Windermere Island Holiday Rentals

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Holiday Rentals in Windermere Island

Our top choices for Windermere Island holiday rentals

Remote Beachfront Treasure 4-bedroom villa WiFi and AC on Windermere Eleuthera

Remote Beachfront Treasure 4-bedroom villa WiFi and AC on Windermere Eleuthera

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

10.0 out of 10, Exceptional, (121)
"Great location. Rustic style with all the necessary amenities. Property owner is nearby and very friendly and knowledgeable. "
The price is NZ$524
includes taxes & fees
29 Sept - 30 Sept
Sea Shanty - Ocean view, Private pool, Walk to Beach, Prime Central Location.

High-end New Home - Large PRIVATE Pool, Snorkeling, Cliff Jumping, Kayaks & SUP

9.8 out of 10, Exceptional, (73)
"We had the most beautiful week in Eleuthera. Property was as described. It was centrally located on the island. Plenty of space to spread out and relax. Loved seeing the turtles visit. Can’t wait to go back."
High-end New Home - Large PRIVATE Pool, Snorkeling, Cliff Jumping, Kayaks & SUP

Oceanfront Deck, Kayak, SUP, Snorkel Mask, AC, Free Wi-Fi, Grill, Great Location

9.8 out of 10, Exceptional, (18)
"We absolutely loved staying here! Comfortable bed, stocked kitchen, and very useful space. We were sad to leave!"
Oceanfront Deck, Kayak, SUP, Snorkel Mask, AC, Free Wi-Fi, Grill, Great Location

BEACHFRONT INFINTY POOL, 4BR/ NEW! 4 BATHROOMS

9.8 out of 10, Exceptional, (80)
"Can’t wait to come back! The care taker Mercy and her husband was amazing! Locals are so friendly! The house is wonderful and the view is so stunning! The owner’s response immediately! Thank you for all the hospitality!!! "
BEACHFRONT INFINTY POOL, 4BR/ NEW! 4 BATHROOMS

Oceanfront- Brand new Eleuthera house

10.0 out of 10, Exceptional, (73)
"We love this house. We have stayed here 4 times and enjoyed our vacations here every time. "
Oceanfront- Brand new Eleuthera house

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

10.0 out of 10, Exceptional, (123)
"Tradewinds was just what we needed as a spot of relaxation before a big wedding. Jethro was so considerate and came by to make sure our stay was going well and to find out if we needed anything. We thoroughly enjoyed the home with comfortable beds and clean refreshing pool. The 3 min walk on the sand path through the palm trees opening to the breathtaking Atlantic beach was a bonus. We hope to come again!"
Trade Winds - Oceanview, Private Pool, Short Walk To Pink Sand Beach, Central.

Pink Sand Studio on DOUBLE BAY beach! "Senza Nome"

9.8 out of 10, Exceptional, (59)
"Friendly welcoming hosts.Accomodation lacking a few niceties like beach chairs, but they were hardly missed.We had two days of much needed rain and still can say: we enjoyed every minute in Double Bay."
Pink Sand Studio on DOUBLE BAY beach! "Senza Nome"

Pineapple Fields Boutique Condo Hotel

3.0 star property
9.8 out of 10, Exceptional, (8)
"Great place to stay"
Pineapple Fields Boutique Condo Hotel

Mika's Resort

3.5 star property
9.4 out of 10, Exceptional, (26)
"Very great location and the facilities are very nice. Location is exceptional. Some very minor challenges but overall very good trip."
The price is NZ$945
includes taxes & fees
9 Sept - 10 Sept
Mika's Resort

Oceanfront Glass House on Private Deserted Pink Sand Beach

9.8 out of 10, Exceptional, (103)
"on the beach which was great for walks"
Oceanfront Glass House on Private Deserted Pink Sand Beach

Romantic Cottage directly on private Double Bay Beach, Bahamas, "Senza Nome"

9.8 out of 10, Exceptional, (126)
"The cottage is in a beautiful setting, very close to the beach."
Romantic Cottage directly on private Double Bay Beach, Bahamas, "Senza Nome"

Villa Allamanda

3.0 star property
9.6 out of 10, Exceptional, (28)
"Great place to stay "
Villa Allamanda

Brand New Estate with Pool & Private Backyard Beach on Calm Caribbean

10.0 out of 10, Exceptional, (4)
"This is by far the best home we've leased in Eleuthra. Well appointed and has everything we needed. Only downside is having to leave it all it all behind. Special thanks to Tenielle (local property manager) and Eleuthra Vacation Rentals."
Brand New Estate with Pool & Private Backyard Beach on Calm Caribbean

Brand New Designer Home w/Private Heated Pool, Golf Cart, Beach, Snorkeling

10.0 out of 10, Exceptional, (7)
"Great location, loved the private pool for the young kids; house was great and the host was very responsive."
Brand New Designer Home w/Private Heated Pool, Golf Cart, Beach, Snorkeling

4-Acre Estate on Banks Rd, House & Guest cottage, Pool, Calm Protected Beach

9.8 out of 10, Exceptional, (69)
"Nice accommodations: close walk to a beautiful ocean beach, nice pool. Well equipped kitchen. All went great."
4-Acre Estate on Banks Rd, House & Guest cottage, Pool, Calm Protected Beach

Beautifully relaxing Beach Front Cottage, Prime Banks Road Location

9.2 out of 10, Wonderful, (78)
"We had an unforgettable second stay at this charming cottage, perfectly situated on one of the most beautiful, pristine pink sand beaches. The turquoise water, framed by rock and coral formations, is absolutely breathtaking—photos don’t do it justice! The location also offers easy access to Governor’s Harbor, making it convenient for dining and exploring the island.The cottage itself is lovely—simple yet spacious, with beautiful decor, impeccably clean, and thoughtfully stocked with all the...
Beautifully relaxing Beach Front Cottage, Prime Banks Road Location

Surrender to your tropical impulse

9.6 out of 10, Exceptional, (49)
"Exceptional , pristine Caribbean beauty!"
Surrender to your tropical impulse

Grand Beachfront Estate on Five Private Acres w/ Kayaks, Hammocks, Snorkeling

9.4 out of 10, Exceptional, (32)
"Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was more than satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: My husband and I along with 2 other couples spent 10 days in this lovely accommodation. My husband and I stayed in the Beach Cottage and listened to the waves at night as we slept. We enjoyed the convenience of the kitchen where we cooked most...
Grand Beachfront Estate on Five Private Acres w/ Kayaks, Hammocks, Snorkeling

Lux Waterfront Villa on Secluded Caribbean Cove w/

9.6 out of 10, Exceptional, (34)
"Bella Mer is absolutely wonderful. It’s spacious, clean and has everything you’d need. Our family had a marvelous time snorkeling, fishing and enjoyed meals as well as drinks right by the sea. Property management was so helpful from the moment we booked should we need informations or assistance. "
Lux Waterfront Villa on Secluded Caribbean Cove w/
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.
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Top Windermere Island Hotel Reviews

Find out more about Windermere Island

Find out more about Windermere Island

Everything you need to know about Windermere Island holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Windermere Island holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Windermere Island holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Windermere Island holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Windermere Island holiday rentals we have selected for you start as low as NZ$524 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Windermere Island rentals

At Expedia, we put the best Windermere Island holiday 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 holiday.

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.