A sunset over a beach with people walking and playing in the water.

Estero Island Vacation Rentals

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Our top choices for Estero Island vacation rentals

Edison Beach House

Edison Beach House
3.5 star property
Fort Myers Beach
9.4 out of 10, Exceptional, (1,801 reviews)
"Every aspect fit our needs for this beach trip!"
United States
Lisa
The price is CA $206
CA $285 total
includes taxes & fees
Jul 7 - Jul 8
Edison Beach House

GullWing Beach Resort

GullWing Beach Resort
3.5 star property
South Island
9.4 out of 10, Exceptional, (955 reviews)
"We really enjoyed our stay here and plan on staying here again!"
United States
Claudia
The price is CA $195
CA $726 total
includes taxes & fees
Jul 27 - Jul 28
GullWing Beach Resort

Flamingo Inn

Flamingo Inn
3.0 star property
Mid Island
7.8 out of 10, Good, (1,010 reviews)
"Very clean and a short walk to the ocean. The property manager accommodated everything we needed and was friendly. Definitely would recommend Flamingo Inn to everyone!"
United States
Cary
The price is CA $172
CA $290 total
includes taxes & fees
Jul 8 - Jul 9
Flamingo Inn

StudioRes by Marriott Fort Myers Airport

StudioRes by Marriott Fort Myers Airport
3.0 star property
Fort Myers
9.4 out of 10, Exceptional, (73 reviews)
"Excellent facility. Favorite place to stay"
United States
Daniel
The price is CA $86
CA $96 total
includes taxes & fees
Jul 8 - Jul 9
StudioRes by Marriott Fort Myers Airport

Island Inn

Island Inn
3.5 star property
West End
9.4 out of 10, Exceptional, (1,139 reviews)
"The place was amazing and the host was very gracious."
United States
Wendy
The price is CA $368
CA $410 total
includes taxes & fees
Jul 5 - Jul 6
Island Inn

Wiggins Pass Chalet

Wiggins Pass Chalet
4.0 star property
Naples
9.6 out of 10, Exceptional, (276 reviews)
"This was in was in a great location! Everything was clean, staff was helpful and friendly. The wife and I will definitely book it again next time we’re in Naples!"
United States
Daniel Luis
The price is CA $158
CA $175 total
includes taxes & fees
Jul 22 - Jul 23
Wiggins Pass Chalet

Bellasera Resort

Bellasera Resort
4.0 star property
Old Naples
9.6 out of 10, Exceptional, (2,287 reviews)
"Everything was great! Nice hotel."
United States
Yuliia
The price is CA $353
CA $455 total
includes taxes & fees
Jul 7 - Jul 8
Bellasera Resort

Lovers Key Resort

Lovers Key Resort
3.0 star property
Fort Myers Beach
8.8 out of 10, Excellent, (1,066 reviews)
"Always a great stay"
United States
Jason
The price is CA $162
CA $414 total
includes taxes & fees
Jul 2 - Jul 3
Lovers Key Resort

Lazy Cuckoo Inn

Lazy Cuckoo Inn
2.0 star property
Fort Myers Beach
8.8 out of 10, Excellent, (291 reviews)
"Clean room, good location, easy check in instructions."
United States
Brooklyn
The price is CA $83
CA $138 total
includes taxes & fees
Jul 16 - Jul 17
Lazy Cuckoo Inn

Matlacha Tiny Village

Matlacha Tiny Village
3.0 star property
Matlacha
8.8 out of 10, Excellent, (292 reviews)
"Very nice alternative to a motel quite clean everything you need for your stay. highly recommend this property"
United States
PETER
The price is CA $156
CA $281 total
includes taxes & fees
Jul 8 - Jul 9
Matlacha Tiny Village

Sleeps 16 Plus Central Cape Coral Family Escape 4 Bedroom Home

Sleeps 16 Plus Central Cape Coral Family Escape 4 Bedroom Home
3.0 star property
Hancock
The price is CA $160
CA $738 total
includes taxes & fees
Jul 8 - Jul 9
Sleeps 16 Plus Central Cape Coral Family Escape 4 Bedroom Home

Cozy Lehigh Extended Stay

Cozy Lehigh Extended Stay
3.5 star property
Lehigh Acres
The price is CA $132
CA $289 total
includes taxes & fees
Jul 2 - Jul 3
Cozy Lehigh Extended Stay

Seaside Serenity Steps to Beach

Seaside Serenity Steps to Beach
3.0 star property
Naples Park
Seaside Serenity Steps to Beach

Tropical Mango Grove Stay Whiskey Creek Area

Tropical Mango Grove Stay Whiskey Creek Area
2.0 star property
McGregor
The price is CA $179
CA $452 total
includes taxes & fees
Jul 2 - Jul 3
Tropical Mango Grove Stay Whiskey Creek Area

Driftwood Inn

Driftwood Inn
4.0 star property
Mid Island
10.0 out of 10, Exceptional, (11 reviews)
"The cottage was well stocked with all we needed. It was also immaculate with a lovely garden. The beach was a 5 minute walk."
United States
Maureen
The price is CA $465
CA $860 total
includes taxes & fees
Jul 2 - Jul 3
Driftwood Inn

Avanti Vacation Rental, Relaxing 3-BR Retreat with Private Pool Minutes from Vanderbilt Beach and Delnor-Wiggins State Park. Enjoy Southern Exposure, BBQ Area, and Pet-Friendly Comfort

Avanti Vacation Rental, Relaxing 3-BR Retreat with Private Pool Minutes from Vanderbilt Beach and Delnor-Wiggins State Park. Enjoy Southern Exposure, BBQ Area, and Pet-Friendly Comfort
3.5 star property
Naples Park
The price is CA $362
CA $1,613 total
includes taxes & fees
Jul 7 - Jul 8
Avanti Vacation Rental, Relaxing 3-BR Retreat with Private Pool Minutes from Vanderbilt Beach and Delnor-Wiggins State Park. Enjoy Southern Exposure, BBQ Area, and Pet-Friendly Comfort

Sundial Beach Resort & Spa

Sundial Beach Resort & Spa
5.0 star property
Mid Island
8.6 out of 10, Excellent, (2,663 reviews)
"Excellent stay and amenities for families. "
United States
Megan
The price is CA $637
CA $788 total
includes taxes & fees
Jul 3 - Jul 4
Sundial Beach Resort & Spa

Sorrento Cabana: 1-Bedroom Cabana Near Vanderbilt Beach – Perfect for a Tranquil Beachside Escape

Sorrento Cabana: 1-Bedroom Cabana Near Vanderbilt Beach – Perfect for a Tranquil Beachside Escape
2.0 star property
Naples Park
The price is CA $121
CA $581 total
includes taxes & fees
Jul 13 - Jul 14
Sorrento Cabana: 1-Bedroom Cabana Near Vanderbilt Beach – Perfect for a Tranquil Beachside Escape

Milano Vacation Rental: Newly Renovated 3-BR Home with Private Pool, Hot Tub, and Pet-Friendly Front Yard. Minutes from Vanderbilt Beach

Milano Vacation Rental: Newly Renovated 3-BR Home with Private Pool, Hot Tub, and Pet-Friendly Front Yard. Minutes from Vanderbilt Beach
3.5 star property
Naples Park
8.0 out of 10, Very good, (5 reviews)
"This home is beautifully maintained in a quiet neighborhood just blocks away from the waterway. Spacious and clean with a nice pool and comfortable rooms. "
United States
Mandolin
The price is CA $165
CA $1,372 total
includes taxes & fees
Jul 2 - Jul 3
Milano Vacation Rental: Newly Renovated 3-BR Home with Private Pool, Hot Tub, and Pet-Friendly Front Yard. Minutes from Vanderbilt Beach

Imola: Newly Remodeled Pool Home Minutes from Vanderbilt Beach. Family-Friendly Retreat with 4 BR, 3.5 Bathrooms, and Private Screened Pool. Perfect Location Near Mercato and Naples Attractions

Imola: Newly Remodeled Pool Home Minutes from Vanderbilt Beach. Family-Friendly Retreat with 4 BR, 3.5 Bathrooms, and Private Screened Pool. Perfect Location Near Mercato and Naples Attractions
3.0 star property
Naples Park
The price is CA $625
CA $2,063 total
includes taxes & fees
Jul 8 - Jul 9
Imola: Newly Remodeled Pool Home Minutes from Vanderbilt Beach. Family-Friendly Retreat with 4 BR, 3.5 Bathrooms, and Private Screened Pool. Perfect Location Near Mercato and Naples Attractions
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

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Estero Island. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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