TOP 10 Relaxing vacation rentals in Estero, Florida

Estero Island Beach Villas offers luxurious beachfront accommodations in Fort Myers Beach, Florida. Our villas provide a tranquil and relaxing retreat for guests looking to escape the hustle and bustle of everyday life. Situated on the beautiful Estero Boulevard, our property boasts stunning views of the Gulf of Mexico and easy access to the pristine white sand beaches. As a lodging institution, we take pride in providing top-notch amenities and services to ensure our guests have a comfortable and memorable stay. Whether you're looking for a romantic getaway, a family vacation, or a solo adventure, Estero Island Beach Villas has something for everyone.

Sun Retreats Estero Bay is a charming lodging and RV park located at 19551 South Tamiami Trail in Fort Myers, Florida. Situated in the beautiful Estero Bay area, this institution offers a serene and peaceful retreat for guests looking to relax and unwind. With spacious RV sites and cozy accommodations, Sun Retreats Estero Bay provides a comfortable and convenient stay for travelers. Enjoy the nearby attractions, pristine beaches, and stunning natural surroundings while staying at this welcoming institution. Whether you're looking for a weekend getaway or a longer stay, Sun Retreats Estero Bay is the perfect destination for your next vacation.

Cornerstone Beach Resort Rentals is a premier lodging destination located at 5480 Estero Boulevard in Fort Myers Beach, Florida. Our resort offers luxurious accommodations with stunning views of the beach and Gulf of Mexico. Guests can choose from a variety of rental options, including spacious condos and beachfront villas. Our resort amenities include a heated pool, hot tub, fitness center, and direct beach access. Whether you're looking for a relaxing getaway or an action-packed vacation, Cornerstone Beach Resort Rentals has everything you need for a memorable stay in sunny Florida.

Paradise Key Vacations is a lodging, real estate, and travel agency located at 8701 Estero Boulevard in Fort Myers Beach, Florida. Whether you're seeking adventure or relaxation, our properties offer a range of options from the pristine Gulf Coast beaches to the serene rural areas of Fort Myers. From state parks to shopping centers, there is something for everyone to enjoy. Stay in one of our homes and experience Florida like a true local. Our Little cottage in Buckingham, family-friendly property in Fort Myers, and cozy condo at Barefoot Beach are just a few of the options available. While repairs are still ongoing at Lovers Key Beach Club due to damages from hurricane Ian, we look forward to welcoming guests back in April 2024. Come stay with us and discover paradise just one Key away!

Gulf Breeze Condos offers luxurious vacation rentals in the heart of Fort Myers Beach, Florida. Our beautifully furnished condos are located right on the beach, providing stunning views of the Gulf of Mexico. Whether you're looking for a relaxing getaway or an action-packed vacation, Gulf Breeze Condos has something for everyone. Our real estate and travel agency experts are dedicated to helping you find the perfect rental for your needs. Come experience the beauty and tranquility of Fort Myers Beach at Gulf Breeze Condos.

Royal Shell Vacations is a premier real estate and travel agency located at 15050 Captiva Drive in Captiva, Florida. With a wide range of vacation rental options available, from Captiva Island to Ocala, Royal Shell makes vacation planning a breeze. Since 1996, we have been the largest vacation rental company in Southwest Florida, offering unique amenities and services to make your stay stress-free and memorable. Our portfolio includes over 500 vacation rental homes and condos in Sanibel and Captiva Islands, with even more options in Cape Coral, Fort Myers, Ocala, and beyond. Whether you're looking for a nightly, weekly, monthly, or annual stay, our variety of styles and sizes ensure the perfect vacation rental for you.

Newlove Vacation Rental is a premier lodging establishment located at 5551 Estero Boulevard in the beautiful Fort Myers Beach, Florida. As a combined real estate and travel agency, we offer a wide range of vacation rental properties for visitors looking to enjoy a relaxing and luxurious stay in this tropical paradise. Our team is dedicated to providing top-notch customer service and ensuring that every guest has a memorable and enjoyable experience during their stay. Whether you're looking for a cozy beachfront condo or a spacious vacation home, Newlove Vacation Rental has the perfect accommodation for your needs. Book your stay with us today and let us help you create the perfect vacation getaway.

Sunny Beach Vacation Rentals & Sales, Inc. is a premier real estate and travel agency located at 1801 Estero Boulevard in Fort Myers Beach, Florida. Specializing in vacation rentals and property sales in the sunny beachfront area, our experienced team is dedicated to helping clients find their perfect getaway or investment property. Whether you're looking for a beachfront condo for a relaxing vacation or a beach house for a permanent residence, we have a wide range of options to suit your needs. Contact us today to start planning your dream beach getaway in beautiful Fort Myers Beach.

Pointe South Condominium Vacation Rentals offers luxurious and comfortable accommodations in Fort Myers Beach, Florida. Located at 5000 Estero Boulevard, this institution provides a perfect getaway for those looking to enjoy the sun, sand, and surf of the Gulf Coast. With spacious condos equipped with modern amenities, guests can relax and unwind in style. Whether you're looking for a romantic retreat, a family vacation, or a group getaway, Pointe South Condominium Vacation Rentals has something for everyone. Enjoy stunning views, easy access to the beach, and a range of activities and attractions nearby. Make your next vacation unforgettable with a stay at Pointe South Condominium Vacation Rentals.

Estero Bay Express is a trusted travel agency located at 7225 Estero Boulevard in Fort Myers Beach, Florida. Specializing in providing top-notch transportation services, the agency offers a wide range of options for exploring the beautiful Estero Bay area and beyond. Whether you're looking to book a scenic boat tour, a thrilling jet ski adventure, or a relaxing sunset cruise, Estero Bay Express has you covered. With experienced and knowledgeable staff, convenient booking options, and excellent customer service, this travel agency is your go-to destination for all your travel needs in the Fort Myers Beach area. Visit Estero Bay Express today and start planning your next unforgettable vacation experience!

Holiday Adventure Tours and Boat Rental is a premier travel agency located at 275 Estero Boulevard in Fort Myers Beach, Florida. We specialize in providing unforgettable adventures and experiences for our clients, including boat rentals for exploring the beautiful waters of Florida. Whether you're looking for a relaxing day on the water or an exciting adventure, our knowledgeable staff is here to help you plan the perfect trip. Come visit us and let us help you create memories that will last a lifetime.

Estero Country Club is a premier institution located in Fort Myers, Florida, offering a wide range of amenities for members and guests. From a state-of-the-art gym and health facilities to a luxurious restaurant serving delicious meals, this institution has something for everyone. Whether you're looking to stay fit, enjoy a gourmet meal, or simply relax in a beautiful setting, Estero Country Club is the perfect destination. Visit us at 19501 Vintage Trace Circle and experience the ultimate in leisure and wellness.

Welcome to Fun In the Sun Rentals Inc, your premier destination for adventure and relaxation in the heart of Fort Myers Beach, Florida. Located at 1661 Estero Boulevard, our family-owned business is dedicated to providing you with top-quality rental equipment to enhance your vacation experience. Whether you're looking to cruise along the pristine sandy beaches on a bicycle, explore the serene waterways by kayak or paddleboard, or simply relax and soak in the breathtaking sunsets, we have something for everyone. At Fun In the Sun Rentals Inc, we offer an array of rental equipment to suit all ages and preferences. Enjoy the convenience of free delivery on all equipment, including bikes, directly to your door. Plus, every bike rental comes with a complimentary helmet, lock, and basket for your safety and convenience. We also offer multi-week and group discounts to make your adventure even more affordable.

Welcome to Estero Blvd @ St Peters Dr Transit Station, your convenient gateway to exploring the beautiful Fort Myers Beach, Florida. Situated in the heart of this vibrant coastal community, our transit station serves as a central hub for locals and visitors alike, providing easy access to the stunning beaches, lively attractions, and charming local businesses that Fort Myers Beach has to offer. Whether you're commuting to work, heading out for a day of sun and sand, or exploring the local dining and shopping scene, our well-connected transit station ensures a seamless and stress-free travel experience. With a commitment to efficiency and customer satisfaction, Estero Blvd @ St Peters Dr is your reliable partner in reaching your destination. Visit us today and discover the convenience and accessibility that our transit station provides in the picturesque setting of Fort Myers Beach.

Welcome to Estero Beach & Tennis 206C, your premier destination for relaxation and adventure in the heart of Fort Myers Beach, Florida. Nestled at 7360 Estero Boulevard, our unique establishment offers a blend of lodging, real estate, and travel services, making it the perfect choice for both short-term getaways and long-term stays. Our beautifully appointed accommodations provide a serene escape with stunning views of the Gulf of Mexico, ensuring a tranquil and rejuvenating experience. Whether you're planning a romantic retreat, a family vacation, or a solo adventure, Estero Beach & Tennis 206C caters to all your needs with exceptional amenities and personalized service.

Welcome to Fort Myers Beach Vacations/Sunny Daze, your premier destination for unforgettable getaways and real estate opportunities on the stunning shores of Fort Myers Beach, Florida. Located at 612 Estero Boulevard, our dedicated team is committed to helping you discover the perfect vacation rental or property investment in this tropical paradise. As both a real estate and travel agency, we offer a unique blend of services to meet all your needs. Whether you're seeking a relaxing beachfront retreat, an adventurous island excursion, or a lucrative real estate investment, we provide personalized assistance and expert advice to turn your vision into reality.

Rebel Water Sports, located at 1010 Estero Boulevard in Fort Myers Beach, Florida, offers an exciting array of water activities for visitors to enjoy. Join their experienced crew on a dolphin tour to explore the back bay and encounter marine wildlife such as dolphins, manatees, and sea turtles. For a thrilling experience, hop on a wave runner or take a ride on a banana boat with up to 6 friends or family members. Forget about lugging beach chairs to the shore - relax under umbrellas with drink trays provided by Rebel Water Sports. Operating from 8am to 5pm daily, weather permitting, this institution promises a fun-filled day on the water. Contact them at (239)-677-6782 to book your adventure today!

Gulfview Manor is a charming lodging institution located at 6530 Estero Boulevard in Fort Myers Beach, Florida. Situated right on the Gulf of Mexico, this tranquil retreat offers stunning ocean views and easy access to the beach. The accommodations at Gulfview Manor are cozy and comfortable, providing guests with a relaxing atmosphere to unwind and enjoy their stay. Whether you're looking for a romantic getaway, a family vacation, or a solo adventure, Gulfview Manor is the perfect place to escape and rejuvenate. With its prime location and welcoming ambiance, Gulfview Manor is the ideal destination for your next Florida vacation.

Edison Beach House, located at 830 Estero Boulevard in Fort Myers Beach, Florida, offers stunning ocean-front views and luxurious accommodations. The institution has recently undergone renovations to improve guest experiences, including the addition of a fully-functioning elevator for convenience. Each suite features in-suite kitchenettes with full-size appliances and in-suite stacked washers and dryers. Guests can enjoy the gorgeous ocean views from their private balconies and relax at the beach-front pool. The hotel is within walking distance to shopping boutiques and restaurants, making it easy to enjoy everything Fort Myers Beach has to offer.

DiamondHead Beach Resort is a luxurious yet affordable lodging option located on Estero Island in Fort Myers Beach, Florida. Guests can relax and recharge with a beach retreat, indulging in activities such as searching for seashells, dining on flavorful cuisine, and exploring the island. The newly updated suites provide spacious accommodations for guests to rest in between activities. With a tropical beachfront pool, volleyball court, bikes for rent, and watersports available through Holiday Water Sports, there is no shortage of things to do. The resort also offers exceptional dining options at Cabañas, where guests can enjoy island cuisine and signature drinks. For those looking to explore the area, the local beach trolley offers easy access to seaside cafes, shops, and dive bars. And with fully furnished balconies overlooking the stunning sunsets, guests can truly unwind and enjoy the beauty of Estero Island. Welcome to island time at DiamondHead Beach Resort!

Tropical Sands Resort is a beachfront lodging located at 7785 Estero Boulevard in Fort Myers Beach, Florida. This charming resort offers guests a tropical oasis with stunning views of the Gulf of Mexico. The resort features spacious and comfortable accommodations, a heated outdoor pool, a hot tub, and direct access to the beautiful white sandy beach. Guests can relax and unwind in the tranquil surroundings or explore the nearby attractions and activities. Whether you're looking for a romantic getaway, a family vacation, or a solo retreat, Tropical Sands Resort is the perfect destination for a memorable stay in paradise.

Located at 1400 Estero Boulevard in Fort Myers Beach, Florida, the Lani Kai Island Resort is a top-notch lodging establishment developed by the Conidaris Family for over 40 years. With a passion for creating a fun and energetic environment, the resort offers beautiful beach views from every room, ensuring guests are always close to the action. Enjoy delicious meals and refreshing cocktails at the resort's amazing restaurants and bars, all while taking in the stunning view. Guests can participate in a variety of beach activities throughout the day, from volleyball to parasailing, and dance the night away to live music acts. The resort also offers event planning services for weddings, business retreats, and more, ensuring a memorable experience for all guests. For those missing the beach, a 24/7 live stream of Fort Myers Beach is available for viewing.

La De Da Beach Bar is a vibrant and lively institution located at 1154 Estero Boulevard in Fort Myers Beach, Florida. As part of the Margaritaville Beach Resort, this bar offers a variety of amenities for guests to enjoy while soaking up the sun and relaxing by the pool. From tasty bites and frozen drinks at the 5 o'Clock Somewhere Bar & Grill to live music and stunning sunsets at the Fins Up! Beach Club, there is something for everyone to enjoy. Guests can also take advantage of watersports activities such as jet skiing and parasailing, as well as spa treatments at the St. Somewhere Spa. The License to Chill Bar & Grill provides a cozy outdoor space with fire pits, daily activities, and live entertainment, perfect for unwinding after a day of fun in the sun.

Bayside Park is a beautiful waterfront park located in Fort Myers Beach, Florida, United States. This serene and picturesque park offers stunning views of the bay and is the perfect place to relax and unwind. Visitors can enjoy a leisurely stroll along the walking paths, have a picnic on the grassy areas, or simply sit and take in the peaceful surroundings. Bayside Park is a popular spot for locals and tourists alike, and is a great place to escape the hustle and bustle of city life. Whether you're looking for a quiet place to read a book or a peaceful spot to watch the sunset, Bayside Park is the ideal destination for nature lovers and outdoor enthusiasts.

Paradise Parasail Inc is a premier tourist attraction and travel agency located at 1160 Estero Boulevard in Fort Myers Beach, Florida. Offering exhilarating parasailing adventures, visitors can soar above the crystal-clear waters of the Gulf of Mexico while taking in breathtaking views of the coastline. With experienced guides and top-of-the-line equipment, Paradise Parasail Inc ensures a safe and unforgettable experience for all guests. Whether you're looking for a thrilling adventure or a relaxing day on the water, this institution is the perfect destination for your next vacation.

Lovers Key Adventures is a convenient and charming institution located at 8720 Estero Boulevard, Fort Myers Beach, Florida. This establishment offers a variety of services including a gift shop, rentals, and beach amenities. In loving memory of Bowser Denmark, the institution provides a welcoming and friendly atmosphere for visitors to enjoy. The gift shop is open from 9 am to 5 pm, with rentals available from 9 am to 4:45 pm. Beach rentals, including chairs and umbrellas, are available from 9 am to 4:30 pm. Paddles, backrests, and life vests are included in the rental price. Additionally, there is a special 2-hour pricing offer valid from June 1st to October 31st.

Lover's Key Beach Club is a charming lodging option located at 6090 Estero Boulevard in Fort Myers Beach, Florida. Situated right on the picturesque shores of the Gulf of Mexico, this beachfront resort offers guests a relaxing and unforgettable stay. With its stunning views, pristine sandy beaches, and luxurious accommodations, Lover's Key Beach Club is the perfect destination for couples looking for a romantic getaway or families seeking a fun-filled vacation. Whether you're lounging by the pool, exploring the nearby attractions, or simply enjoying the sunsets over the water, this hidden gem is sure to make your stay in Florida truly special.

Lovers Key Resort is a charming lodging institution located at 8771 Estero Boulevard in Fort Myers Beach, Florida. This resort offers stunning water views, luxurious amenities, and spacious accommodations perfect for romantic getaways, family vacations, or girls' weekends. Guests can explore nearby nature parks, relax on the beach, or enjoy beautiful sunset views from their private balconies. The resort features large suites with kitchens for added convenience, as well as a waterfront restaurant, Flipper's on the Bay, known for its delicious American cuisine and seafood dishes. Guests can take advantage of special deals, such as the Advance Purchase Rate for 20% off or the Florida Residents Deal for 15% off. With island-inspired elegance and contemporary convenience, Lovers Key Resort is the perfect destination for a memorable stay in Fort Myers Beach.

Windward Passage Resort, located at 418 Estero Boulevard in Fort Myers Beach, Florida, is a beautiful vacation ownership resort offering a perfect blend of sand, sun, water, and fun. Unfortunately, the resort is currently closed until further notice due to extensive damage from Hurricane Ian on September 28, 2022. The recovery process is expected to extend through 2023 and possibly longer. Despite the closure, Windward Passage Owners can access the OWNER’S PROTECTED SECTION OF THE WEBSITE for updates and photos as the resort moves through the recovery process. When the resort reopens, guests can look forward to relaxing in the hot tub, taking a dip in the heated pool, and enjoying a variety of amenities. Guests can also explore the charm of Ft. Myers Beach by taking a bike out or going for a stroll to Times Square.

Located at 6620 Estero Boulevard in Fort Myers Beach, Florida, GullWing Beach Resort offers homelike vacation rentals perfect for a beach getaway. With a contemporary tropical flair and luxurious island elements, our modern beachfront rentals are the perfect place to relax and unwind. Enjoy the tropical pool area, swim in the ocean, or take a stroll along the sandy shores in search of seashells. Conveniently located with a stop directly in front of the resort, guests can easily explore nearby shops, cafes, and bars. Watch spectacular sunsets from your private balcony, fully furnished and screened-in for your comfort. Whether you want to relax by the pool or venture out to discover the local attractions, GullWing Beach Resort has something for everyone.