Beachfront holiday rentals in Estero Island

4.98 out of 5 average rating, 43 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!

4.82 out of 5 average rating, 112 reviews

Oceanfront Views + Balcony Sunsets Bikes Included

“Caihlin, you were a phenomenal host.” – Sandy, May 2025 ☀️ What You’ll Love: • Unbeatable Views: Floor-to-ceiling glass sliders open to the Gulf—watch dolphins, sunsets, and seabirds from your private balcony. • Free Beach Bikes: Cruise the beach or explore nearby Lovers Key with the 2 bikes we provide. • Updated Interior: Modern kitchen, stainless appliances, granite countertops, and a cozy living area with coastal decor. • Comfy King Bed: Sleep to the sound of waves in a plush king-size

4.95 out of 5 average rating, 111 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.

Top guest favourite

Home in Fort Myers Beach

5 out of 5 average rating, 49 reviews

Beyond The Sea · Newer House · Walk to Beach-Town

A stylish coastal home with lush banana and palm trees only a 6 min walk to the powdery sugar sand beach. In the morning, enjoy sipping coffee on the covered front porch with the bay breeze. During the day, relax by the saltwater heated pool on sun loungers with a good book! At night, enjoy the tropical backyard and grill out on our comfy outdoor living set with an evening fire! The best part.. you can take a sunset stroll to the beach bars, open air restaurants or local ice cream shoppes🍦

4.94 out of 5 average rating, 35 reviews

Newly Renovated Second Floor 1 Bedroom Condo

We are back! Everything in the apartment is all brand new - be the first to experience our newly renovated space! Vacation Villas is the northernmost building on the island, with a secluded beachfront for your enjoyment, but only a short one mile walk to 'Times Square' - the heart of the island. Outdoor living at its best: on the beach, at the pool, on the private lanai, or cooking in the grilling area. Sink your toes in the powdered sugar sand and you will never want to go anywhere else!

4.9 out of 5 average rating, 121 reviews

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.

Top guest favourite

5 out of 5 average rating, 53 reviews

Relax FMB Gulf views/ pool Beautiful 2B/2B condo

White Cap Beach condo is just steps away from the gulfs white sandy beach. Relax, unwind, and create beautiful memories in this 2b/2b condo! The master bedroom oasis has a king size bed, full bathroom, private balcony, and a streaming TV. The second bedroom boasts a beachy feel with two twin beds and a streaming TV. The living room has a pull out queen sofa and a new 60 inch 4k TV. The fully loaded kitchen contains all your cooking needs. Enjoy Gulf views from your front balcony.

4.94 out of 5 average rating, 105 reviews

Apartment in Captiva

South Seas Resort Beach Villa 🌴 On The Beach !

South Seas 2527 is located in the Beach Villas area of the South Seas Resort, the Gulf of Mexico and pool can be viewed from the private lanai. This second floor unit has one king size bed located in the bedroom and pull out queen size sleeper sofa. The kitchen is fully stocked, there is an inside and outside dining table for your enjoyment. Beach chairs, umbrella and beach towels are provided with this unit since resort amenities are not available when you rent through an owner.

4.84 out of 5 average rating, 176 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,

4.92 out of 5 average rating, 103 reviews

Lovers Key Beach Club Private Beach

* Minimum age to book is 25 please. * 7 night minimum Lovers Key beach front, with all of Lovers Key State Park just across the street which also has beautiful white, sand beaches. Beach...Dolphins...Fishing...Kayaking...Biking...right out your door! Beautiful sunrise and sunsets from the condo. Private beach with private pool. Next door to multiple beaches, restaurants and bars within short distance. Private enough to be out of the hustle and bustle.

4.97 out of 5 average rating, 29 reviews

Apartment in Sanibel

"Seaspray" - beachfront, Amazing GULF VIEWS!

Hurricane Update: When Hurricane Ian hit on September 28, 2022 it devastated the island. Many complexes are still recovering. There is a likelihood that you will hear construction noises throughout your stay from our complex or neighboring complexes depending on the dates of your stay. We appreciate you being part of the healing process. There are plenty of local restaurants and shops to experience during your stay! #SanibelStrong