Vacation rentals with a pool in Estero Island

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Top-rated rentals with a pool in Estero Island

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Guest favorite

Guesthouse in Fort Myers

4.98 out of 5 average rating, 622 reviews

Hints of Key West in Fort Myers' Historic District

Tucked away in tranquil Dean Park Historic District. Built in 1925, this carriage house has been completely renovated in 2016. It is over a garage, there are stairs. Stroll to downtown Fort Myers River District, and enjoy the restaurants, nightlife, and cultural events. Take advantage of all the activities the area has to offer, and at the end of the day come back to this peaceful oasis. Our place can accommodate couples, older child (twin air mattress available), business travelers. No pets.

Apr 12 – 19

ﺩ.ﺇ582 per night

Guest favorite

Home in Fort Myers Beach

5.0 out of 5 average rating, 26 reviews

5 O’Clock at Miramar

It’s always five o’ clock at our cozy oasis located just steps from FMB! Quaint street close to the iconic Times Square & dozens of restaurants. Short 5 min walk to deeded walkway to Fort Myers Beach. Boating your thing? Canal access at the end of the street. Ranch home (no steps!) that currently sleeps up to six with two king bedrooms, one Murphy queen bed, two full baths, stocked kitchen, wifi, onsite laundry, ample parking! Brand new pool. Kick back & relax your cares away! FMB STR# 22-0240

Sep 24 – Oct 1

ﺩ.ﺇ1,274 per night

Guest favorite

Home in Fort Myers

4.93 out of 5 average rating, 161 reviews

*Relaxing and Fun Pyramid Home in Ft Myers (7048)

Get ready for a unique vacation in a fully equipped pyramid home!! Enjoy exploring all of southwest Florida and then return home where you can relax on your own private patio or jump in the natural spring water lake! Located in south Ft Myers, easy distance to most attractions, 15 miles to beaches!! -Free WIFI -washer dryer -full kitchen -2 patios with dining area -self check in with lock box -perfect for families, great friends, couples -Beach gear provided -2 bedrooms/ 1 bathroom unit

Aug 8 – 15

ﺩ.ﺇ571 per night

Guest favorite

Apartment in Fort Myers Beach

5.0 out of 5 average rating, 6 reviews

Sun and fun! Adorable 1 bedroom condo on the beach

If you are craving some sunshine and blue waters, come on down! Morning walks with your toes in the sand set the tone for another day in Paradise. Spend the day in the surf and sun, then finish off another perfect day quietly entranced by another unique and spectacular sunset. Whether you want to relax on the balcony and enjoy looking at the gulf, play in the surf, lay out on the beach or pick shells, lounge by the pool or enjoy a few rounds of tennis and pickle ball, you won't be bored.

Oct 13 – 20

ﺩ.ﺇ716 per night

Guest favorite

Home in Fort Myers Beach

4.96 out of 5 average rating, 120 reviews

Coastal Oasis of Fort Myers Beach

Welcome to Fort Myers Beach Florida. This stunning, waterfront, contemporary ranch offers 5 bedrooms & 3 bathrooms. You will be impressed with the 2024 renovation from top to bottom. It will meet even the most discriminating of client's wish list. Pulling into the driveway you will notice beautiful, tropical landscaping. Entering the home through large French doors, you will be captivated by the elegant decor & immediate views of the stunning infinity pool and deep canal.

Apr 23 – 30

ﺩ.ﺇ3,476 per night

Guest favorite

Apartment in Fort Myers Beach

4.9 out of 5 average rating, 194 reviews

Mermaid Oasis

Ft Myers beach Bonita Mermaid Oasis’s dream getaway! 1 bedroom King bed , full kitchen, spacious living room, sofa sleeper couch, beautiful balcony. Bathroom with a Jacuzzi tub, walk-in shower, private toilet area. The beautiful bay and pool invite you to come play. Flippers 5-star restaurant on the property. You can enjoy water sports long walks on Lovers Key Beach across the street. Only minutes to Bonita Naples and Ft. Myers beach, reviews say it all!

Jun 13 – 20

ﺩ.ﺇ468 per night

Guest favorite

Tiny home in Fort Myers

5.0 out of 5 average rating, 48 reviews

Tiny Home close to beach- Sun Kissed Hide-A-Way

Welcome to our SunKissed Hide-a-way! Located 3 short miles from beautiful Fort Myers’ beaches. This Tiny Home (built in 2014) can sleep 4. One bedroom- queen bed and in the living room a queen sized pull out couch (super comfy- I promise). Two smart TV’s and Wi-Fi. Full kitchen with table seating for 4. Outdoor patio dining area. Beach chairs, towels, & toys available for use. Located 30 minutes from RSW airport. **The community has been affected by Hurricane Ian**

Jul 20 – 27

ﺩ.ﺇ405 per night

Guest favorite

Home in Fort Myers

4.94 out of 5 average rating, 273 reviews

Whole cozy house

Entire cozy house just for you friends and family. Perfect to spend a pleasant and relaxed moment. If you plan to have a party or event, this place is NOT for you. The neighbors are very strict in terms of noise and large groups of people. Well maintained house. CLEAN POOL BUT NOT HEATED. Walk in to a living area and separated dining. 20 minutes to airport, 25 minutes to the beach, fine dining and entertainment. For a virtual tour, click on the cover photo twice.

Jun 2 – 9

ﺩ.ﺇ669 per night

Guest favorite

Apartment in Fort Myers Beach

4.98 out of 5 average rating, 94 reviews

Island Oasis Steps From the Sugar Sand Beach

Home was completely restored after Hurricane Ian. Lots of work happening in the area to repair our beautiful paradise. Beaches are beautiful and our brand new pool is complete and ready to enjoy. Be one of the first to enjoy this complete remodel renovation. No expense was spared here. Top quality memory foam mattresses with high end bed linens for a restful sleep. Fresh and fluffy hospitality towels for both bath and beach. One block away from beach

Jul 15 – 22

ﺩ.ﺇ797 per night

Guest favorite

Home in Fort Myers Beach

4.89 out of 5 average rating, 219 reviews

La Casa On Mango, heated pool-5 min walk to Beach

The house, officially registered under FMB Reg 19-1316, is located at the northern end of the Island, just a leisurely 3-5 minute stroll to Public Beach Access No. 27 at the end of Mango street, providing easy access to the white-sand beach of the Gulf of Mexico. Its lush landscaping and a fully equipped beach cottage comfortably blend modern living with tropical leisure, making this house a perfect place for relaxation and enjoyment.

Apr 21 – 28

ﺩ.ﺇ1,822 per night

Guest favorite

Home in Fort Myers Beach

4.94 out of 5 average rating, 108 reviews

Luxury Waterfront Escape Near The Beach C1

2023 Fully renovated DBOW Paradise on Cutlass C1 is located on a canal with direct gulf access. The beach, dining, shopping and activities are all under 3 miles away. A modern, open concept home that opens right up to an outdoor living space and pool. Families, couples, and groups will love the privacy of the bedrooms and bathrooms at the end of a day of playing or relaxing. This is the best that Fort Myers Beach has to offer!!

Mar 1 – 8

ﺩ.ﺇ3,911 per night

Guest favorite

Home in Fort Myers Beach

5.0 out of 5 average rating, 7 reviews

Crain's Perch will WOW you!

You've had to put your vacation at the Beach on hold, we are ready for you now! While our rental homes may look a little different, yards may not be as lush as Fort Myers Beach rebuilds, we can tell you that all our homes that have been either renovated or rebuilt and have been inspected thoroughly to meet your needs. When choosing your home, please be sure to read the descriptions carefully.

Dec 11 – 18

ﺩ.ﺇ1,148 per night