Beachfront holiday rentals in Estero

4.96 out of 5 average rating, 136 reviews

A serene beach scene features soft, white sand leading to gentle waves. A long wooden pier extends into the calm water, framed by a vibrant sunset sky filled with hues of orange and purple. The atmosphere conveys tranquility as clouds float overhead.

Home in Naples Park

Beach Bliss Haven|Steps to Vanderbilt| Free HotTub

Welcome to your Naples getaway, just steps from Vanderbilt Beach! Our home combines comfort & convenience, perfect for families or couples. Inside, enjoy a fully-equipped kitchen, cozy living space, and plush bedrooms. Outdoors, your private hot tub awaits—ideal for unwinding after a day at the beach. Amenities include high-speed Wi-Fi, washer/dryer, and beach essentials. Within walking distance, you'll find great dining, shopping, and water activities. Book now for the ultimate Florida escape!

4.97 out of 5 average rating, 35 reviews

A heated swimming pool area features lounge chairs surrounded by palm trees and tropical plants. The clear water glistens under the sun, while a private dock extends nearby along the canal, offering a serene waterfront view.

Home in Fort Myers Beach

Island getaway, dock, heated pool, walk to beach

Experience Fort Myers Beach by staying in this spacious 1BR 1Bath home (within a triplex), situated in the serene, peaceful neighborhood right on the canal. Its prime location offers a relaxing retreat in a resort like setting while allowing quick access to beautiful, sunny beaches. The stylish design and rich amenity list will satisfy your every need. ✔ 1 Comfy BR w/Queen Bed ✔ Full Kitchen ✔ Patio ✔ Heated Pool ✔ High-Speed Wi-Fi ✔ Workstation ✔ 2 Smart TVs ✔ Free Parking See More below!

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.

4.96 out of 5 average rating, 114 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.

A modern living area is depicted with a light blue couch and a wooden coffee table. Large glass doors provide access to a balcony with outdoor seating, allowing natural light to fill the space. Curtains frame the windows, and a tasteful lamp adds ambient lighting.

5 out of 5 average rating, 16 reviews

Beachfront condo on 10 acres of pristine beach.

Enjoy the Beach Life! This beautiful one-bedroom condo on the beach with partial ocean views for breathtaking sunsets situated on 10 acres of beauty. Estero Beach & Tennis is ready for a new vacation experience BRAND NEW- heated pool, lobbies, laundry rooms, pool area, BBQ areas, tennis courts, pickleball and bocce ball. Across the street from Santinis Plaza! Our Island is 7 miles of paradise, plenty to do here-enjoy walks on the beach, fishing & watching the dolphins & shelling! Paradise

5 out of 5 average rating, 21 reviews

Home in Fort Myers Beach

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.

4.9 out of 5 average rating, 121 reviews

A two-story beach house features a bright blue exterior and large windows, surrounded by palm trees and lush greenery. A wooden staircase leads to the entrance, with a deck visible on the upper level. The sandy area offers a welcoming beach environment.

Home in Captiva

Blue Laguna - Vacation in paradise!

Beautiful and welcoming are just two words to describe this magnificent, 4 story home with heated private pool and sweeping 360 degree water views from the observation deck. Blue Laguna features 3 bedrooms and 3 full baths allowing this home to sleep up to 6 people. Two screened in lanai's so you can sit and enjoy the island breeze and leave the sliding doors open for a true island nature experience during the colder seasons. A golf cart for 4 persons is also included in the rental.

Superhost

Flat in Sanibel

5 out of 5 average rating, 4 reviews

Sundial E304: Gulf Front 3BR w/Stunning Ocean View

BRAND NEW - RIGHT ON THE BEACH! Enjoy stunning direct gulf-front views from nearly every room at this relaxing 3BR coastal retreat. This luxury residence was fully renovated to include a custom expanded kitchen, 2 gorgeous bathrooms, and washer & dryer. Top of the line coastal furnishings in every room. The large master bedroom offers spectacular gulf views & a full-size desk in case you need a quiet space to work. WiFi has been fully upgraded to make streaming and video a breeze.

Apartment in Bonita Springs

A vibrant sunset is captured over the Gulf of Mexico, blending oranges and yellows as the sun meets the horizon. Silhouettes of palm trees and people can be seen in the foreground, adding depth to the serene coastal view.

4.95 out of 5 average rating, 41 reviews

Half-Way To Heaven II, The Best on Bonita Beach!!!

Our proximity to one of the best beaches in the world on the Gulf of Mexico as well as our flexible rental program is unique in Southwest Florida. We are dedicated to insuring you have a relaxing, enjoyable and unforgettable stay with us and that you will return year after year!!! We are located on the beautiful six-mile Bonita Beach in Florida. We are close to Southwest Florida International Airport (RSW). Ours is a friendly and welcoming community of owners and their Guests.

4.83 out of 5 average rating, 186 reviews

Home in Fort Myers

Blue Beach Bungalow

3 large bedrooms (3 king sized beds) with TV in everyroom, plus a full den, laundry room, HEATED pool and the house has its own beach with an in-ground fire pit that seats 12, lounge chairs, and sunset views! Walking distance to shopping centers, great restaurants, 20 minutes to RSW Airport and Fort Myers' white-sand beaches, perfect for a romantic get-away and 10 minutes from downtown Fort Myers Completely remodeled in July of 2021 with brand new appliances electronics,

Superhost

5 out of 5 average rating, 4 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, 114 reviews

Beachfront Condo • Direct Gulf Views + 2 Bikes

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, and high-speed WiFi to pool, tennis, and stocked beach gear. Steps from the sand with sunsets you’ll never forget.