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, (1593)
"Awesome stay "
United States
mary
The price is AU$351
includes taxes & fees
1 Jan - 2 Jan 2026
Edison Beach House

GullWing Beach Resort

GullWing Beach Resort
3.5 star property
South Island
9.4 out of 10, Exceptional, (932)
"The view of the beach was spectacular. "
United States
Carol
The price is AU$997
includes taxes & fees
4 Jan - 5 Jan 2026
GullWing Beach Resort

The Pina Colada at the Anchorage

The Pina Colada at the Anchorage
Mid Island
9.6 out of 10, Exceptional, (21)
"Perfect for the 3 of us"
United States
kelly m.
The price is AU$661
includes taxes & fees
28 Dec - 29 Dec
The Pina Colada at the Anchorage

Studio apartment across from the beach

Studio apartment across from the beach
South Island
10.0 out of 10, Exceptional, (2)
"Valerie was great as was the studio we stayed in in FM Beach. Immaculate, pool with hot-tub, beach across the street. A great getaway from the freezing temps up north. 5-star "
United States
Anonymous traveller
The price is AU$768
includes taxes & fees
5 Jan - 6 Jan 2026
Studio apartment across from the beach

Casa Playa #205- Toes in the Sand - Pet Friendly

Casa Playa #205- Toes in the Sand - Pet Friendly
Fort Myers Beach
10.0 out of 10, Exceptional, (8)
"We had an excellent stay at Casa Playa. The room was super clean and had everything we needed. The beach was beautiful and we enjoyed the pool as well. The staff were friendly and very responsive. We will definitely return!"
United States
Kelly
The price is AU$544
includes taxes & fees
28 Dec - 29 Dec
Casa Playa #205- Toes in the Sand - Pet Friendly

Redfish Retreat - South End Pool Home

Redfish Retreat - South End Pool Home
South Island
10.0 out of 10, Exceptional, (2)
"We were here for a long weekend to see the Minnesota Twins. Great place and location, easy walk to the beach. Clean and spacious. Highly recommend."
United States
Frank S.
The price is AU$1,145
includes taxes & fees
4 Jan - 5 Jan 2026
Redfish Retreat - South End Pool Home

Heated Pool Home steps to the beach

Heated Pool Home steps to the beach
South Island
9.8 out of 10, Exceptional, (9)
"My daughter and I had a great time in Fort Myers. The accommodations were perfect. Great location and easy beach access. Would definitely stay there again."
United States
Lisa K.
The price is AU$777
includes taxes & fees
5 Jan - 6 Jan 2026
Heated Pool Home steps to the beach

The Lime Margarita at the Anchorage

The Lime Margarita at the Anchorage
Mid Island
9.6 out of 10, Exceptional, (12)
"Close to the beach"
United States
BO
The Lime Margarita at the Anchorage

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)
"Great stay good location nice property "
United States
George T.
The price is AU$929
includes taxes & fees
4 Jan - 5 Jan 2026
Stunning 2/2 with balcony in the Heart of Downtown Fort Myers Beach!

Quaint beautiful backyard sanctuary

Quaint beautiful backyard sanctuary
Fort Myers Beach
9.0 out of 10, Wonderful, (2)
"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$790
includes taxes & fees
6 Jan - 7 Jan 2026
Quaint beautiful backyard sanctuary

Flamingo Inn

Flamingo Inn
3.0 star property
Mid Island
7.8 out of 10, Good, (983)
"Will definitely stay here again!"
United States
Sasha
The price is AU$331
includes taxes & fees
5 Jan - 6 Jan 2026
Flamingo Inn

720 ft to beach, 2 BR 2 BA, Pool, Beach Gear, Deck, BBQ, W/D, sleeps 6.

720 ft to beach, 2 BR 2 BA, Pool, Beach Gear, Deck, BBQ, W/D, sleeps 6.
4.0 star property
Fort Myers Beach
9.6 out of 10, Exceptional, (29)
"It was a great place. Wish we had had more time there!"
United States
Fred M.
The price is AU$953
includes taxes & fees
27 Jan - 28 Jan 2026
720 ft to beach, 2 BR 2 BA, Pool, Beach Gear, Deck, BBQ, W/D, sleeps 6.

Dockside Dream Lower Unit - Canal Front - Spa/Pool

Dockside Dream Lower Unit - Canal Front - Spa/Pool
TP Hill's
10.0 out of 10, Exceptional, (3)
"Great spot, so close to the beach and the action"
United States
Chad K.
The price is AU$550
includes taxes & fees
3 Jan - 4 Jan 2026
Dockside Dream Lower Unit - Canal Front - Spa/Pool

The Tequila Sunrise at Lazy Way

The Tequila Sunrise at Lazy Way
Mid Island
10.0 out of 10, Exceptional, (5)
" Long weekend to visit family! Place is as advertised. Great location - although Fort Myers Beach is still in process of rebuilding - was perfect for our needs - great communication with manager - highly recommend!"
United States
Evamarie W.
The price is AU$768
includes taxes & fees
1 Jan - 2 Jan 2026
The Tequila Sunrise at Lazy Way

Stunning 1/1 with Heated pool and Spa in the Heart of Downtown Fort Myers Beach!

Stunning 1/1 with Heated pool and Spa in the Heart of Downtown Fort Myers Beach!
Fort Myers Beach
10.0 out of 10, Exceptional, (2)
"Great location. "
United States
Dexter S.
The price is AU$698
includes taxes & fees
8 Jan - 9 Jan 2026
Stunning 1/1 with Heated pool and Spa in the Heart of Downtown Fort Myers Beach!

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, (110)
"Great place"
United States
Glenn H.
The price is AU$1,053
includes taxes & fees
5 Jan - 6 Jan 2026
Beach Bungalow 2B/2B Private Pool/Spa, North End, Newly Renovated

Times Square Hideaway By FL Vibes

Times Square Hideaway By FL Vibes
2.0 star property
Downtown Fort Myers Beach
9.8 out of 10, Exceptional, (19)
"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$729
includes taxes & fees
7 Jan - 8 Jan 2026
Times Square Hideaway By FL Vibes

Bahia Tide • Lower Unit • New Intro Pricing • Pool • Steps to Beach

Bahia Tide • Lower Unit • New Intro Pricing • Pool • Steps to Beach
2.0 star property
South Island
10.0 out of 10, Exceptional, (1)
"We had a great stay! Walking distance to the beach, and the kids loved the pool. The host was very helpful also. We plan to come back next year. "
United States
Noah L.
The price is AU$704
includes taxes & fees
8 Jan - 9 Jan 2026
Bahia Tide • Lower Unit • New Intro Pricing • Pool • Steps to Beach

Beach Bliss~Private Pool~Steps to Fort Myers Beach Sleeps 7

Beach Bliss~Private Pool~Steps to Fort Myers Beach Sleeps 7
Fort Myers Beach
10.0 out of 10, Exceptional, (5)
"Great location, convenient and very well decorated."
United States
Andrea N.
The price is AU$1,308
includes taxes & fees
2 Jan - 3 Jan 2026
Beach Bliss~Private Pool~Steps to Fort Myers Beach Sleeps 7

Peace and quiet; Private pool - 3BR/3BA

Peace and quiet; Private pool - 3BR/3BA
South Island
9.2 out of 10, Wonderful, (79)
"Description fit the bill, perfect for three couples looking for some R and R! Close enough to beach, quiet canal, great scenery. "
United States
Anonymous traveller
The price is AU$1,262
includes taxes & fees
5 Jan - 6 Jan 2026
Peace and quiet; Private pool - 3BR/3BA
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$331 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.