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Holiday Rentals in Estero Island

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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, (1586)
"Awesome stay "
United States
mary
The price is €181
includes taxes & fees
23 Dec - 24 Dec
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 €477
includes taxes & fees
3 Jan - 4 Jan 2026
GullWing Beach Resort

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 €197
includes taxes & fees
12 Jan - 13 Jan 2026
Flamingo Inn

Docked at Dakota Sunset - Mid Island Pool Home

Docked at Dakota Sunset - Mid Island Pool Home
2.0 star property
Mid Island
The price is €813
includes taxes & fees
3 Jan - 4 Jan 2026
Docked at Dakota Sunset - Mid Island Pool Home

Redfish Retreat - South End Pool Home

Redfish Retreat - South End Pool Home
2.0 star property
South Island
The price is €753
includes taxes & fees
3 Jan - 4 Jan 2026
Redfish Retreat - South End Pool Home

Docked at Dakota Sunrise

Docked at Dakota Sunrise
2.0 star property
Mid Island
The price is €925
includes taxes & fees
11 Jan - 12 Jan 2026
Docked at Dakota Sunrise

Hyatt Vacation Club at Coconut Cove, Bonita Springs

Hyatt Vacation Club at Coconut Cove, Bonita Springs
4.0 star property
Bonita Springs
9.2 out of 10, Wonderful, (736)
"Room great clean, staff great.loved pool"
United States
Dennis
The price is €215
includes taxes & fees
5 Jan - 6 Jan 2026
Hyatt Vacation Club at Coconut Cove, Bonita Springs

StudioRes Fort Myers Airport

StudioRes Fort Myers Airport
3.0 star property
Fort Myers
8.8 out of 10, Excellent, (15)
"Clean room, staff, amenities, easy check in, easy access to gas stations, restaurants, and retail. "
United States
Gina
The price is €96
includes taxes & fees
30 Dec - 31 Dec
StudioRes Fort Myers Airport

Wiggins Pass Chalet

Wiggins Pass Chalet
4.0 star property
Naples
9.6 out of 10, Exceptional, (243)
"Room was very clean, staff was awesome, and the location was perfect. I will definitely stay here again."
United States
Tamisha
Wiggins Pass Chalet

Island Inn

Island Inn
3.5 star property
West End
9.4 out of 10, Exceptional, (1122)
"Really nice, updated, and clean room with a screened waterfront balcony in a perfect place on the island (far enough away from the big resorts to be in a quieter area, but close enough to the center area of the island to be convenient). "
United States
Chris
The price is €247
includes taxes & fees
4 Jan - 5 Jan 2026
Island Inn

Lovers Key Resort

Lovers Key Resort
3.0 star property
Fort Myers Beach
8.8 out of 10, Excellent, (1017)
"Nice place"
United States
patrick
Lovers Key Resort

Sundial Beach Resort & Spa

Sundial Beach Resort & Spa
5.0 star property
Mid Island
8.6 out of 10, Excellent, (2584)
"wonderful family friendly and spotless resort"
United States
Mary Anne
The price is €414
includes taxes & fees
20 Jan - 21 Jan 2026
Sundial Beach Resort & Spa

Matlacha Tiny Village

Matlacha Tiny Village
3.0 star property
Matlacha
8.8 out of 10, Excellent, (268)
"Very nice place with all necesary accommodations for a Pleasant stay. "
United States
isabel
The price is €183
includes taxes & fees
5 Jan - 6 Jan 2026
Matlacha Tiny Village

Resort Harbour Properties

Resort Harbour Properties
3.5 star property
Punta Rassa
9.6 out of 10, Exceptional, (364)
"10/10 would stay there again"
United States
Kristie
Resort Harbour Properties

Hibiscus House Bed Breakfast Citrus Room

Hibiscus House Bed Breakfast Citrus Room
2.0 star property
Fort Myers River District
10.0 out of 10, Exceptional, (1)
"Absolutely beautiful room and amenities and the breakfast was delicious and with so many options. Loved the communication and cannot wait to come back! "
United States
Crissa
The price is €190
includes taxes & fees
22 Dec - 23 Dec
Hibiscus House Bed Breakfast Citrus Room

Lazy Cuckoo Inn

Lazy Cuckoo Inn
2.0 star property
Fort Myers Beach
9.0 out of 10, Wonderful, (225)
"Room was very clean, and spacious. Very convenient location for Ft. Myers’s beach and Sanibel. "
United States
ANNA
The price is €85
includes taxes & fees
21 Dec - 22 Dec
Lazy Cuckoo Inn

Modern 2BR Fort Myers Condo Pool, BBQ & Near Beaches

Modern 2BR Fort Myers Condo Pool, BBQ & Near Beaches
3.0 star property
Three Oaks
The price is €296
includes taxes & fees
6 Jan - 7 Jan 2026
Modern 2BR Fort Myers Condo Pool, BBQ & Near Beaches

Hibiscus House Bed Breakfast Seashell Room

Hibiscus House Bed Breakfast Seashell Room
2.0 star property
Fort Myers River District
The price is €227
includes taxes & fees
3 Jan - 4 Jan 2026
Hibiscus House Bed Breakfast Seashell Room

Hibiscus House Bed Breakfast Inn Flamingo Suite

Hibiscus House Bed Breakfast Inn Flamingo Suite
2.0 star property
Fort Myers River District
The price is €190
includes taxes & fees
21 Dec - 22 Dec
Hibiscus House Bed Breakfast Inn Flamingo Suite

Hibiscus House Bed Breakfast Inn Turtle Room Bed-ada

Hibiscus House Bed Breakfast Inn Turtle Room Bed-ada
2.0 star property
Fort Myers River District
The price is €195
includes taxes & fees
3 Jan - 4 Jan 2026
Hibiscus House Bed Breakfast Inn Turtle Room Bed-ada
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, apart-hotels, 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 favorite 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 depends 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 €181 per night. Entering your travel dates in the search wizard you might find 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.