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

Estero Island Holiday Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Estero Island holiday rentals

1. GullWing Beach Resort

GullWing Beach Resort
3.5 star property
South Island
9.6 out of 10, Exceptional, (974 reviews)
"Highly recommended, coastal by the sea, good for family outings."
United States
MARYTE
The price is NZ$956
includes taxes & fees
1 Oct - 2 Oct
GullWing Beach Resort

2. Flamingo Inn

Flamingo Inn
3.0 star property
Mid Island
8.0 out of 10, Very good, (1,025 reviews)
"Great location and cleanliness was excellent"
United States
J
The price is NZ$305
includes taxes & fees
28 Sept - 29 Sept
Flamingo Inn

3. Edison Beach House

Edison Beach House
3.5 star property
Fort Myers Beach
9.4 out of 10, Exceptional, (1,921 reviews)
"Great stay."
United States
Angie
The price is NZ$321
includes taxes & fees
28 Sept - 29 Sept
Edison Beach House

4. Getaway beach house, Downstairs unit

Getaway beach house, Downstairs unit
South Island
10.0 out of 10, Exceptional, (2 reviews)
"Very clean, quiet neighborhood. "
United States
Vickey C.
The price is NZ$525
includes taxes & fees
4 Oct - 5 Oct
Getaway beach house, Downstairs unit

5. Studio apartment across from the beach

Studio apartment across from the beach
South Island
10.0 out of 10, Exceptional, (2 reviews)
"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 NZ$722
includes taxes & fees
7 Oct - 8 Oct
Studio apartment across from the beach

6. The Strawberry Daiquiri at Lazy Way

The Strawberry Daiquiri at Lazy Way
Mid Island
10.0 out of 10, Exceptional, (20 reviews)
"Great experience, very nice place close to everything!"
United States
Harry M.
The price is NZ$700
includes taxes & fees
28 Sept - 29 Sept
The Strawberry Daiquiri at Lazy Way

7. Heated Pool Home steps to the beach

Heated Pool Home steps to the beach
South Island
9.8 out of 10, Exceptional, (9 reviews)
"Great place, clean and quiet. Owner was very responsive to questions."
United States
Scott S.
Heated Pool Home steps to the beach

8. Paradise Beach Getaway Steps to Sand & Gulf Views King Bed + Sofa Bed

Paradise Beach Getaway Steps to Sand & Gulf Views King Bed + Sofa Bed
Mid Island
10.0 out of 10, Exceptional, (1 review)
"This home was so comfy, well organized and stocked with the best smelling towels and linens. The walk to the beach was a breeze, and they had chairs, umbrellas, and toys to use on your trip. Groceries were a short walk away and communication was quick and easy. I would love to visit again."
United States
Adrienne
The price is NZ$613
includes taxes & fees
28 Sept - 29 Sept
Paradise Beach Getaway Steps to Sand & Gulf Views King Bed + Sofa Bed

9. Beach view Pool Home

Beach view Pool Home
South Island
10.0 out of 10, Exceptional, (4 reviews)
"The host was very nice! The place was very clean and a great place to stay! There are a good amount of shops and places to eat nearby as well!"
United States
Elyse M.
The price is NZ$684
includes taxes & fees
28 Sept - 29 Sept
Beach view Pool Home

10. Times Square Hideaway By FL Vibes

Times Square Hideaway By FL Vibes
Downtown Fort Myers Beach
9.8 out of 10, Exceptional, (35 reviews)
"We enjoyed our stay. Plenty of things to do. If you love to karaoke, there is a karaoke bar right next door."
United States
Amy C.
The price is NZ$555
includes taxes & fees
28 Sept - 29 Sept
Times Square Hideaway By FL Vibes

11. The Tequila Sunrise at Lazy Way

The Tequila Sunrise at Lazy Way
Mid Island
10.0 out of 10, Exceptional, (12 reviews)
"We just had a quick one night stay and it was perfect. It's close proximity to the beach within walking distance downtown. We took a golf cart and had a blast."
United States
adrian r.
The price is NZ$700
includes taxes & fees
28 Sept - 29 Sept
The Tequila Sunrise at Lazy Way

12. The Pina Colada at the Anchorage

The Pina Colada at the Anchorage
Mid Island
9.6 out of 10, Exceptional, (28 reviews)
"Super cute, clean and convenient to the beach. "
United States
Allison S.
The price is NZ$700
includes taxes & fees
28 Sept - 29 Sept
The Pina Colada at the Anchorage

13. The Lime Margarita at the Anchorage

The Lime Margarita at the Anchorage
Mid Island
9.6 out of 10, Exceptional, (14 reviews)
"Great location!"
United States
Brian S.
The price is NZ$700
includes taxes & fees
28 Sept - 29 Sept
The Lime Margarita at the Anchorage

14. Beach house with POOL and fenced in yard

Beach house with POOL and fenced in yard
South Island
10.0 out of 10, Exceptional, (3 reviews)
"Everything was clean, comfortable, and exactly as described, making it feel like a home away from home. We really appreciate the care and attention that was put into making our visit so enjoyable. we would gladly stay here again and will happily recommend your place to others!"
United States
Eduardo P.
The price is NZ$957
includes taxes & fees
15 Oct - 16 Oct
Beach house with POOL and fenced in yard

15. SEASIDE 302. Solmate is a luxurious BEACHFRONT 2BR / 2BA Condo in FMB

SEASIDE 302. Solmate is a luxurious BEACHFRONT 2BR / 2BA Condo in FMB
Mid Island
10.0 out of 10, Exceptional, (107 reviews)
"Awesome place with amazing location. Super clean with great amenities. Would definitely book again!"
United States
Jason R.
The price is NZ$969
includes taxes & fees
20 Oct - 21 Oct
SEASIDE 302. Solmate is a luxurious BEACHFRONT 2BR / 2BA Condo in FMB

16. Charming suite w/ private deck Downtown FMB

Charming suite w/ private deck Downtown FMB
Fort Myers Beach
10.0 out of 10, Exceptional, (4 reviews)
"Beautiful place , welcoming people, so close to town and beach!"
United States
Jacquelyn B.
The price is NZ$627
includes taxes & fees
28 Sept - 29 Sept
Charming suite w/ private deck Downtown FMB

17. Beach Bliss~Walk to Beach & Times Square~Private Pool

Beach Bliss~Walk to Beach & Times Square~Private Pool
Fort Myers Beach
9.8 out of 10, Exceptional, (22 reviews)
"Perfect location, great long weekend with friends."
United States
Jennifer B.
The price is NZ$881
includes taxes & fees
23 Oct - 24 Oct
Beach Bliss~Walk to Beach & Times Square~Private Pool

18. SEASIDE 204. Luna Sea is a luxurious BEACHFRONT 2BR / 2BA Condo in FMB

SEASIDE 204. Luna Sea is a luxurious BEACHFRONT 2BR / 2BA Condo in FMB
Mid Island
10.0 out of 10, Exceptional, (149 reviews)
"Easy beach access. Quieter part of Ft Myers Beach, it was never overly crowded."
United States
Steven M.
The price is NZ$914
includes taxes & fees
8 Oct - 9 Oct
SEASIDE 204. Luna Sea is a luxurious BEACHFRONT 2BR / 2BA Condo in FMB

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

Peace and quiet; Private pool - 3BR/3BA
South Island
9.2 out of 10, Wonderful, (86 reviews)
"The property was perfect for our family. The kids loved the pool and it was a short walk to the beach. Communication with the owner was excellent as well."
United States
Ben L.
The price is NZ$1,479
includes taxes & fees
28 Sept - 29 Sept
Peace and quiet; Private pool - 3BR/3BA

20. Approx.720 ft to Beach, Pool, Walk to restaurants, Beach Gear, Full Kit, WD, BBQ

Approx.720 ft to Beach, Pool, Walk to restaurants, Beach Gear, Full Kit, WD, BBQ
Fort Myers Beach
10.0 out of 10, Exceptional, (31 reviews)
"Very nice accommodations, great location!"
United States
Tammy M. A.
The price is NZ$835
includes taxes & fees
28 Sept - 29 Sept
Approx.720 ft to Beach, Pool, Walk to restaurants, Beach Gear, Full Kit, WD, BBQ
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Estero Island Hotel Reviews

Find out more about Estero Island

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Estero Island holiday 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. 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 holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Estero Island. 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 Estero Island. 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 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 holiday 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 Estero Island short-term rentals, that won’t be hard to do.

Explore a world of travel with Expedia