island vacation rentals

A wooden deck with a table and chairs, overlooking a lush landscape and a body of water.

1. Villa Allamanda

Governor's Harbour

Daniel

$257 nightly

Oct 3 - Oct 4

Total with taxes and fees

A pool area with lounge chairs and umbrellas, surrounded by palm trees and a view of the beach.

2. Laughing Bird Suites

Governor's Harbour

Nicole

$252 nightly

Oct 7 - Oct 8

Total with taxes and fees

A beach with a thatched roof structure, sandy beach, and clear blue ocean.

3. Pineapple Fields Boutique Condo Hotel

Governor's Harbour

Randi

$271 nightly

Sep 30 - Oct 1

Total with taxes and fees

A bright kitchen with large windows overlooking the ocean, a white countertop, and bar stools.

4. Mika's Resort

Governor's Harbour

"Excellent place to relax, unwind, and disconnect! Reynaldo was very kind and attentive, and he gave us some great recommendations about the area. The beach is absolutely beautiful, with crystal-clear, warm water. We had the beach almost entirely to ourselves, which made the experience even more special. Bring your own food, as the kitchen is fully equipped with all the utensils you need. Overall, a wonderful place for a peaceful and relaxing getaway. Highly recommended!."

Fernando

$463 nightly

Sep 30 - Oct 1

Total with taxes and fees

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Top Windermere Island Hotel Reviews

La Bougainvillea Hotel and Villas

10/10 Excellent

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Sky Beach Club

8/10 Good

"I thoroughly enjoyed my stay af the Beach Club, Bungalow 1. Mr. Rolle, manager, and Virginia, staff, were very professional and courteous and ensured all my needs were met. The road to bungalows however could use some renovation works - a rental car however is still fine for transportation back and forth. I highly recommend the Sky Beach Club and would most definitely stay there again."

BEACHFRONT HOME AND POOL, 4BR/4 BATHROOMS

10/10 Excellent

"Amazing view , beach all to ourselves. We didn’t realize Sept 5 was beginning of low season so almost all restaurants closed. Grocery store open. If you want a totally relaxing week , it is perfect. Pool is being renovated next month but was cool and refreshing. Had an awesome day with Cpt bubba and fishbone tours!! Everyone was so nice and kind, house was perfect for our group of 4. Prepared to relax and unplug !!!!We will be back. !!"

High-End Caribbean-Front Home in Top location-Large Pool, Great Views-Generator!

10/10 Excellent

"What a very unique property. So very cool to be able to snorkel reefs right from your front yard. Water was a little rough the week we stayed, with poor visibility, but we did see a few tropical fish throughout the week. Jumping off the cliffs was also fun! Romell was very kind and accommodating- he graciously helped my husband and son out of a bind when they got stuck. The Jeep Liberty we rented from him was awesome…my son loved it so much he wants to get one for camping. The house was fine for our needs. I will say it is not quite as new as the pictures made it look, especially the kitchen and bedding, but certainly nothing I would leave a bad rating for, as who can complain about paradise. The views, the colors of the water, and the islanders we met are unforgettable. We have visited 6 of the out islands so far, and Eleuthera is now one of our favorites. We did spend much time up in Spanish Wells, as that is where we rented the boat - from research, fishing and snorkeling from Spanish Wells proved to be the best. A bit of a drive and a ferry each day to get there, but also very worth the effort. We hit many of the beaches both north and south of the rental- there are just too many to visit. Deborah was amazing at communicating, and provided so much information about places to visit and where to get essentials. This is a very special rental that I would have no problem recommending to future guests."

Sea Shanty - Ocean view, Private pool, Walk to Beach, Prime Central Location.

10/10 Excellent

"A cozy and comfortable home! We thoroughly enjoyed our stay. Jethro was very responsive, accommodating, and easy to communicate with throughout our visit. The home had everything we needed for a relaxing stay in Eleuthera, and we truly appreciated the hospitality. We would definitely recommend it to others and would happily stay again!"

Find out more about Windermere Island

Everything you need to know about Windermere Island vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Windermere Island vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Windermere Island vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Windermere Island vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Windermere Island. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Windermere Island in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $271 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Windermere Island rentals

At Expedia, we put the best Windermere Island vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Windermere Island rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Windermere Island vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Windermere Island. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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Check prices for these dates

Our top choices for Windermere Island vacation rentals

1. Villa Allamanda

2. Laughing Bird Suites

3. Pineapple Fields Boutique Condo Hotel

4. Mika's Resort

Find vacation rentals that suit your style

Top Windermere Island Hotel Reviews

La Bougainvillea Hotel and Villas

Pineapple Fields Boutique Condo Hotel

Hilton's Haven

Sky Beach Club

BEACHFRONT HOME AND POOL, 4BR/4 BATHROOMS

High-End Caribbean-Front Home in Top location-Large Pool, Great Views-Generator!

Private family beach bungalow - on a beautiful swimming beach

Sea Shanty - Ocean view, Private pool, Walk to Beach, Prime Central Location.

Trade Winds - Oceanview, Private Pool, Short Walk To Pink Sand Beach, Central.

Find out more about Windermere Island

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