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

Holiday Rentals in Estero Island

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Our top choices for Estero Island holiday rentals

1. Edison Beach House

Edison Beach House
3.5 star property
Fort Myers Beach
9.4 out of 10, Exceptional, (1,958 reviews)
"One of the best locations on Ft Myers Beach"
United States
mark
The price is €200
includes taxes & fees
9 Nov - 10 Nov
Edison Beach House

2. GullWing Beach Resort

GullWing Beach Resort
3.5 star property
South Island
9.4 out of 10, Exceptional, (984 reviews)
"Gullwing is an excellent beach front condo property. Very well maintained, friendly staff and close to amenities."
United States
Jennifer
The price is €503
includes taxes & fees
1 Dec - 2 Dec
GullWing Beach Resort

3. Flamingo Inn

Flamingo Inn
3.0 star property
Mid Island
8.0 out of 10, Very good, (1,028 reviews)
"Cute, clean, beachside inn. Will definitely be back!"
United States
Emily
The price is €156
includes taxes & fees
3 Nov - 4 Nov
Flamingo Inn

4. Harbour House at the Inn 308

Harbour House at the Inn 308
3.0 star property
Fort Myers Beach
The price is €476
includes taxes & fees
3 Nov - 4 Nov
Harbour House at the Inn 308

5. Lovers Key Resort

Lovers Key Resort
3.0 star property
Fort Myers Beach
8.8 out of 10, Excellent, (1,097 reviews)
"Room location had a amazing view"
United States
Joanne
The price is €266
includes taxes & fees
3 Nov - 4 Nov
Lovers Key Resort

6. Lazy Cuckoo Inn

Lazy Cuckoo Inn
2.0 star property
Fort Myers Beach
8.8 out of 10, Excellent, (304 reviews)
"Great place!"
United States
Bruce
The price is €88
includes taxes & fees
3 Nov - 4 Nov
Lazy Cuckoo Inn

7. StudioRes by Marriott Fort Myers Airport

StudioRes by Marriott Fort Myers Airport
3.0 star property
Fort Myers
9.4 out of 10, Exceptional, (180 reviews)
"Location was great."
United States
Joseph
The price is €84
includes taxes & fees
8 Nov - 9 Nov
StudioRes by Marriott Fort Myers Airport

8. Island Inn

Island Inn
3.5 star property
West End
9.4 out of 10, Exceptional, (1,167 reviews)
"Great location"
United States
Nicole
The price is €269
includes taxes & fees
30 Nov - 1 Dec
Island Inn

9. Wiggins Pass Chalet

Wiggins Pass Chalet
4.0 star property
Naples
9.6 out of 10, Exceptional, (297 reviews)
"Great location very close to beach and restaurants."
United States
Maribel
The price is €118
includes taxes & fees
3 Nov - 4 Nov
Wiggins Pass Chalet

10. Sundial Beach Resort & Spa

Sundial Beach Resort & Spa
5.0 star property
Mid Island
8.6 out of 10, Excellent, (2,717 reviews)
"Love the resort and great access to beach"
United States
Lisa Renee
The price is €408
includes taxes & fees
29 Nov - 30 Nov
Sundial Beach Resort & Spa

11. 3 Mi to Fort Myers Beach! Family Getaway w/ Pool

3 Mi to Fort Myers Beach! Family Getaway w/ Pool
3.0 star property
Iona
3 Mi to Fort Myers Beach! Family Getaway w/ Pool

12. Lakeside Oasis Fort Myers

Lakeside Oasis Fort Myers
2.0 star property
Iona
The price is €225
includes taxes & fees
15 Nov - 16 Nov
Lakeside Oasis Fort Myers

13. Driftwood Inn

Driftwood Inn
4.0 star property
Mid Island
10.0 out of 10, Exceptional, (11 reviews)
"Great place to stay on sanibel"
United States
Terri
The price is €410
includes taxes & fees
5 Nov - 6 Nov
Driftwood Inn

14. Starfish Cottage by Avantstay Naples Studio Private Patio Near Vanderbilt Beach + Mercato

Starfish Cottage by Avantstay Naples Studio Private Patio Near Vanderbilt Beach + Mercato
3.0 star property
Naples Park
The price is €270
includes taxes & fees
3 Nov - 4 Nov
Starfish Cottage by Avantstay Naples Studio Private Patio Near Vanderbilt Beach + Mercato

15. Fort Myers Coastal Retreat Hot Tub Yard Games

Fort Myers Coastal Retreat Hot Tub Yard Games
2.0 star property
San Carlos Park
The price is €431
includes taxes & fees
10 Nov - 11 Nov
Fort Myers Coastal Retreat Hot Tub Yard Games

16. Matlacha Tiny Village

Matlacha Tiny Village
3.0 star property
Matlacha
9.0 out of 10, Wonderful, (299 reviews)
"So cute and clean nice dock to sit and relax or fish. Kayaks available to use free as well with life jackets paddles, etc. well equipped rental we can’t wait to go again! Great communication with hosts."
United States
Lori
The price is €195
includes taxes & fees
3 Nov - 4 Nov
Matlacha Tiny Village

17. Park Shore Resort

Park Shore Resort
3.0 star property
Park Shore
8.8 out of 10, Excellent, (733 reviews)
"I have been going there for over 30 years, and park shore never disappoints. We love the atmosphere and the tranquility."
United States
nathaly
The price is €212
includes taxes & fees
5 Nov - 6 Nov
Park Shore Resort

18. Bellasera Resort

Bellasera Resort
4.0 star property
Old Naples
9.6 out of 10, Exceptional, (2,344 reviews)
"Really enjoyed the stay, the staff was very friendly. And the property is very conveniently located"
United States
vasilisa
The price is €373
includes taxes & fees
3 Nov - 4 Nov
Bellasera Resort

19. Coastal Paradise

Coastal Paradise
3.0 star property
Old Naples
Coastal Paradise

20. Pineapple Cottage by Avantstay Cozy Cottage + BBQ Patio Private Entrance Beach + Mercato Nearby

Pineapple Cottage by Avantstay Cozy Cottage + BBQ Patio Private Entrance Beach + Mercato Nearby
3.0 star property
Naples Park
The price is €270
includes taxes & fees
3 Nov - 4 Nov
Pineapple Cottage by Avantstay Cozy Cottage + BBQ Patio Private Entrance Beach + Mercato Nearby
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 €156 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. 

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