Luxury rentals in Estero Island

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Top-rated luxury holiday rentals in Estero Island

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Luxe
A charming two-story home is showcased with a light blue exterior. The structure features a welcoming front porch, adorned with white railings. A paved driveway leads to a two-car garage, surrounded by lush greenery and colorful plants for an inviting approach.
Villa in Naples

Vanderbilt II

Rippling ocean views greet you from the balcony at this charming Naples home. As the sun sets over the horizon, sip a cocktail and watch the sky transform with an array of pastel hues. Expansive glass doors open from the living room onto the terrace where you’ll find a heated pool. A 5-minute stroll lands you at the white-sand beach. Golf courses, high-end shops, and seaside eateries await nearby. Copyright © Luxury Retreats. All rights reserved. BEDROOM & BATHROOM • Bedroom 1 - Primary=: King size bed, Ensuite bathroom with stand-alone shower, Jetted hot tub, Walk-in closet • Bedroom 2: Queen size bed, , Jack & Jill bathroom shared with Bedroom 3, Stand-alone shower • Bedroom 3: Queen size bed, Twin over twin size bunk bed, Jack & Jill bathroom shared with Bedroom 2, Stand-alone shower Additional bedding: • Queen size sofa bed (Bedroom 4) STAFF & SERVICES Included: • Concierge service Extra Cost (advance notice may be required): • Activities and excursions • Babysitting service

Luxe
A three-story coastal home is showcased, featuring a light blue exterior with white trim. Balconies adorn the upper levels, and the front includes a covered porch and a spacious driveway leading to the two-car garage.
Home in Fort Myers Beach
5 out of 5 average rating, 6 reviews

673 White Sands Retreat: Bay Views, Pool, Elevator

Welcome to your dream escape—a brand-new, three-story canal-front masterpiece offering five bedrooms, five bathrooms, and all the high-end amenities you could want for a luxurious getaway. This private home boasts a heated pool, hot tub, and expansive pool deck backing up to the tranquil waters of the canal, with stunning bay views and just steps across the street from seven miles of sugar-soft sand on Estero Island. With a 4-car driveway, an elevator, and incredible indoor-outdoor living spaces

Luxe
Home in Fort Myers Beach
4.86 out of 5 average rating, 7 reviews

3134 Gulf-Front 5BR: Pool, Spa, Stunning Views

3134Check out this stunning luxury rental property on the Gulf of Mexico! This property is one-half of a duplex with a private heated pool and spa. This property boasts 5 bedrooms and 4 full & 1 half bathrooms making it a spacious, comfortable place for all your entourage to enjoy. Private elevator, heated pool, spa, and large balconies with amazing views contribute to a luxurious living experience. You will walk right out the back door onto the famous 7-mile stretch of white, sugar sand beach!

Luxe
A spacious kitchen and dining area features a large island with bar stools, complemented by warm pendant lighting. The dining table, crafted from wood, accommodates several guests. The modern kitchen boasts sleek cabinetry and a chic backsplash, creating an open and inviting space.
Home in Naples
5 out of 5 average rating, 7 reviews

Brand New Gulf Coast Luxury Getaway

Escape to luxury in Naples, Florida! Our well appointed vacation BRAND NEW 2025 built rental home features a heated private pool and spa, an outdoor kitchen with a sprawling outdoor oasis and luxurious accommodations. Enjoy a gourmet kitchen, elegant dining indoors and out, and multiple living areas with large Alexa enable TV's throughout. Just minutes from beaches, dining, and more, it’s the perfect Florida getaway. Bikes, beach chairs, a universal EV charger and more provided!

Luxe
Home in Naples

Luxe 20 P Hot Tub/Pool/ Cinema/Pickle ball

Welcome to your dream getaway! Nestled in a serene, private community in sunny Florida, this brand new, luxury home offers the perfect blend of elegance and comfort. With four spacious bedrooms and high end finishes throughout, you'll enjoy a truly indulgent experience. Additional amenities include: - Spacious master suite with a luxurious en-suite bedroom - Elegant dining area and cozy livingroom - High speed wi-fi and smart home features - Ample parking and private entrance

Luxe
An open-concept living area showcases a modern kitchen with a large island and bar seating. Floor-to-ceiling windows frame panoramic ocean views. A spacious dining table accommodates multiple guests, while a comfortable seating area invites relaxation, enhanced by natural light throughout the space.
Home in Captiva

Eden - Iconic Beachfront Villa Captiva

Welcome to Eden, an architectural masterpiece that embodies the essence of bliss. Nestled in the heart of Captiva, this premier 6-BRs, 5-BAs beachfront estate was the home of the late artist Robert Rauschenberg. Every detail of Eden exudes luxury and relaxation with its breathtaking panoramic ocean views, private beach access, heated pool/spa, this is the perfect retreat for families, friends, or special gatherings. Book your stay today and indulge in the ultimate coastal luxury!

Luxe
Home in Captiva

Casa Captiva - 5 BR Villa, Steps to Beach

Located in the heart of Captiva Island’s charming downtown, this exquisite Spanish-style villa offers the perfect mix of luxury and serenity. Featuring five spacious bedrooms and four beautifully renovated bathrooms, the home comfortably sleeps up to 12 guests. Just steps from white sugar sand beaches and turquoise waters, it’s the ideal getaway. More than just a vacation home, this retreat offers an elevated experience in one of Florida’s most scenic coastal destinations.

Luxe
A modern home is displayed with a circular balcony atop the second floor. The driveway, paved with bricks, is bordered by lush greenery and palm trees. Two garage doors offer practical access, while sunlight brightens the exterior of the property.
Villa in Naples
4.67 out of 5 average rating, 3 reviews

Vanderbilt I

If you have to be isolated, do it in style. Welcome to the exclusive destination with our unique Triple-Cleaned Promise - your assurance of a thoroughly disinfected environment. just steps away from Vanderbilt Beach, this magnificent home has been meticulously deep-cleaned 3 times for your comfort and protection. Now you can enjoy “social distancing” with spectacular scenery, luxurious amenities, and many healthy outdoor activities, all with confidence and peace of mind.

Luxe
A spacious outdoor area features a serene swimming pool and spa, surrounded by a screened lanai. Direct views of intersecting canals are visible, adding to the environment. The nearby dining area is accessible from the pool, promoting a seamless flow between indoor and outdoor living.
Home in Cape Coral

Villa Indian Summer - Luxury Lifestyle

Welcome to "Villa Indian Summer," a modern, two-story newly built home nestled in the highly sought-after Southwest of Cape Coral. This exquisite vacation villa boasts an unparalleled southern panoramic location with captivating views of intersecting canals. The prime location ensures effortless access to everyday conveniences. Essential shopping – groceries, pharmacy, postal services, etc. – can be found less than two miles away at the Camelot Isles Shopping Plaza.

Luxe
Home in Bonita Springs
5 out of 5 average rating, 9 reviews

Beachfront Mansion - Pool, Theater, Game Room

Welcome to Your Private Beachfront Getaway Wake up to breathtaking Gulf views and soft white sand just steps away. Spend your days lounging by the private pool, soaking in the hot tub, or watching a movie in the in-home theater. Enjoy coffee on the balcony, sunsets on the beach, and starry nights with loved ones. Whether it's adventure or relaxation, this luxurious retreat is all about comfort, connection, and memories.

Luxe
A covered outdoor living room features a curving sectional sofa and a circular fire table at its center. Large screens offer views of the heated swimming pool and a vibrant sunset sky, framed by spacious sliding glass doors that open to the lanai.
Home in Marco Island
5 out of 5 average rating, 4 reviews

Begonia Bay | Luxe Waterfront • Pool • Hot Tub

Modern coastal elegance meets effortless island living at Begonia Bay—a 2020-built waterfront retreat in a prime South Marco Island location. Designed to host large families in comfort and style, this spacious residence blends high-end design with all the sought-after amenities for a memorable Gulf Coast escape.

Luxe
A spacious living area is highlighted by a large sectional sofa adorned with decorative pillows. A glass coffee table is positioned in the center, reflecting the bright interior. Open spaces are visible in the background, leading to a well-lit kitchen and dining area.
Home in Captiva

Wine Down - Ultimate Captiva Vacation!

The ultimate Captiva vacation home! Enjoy breathtaking water views as this home offers 200 ft. of bay-frontage overlooking the Blind Pass.

Popular amenities for Estero Island luxury holiday rentals

Destinations to explore

  1. Airbnb
  2. United States
  3. Florida
  4. Lee County
  5. Fort Myers Beach
  6. Estero Island
  7. Luxury rentals