Holiday houses in Estero Island

4.92 out of 5 average rating, 198 reviews

Ft Myers Beach & Lovers Key State Park- FANTASTIC!

BEACHES ARE OPEN! Beautiful Views, large unit, Enjoy the sun, beach, and excitement of Florida. Lovers Key State Park, beautiful beaches, hiking & biking trails, Ft Myers Beach, white sand, many activities. Views of the gulf & bay area. Exercise room, wifi, great swimming pool- the beaches & trails you come to Florida for. Ft Myers beach has the white sand you think of when visiting Florida. The Gulf Coast Beach, and Lovers Key State Park are there for your enjoyment. Great place for Memories

4.98 out of 5 average rating, 115 reviews

Island Oasis Steps From the Sugar Sand Beach

Important Note: This apartment had no damage from hurricanes in 2024. Everything is perfect here. Beaches are beautiful, pool is relaxing and welcoming. Thankfully the island restaurants and bars are also back up and going in fun island style! Beaches are beautiful and our brand new pool is complete and ready to enjoy. Be one of the first to enjoy this complete remodel renovation. No expense was spared here. Top quality memory foam mattresses with high end bed linens for a restful sleep. F

4.99 out of 5 average rating, 216 reviews

Home in Cape Coral

LUX Villa w/ Private Salt Water Pool, Lanai, Canal

Are you looking to swim, relax outdoors, fish and take in beautiful sunsets on a wide gulf access canal? If so you will fall in love with this stunning newly constructed custom built home! The 2750 square foot home is bright & airy with two main bedroom on-suites & a separate family wing! The gourmet kitchen, dining room & great room open via large sliders to the lanai & pool w/ views of the canal in much desired SW Cape! Beach inspired villa! Large captains walk & Tiki! Check out our reviews!

4.93 out of 5 average rating, 30 reviews

Beachfront Lovers Key Beach Club Condo 1002

Our remodeled 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!

5 out of 5 average rating, 27 reviews

Home in Fort Myers Beach

Luxury Beachside House W/ Heated Pool & Elevator

261 Key West is a luxurious Oceanside single-family pool home with private elevator that will satisfy the most exquisite taste. You will not only enjoy the fine quality and style of the home, you will enjoy the Gulf waters and the soft white sandy beaches of the Gulf just footsteps from your door. Your stay will include beach chairs, umbrellas, sand toys, fishing rods, kayak, paddle boards, and bicycles for your enjoyments. Enjoy a stylish experience at this centrally-located place.

4.98 out of 5 average rating, 118 reviews

Ready to Enjoy again! Everything is brand new!

This vacation rental unit has been totally rebuilt and is now ready to welcome guests again! Nearly everything is brand new and it is likely one of the nicest studio apartments now available on the entire island. Skip the dated condos and hotels and get ready to enjoy this newer, nicer option, located just 1 short block (800 feet) from the sand. As you’ll see from the reviews it had a great track record before the storm, and it’s been rebuilt even better! Enjoy NEW!

Guesthouse in Fort Myers Beach

4.85 out of 5 average rating, 61 reviews

Beachside Living – Walk to the Water!

Escape to our cozy one-bedroom beach retreat! Located on the lower level with a private entrance, enjoy your own living room, bathroom, and peaceful privacy. Just a 5-minute walk to the beach and 10 minutes to the island center. Relax outdoors with seating and a refreshing outdoor shower. Parking is available, plus boat parking on the canal. The perfect mix of comfort and convenience for your island getaway. Book now and enjoy sun, sand, and serenity just steps away!

5 out of 5 average rating, 6 reviews

Beachfront Bliss!

Experience the ultimate Fort Myers Beach getaway in our charming 2B/2Ba condo overlooking the beach! This retreat features a king master suite and second bedroom with full and twin beds. Enjoy modern walk-in showers, fully equipped kitchen boasting SS appliances and quartz tops. Stay connected with high-speed Wi-Fi, unwind on the balcony with stunning Gulf views, stroll along the beach, or explore the vibrant Times Square area. Your perfect beach escape awaits!

5 out of 5 average rating, 4 reviews

Seaside 302 - Beachfront 2BR/2BA - Solmate on FMB

Solmate is a well-appointed, breathtaking beach front condo located mid-island on beautiful Fort Myers Beach, FL. This is a 2br/2ba third floor unit with direct beach front views. The condo sleeps up to 6 people. The full kitchen has everything you need from pans to an air fryer and everything else in between. The bedrooms and living room have flat screen 4K HD Smart Tvs for your entertainment. Supermarket is located literally across the street.

4.96 out of 5 average rating, 250 reviews

Home in Cape Coral

Dolphin beach house 2

ONE OF THE BEST WATERFRONTS IN CAPE CORAL! A short walk to the beach a. This 2,500+sq ft home has stunning sunsets and South Western water views from all main living areas,as well as the Master Suite. Heated pool w/ LED colored lighting, built in Spa,Pool bath, full laundry facility, Lanai,Fireplace ,Wi-fi and TVs in every bedroom, private dock . Boat on lift for rent w/RPM rentals . Large 2-car garage w/5 bicycles,beach wagon & cooler on site.

4.81 out of 5 average rating, 107 reviews

EBT 206C Exceptional Panoramic Gulf Views +2 Bikes

“Caihlin, you were a phenomenal host.” – Sandy, May 2025 Unit 206C at Estero Beach & Tennis Club offers the ultimate beachfront escape in Fort Myers Beach’s exclusive South End. With direct ocean views, pristine interiors, and steps to the sand, it’s perfect for relaxing, dolphin watching, and soaking up beach vibes. Thoughtfully designed and packed with top-tier amenities, it’s no surprise this clean, luxurious condo is a 5-star favorite.

4.9 out of 5 average rating, 79 reviews

Boutique condo on the bay, short walk to the beach

This beautifully updated Condo sits right on Estero Bay with a beautiful view of the water right outside the back door. The beach, shopping plaza, drugstore, and Marina are within a very short walking distance making this condo perfectly situated in the quiet end of Fort Myers Beach. Kick back, relax, and unwind in this elegant yet casual Condo.

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Popular amenities for Estero Island holiday rentals

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Pool

Free parking on premises

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Other great holiday rentals in Estero Island

4.99 out of 5 average rating, 96 reviews

Villa in Cape Coral

LAST Minute! NEW Villa-Heated Saltwater Pool & Spa

JimRating, 5 stars4 days ago

Vincent was very on target with his property description, and he was responsive quickly to questions. Very nice home, very clean as well

5 out of 5 average rating, 9 reviews

Beachfront @ Elevate in the Sun!

TaylorRating, 5 stars3 weeks ago

There were extensive directions, which made everything very easy! The host also checked in with us after we got there and was super responsive. We loved how close and accessible the beach was! We would stay here again!

4.83 out of 5 average rating, 6 reviews

Estero Beach & Tennis | Gulf Front + Resort Pool!

BarbaraRating, 5 stars11 months ago

It was a great place for my husband and I to stay for a week. The beach was great!

4.97 out of 5 average rating, 35 reviews

Your Home at the Beach!

MeganRating, 5 stars1 week ago

Sylvia’s home was beautiful, very clean and stocked with everything we could have possibly needed!

4.96 out of 5 average rating, 53 reviews

Summer Discount - Direct BEACH FRONT - Ocean Views

AmyRating, 5 stars1 month ago

Adorable beach condo with amazing beach, gulf and sunset views. The hosts were very responsive. Close to grocery stores, souvenir shops and restaurants. A perfect island getaway.

Home in Fort Myers Beach

5 out of 5 average rating, 4 reviews

Beach Cottage

KarenRating, 5 stars3 days ago

What a wonderful week in this beautiful home!! This home is well stocked with all that you will need for a great get-away. The recliners were perfect for us. The kitchen had plenty of dishes, utensils, cooking utensils and a beautiful island. There were surplus towels & linens as well as supplies for the beach and pool. We'd be back in a heartbeat!! Jamie was very helpful and friendly. We loved the location with easy access to the beach in less than 10 minutes. Summerlin's Cafe and Yoder's Homemade Ice Cream were some of our favorites.

5 out of 5 average rating, 11 reviews

Condo in Sanibel

Sundial G406 - Brand New w/Beautiful Beach Views

AliRating, 5 stars1 week ago

My husband and I had the most wonderful week here! Every detail of the condo is thoughtful and beautiful, down to the color of the pots and pans. The whole space was absolutely pristine, and we had everything we needed for the week. The beach right in front of this unit’s building was super peaceful. If we wanted a cocktail or more of an upbeat vibe, we’d walk down the beach to the larger pool and Turtle’s (which had wonderful food, drinks, and staff!). We’ve already been talking about another trip back when the second pool closer to this unit opens back up. Rebecca’s instructions were very clear, and everything about our stay was easy. Whenever we did have questions, she was so quick and helpful in her responses (even with recommendations around the island). We are already looking forward to a trip back here and would definitely book this condo again!!!