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Estero Island Vacation Rentals

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Our top choices for Estero Island vacation rentals

1. Edison Beach House

Edison Beach House
3.5 star property
Fort Myers Beach
9.4 out of 10, Exceptional, (1,973 reviews)
"Best place ever"
United States
Joshua
The price is CA $219
CA $300 total
includes taxes & fees
Nov 17 - Nov 18
Edison Beach House

2. GullWing Beach Resort

GullWing Beach Resort
3.5 star property
South Island
9.6 out of 10, Exceptional, (987 reviews)
"Gullwing is an excellent beach front condo property. Very well maintained, friendly staff and close to amenities."
United States
Jennifer
The price is CA $239
CA $777 total
includes taxes & fees
Dec 16 - Dec 17
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 CA $133
CA $243 total
includes taxes & fees
Nov 16 - Nov 17
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 CA $498
CA $741 total
includes taxes & fees
Nov 16 - Nov 17
Harbour House at the Inn 308

5. The June

The June
2.0 star property
Mid Island
9.8 out of 10, Exceptional, (8 reviews)
"The stay was great the place was nice, clean, and in a great location!"
United States
Alexzandria
The price is CA $184
CA $483 total
includes taxes & fees
Nov 25 - Nov 26
The June

6. 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, (112 reviews)
"Place is great. Great location and beautiful ocean views everything we needed for a great vacation"
United States
Mordechai S.
The price is CA $250
CA $760 total
includes taxes & fees
Nov 16 - Nov 17
SEASIDE 302. Solmate is a luxurious BEACHFRONT 2BR / 2BA Condo in FMB

7. The "Tommy Suite". North end of the Island! 350 yrds. from The Gulf of America!

The "Tommy Suite". North end of the Island! 350 yrds. from The Gulf of America!
Fort Myers Beach
9.6 out of 10, Exceptional, (35 reviews)
"Awesome place, would stay again!"
United States
David A.
The price is CA $213
CA $606 total
includes taxes & fees
Nov 16 - Nov 17
The "Tommy Suite". North end of the Island! 350 yrds. from The Gulf of America!

8. Times Square Hideaway By FL Vibes

Times Square Hideaway By FL Vibes
Downtown Fort Myers Beach
9.8 out of 10, Exceptional, (36 reviews)
"Place was amazing and in the perfect location for everything!"
United States
Jacob S.
The price is CA $228
CA $488 total
includes taxes & fees
Nov 16 - Nov 17
Times Square Hideaway By FL Vibes

9. 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, (28 reviews)
"Perfect location, great long weekend with friends."
United States
Jennifer B.
The price is CA $213
CA $597 total
includes taxes & fees
Nov 16 - Nov 17
Beach Bliss~Walk to Beach & Times Square~Private Pool

10. 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 CA $232
CA $549 total
includes taxes & fees
Nov 16 - Nov 17
The Pina Colada at the Anchorage

11. 2 BR 2 BA, 720 ft to beach, Pool, 75" TV, Beach Gear, Deck, BBQ, W/D, sleeps 6

2 BR 2 BA, 720 ft to beach, Pool, 75" TV, Beach Gear, Deck, BBQ, W/D, sleeps 6
Fort Myers Beach
9.6 out of 10, Exceptional, (36 reviews)
"We had a lovely stay at this wonderful home hosted by Sandy and Brian. It had all the comforts of home and thensome! They thought of everything. Would definitely stay there again! "
United States
Bob L.
The price is CA $213
CA $662 total
includes taxes & fees
Nov 16 - Nov 17
2 BR 2 BA, 720 ft to beach, Pool, 75" TV, Beach Gear, Deck, BBQ, W/D, sleeps 6

12. 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 CA $231
CA $568 total
includes taxes & fees
Dec 7 - Dec 8
Paradise Beach Getaway Steps to Sand & Gulf Views King Bed + Sofa Bed

13. 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 CA $232
CA $549 total
includes taxes & fees
Nov 16 - Nov 17
The Tequila Sunrise at Lazy Way

14. Heated Pool Home steps to the beach

Heated Pool Home steps to the beach
South Island
9.8 out of 10, Exceptional, (9 reviews)
"Very nicely decorated and great location."
United States
Karri W.
The price is CA $195
CA $547 total
includes taxes & fees
Nov 16 - Nov 17
Heated Pool Home steps to the beach

15. 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 CA $232
CA $549 total
includes taxes & fees
Nov 16 - Nov 17
The Lime Margarita at the Anchorage

16. Peaceful Coastal Suite • King Bed + Kitchenette

Peaceful Coastal Suite • King Bed + Kitchenette
Fort Myers Beach
The price is CA $189
CA $482 total
includes taxes & fees
Dec 13 - Dec 14
Peaceful Coastal Suite • King Bed + Kitchenette

17. 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 CA $141
CA $428 total
includes taxes & fees
Nov 16 - Nov 17
Getaway beach house, Downstairs unit

18. Paradise Primo Lower: 5-Min Walk to Fort Myers Beach, 1 Pet OK

Paradise Primo Lower: 5-Min Walk to Fort Myers Beach, 1 Pet OK
Fort Myers Beach
10.0 out of 10, Exceptional, (2 reviews)
"Property was clean and ready. Great location and host was great."
United States
Patrick A.
The price is CA $284
CA $718 total
includes taxes & fees
Nov 16 - Nov 17
Paradise Primo Lower: 5-Min Walk to Fort Myers Beach, 1 Pet OK

19. Extended Family Dream Entire Property! 6 Bedroom!

Extended Family Dream Entire Property! 6 Bedroom!
Mid Island
The price is CA $445
CA $1,067 total
includes taxes & fees
Nov 16 - Nov 17
Extended Family Dream Entire Property! 6 Bedroom!

20. 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 CA $176
CA $524 total
includes taxes & fees
Nov 18 - Nov 19
Studio apartment across from the beach
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.