Luxury rentals in Estero Island

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Top-rated luxury holiday rentals in Estero Island

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Luxe

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

Home in Fort Myers Beach

5 out of 5 average rating, 4 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

New place to stay

5350 Chasing Sunshine: 5BD/4.5BA Pool Home!

Welcome to Chasing Sunshine, a brand-new beachfront retreat located on Fort Myers Beach. This stunning five-bedroom, four-and-a-half-bathroom home offers the perfect blend of modern comfort and coastal charm, with direct beach access right from your backyard. Just beyond your private heated pool and hot tub lies the soft, white sand of the Gulf of Mexico, making this one of the most sought-after locations on the island. Situated mid-island, Chasing Sunshine offers peaceful surroundings while kee

Luxe

Home in Fort Myers Beach

4 out of 5 average rating, 3 reviews

61 Once Upon A Tide: 4BR Beachfront w/ Pool & Spa!

Welcome to Once Upon A Tide - 61 Delmar Avenue, an amazing four bedroom, four bath multi-level private home situated beach front right on the Gulf of Mexico! This property is located at the northern end of the island and features unbelievable views of the palm trees and white sugar sand beach. You'll love the convenience of being able to walk to everything. Shops, restaurants, night life and so much more are just a short walk away. Seven miles of sugar sand beach is right at your back door.

Luxe

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

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

Home in Naples

New place to stay

Spacious Luxury Waterfront Retreat with Pool & Spa

Experience waterfront luxury in Naples’ Conners at Vanderbilt Beach. This stunning home features soaring ceilings, a gourmet kitchen with soaring quartz counters, a heated pool with spillover spa, and expansive balconies with sweeping canal views. Just minutes to the Mercato, Waterside Shops, white-sand beaches, and fine dining, it’s the perfect blend of indoor elegance and outdoor relaxation.