Beach house holiday rentals in Estero Island

Pelican House 4 bedrooms Free Heated Pool

Welcome to Pelican House, a bright and spacious Florida getaway designed for family fun and total relaxation. This beautiful 4-bedroom, 2-bathroom home features a free heated pool and a sunny open layout, perfect for enjoying Cape Coral’s tropical lifestyle. Large sliding doors from the dining room, great room, kitchen, and master bedroom fill the home with natural light and provide direct access to the pool area — where you can swim, sunbathe, or enjoy meals al fresco. The screened lanai and c

Value · Location · Beach

Island retreat - canal, heated pool, walk to beach

Experience Fort Myers Beach by staying in this cozy 2BR 2Bath home (within a triplex), situated in the serene waterfront neighborhood right on the canal. Its prime location offers a relaxing retreat in a resort like setting while allowing quick access to beautiful and sunny beaches. The design and rich amenity list will satisfy your every need. ✔ Waterfront ✔ Beach Access ✔ 2 Comfy BRs ✔ Full Kitchen ✔ Heated Pool ✔ Outside Patio ✔ High-Speed Wi-Fi ✔ 3 Smart TVs ✔ Free Parking See More below!

Family · Location · Laundry

Short walk to beach and Time Square

Relax by the pool with the whole family at this peaceful place to stay. Highly desirable North End of Fort Myers Beach. Large heated pool. 3 bedroom and 1 bathroom. ++Please note that the pool/exterior is shared space with the converted garage (up to 2 other guests) The Bed Setup Bedroom 1 King bed Bedroom 2 King bed Bedroom 3 open bunk room (twin, full, twin trundle) This tropical oasis home features a bright, open-concept living area designed for comfort and gathering with family and friends.

Location · Family · Beach

Bahia Villa | Coastal Waterfront Retreat Pool

Discover Bahia Villa, a private waterfront retreat on Fort Myers Beach with pool, dock, and space for up to 10 guests. The Villa is the entire home (both Penthouse & Poolside units) for the ultimate coastal getaway. Enjoy two kitchens, two living areas, and four bedrooms — perfect for families or groups seeking comfort and privacy under one roof. Lounge by the pool, fish from your private dock, or stroll just four minutes to the beach. Modern coastal interiors, open-concept living, and tropic

Location · Family · Kitchen

New! Beachside cottage style cutie-host pays fees

Welcome to Sandy Cay!! Located just steps to the beach and walking distance to Times Square, Sandy Cay is a cute, beachy green colored two-story cottage style home with 4 bedrooms, 4 1/2 baths. Each bedroom has a private ensuite bathroom. Open concept living and fully equipped kitchen with induction cooktop, oven, microwave, dishwasher. Breakfast nook/dining area has shiplap covered walls and seating for up to 8. This home offers all the charm of an iconic beach cottage ... on stilts!

Family · Location · Walkability

FMB Farmhouse

Relax at this new, 3 bedroom home. 3 minute walk or bike ride to the beach or restaurants. Large Master bedroom with king bed and en suite bathroom. Second bedroom has a queen bed and shared guest bath. Third bedroom has two sets of bunk beds. Amenities include Wi-Fi, flat screens in living and bedrooms, heated pool, hot tub, grill and AC. 3 bedrooms, a stocked kitchen, washer/dryer, outdoor dining and a cozy living room make this property perfect for families, couples or friends.

Family · Location · Beach

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,

Value · Family · Barbecue

Tommy Bahama House | 3-Bedroom Beachfront Retreat

The one and only Tommy Bahama House, bedrooms and three bathrooms, located directly on Bonita Beach in Bonita Springs, Florida. The elegance and beauty of Tommy Bahama House is apparent when you turn off Hickory Blvd. onto the paver driveway and see the ginger bread trim and lattice garage door's. You will immediately know why you choose to spend your vacation or Holiday on this beach front treasure. Look no more for that perfect beach front private home!

Value · Family · Comfort

Plunge Pool + 8-Person Jet Spa + Sundeck

You’re renting the entire Sunset by the Sea duplex—two identical 2BR/1BA units, each with a full kitchen, two arcade games, and private patio. Perfect for large groups needing both space and privacy. Enjoy double the amenities plus exclusive access to the full property: 8-person jet swim spa + separate plunge pool with sundeck, putting green, outdoor gym with free weights, and a spacious resort-style backyard. Full private compound just minutes from th

Family · Nearby · Walkability

Grace by The Sea · 2025 Build · Steps to Beach

This stylish coastal home offers a brand-new experience with a spacious lanai and backyard, all with just a 6-minute walk to the sugar sand beach. Start your morning with coffee on the covered front porch, enjoying Gulf breezes. Relax by the pool with a book throw something on the blackstone grill, play corn hole or enjoy cozy outdoor seating for lounging and dining. End the day with a sunset stroll or a short drive to nearby bars and restaurants.

Value · Location · Walkability

Pink Star | Coastal Chic - Walk to Town Square

Welcome to The Pink Pearl, a cheerful 4-bed, 4-bath newly built haven in Fort Myers Beach. This charming home offers tropical elegance and laid-back luxury. Enjoy an open-plan living, multiple balconies, and a private pool with a spill-over spa. Each bedroom features a private en-suite. Located right off Estero Blvd, you're mere steps from the wide sandy beach and a stroll to Times Square. Pairs perfectly with Blue Stars next store!

Family · Location · View

"The Osprey" - New Construction, Gulf-Side, Pool!

Have fun with your perfect beach getaway! Pool, Tiki Bar, Gulf-side, Ocean!| Brand new construction with pool on premier gulf-side location of Fort Myers Beach. Rebuilt after Hurricane Ian--same great location, same great host! Professionally decorated and just steps from the ocean! Updated with quality finishing, this 4BR, 4BA home is fully outfitted with everything you'll need for your beach getaway.

Family · Location · Pool