Estero Island Holiday Rentals

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Our top choices for Estero Island holiday rentals

Edison Beach House

Edison Beach House
3.5 star property
Fort Myers Beach
9.4 out of 10, Exceptional, (1,645 reviews)
"Staff is very friendly & accommodating. Location is great. Close to bars, restaurants, shopping and right on the beach. "
United States
Ellen
The price is AU$602
includes taxes & fees
24 Feb - 25 Feb
Edison Beach House

GullWing Beach Resort

GullWing Beach Resort
3.5 star property
South Island
9.4 out of 10, Exceptional, (932 reviews)
"The view of the beach was spectacular. "
United States
Carol
GullWing Beach Resort

Flamingo Inn

Flamingo Inn
3.0 star property
Mid Island
7.8 out of 10, Good, (987 reviews)
"Quiet, clean and updated room. Easy walk to the beach."
United States
KATHLEEN
The price is AU$416
includes taxes & fees
1 Mar - 2 Mar
Flamingo Inn

Villa Del Mar 402

Villa Del Mar 402
3.0 star property
Mid Island
The price is AU$1,239
includes taxes & fees
11 Mar - 12 Mar
Villa Del Mar 402

Owners Featured on HGTV- Private Terrace - Private Beach Path - Mid Island Luxry

Owners Featured on HGTV- Private Terrace - Private Beach Path - Mid Island Luxry
Mid Island
10.0 out of 10, Exceptional, (22 reviews)
"Very nice stay in a clean and quiet unit with a "
United States
Ron T.
The price is AU$915
includes taxes & fees
24 Feb - 25 Feb
Owners Featured on HGTV- Private Terrace - Private Beach Path - Mid Island Luxry

Grace by The Sea · 2025 Build · Steps to Beach

Grace by The Sea · 2025 Build · Steps to Beach
Mid Island
10.0 out of 10, Exceptional, (2 reviews)
"Perfect property for 6 friends. Great location and amenities."
United States
Michele M.
The price is AU$1,854
includes taxes & fees
14 Feb - 15 Feb
Grace by The Sea · 2025 Build · Steps to Beach

Stunning 2/2 with balcony in the Heart of Downtown Fort Myers Beach!

Stunning 2/2 with balcony in the Heart of Downtown Fort Myers Beach!
Fort Myers Beach
10.0 out of 10, Exceptional, (4 reviews)
"Great stay good location nice property "
United States
George T.
Stunning 2/2 with balcony in the Heart of Downtown Fort Myers Beach!

Beach Cottage With Heated Pool - The Beach Is In Sight!

Beach Cottage With Heated Pool - The Beach Is In Sight!
Mid Island
10.0 out of 10, Exceptional, (1 review)
"Beautiful and peaceful. Close to everything. Pool and outdoor space was perfect. "
United States
Erica C.
Beach Cottage With Heated Pool - The Beach Is In Sight!

Villa Capri · 2025 Luxury Build · Steps to Beach

Villa Capri · 2025 Luxury Build · Steps to Beach
Mid Island
10.0 out of 10, Exceptional, (4 reviews)
"Location to beach. Beautiful house! "
United States
Clayton C.
The price is AU$2,928
includes taxes & fees
24 Feb - 25 Feb
Villa Capri · 2025 Luxury Build · Steps to Beach

Dockside Dream Upper Unit - Canal front - Spa/Pool

Dockside Dream Upper Unit - Canal front - Spa/Pool
TP Hill's
10.0 out of 10, Exceptional, (1 review)
"Host was amazing! We had a great time. Home was perfect for our needs and walking distance to everything we wanted!! Perfect location! "
United States
Ashley W.
The price is AU$1,288
includes taxes & fees
11 Feb - 12 Feb
Dockside Dream Upper Unit - Canal front - Spa/Pool

Beach Bungalow 2B/2B Private Pool/Spa, North End, Newly Renovated

Beach Bungalow 2B/2B Private Pool/Spa, North End, Newly Renovated
Fort Myers Beach
9.8 out of 10, Exceptional, (115 reviews)
"Great place"
United States
Glenn H.
The price is AU$870
includes taxes & fees
22 Feb - 23 Feb
Beach Bungalow 2B/2B Private Pool/Spa, North End, Newly Renovated

Vacation Villas #633: Coastal Beachfront Condo on the North Tip of Island

Vacation Villas #633: Coastal Beachfront Condo on the North Tip of Island
Fort Myers Beach
10.0 out of 10, Exceptional, (1 review)
"Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: The condo was wonderful - great location, great view, we had a wonderful time. The biggest issue was trying to figure out the TV, some instructions would have been helpful. Also, the lights in the dining and living room were really bright, it would...
United States
Tim D.
The price is AU$1,823
includes taxes & fees
17 Feb - 18 Feb
Vacation Villas #633: Coastal Beachfront Condo on the North Tip of Island

Mango Margarita- Beach Home with Pool, Sleeps 12

Mango Margarita- Beach Home with Pool, Sleeps 12
Fort Myers Beach
9.8 out of 10, Exceptional, (9 reviews)
"Easy check in and out, good location to the beach, lots of space. "
United States
Deidre M.
The price is AU$1,951
includes taxes & fees
14 Feb - 15 Feb
Mango Margarita- Beach Home with Pool, Sleeps 12

Beyond The Sea · Newer House · Walk to Beach-Town

Beyond The Sea · Newer House · Walk to Beach-Town
Fort Myers Beach
10.0 out of 10, Exceptional, (16 reviews)
"Location was perfect for us "
United States
Tadd H.
The price is AU$1,779
includes taxes & fees
4 Mar - 5 Mar
Beyond The Sea · Newer House · Walk to Beach-Town

Casa Playa Resort #201 - "Paradise Palms"

Casa Playa Resort #201 - "Paradise Palms"
Fort Myers Beach
10.0 out of 10, Exceptional, (2 reviews)
"This spot is truly awesome!Clean, great seating area and kitchen. "
United States
Mark T.
The price is AU$817
includes taxes & fees
4 Mar - 5 Mar
Casa Playa Resort #201 - "Paradise Palms"

Flip Flop Paradise - 3 Bdrms, Pool, Steps to the Beach

Flip Flop Paradise - 3 Bdrms, Pool, Steps to the Beach
Mid Island
10.0 out of 10, Exceptional, (6 reviews)
"Big, comfortable, and truly just a few steps from the beach. The place is on the main road but it's on the quiet end of the island and is actually very quiet. We would definitely stay here again."
United States
Charles R.
The price is AU$1,554
includes taxes & fees
28 Feb - 1 Mar
Flip Flop Paradise - 3 Bdrms, Pool, Steps to the Beach

Times Square Hideaway By FL Vibes

Times Square Hideaway By FL Vibes
Downtown Fort Myers Beach
9.8 out of 10, Exceptional, (20 reviews)
"This vrbo is in the perfect location. It's steps from the beach, food trucks, restaurants, and Margarittaville's public areas."
United States
Trudy C.
The price is AU$843
includes taxes & fees
4 Mar - 5 Mar
Times Square Hideaway By FL Vibes

Quaint beautiful backyard sanctuary

Quaint beautiful backyard sanctuary
Fort Myers Beach
9.0 out of 10, Wonderful, (2 reviews)
"The house was clean and neat. They are currently putting a pool in to make future stays even more relaxing! The construction was no bother at all, we spent most of our time at the beach anyways. Cant wait to stay here again and enjoy the pool on the next go around."
United States
Kyle K.
The price is AU$1,146
includes taxes & fees
25 Feb - 26 Feb
Quaint beautiful backyard sanctuary

Luxury Coastal Retreat | Stunning Ocean Views & Walk to Times Square

Luxury Coastal Retreat | Stunning Ocean Views & Walk to Times Square
Fort Myers Beach
8.0 out of 10, Very good, (1 review)
"It was a beautiful home in a great location. Steps away from Time Square, but far enough away to enjoy quiet time. "
United States
Lori L.
The price is AU$1,950
includes taxes & fees
5 Mar - 6 Mar
Luxury Coastal Retreat | Stunning Ocean Views & Walk to Times Square

Villa Sorrento · 2026 Luxury · 4 Kings · Near Town

Villa Sorrento · 2026 Luxury · 4 Kings · Near Town
Fort Myers Beach
10.0 out of 10, Exceptional, (7 reviews)
"We absolutely loved our stay at Villa Sorrento. The house and decor was absolutely gorgeous! We loved hanging out in the pool and the beach was beautiful and just a short walk down the road. The house was stocked with Tommy Bahama beach chairs and umbrellas, a cooler, a beach wagon, toys and the most kitchen cookware and supplies we have ever seen. We will definitely be back!!"
United States
Nicole C.
Villa Sorrento · 2026 Luxury · 4 Kings · Near Town
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 Estero Island Hotel Reviews

Find out more about Estero Island

Everything you need to know about Estero 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 Estero 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 Estero Island holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Estero Island holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Estero 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 depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Estero 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 Estero Island holiday rentals we have selected for you start as low as AU$416 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Estero Island rentals

At Expedia, we put the best Estero 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 Estero 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 Estero 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 Estero 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.