Holiday rentals with a pool in Estero Island

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Top-rated rentals with a pool in Estero Island

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Top Guest favourite
A contemporary living space features a comfortable sofa and a coffee table adorned with decorative items. Large glass doors open to a private balcony with ocean views, allowing natural light to fill the room. Soft colors and minimalistic decor create an inviting ambiance.
Condo in Fort Myers Beach
4.98 out of 5 average rating, 50 reviews

Beach Sanctuary Condo

Wake up to the Gulf's gentle breezes and breathtaking views from your private balcony! Sip morning coffee or unwind with a cocktail while a stunning sunset paints the sky. Keep an eye out for playful dolphins and watch the fascinating dance of pelicans and seabirds in the protected sanctuary below – it's nature's daily show! Our beach sanctuary is ready for you, although the island is still rebuilding, convenience is just moments away. Book your escape now and experience the magic of the Gulf!

Guest favourite
Two comfortable reclining chairs are positioned on a private balcony, facing the beach. A small table is set between them, featuring a pitcher with a garnish and a couple of glasses. Palm trees are visible beyond the railing, framing a distant view of the ocean.
Apartment in Fort Myers Beach
4.94 out of 5 average rating, 16 reviews

Salt Air Gulf View Pool Condo Steps from the Beach

This 2-bed, 2-bath condo has EVERYTHING for your sunny beach getaway! The master bedroom has a king bed and ensuite bathroom for privacy, while the second bedroom has 2 twins next to another full bathroom. Just steps from the white sand beaches with beach towels and chairs provided. Enjoy the pool or private balconies while you unwind and soak up the sunshine. A short walk to Publix and the island's favorite hangout, Junkanoo. Note: this second-floor unit’s elevator is currently out of order.

Top Guest favourite
Aerial view of a stunning coastline, featuring soft white sand intertwined with turquoise waters. Small boats are anchored near the shore, where a few individuals enjoy the beach. Lush greenery and houses are visible in the background, contributing to the serene landscape.
Condo in Fort Myers Beach
4.98 out of 5 average rating, 56 reviews

Luxury Beach Condo On The Bay In A tropical Oasis!

Stylish beach condo located on the bay in Estero Island is one of the most beautiful places in all of Florida. There is activities for all ages from fishing, boating, swimming, bicycling and kayaking. You can enjoy World Famous Seafood Restaurants or hang out in the tropical laid back downtown. The condo is walking distance to the beach or a short drive to Lovers Key. Where you can find dolphins exotic shells, manatees, live conch and sea dollars. Memories made here will last a life time!!

Top Guest favourite
An open living area features a kitchen island with seating for four, surrounded by white cabinetry and stainless steel appliances. A comfortable seating area with light gray furniture invites relaxation, complemented by natural light streaming through multiple windows. Decorative accents add a welcoming touch.
Home in Fort Myers Beach
4.95 out of 5 average rating, 19 reviews

Paradise Found

Located in Sun Retreats Fort Myers Beach (formerly Indian Creek), just 3 miles from Fort Myers Beach, Bunche, and Sanibel Island, and Margaritaville. The property offers amenities, including pools, pickleball, tennis, and numerous activities. It’s a great location, away from the main beach traffic but still close to shopping, and you can bike or walk to the beach. The trolley also stops right at the entrance. The bungalow features a fully equipped kitchen. Must be 35 to book, park rules.

Top Guest favourite
Home in Fort Myers Beach
5 out of 5 average rating, 27 reviews

Just Beachy • Pool • 2 Kings+ • 3 Min to Beach

Personally hosted by Paul & Alicia of Dancing Palms Vacations, this brand-new home offers Gulf views from the front porch—just steps from the white-sand beach. The 3BR/2BA retreat sleeps 8 with 2 KING bedrooms, a private heated pool, and a fenced outdoor living/dining area with TV and boutique coastal hotel vibe. Enjoy all-new furnishings, games, and beach gear. Open-concept living/kitchen/dining with 85” smart TV. Family-friendly and walkable to bars, restaurants, shops, and the marina.

Top Guest favourite
The outdoor area features a spacious paved patio surrounding a private heated pool. Lounge chairs are positioned by the poolside, and a grill is visible nearby. The pink-hued villa and a screened lanai area can be seen in the background.
Cottage in Fort Myers Beach
4.97 out of 5 average rating, 134 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 favourite
Condo in Fort Myers Beach
4.91 out of 5 average rating, 11 reviews

Gorgeous condo with pool and spa

Welcome to Margarita Mansion! This intimate four-condo development features a large heated pool, spa, free bikes and is within walking distance to the beautiful white sandy beaches of Fort Myers Beach, FL. This listing is for unit 5 at Margarita Mansion, which features two bedrooms and two bathrooms. Pet friendly with a sleeping capacity of up to seven guests, with a patio and bikes this listing is perfect for guests seeking an amenity rich experience that is close to the beach!

Top Guest favourite
A serene pool area features a champagne-style hot tub connected to a shimmering pool, surrounded by a marble deck. A vibrant mural of a sea turtle decorates the wall, while lounge chairs are positioned nearby, inviting relaxation amidst lush tropical landscaping.
Home in Bonita Springs
4.98 out of 5 average rating, 146 reviews

Luxe Unique: Close to Beach, Hot Tub, Heated Pool

Step into the luxurious 2BR 2BA oasis in the heart of Bonita Springs, FL. It promises a relaxing retreat just a few minutes from the pristine Bonita Beach, restaurants, shops, exciting attractions, and natural landmarks. The stylish design and a rich amenity list will leave you in awe. ✔ 2 Comfortable Bedrooms ✔ Open Design Living ✔ Fully Equipped Kitchen ✔ Backyard (Pool, Hot Tub, Swim-Up Bar, BBQ) ✔ Lounge Pool House ✔ Workspace ✔ Smart TVs ✔ Wi-Fi ✔ Parking See more below!

Top Guest favourite
The living room features a spacious sectional sofa, providing ample seating. Large glass doors open to the outdoor area, enhancing natural light. A mounted TV displays beach scenery, while a modern fireplace adds a touch of warmth. The room's design promotes comfort and relaxation for guests.
Home in Cape Coral
4.98 out of 5 average rating, 121 reviews

2 Kings, Pool, Gulf Canal, Game Room and Kayaks

Unwind Cape Coral welcomes you to sunny southwest Florida, close to magnificent beaches, fishing, shelling, Minnesota Twins Spring Training & much more. Come enjoy this new construction home with heated pool, Kayaks, heated and cooled game room (PlayStation 5), gulf access - salt water canal, 4k oled tv's & many more refreshing amenities. You will love this clean & bright home with lovely décor. Located in the highly sought after Pelican neighborhood of Southwest Cape Coral!

Top Guest favourite
Condo in Fort Myers Beach
4.83 out of 5 average rating, 118 reviews

Gulf Water Views + 2 bikes, beach gear weekly stay

Beachfront & Gulf Water Views at Estero Beach & Tennis Club 206C Wake up to unobstructed Gulf views in this 5-star Fort Myers Beach condo! Enjoy early check-in, no checkout chores, and every comfort—from a king GhostBed, full kitchen with dishwasher, free high-speed WiFi, heated pool, tennis/pickleball courts, BBQ grills, free parking, and stocked beach gear. Steps from the sand with sunsets you’ll never forget.

Top Guest favourite
An open kitchen and dining area features a round glass table surrounded by rattan chairs adorned with tropical patterns. Stainless steel appliances are positioned next to light cabinetry. Expansive windows invite natural light, providing a view of the outdoor scenery.
Condo in Bonita Springs
4.99 out of 5 average rating, 148 reviews

Casa Bonita - Relax @ The Beach (Newly Remodeled)

Beach within steps of this beautifully remodeled condo! DOC's restaurant & jet ski rentals, directly across the street. Beach gear available along with a cart to transport. Luxurious king size bed with extra plush mattress topper. Queen size sofa bed. Our studio will sleep up to 3 people (2 adults, 1 child) Newly refurbished pools opened April 2nd 2025.

Top Guest favourite
The eight-story building stands prominently along the vibrant green waters of Lovers Key State Park. Lush landscaping surrounds the property, with residential docks and a restaurant visible along the water's edge, enhancing the serene coastal environment.
Condo in Fort Myers Beach
4.93 out of 5 average rating, 168 reviews

Lovers Key Resort/Ft Myers Beach/Condo/Pool/View

HIGH FLOOR Located on the 8th floor of Lovers Key Resort Unit 803, 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 your balcony. Pool / Hot tub / gym

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