Vacation rentals with a pool in Estero Island

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Top-rated rentals with a pool in Estero Island

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Guest favorite

Condo in Fort Myers Beach

4.8 out of 5 average rating, 100 reviews

Lux condo w/ direct Beach View + beach gear

206C is not your average beach condo. Located just a matter of feet from the beach and meticulously designed with the beach lover in mind. It's the perfect place for guests to unplug, relax and enjoy time with loved ones. The perfect location for shelling, sunbathing, and walking to the local restaurants. Steps to the sugar sand Beach Across the street Santini Plaza Restaurants 6 Min Drive to Lovers Key State Park 10 Min Drive to Ft Myers Times Square Experience EBT with us & learn more below

Guest favorite

Guest suite in Naples

5 out of 5 average rating, 148 reviews

By the Beach and 5th - Studio Guest Home & Pool

Great location! Newly renovated! A studio guest home with your own private entrance & your own full kitchen & bath! A non-smoking home only 1 mile from the beach, 5th Ave dining and shops, the mall, the zoo, beautiful Baker Park, and that's not all- Only steps away are local restaurants and shops! Bikes and beach equipment included! Did we mention the pool? Or that you can sing along to your fave tunes in the shower via a Bluetooth shower speaker? This home is 350 square feet of clean cuteness!

Guest favorite

Rental unit in Fort Myers Beach

5 out of 5 average rating, 7 reviews

Sunset & Ocean Front Views-FM-Beach(Pool is Open)

Relax with a tranquil getaway. It's a lovely 1-king & 1-queen cabinet bed in living room(memory foam mattresses) 1 bath unit with a fully equipped kitchen. Balcony looks directly on the ocean.The unit faces west, for incredible, sunsets from your balcony and it's in the shade from hot Florida sun until afternoon.Located directly on the beach, yet close to public transport, nightlife, family-friendly activities, and airport.The unit comes with pool passes, free parking, use of tennis/pickelball

Guest favorite

Home in Fort Myers

4.95 out of 5 average rating, 128 reviews

Paradise on Estero Bay

Welcome to Mullock Creek a Boater's dream! Southwest views boasting breathtaking sunsets overlooking gulf access canal from your spacious backyard, just minutes away from shopping and dining at Coconut Point, and Gulf Coast Town Center. This stunning Key West Style home has been beautifully maintained and updated offering a lovely front entrance, fully equipped kitchen, spacious Living Room, dining room, Wi-Fi, private driveway with access to the open garage, fully furnished and private pool.

Guest favorite

Home in Captiva

4.97 out of 5 average rating, 114 reviews

The Pearl Beach House, North Captiva Island,FL

This water-front property offers designer furniture and panoramic views of the Gulf of Mexico throughout the home. Experience unprecedented privacy with direct walking access to the beach, and a very secluded location suitable for couples, friends or families. The property has a Main House and Guest Cottage, both with expansive decking and panoramic windows and doors providing spectacular views of the water and sunsets. StarLink WiFi and Samsung QLED smart TV. We allow dogs up to 50 lbs

Guest favorite

Condo in Fort Myers

4.92 out of 5 average rating, 154 reviews

Ft. Myers Quaint Getaway! Minutes from Beach!

My condo is close to the beach, nightlife, public transport, and family-friendly activities. It is good for couples, solo adventurers, business travelers, and families (with kids). It's minutes from Ft. Myers and Sanibel Beach. It has a King size bed in the master bedroom and two twin murphy beds in the guest room. Walking distance from a Super Target and trolley. Several outlet malls, closest is 2 miles. FYI, not handicap accessible (second floor unit). A few steps to the pool and grill.

Guest favorite

Cottage in Fort Myers Beach

4.96 out of 5 average rating, 103 reviews

Coral Reef Villa - Steps from beach / Private Pool

We're Back! Fully Renovated in 2023! Welcome to the Coral Reef Villa located at 213 Fairweather Lane, Fort Myers Beach. 2 bedroom and 1 full bathroom villa. Steps away from the beach where paradise is waiting for you. Centrally located at the North end of the island. Walk to Times Square to enjoy shopping and dining. Close to all Fort Myers Beach has to offer while also located on a quiet residential street, this home is perfect for those that demand both proximity and tranquility!

Guest favorite

Home in Fort Myers Beach

4.96 out of 5 average rating, 128 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.

Guest favorite

Rental unit in Fort Myers Beach

4.98 out of 5 average rating, 106 reviews

Island Oasis Steps From the Sugar Sand Beach

Note: This apartment had no damage from hurricanes in 2024. 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

Guest favorite

Condo in Fort Myers Beach

4.9 out of 5 average rating, 103 reviews

Lovers Key Resort/Stunning water & Sanctuary views

HIGH FLOOR Located on the 8th floor of Lovers Key Resort Unit 803 n Fort Myers / Bonita Springs Fl. Private balcony overlooking the stunning water views of Lovers Key State Park and its beautiful environment Dolphins, Manatees, exotic birds and more spotted right from the balcony. POOL IS CLOSED UNTILL FURTHER NOTICE DUE TO FLOODING FROM 10/10/24 STORM

Guest favorite

Home in Fort Myers Beach

4.95 out of 5 average rating, 125 reviews

Blue Lagoon w/ heated pool-2 min walk to beach

FMB Reg 19-1212 . Hurricane Ian caused damage to the island but the home is back fully operational as it was prior to the storm & beaches look great! Come be part of #FMBStrong! Check the Town of FMB or Chamber Websites for more info. No refunds outside our cancelation policy. TRAVEL INSURANCE IS HIGHLY RECOMMENDED FOR TRAVEL DISRUPTION.

Guest favorite

Condo in Sanibel

4.88 out of 5 average rating, 234 reviews

Rare walkout condo on Sanibel beach-Fully Restored

FULLY RESTORED AND READY FOR YOUR SANIBEL VACATION! Everything you need in this recently updated, comfortable 2 bedroom, 2 bath condo on beautiful Sanibel Island, Breakers West Unit A-6. Rare ground floor location; private walk-out patio leaves you just steps to the pool or to the world famous Sanibel beach on the Gulf of Mexico.