Waterfront holiday rentals in Estero Bay

4.88 out of 5 average rating, 123 reviews

The modern exterior of the home is highlighted by a manicured lawn and tropical landscaping, featuring palm trees and colorful shrubs. A paved driveway leads to a two-car garage, while a covered entrance invites guests into the villa.

Villa in Cape Coral

Heated Pool | Canal | Modern | New | Southern Exp.

Welcome to the brand new, absolutely stunning, Villa Southbreeze! This 3 bedroom, 2 bathroom vacation rental is fully furnished &equipped. Stunning high ceilings, huge 72" fireplace, office, laundry room all Samsung stainless-steel appliances, and much more. Out by the huge screened-in pool area you'll find a private electric heated pool, BBQ propane grill, several loungers, large table + chairs. The heated pool features two fountains and a shallow "beach area". Welcome to the villa Southbreeze!

Cottage in Bonita Springs

A covered outdoor seating area features two lounge chairs beside a natural rug. String lights hang from the wooden ceiling, providing soft illumination. The view of the canal, adorned with lush greenery, is visible beyond the inviting space, enhancing the tranquil atmosphere.

4.89 out of 5 average rating, 54 reviews

The Bonita Bitty Beach Cottage

Welcome to the Bonita Bitty! This 2 bed, 1 bath direct waterfront cottage is the perfect getaway spot to relax & recharge. Outdoor dining and lounge area with private canal mangrove views with the occasional manatee & dolphin visit. Unbeatable location in a quaint neighborhood only 1 mile to walk/bike to the beautiful beaches. Downtown, parks, restaurants, cafes, & breweries minutes away. Explore all Bonita, Naples, & Fort Myers paradises have to offer from this Bonita duplex. Estero Bay fishing

4.97 out of 5 average rating, 127 reviews

A clear blue pool is surrounded by a spacious patio, featuring comfortable loungers partially immersed in the water. The inviting outdoor space overlooks the serene canal, while the covered lanai offers additional seating options. Lush palm trees sway gently in the background under a bright sky.

Home in Cape Coral

Boater’s Paradise-Stunning Sunsets! Games Room!

Renovated lanai! This 3 bed/4 bath home is on the nicest canal with 200+ ft of frontage & gorgeous views of the canal & sunset. The pool, tiki hut & docks have full sun all day. Each bedroom has a private bath & there's a 2 pc powder room off the laundry. The primary has a king bed & walkout to pool. The 2nd bedroom has a queen bed & pool access. Bedroom 3 has a queen & private bath. Fully equipped kitchen with everything you need. And a games room! Enjoy stunning sunsets under the tiki hut.

4.97 out of 5 average rating, 410 reviews

A private patio area features a smooth surface bordered by lush tropical plants and colorful flowers. A three-tiered blue water fountain adds a calming element, accompanied by comfortable seating arrangements. The space is set against a backdrop of vibrant greenery, presenting a serene outdoor escape.

Guest suite in Naples

Tropical Garden Studio Cottage (2 miles to beach)

Studio beach cottage experience in North Naples. Take one of the two complementary bicycles on an easy 15 min bike ride to the beautiful Wiggins Pass State Park or Vanderbilt beach. Just 3 miles from the popular Mercado shops, restaurants and theater. Prefer to walk? It's less than 10 mins walking to multiple great restaurants, grocery stores, and even paddle board/boat rentals, fishing trips, dolphin eco sunset & tours. Feeling adventurous? Take one of double kayaks from the dock to the beach.

4.93 out of 5 average rating, 15 reviews

Beachfront, Estero Beach Tennis 708A Weekly Stays

Wake up to stunning sunrises and wind down with breathtaking sunsets in this beautifully renovated beachfront condo on the South End of Ft Myers Beach. Enjoy luxury finishes throughout, including a sleek quartz countertop kitchen, modern appliances, and a spa-inspired walk-in shower. The layout and private balcony offer unbeatable ocean & bay views, making it the perfect escape for relaxation, comfort, and coastal elegance—all just steps from the sand. 708A is where your dream vacation starts!

4.93 out of 5 average rating, 67 reviews

A spacious open-concept living area is showcased, featuring a modern kitchen with an island and sleek cabinetry. Large glass doors provide abundant natural light and views of the outdoors. Rustic wooden beams contrast with the contemporary décor, highlighting both elegance and comfort.

Home in Cape Coral

AquaLux Smart Home

Unwind in style in this spacious and modern home. Here's what awaits you: Smart Home Technology: Control lights, temperature, and even the front door with voice commands or your smartphone for a seamless experience. Heated Saltwater Pool: Take a refreshing dip in the sparkling pool, perfect for year-round enjoyment. Dedicated Workout Area: Maintain your fitness routine with a private space equipped for exercise. Freshwater Canal Views: Wake up to calming water views and the sounds of nature.

A private balcony offers a panoramic view of the Gulf of Mexico at sunset. The tranquil water reflects hues of orange and pink, while the distant shoreline features a pier extending into the bay. Two lounge chairs are positioned to enhance the outdoor experience.

4.94 out of 5 average rating, 36 reviews

Beachfront Gulf View Lovers Key Beach Club #1002

Our beautiful 1BR condo is located directly on a private, white sugar-sand beach with beautiful Gulf and bay views from a private balcony. Modern amenities and new furnishings including two 40" flat screen smart TVs. Enjoy the heated swimming pool, gas grills and our uncrowded beach, with lovely Lovers Key State Park Beach connected directly to ours. Easy access to shopping, dining, and the trolley. There are many activities/watersports here or simply relax. Keep an eye out for the dolphins!

A living area is seen featuring large glass doors that offer a view of the waterfront. Rattan furniture, including a sofa and coffee table, complements the room. Decorative sea-themed artwork adorns the walls, creating a bright and airy atmosphere.

4.95 out of 5 average rating, 115 reviews

Romance! Awesome Beach & Views! 5 Stars

Feeds the senses & nourishes the soul! Away from the crowds and noise is this spectacular, waterfront (on the beach) 5 Star corner condo allowing you private unobstructed views of the Gulf, San Carlos Pass, Fort Myers Beach, City Lights, Back Bays, wildlife and is on Lover’s Key State Park Beach (#4 in US & 3 miles of pristine white sand shelling beach and 700 acres of nature). Don't risk your chance for a lifetime memorable experience anywhere else. There is bridge construction currently.

4.99 out of 5 average rating, 166 reviews

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 Naples

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.

5 out of 5 average rating, 6 reviews

Tide & Seek: Beach-front and Resort Amenities

Welcome to Tide & Seek! This stylish 2 bedroom, 2 bath condo at Gull Wing Beach Resort is perfectly situated on the peaceful south end of Fort Myers Beach. Sleeping 6, this 8th-floor retreat features an open living space, full kitchen with coffee & wine bar, and a screened balcony with angled Gulf views. With resort amenities including a heated pool, spa, grilling area, and direct beach access, it’s the ideal spot for families or friends to unwind in coastal comfort.

4.82 out of 5 average rating, 33 reviews

The exterior of the cottage is showcased against a vibrant sunset sky. A manicured lawn with colorful shrubs surrounds the property. Large windows reflect the evening light, while a modern metal roof complements the inviting design. A paved pathway leads to the entrance.

Home in Bonita Springs

Stunning Beach Cottage!

Welcome to paradise. Stunning cottage one mile from the beach! Three bedrooms, two bathroom, one with a brand new steam shower. This house is immaculately appointed and sits on a little lake. Enjoy the fire pit on any cold nights. Relax in the heated pool and hot tub or enjoy the patio which is screened in and includes a BBQ and relaxing seating. This really is a fantastic location, close to shopping, restaurants and the beach. Small dog ok with pet fee.