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Holiday rentals in Estero Bay

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Top-rated holiday rentals in Estero Bay

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top guest favourite
Home in Bonita Springs
5.0 out of 5 average rating, 101 reviews

Remodeled 4 BR 3 Full Bath Sunshine Getaway

A perfect place for couple's or families. This home boasts 2 master suites with large, covered Lani with heated pool (Nov-March 85°). A total of 7 smart TVs. Enjoy preparing a family meal in the large fully equipped kitchen with double oven and plenty of counter space. Enjoy a bike ride on one of 4 bikes or Cornhole that's provided as well as other games and beach accessories. House sits on a quiet cul-de-sac for relaxing. Absolutely no parties or events! Max Guests on property at ANY time is 8!

Top guest favourite
A private backyard features a heated saltwater pool surrounded by a spacious patio. Two loungers are positioned beside the water, while a dining table with an umbrella is visible in the distance. Tropical landscaping and trees provide a serene backdrop.
Home in North Naples
4.97 out of 5 average rating, 67 reviews

Newly Renovated Home Just Minutes From The Beach!

Welcome to the "Bonita Shores House" presented by TTM Luxury Rentals! Enjoy your time in this fully renovated 3 bedroom + Den, 2 Full Bath home, with a brand new heated saltwater pool, located in the highly desirable Bonita Shores neighborhood! Everything is new and the home is fully stocked with household supplies. Only a few minutes to Bonita Beach and lots of great restaurants & shopping nearby! This extremely comfortable & peaceful house is definitely a favorite for everyone who visits it!

Top guest favourite
Home in Bonita Springs
5.0 out of 5 average rating, 35 reviews

Estero Bay Modern Oasis

Welcome to Modern Oasis Estero Bay - a serene retreat designed to give you the ultimate vacation experience! This beautiful home has 4 bedrooms plus a bunk room, 2 bathrooms, and a great room overlooking the backyard oasis. Relax & unwind in the heated salt water pool & hot tub, grill & dine in the covered patio and enjoy the sunset views over Estero Bay. The home backs onto a golf course and is minutes to shops & restaurants at Coconut Point, and a short drive to the beautiful Barefoot Beach.

Top guest favourite
Home in Burnt Store
5.0 out of 5 average rating, 22 reviews

Villa510~3 En-Suites~Gulf Access, Heated spa~pool

Villa510 is a newly built waterfront retreat ideal for extended stays in Cape Coral. Enjoy peaceful salt canal water views and manatees from the lanai, then relax in your private heated pool and spa—perfect year-round. The outdoor kitchen and lanai create an easy, comfortable daily routine. Inside offers three private en-suite bedrooms, a den with optional airbed, open living space, and TVs in every room. Close to shopping, dining, and beaches—perfect for snowbirds seeking comfort and ease.

Top guest favourite
A spacious stilt home features large windows that provide ample natural light. An outdoor deck with seating overlooks the canal, surrounded by palm trees. A boat dock is visible alongside smooth stone pathways leading to the house, creating a tranquil waterside setting.
Home in North Naples
4.99 out of 5 average rating, 186 reviews

Waterfront ocean access canal, Kayaks, Bikes Beach

We renovated a key west style home into a modern beachy oasis. You can kayak, bike and boat to the beach right from the house! This safe waterfront neighborhood has tons of friendly people out walking, running, biking, dog walking, etc. The house is 1/4 mile to the beach as the crow flys. Beach entrances are 2 miles away. We have 2 nice adult bicycles, kayaks and fishing rods for you to use. Located just off Wiggins Pass Road between 41 and the ocean. Stilt home. Don’t even need a car.

Guest favourite
An aerial view captures a charming beach house surrounded by palm trees and sandy areas. The tranquil coastline is visible in the background, showcasing the proximity to the beach. Several residential structures line the street, enhancing the beachside community ambiance.
Home in Bonita Beach
5.0 out of 5 average rating, 8 reviews

Walk to the Beach | 2-Bedroom Tropical Oasis

Walk to the Beach | Escape to paradise! Welcome to Walk to the Beach, a charming tropical retreat located directly across from Bonita Beach Access #8. Perfect for small families, couples, or friends, this single-level beach house offers the ultimate in relaxation—no stairs required! Your tropical beachside getaway is calling! Whether you’re lounging in the backyard, exploring Bonita Beach, or making memories with loved ones, this tropical oasis is the perfect place to unwind and recharge.

Guest favourite
A spacious two-story home showcases a large outdoor deck and a well-maintained landscape featuring various tropical plants. The exterior features light-colored siding, a brown shingled roof, and ample windows that allow natural light. Pathways lead through the surrounding greenery.
Home in Bonita Beach
4.91 out of 5 average rating, 57 reviews

Elegant Beachside Luxury Home Awaits!

This stunning Bonita home is steps from the beach. It combines modern luxury with artistic flair. The home features a striking wave stained-glass window and cozy sitting nook which provides an ideal spot to watch mesmerizing sunsets. The chef’s kitchen flows into the great room and dining area, where a large picture window frames serene views of palms. The home has a generous outdoor deck. It features three beautiful bedrooms and two full bathrooms, each designed luxuriously.

Guest favourite
Home in Bonita Springs
5.0 out of 5 average rating, 7 reviews

Palm Paradise Retreat | Pool Oasis

Welcome to your private Southwest Florida retreat. This beautifully appointed 4-bedroom, 2-bathroom home features a screened-in pool, outdoor kitchen, covered lanai, and spacious indoor-outdoor living areas designed for relaxation and entertaining. Whether you're enjoying a day by the pool, grilling dinner outdoors, or exploring the area's beaches, shopping, and dining, this home offers the perfect setting for a memorable Florida getaway with family and friends.

Guest favourite
A screened pool area features a sparkling blue pool with built-in loungers for relaxation. Comfortable outdoor seating is available, with a hot tub in the corner. Bright blue skies filled with clouds enhance the vibrant atmosphere, while greenery stands tall in the background.
Home in Bonita Springs
4.76 out of 5 average rating, 17 reviews

Cozy 2 bedroom on the canal with pool and hot tub!

Welcome to your relaxing retreat in beautiful Bonita Springs, Florida. This comfortable home is located in a quiet neighborhood, offering a peaceful stay with easy access to everything Southwest Florida has to offer. Perfect for families, couples, or business travelers. You’re just a short drive from Bonita Beach, Barefoot Beach, Coconut Point shopping, and great local dining. Enjoy nearby boating, fishing, golf, and nature preserves, all within minutes.

Top guest favourite
A bright living room features a reclining sectional sofa facing an 85-inch Sony smart TV mounted on the wall. An elegant shelving unit holds decorative items. Large sliding doors lead to the pool area, enhancing natural light in the space.
Home in Bonita Springs
5.0 out of 5 average rating, 44 reviews

Barefoot Breeze 2

Welcome to Imperial Shores and the beaches of Bonita Springs and southwest Florida. This 2023 BRAND NEW home includes a Master Suite with a king bed and 3 more bedrooms with queen beds. There are three full bathrooms. Barefoot Beach is a mile away. The backyard offers a 3'-6' deep, 12' W x 37' L heated pool, patio furniture and BBQ grill. Less than 30 mins away from RSW (Airport), 10 mins from Coconut Point Mall, and 25 mins from downtown Naples.

Superhost
Home in Bonita Beach
5.0 out of 5 average rating, 4 reviews

Barefoot Bay House | Steps to Beach

Welcome to Barefoot Bay House — a Bonita Springs vacation rental near Bonita Beach and Estero Bay with bay views, beach access nearby, covered outdoor living space, and room for up to 10 guests. This 3-bedroom, 2-bath home is a great fit for families or groups looking for a relaxed Southwest Florida beach stay close to dining, boat rentals, kayaking, paddleboarding, fishing, sunset cruises, and local attractions.

Guest favourite
Home in North Naples
5.0 out of 5 average rating, 13 reviews

Naples Dream Getaway w/ a view !

!!Book with us and avoid paying Airbnb Fees!!! Luxury Lakeside Villa in Naples – Your Perfect Coastal Escape Welcome to your dream retreat in beautiful Naples, Florida! This stunning luxury villa is perfectly located just 15 minutes from the white sands of Vanderbilt Beach and close to top-tier shopping, dining, and entertainment.

Popular amenities for Estero Bay holiday rentals