TOP 30 Best Island getaway rentals in Holiday, Florida

Island Ventures is a premier institution located at 13 Seagate Boulevard in Key Largo, Florida, United States. Specializing in SCUBA and snorkel tours, we offer the finest personal experiences on the Key Largo reef. Our knowledgeable crews will guide you 6 miles offshore to explore vibrant coral reefs and encounter marine life up close. Our commitment to top-tier customer service ensures that your journey is not only memorable but also enriched with information and care. Embark on an underwater adventure with our SCUBA tours, where expert guides will take you to the best and safest parts of the reef. Alternatively, dive into crystal-clear waters with our Key Largo Snorkel Tours, where you can experience the breathtaking beauty of coral reefs and colorful marine life.

the elevator to be at the lazy river or the beach in just seconds. This unit has two master suites and an additional bunkroom, making it perfect for families or groups. With a view of the pool and a partial view of the Gulf, B203 offers a peaceful and relaxing atmosphere for your vacation. B205 is a second floor unit with a beautiful view of the pool and a partial view of the Gulf of Mexico. This condo has two master suites and a bunkroom, providing plenty of space for your family or friends. With easy access to the pool and beach, B205 is the perfect spot for a fun and relaxing getaway. B307 is a third floor unit with a stunning view of the pool and the Gulf of Mexico. This condo has two master suites and a bunkroom, offering plenty of space for your group. With easy access to the pool and beach, B307 is the ideal spot for a memorable vacation. B313 is a third floor unit with a view of the pool and a partial view of the Gulf of Mexico. This condo has two master suites and a bunkroom, providing ample space for your family or friends. With easy access to the pool and beach, B313 is the perfect place to unwind and enjoy a beach vacation.

Grace River Island Resort is a hidden gem located at 14524 Riverside Drive in Fort Myers, Florida. This private tropical island vacation home is nestled on the Caloosahatchee River, accessible via a land bridge that transforms it into a peninsula. Whether you are looking for a memorable family vacation, a romantic honeymoon, an intimate wedding venue, or simply some time away, Grace River Island Resort offers the perfect setting. The resort features a spacious 6-bedroom, 8-bathroom house that can accommodate up to 20 guests, making it ideal for family reunions or group getaways. Guests can enjoy a large air-conditioned bonus room, a 2000 sq ft deck overlooking the river with market lighting, a heated swimming pool, a beautiful gazebo, an upscale courtyard, and a grassy point with stunning sunsets. The bridal suite upstairs is perfect for wedding preparations, while the groomsman area downstairs provides a space for the guys to relax before the ceremony.

Kingfisher Vacation Rentals offers a wide range of vacation rentals on the beautiful Sanibel and Captiva Islands in Florida. Located at 2402 Palm Ridge Road, Sanibel, this real estate and travel agency provides luxurious accommodations for visitors looking to experience the stunning beaches and natural beauty of the Gulf Coast. Whether you're looking for a cozy beachfront cottage or a spacious waterfront villa, Kingfisher Vacation Rentals has the perfect option for your island getaway. With personalized service and local expertise, they are dedicated to helping you make the most of your vacation in paradise.

Stay & Play Vacation Rentals and Watersports Clearwater Beach is a dynamic hospitality concept located at 657 Bay Esplanade in Clearwater, Florida. This all-inclusive vacation destination offers waterfront vacation rentals and a wide range of on-site activities and amenities. From jet skiing and parasailing to kayaking, paddle boarding, and fishing expeditions, there is something for everyone to enjoy. Guests can also explore the local sights with golf cart rentals. The institution also offers a unique stay-and-play experience with a custom-built houseboat rental located on the intracoastal Mandalay Bay, just two blocks from the Gulf of Mexico. Complimentary kayak and paddle board rentals, beach cruiser bikes, and beach equipment are provided to ensure a comfortable and enjoyable stay.

Island Time Charter is a unique establishment located on 11th Street in Sarasota, Florida, United States. This dual-purpose venue serves as both a bar and a travel agency, offering patrons the opportunity to enjoy a refreshing drink while planning their next adventure. Whether you're looking to unwind with a cocktail or book a thrilling excursion, Island Time Charter has you covered. With a laid-back atmosphere and friendly staff, this is the perfect place to kick back and relax while making plans for your next getaway.

Island Adventures is a premier travel agency located at 80500 Overseas Highway in Islamorada, Florida. Specializing in creating unforgettable island getaways, our dedicated team of travel experts can help you plan the perfect vacation to tropical destinations around the world. From luxurious beach resorts to thrilling outdoor excursions, Island Adventures offers a wide range of travel options to suit every traveler's preferences. Let us help you turn your dream island getaway into a reality. Book your next adventure with Island Adventures today!

Island Bay Resort is a tropical oasis located at 92530 Overseas Highway in Tavernier, Florida, United States. Our beachfront location on the Florida Bay offers stunning sunsets and a relaxing atmosphere surrounded by palm trees and flowering plants. Whether you're looking to unwind and escape everyday stress or seeking adventure in the Florida Keys, our resort has something for everyone. Centrally located between Key Largo and Islamorada, just two hours from Key West or the Miami/Ft. Lauderdale area, Island Bay Resort is the perfect destination for your next vacation. Enjoy our tiki huts, hammocks, swimming, snorkeling, boating, and sunbathing on our private beach.

Virgin Island Sailing® is a renowned travel agency located at 8900 North Armenia Avenue in Tampa, Florida, United States. With over 30 years of experience, we specialize in providing world-class yacht charters and sailing vacations in destinations such as the Caribbean, Mediterranean, South Pacific, and more. Our team is dedicated to ensuring that your sailing trip is trouble-free and unforgettable. Whether you're looking for a romantic retreat, a family adventure, or a fun getaway with friends, Virgin Island Sailing® offers a wide selection of sailboats, catamarans, motor yachts, and luxury yachts to suit your preferences. Our partnerships with reputable charter companies and crewed yacht management companies ensure that we only recommend the best yachts and crews in the industry.

Paradise Island Charters is a premier lodging and travel agency located at 105 Laguna Avenue in Key Largo, Florida. Offering luxurious accommodations and personalized travel experiences, Paradise Island Charters is the perfect destination for those seeking a tropical getaway. From arranging private charters to planning excursions to nearby islands, our experienced team is dedicated to providing top-notch service and creating unforgettable memories for our guests. Come discover the beauty of Key Largo with Paradise Island Charters.

Welcome to Ana Maria Island, your premier tourist attraction located at Florida 789, Bradenton Beach, Florida. Nestled in the heart of the beautiful Gulf Coast, Ana Maria Island offers a unique blend of natural beauty, vibrant culture, and endless recreational opportunities. Whether you're seeking a relaxing beach retreat or an adventure-filled getaway, our island paradise has something for everyone. Explore pristine white sand beaches, crystal-clear turquoise waters, and stunning sunsets that paint the sky with breathtaking colors. Enjoy a variety of outdoor activities, including swimming, snorkeling, fishing, and kayaking. Discover charming boutiques, local art galleries, and delightful dining options that showcase the rich flavors of Florida cuisine.

Anna Maria Island Getaway is a premier real estate and travel agency located in Bradenton Beach, Florida. Our dedicated team is committed to helping you find the perfect getaway on the beautiful Anna Maria Island. Whether you're looking for a beachfront vacation rental, a cozy cottage, or a luxurious villa, we have a wide selection of properties to choose from. Our experienced staff is here to assist you every step of the way, from booking your accommodation to planning your itinerary. Come experience the beauty and tranquility of Anna Maria Island with us at Anna Maria Island Getaway.

Anchor Down Real Estate & Rentals on Anna Maria Island offers top Bradenton & Anna Maria Island vacation rentals. Located at 9801 Gulf Drive in Anna Maria, Florida, this institution serves as a lodging, real estate, and travel agency. With a "No Worry Guest Guarantee" from reservation to check-out, Anchor Down Vacation Rentals provides the finest homes on the Florida Gulf Coast. Guests can enjoy spacious accommodations, beautiful outdoor areas, and excellent customer service. Whether you're looking for a family gathering, a romantic getaway, or a relaxing vacation, Anchor Down Vacation Rentals has the perfect property for you. Book today and experience the beauty of Anna Maria Island with Anchor Down!

Island Real Estate Vacations on Anna Maria Island is a premier real estate and travel agency located at 3909 East Bay Drive in Holmes Beach, Florida. With a wide range of vacation rental properties available, they provide visitors with the perfect accommodations to enjoy all that this beautiful island has to offer. Whether you're looking for a beachfront villa, a cozy cottage, or a luxurious condo, Island Real Estate Vacations has something for everyone. Their knowledgeable staff is dedicated to ensuring a seamless and memorable vacation experience for all guests. Experience the beauty and tranquility of Anna Maria Island with Island Real Estate Vacations.

Island Charters: Fishing Tours is a premier travel agency located at 319 East Sawyer, Saint George Island, Florida, United States. We offer a variety of fishing charters and guided tours for visitors looking to explore the beautiful waters surrounding the island. Whether you're a seasoned angler looking for the perfect catch or a tourist wanting to experience the natural beauty of the area, our experienced guides will ensure you have a memorable and enjoyable experience. Join us for an unforgettable adventure on the waters of Saint George Island!

Clausen Properties offers luxurious vacation rentals on the beautiful Marco Island in Florida. With a wide range of properties to choose from, guests can escape to paradise and enjoy stunning views of the Gulf of Mexico. Whether you're looking for a beachfront condo or a spacious villa, Clausen Properties has the perfect accommodation for your getaway. Their dedicated team of real estate and travel experts are committed to ensuring a seamless and unforgettable vacation experience for all their guests. Visit escapetomarco.com to book your dream vacation today!

Holiday Beach Resort - Soundside is a charming lodging institution located in Pensacola Beach, Florida. Situated on the beautiful Soundside of the island, this resort offers guests a peaceful and relaxing getaway with stunning views of the water. The resort features comfortable accommodations, including spacious rooms and suites, as well as amenities such as a swimming pool, fitness center, and on-site dining options. Guests can enjoy easy access to the beach, as well as nearby attractions such as restaurants, shops, and water sports activities. Whether you're looking for a romantic retreat or a fun-filled family vacation, Holiday Beach Resort - Soundside is the perfect destination for your next trip to Pensacola Beach.

The St George Island Florida Beach Cam is a must-visit destination located on the beautiful Saint George Island in Florida, United States. This institution offers a unique experience for visitors to enjoy the stunning views of the beach through their live webcam. Whether you're planning a trip to the area or simply want to take in the beauty of the beach from afar, the St George Island Florida Beach Cam is the perfect place to do so. Stop by this store and travel agency to get all the information you need for your visit to this picturesque location.

Island Paradise Cottages of Madeira Beach offers a relaxing and picturesque retreat for visitors to the sunny shores of Florida. Nestled in the heart of Madeira Beach, this charming lodging institution provides cozy and well-appointed cottages for guests to enjoy during their stay. Just a short walk from the beach, guests can soak up the sun, swim in the crystal-clear waters, or simply unwind on the sandy shores. With its convenient location and comfortable accommodations, Island Paradise Cottages is the perfect choice for a memorable beach getaway in Madeira Beach.

Suntide Island Beach Club is a charming beachfront lodging institution located at 850 Benjamin Franklin Drive in Sarasota, Florida, United States. This tropical oasis offers guests a relaxing and rejuvenating stay with its cozy accommodations and stunning views of the Gulf of Mexico. The resort features a variety of amenities including a heated outdoor pool, beach access, BBQ grills, and complimentary Wi-Fi. Whether you're looking to unwind on the sandy shores, explore the local attractions, or simply soak up the sun, Suntide Island Beach Club is the perfect destination for your next vacation getaway.

Windsong Charters & Boat Rentals is a premier institution located in New Port Richey, Florida, offering a wide range of services for boating enthusiasts. As a storage and travel agency, we provide secure and convenient storage solutions for boats of all sizes, along with expert guidance and assistance for planning unforgettable boating adventures. Our experienced team is dedicated to ensuring that every customer has a seamless and enjoyable experience on the water. Visit us at 5011 U.S. Highway 19 to learn more about our services and start your next boating journey with Windsong Charters & Boat Rentals.

Sunshine Island Inn is a charming lodging located at 642 East Gulf Drive in Sanibel, Florida. This cozy inn offers a peaceful retreat for guests looking to relax and unwind in a tropical paradise. With its convenient location just steps away from the beach, guests can enjoy easy access to the sun, sand, and surf. The inn features comfortable accommodations, friendly staff, and a welcoming atmosphere that will make you feel right at home. Whether you're seeking a romantic getaway or a family vacation, Sunshine Island Inn is the perfect destination for your next trip to Sanibel.

Holiday Inn Club Vacations Sunset Cove Resort is a luxurious lodging destination located at 571 West Elkcam Circle in Marco Island, Florida, United States. This resort offers a peaceful and relaxing atmosphere with stunning views of the sunset over the Gulf of Mexico. Guests can enjoy spacious accommodations, top-notch amenities, and personalized service during their stay. Whether you're looking to relax by the pool, explore the nearby attractions, or simply unwind on the beach, Sunset Cove Resort is the perfect choice for your next vacation getaway.

Island House Beach Resort is a charming lodging located at 6150 Midnight Pass Road in the beautiful Siesta Key, Florida. This beachfront resort offers guests a peaceful retreat with stunning views of the Gulf of Mexico. The resort features cozy accommodations, a sparkling outdoor pool, and direct access to the white sandy beaches. Guests can relax in the tropical gardens, take a dip in the ocean, or explore the nearby shops and restaurants. Whether you're looking for a romantic getaway or a fun family vacation, Island House Beach Resort is the perfect destination for a relaxing stay in paradise.

Marco Escapes is a premier real estate and travel agency located on beautiful Marco Island, Florida. Our vacation rentals offer luxurious accommodations with stunning ocean views and top-notch amenities. Whether you're looking for a beachfront condo or a spacious villa, we have the perfect rental for your getaway. Our friendly staff are dedicated to providing exceptional customer service and ensuring that your vacation is a memorable one. Book with us today and experience the ultimate escape on Marco Island.

The Holiday Life, located in Naples, Florida, is a real estate and travel agency specializing in upscale vacation and seasonal home rentals along Southwest Florida’s Paradise Coast. Each property in their portfolio offers guests a unique and authentically local experience with hotel-like service and amenities. They manage the entire rental process for absentee vacation homeowners, from marketing to cleaning to financial reporting. Their local team is available seven days a week to ensure guest needs are promptly met. One of their offerings, SoCe Flats, is a luxurious condominium development in the desirable Olde Naples neighborhood, within walking distance to the beach and 5th Ave S shopping district. Another option is GreenLinks Resort, centrally located in a resort community with fully furnished villas surrounded by championship golf courses and a resort-style pool. They also manage privately owned hotel condos on Marco Island’s white sand beach, with onsite dining options.

Sand Dollar Vacation Rentals and Property Management is a premier real estate and travel agency located in Fernandina Beach, Florida. Our team specializes in providing top-notch vacation rental properties for visitors looking to experience the beauty of the Amelia Island area. With a wide range of luxurious accommodations to choose from, we strive to make your vacation unforgettable. In addition to vacation rentals, we also offer property management services for homeowners looking to rent out their properties. Whether you are looking for a relaxing beachfront getaway or a cozy cottage in the historic district, Sand Dollar Vacation Rentals and Property Management has the perfect option for you. Visit us at 1963 South 8th Street to start planning your dream vacation today.

Welcome to Pine Island Cove, a hidden gem nestled on Pine Island near Flamingo Bay in Saint James City, Florida. Located at 7290 Ladyfish Drive, our charming lodging and RV park offers a serene escape into Old Florida's nature. Surrounded by the abundant wildlife, including majestic eagles and ospreys, Pine Island Cove is the perfect destination for nature enthusiasts and those seeking tranquility. Renowned for some of the best fishing spots in the world, our over-55 community attracts visitors from across the country and beyond, many of whom have come to affectionately call it "The Cove" or simply "Home." Whether you’re looking to relax or explore, Pine Island Cove provides a welcoming atmosphere where you can unwind and connect with the natural beauty of Florida. Come experience the charm and tranquility of Pine Island Cove, where every stay feels like coming home.

Amelia Island Premier Beach Rentals is a top-rated real estate and travel agency located in Fernandina Beach, Florida. Situated at 311 North 14th Street, this institution specializes in providing luxurious beachfront properties for vacation rentals on Amelia Island. With a wide range of rental options to choose from, guests can enjoy a relaxing and unforgettable beach getaway with stunning ocean views and top-notch amenities. Whether you're looking for a cozy condo for a romantic retreat or a spacious beach house for a family vacation, Amelia Island Premier Beach Rentals has the perfect accommodation for you. Book your dream beach rental today and experience the ultimate island paradise on Amelia Island.

Barefoot Rentals is a charming store located at 1808 U.S. 98 in Mexico Beach, Florida. Specializing in beach rentals, this institution offers everything you need for a fun and relaxing day at the beach. From umbrellas and beach chairs to paddle boards and snorkeling gear, Barefoot Rentals has you covered. Their friendly staff is always ready to assist you in finding the perfect rental for your beach day. Visit Barefoot Rentals and enjoy a hassle-free beach experience in beautiful Mexico Beach.