Holiday rentals in Estero Bay

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Top-rated holiday rentals in Estero Bay

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Top guest favourite
A spacious living area features modern white armchairs positioned beside a stylish sofa. A table is set with decorative placements, and light enters through large sliding glass doors, framing views of lush greenery outside.
Apartment in Naples
4.92 out of 5 average rating, 169 reviews

Park Shore Resort Modern Top Floor 2 Bed 2 Bath

You have found THE BEST condominium in Naples! This wonderful and tranquil get-away is set in a tropical paradise in the heart of Park Shore. A modern 2 bedroom, 2 bath with one king bed, two twin beds and one sofa bed, sleeps 6 people. This top floor unit with elevator gives you a breath-taking view over a beautiful resort which offers heated pool, tennis, pickleball, and poolside restaurant Hogfish Harry. The beach is only a mile away! Let us welcome you to your own personal piece of paradise!

Superhost
Home in Naples
4.82 out of 5 average rating, 55 reviews

Heated Pool Beach Family Escape

Welcome to your relaxing Naples getaway just minutes from Vanderbilt Beach, Mercato, and the best dining in town. This beautifully updated 3-bedroom home is designed for easy, sun-filled days and laid-back evenings with family and friends. The highlight? Your private heated pool, perfect year-round, whether you're enjoying a morning swim, lounging in the Florida sunshine, or unwinding after a beach day. And yes - pets are welcome, because vacations are better when the whole family comes along.

Top guest favourite
A clear blue pool is surrounded by a spacious patio, featuring comfortable loungers partially immersed in the water. The inviting outdoor space overlooks the serene canal, while the covered lanai offers additional seating options. Lush palm trees sway gently in the background under a bright sky.
Home in Cape Coral
4.97 out of 5 average rating, 132 reviews

Boater’s Paradise-Stunning Sunsets! Games Room!

Renovated lanai! This 3 bed/4 bath home is on the nicest canal with 200+ ft of frontage & gorgeous views of the canal & sunset. The pool, tiki hut & docks have full sun all day. Each bedroom has a private bath & there's a 2 pc powder room off the laundry. The primary has a king bed & walkout to pool. The 2nd bedroom has a queen bed & pool access. Bedroom 3 has a queen & private bath. Fully equipped kitchen with everything you need. And a games room! Enjoy stunning sunsets under the tiki hut.

Guest favourite
A sandy backyard features a fire pit surrounded by several black chairs, with a canal lining the edge. Lush greenery and palm trees provide a tropical setting, while a spacious home stands in the background, framed by clear blue skies.
Home in Bonita Springs
4.97 out of 5 average rating, 102 reviews

Canal Home- Gulf Access- PET friendly-Fenced yard

Waterfront home with Gulf access. Recently renovated 3 BR, 3 BA home on a canal off the Imperial river. Two en-suite bedrooms. The home can comfortably sleep 8 guests. Kayaks, bikes, fishing poles, yard games, backyard beach, and fire pit available for your use. Fenced in yard. Centrally located about 20 minutes from the airport, Naples, Fort Myers and only 3 miles from the beach! Close to several breweries, wine loft, local coffee shop, cocktail lounge, parks, churches, and many restaurants.

Top guest favourite
A screened patio overlooks a serene swimming pool surrounded by lush greenery. Two lounge chairs are positioned nearby, with a small table featuring colorful drinks. A few inflatable toys float in the water, offering a casual ambiance for relaxation.
Home in Bonita Springs
4.97 out of 5 average rating, 115 reviews

3BR w/HUGE 2k sq ft Lanai & Seasonally Heated Pool

Welcome to your peaceful Bonita Springs retreat, perfectly located near Naples, Ft. Myers, shopping & beaches! This isn’t just a rental, it’s our 2nd home and we treat it as such. You'll experience "exceptional" the minute you enter this stunning, open concept interior. Further, it boasts a striking 2000 sq ft screened-in lanai w a seasonally heated pool. This outdoor oasis doubles your living space and offers a flying pest barrier and significant UV protection. Breathe/Smile/Unwind

Guest favourite
A cozy living area features a comfortable couch adorned with a patterned pillow. A modern electric fireplace is positioned beneath a flat-screen TV, with large windows allowing natural light to fill the space. A decorative area rug adds warmth to the neutral-toned flooring.
Camper van/Motorhome in Bonita Springs
4.94 out of 5 average rating, 69 reviews

Spacious Luxury one bedroom RV @ Coconut point.

You won’t forget your time in this romantic, luxurious 1 bedroom RV with indoor fireplace. Just 1.9 miles away from Coconut Point Mall and less than 1 mile away from the Hyatt Regency Resort and Spa. Super spacious with open kitchen floor residential appliances, tall ceilings, large scenic windows areas. Great amount of storage throughout for your food, clothing & bathroom items, and flatscreens TVs in Living and bedroom. Enjoy your stay with complimentary bikes, BBQ grill, cooler.

Guest favourite
Home in Bonita Springs
5 out of 5 average rating, 5 reviews

Spring Creek Hideaway, "Our Secluded Gem" Pool

Welcome to "Our Secluded Gem", your home away from home. Surrounded by fresh air, luscious gardens, tropical palms, and native plants throughout the property. Located on a Canal that leads to the Spring Creek Channel flowing out to the Gulf of Mexico in Bonita Springs. We've taken pride in ourselves to make sure you feel at home and relax while you're on vacation. Bring the whole family, including your fur family to this great place with lots of sun-n-fun. SEE YA SOON!

Guest favourite
Home in Bonita Springs
4.91 out of 5 average rating, 11 reviews

Bonita Springs Coastal Retreat | Pool Home

Relax and unwind in this beautiful 4-bedroom, 3-bath home featuring a heated pool with a sunshelf, perfect for soaking up the Florida sunshine. Centrally located near Coconut Point Mall, you’re just minutes from great shopping, dining, and only 15 minutes from Bonita Beach. Inside, spacious coastal-inspired living areas provide plenty of room for family and friends to gather. Your private getaway awaits, book today for an unforgettable stay!

Guest favourite
A refreshing pool area features a heated pool surrounded by lounge chairs and a dining table. An inflatable pink flamingo floats in the water, while colorful umbrellas provide shade. Lush greenery frames the outdoor space, creating a bright and inviting atmosphere.
Home in Naples
4.92 out of 5 average rating, 160 reviews

675 FantaSea | New Heated Resort Pool & Fire Pit

Spend the day outside morning, noon & night and live out your FantaSea vacation! Lounge on the deck or in the heated pool on the sun shelf. On a cool night sit by the fire and relax in the Adirondack chairs. Desirable designer interior with coastal decor has the comfort of home with the feel of the sea. We are just a few minutes away from white sandy beaches with beautiful sunsets, amazing restaurants and upscale shopping centers.

Guest favourite
Flat in Fort Myers Beach
4.88 out of 5 average rating, 89 reviews

Southern Comfort - Updated Waterfront Condo

Discover paradise at Lovers Key Resort on Fort Myers Beach! The resort offers unforgettable water views, spectacular amenities and spacious accommodations. Watch the dolphins play from the floor to ceiling bayfront windows or your private open-air balcony! Located on the 3rd floor, this suite features one bedroom, one bathroom and a full size kitchen with all appliances.

Guest favourite
A serene pool area is framed by elegant columns and surrounded by lush greenery. The light yellow exterior of the building complements the turquoise water, which reflects the blue sky. Steps lead from the pool to the entrance, enhancing the inviting atmosphere.
Guest suite in Naples
4.9 out of 5 average rating, 121 reviews

Southern Charmer, a handsome beach studio (Naples)

Come vacation in beautitful Naples, Florida! This guest house is perfect for a couples get away or some much needed R&R. The property boasts a pool, side yard, and is just across the street from the beach. Enjoy fine dining, shopping, and entertainment in downtown Naples located in just a 20 minute walk or 5 minute car ride.

Top guest favourite
A welcoming entrance features a covered patio with seating options, including a cozy sofa and rocking chairs. The surrounding outdoor area is landscaped with plants and decorative stones. The exterior walls are painted in calming shades, contributing to a relaxing atmosphere.
Home in Bonita Springs
5 out of 5 average rating, 49 reviews

Coastal Breeze Cottage

Welcome to our newly renovated charming coastal retreat! This adorable 2-bedroom, 1-bath home with a den offers a delightful coastal decor that will transport you to a world of relaxation and tranquility. Situated right on the canal front, it's the perfect destination for boating enthusiasts and water lovers.

Popular amenities for Estero Bay holiday rentals

  1. Airbnb
  2. United States
  3. Florida
  4. Lee County
  5. Estero Bay