The 30 Best Florida keys vacations in Holiday, Florida

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Perdido Beach, located at 14405 Perdido Key Drive in Pensacola, Florida, is a tourist attraction that truly lives up to its name, which means "lost island" in Spanish. This Southern sanctuary is a barrier island that offers a unique blend of natural beauty, coastal living, and southern charm. With its white-sand dunes, calm Gulf waters, and abundant wildlife, Perdido Key is the perfect destination for beach lovers and nature enthusiasts alike. Visitors can enjoy dining at waterfront restaurants, stay in beachfront resorts or cozy cottages, and partake in a variety of beach adventures such as fishing charters, jet ski rentals, and kayaking. With miles of beaches to explore, including popular spots like Johnson Beach and Perdido Key State Park, there is no shortage of outdoor activities to enjoy.

Skiers' Island is a thrilling park located on Siesta Key Circle in beautiful Siesta Key, Florida. This unique institution offers a wide range of activities for skiers of all levels, from beginners to experts. Visitors can enjoy water skiing, wakeboarding, and other exciting water sports in a safe and supervised environment. With stunning views of the surrounding area and top-notch facilities, Skiers' Island is the perfect destination for those looking for an adrenaline-filled day out on the water. Come and experience the excitement at Skiers' Island today!

Sunshine Watersports is a premier travel agency located in Key Largo, Florida, United States. Situated at 107900 Overseas Highway, this institution offers a wide range of exciting water-based activities and adventures for tourists visiting the beautiful Florida Keys. From jet ski rentals to snorkeling tours, Sunshine Watersports provides unforgettable experiences for visitors looking to explore the crystal-clear waters and vibrant marine life of the area. With knowledgeable staff, top-notch equipment, and excellent customer service, Sunshine Watersports is the perfect choice for travelers seeking thrilling aquatic adventures in Key Largo.

Interiors by Maite Granda Inc is a multifaceted institution located at 200 Crandon Boulevard in Key Biscayne, Florida, United States. As a general contractor, they offer a wide range of services for home improvement projects. Additionally, they operate as a home goods store, providing customers with high-quality furniture and decor items. As a real estate agency, they assist clients in finding their dream homes or investment properties. Their store also offers a curated selection of products for sale. Furthermore, they operate as a travel agency, helping clients plan unforgettable vacations and getaways. With a diverse range of services, Interiors by Maite Granda Inc is a one-stop destination for all your home and travel needs.

Resort & Luxury Home Title Inc is an insurance agency located at 13700 Perdido Key Drive in Pensacola, Florida. We specialize in providing title insurance for high-end resort properties and luxury homes, ensuring that our clients have peace of mind when purchasing or refinancing their valuable investments. Our experienced team of professionals is dedicated to providing top-notch service and protection for your property transactions. Trust Resort & Luxury Home Title Inc to safeguard your real estate assets with the highest level of expertise and care.

Experience luxury beachfront living at this stunning 2BR/2BA condo with a private Jacuzzi. Located at 14511 Perdido Key Drive in Pensacola, Florida, this beautifully appointed lodging offers breathtaking ocean views and direct access to the sandy shores. The spacious two-bedroom, two-bathroom layout provides ample room for relaxation and entertainment, while the Jacuzzi offers the perfect spot to unwind after a day of sun and surf. With modern amenities and a prime location, this beachfront oasis is the perfect destination for your next vacation.

Villa #3 Seahorse is a charming lodging establishment located at 3605 Gulf Drive in Holmes Beach, Florida, United States. This cozy villa offers a relaxing tropical atmosphere with stunning views of the Gulf of Mexico. Guests can enjoy a peaceful getaway with easy access to the beach, as well as nearby dining and shopping options. The villa features comfortable accommodations, a fully equipped kitchen, and a private outdoor patio for guests to unwind and soak up the sunshine. Whether you're looking for a romantic retreat or a family vacation, Villa #3 Seahorse is the perfect destination for a memorable stay on Anna Maria Island.

The Penthouses at Gulf Stream offer luxurious and spacious accommodations in the heart of Anna Maria, Florida. Located at 1501 Gulf Drive, this upscale lodging option provides stunning views of the Gulf of Mexico and easy access to the pristine beaches of the area. Each penthouse is elegantly furnished and equipped with modern amenities to ensure a comfortable stay. Guests can enjoy the convenience of nearby dining and shopping options, as well as outdoor activities such as fishing, kayaking, and beachcombing. Whether you're looking for a relaxing getaway or an adventurous vacation, the Penthouses at Gulf Stream are the perfect choice for your stay in Anna Maria.

The Lido Islander is a premier institution located at 528 South Polk Drive in Sarasota, Florida. As a multi-faceted establishment, it serves as a lodging facility, real estate agency, and travel agency all in one. Whether you are looking for a luxurious place to stay, seeking to invest in property on Lido Key, or planning your next vacation, the Lido Islander offers a one-stop solution for all your needs. With a prime location in the beautiful city of Sarasota, the Lido Islander provides top-notch services and accommodations to ensure a memorable experience for all guests and clients.

Jamaica Royale is a charming lodging institution located at 5830 Midnight Pass Road in Siesta Key, Florida, United States. Nestled in the heart of one of Florida's most popular beach destinations, Jamaica Royale offers guests a relaxing and comfortable stay just steps away from the beautiful white sands of Siesta Key Beach. With a range of accommodations to choose from, including cozy condos and spacious villas, guests can enjoy all the comforts of home while experiencing the beauty of the Gulf Coast. Whether you're looking for a romantic getaway, a family vacation, or a solo retreat, Jamaica Royale is the perfect choice for your next Siesta Key adventure.

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.

South Palm Suites is a charming lodging institution located at 1401 Federal Highway in the picturesque Lake Worth Beach, Florida. Nestled in a prime location, just a stone's throw away from the beach, this cozy establishment offers comfortable and affordable accommodations for travelers looking to unwind and relax in the sunshine state. With its convenient location, friendly staff, and well-appointed rooms, South Palm Suites is the perfect choice for a memorable stay in beautiful Lake Worth Beach.

Little Havana is a charming lodging institution located in the vibrant neighborhood of Miami, Florida. Situated in the heart of the city, this cozy establishment offers guests a comfortable and convenient place to stay while exploring all that Miami has to offer. With its close proximity to the city's top attractions, restaurants, and nightlife, Little Havana is the perfect choice for travelers looking to immerse themselves in the rich culture and lively atmosphere of this iconic neighborhood. Whether you're visiting for business or pleasure, Little Havana provides a welcoming and relaxing retreat for your stay in Miami.

Topsiders Resort is a charming lodging establishment located at 75500 Overseas Highway in the picturesque town of Islamorada, Florida. This tropical oasis offers guests a relaxing and comfortable stay in the heart of the Florida Keys. The resort features spacious and well-appointed rooms, a sparkling swimming pool, and stunning views of the surrounding landscape. Whether you're looking for a romantic getaway, a family vacation, or a solo retreat, Topsiders Resort is the perfect destination for your next trip to paradise. With its convenient location and top-notch amenities, this resort is sure to provide a memorable and enjoyable experience for all guests.

CaliFlorida Dreamin' STR is a premier real estate agency located at 7935 Sweet Retreat Lane in Perdido Key, Florida. Specializing in vacation rentals and investment properties, our team of experienced agents is dedicated to helping clients find their dream home or rental property in the beautiful coastal area of Perdido Key. With a focus on personalized service and attention to detail, we strive to make the buying or renting process as smooth and stress-free as possible. Whether you're looking for a beachfront condo, a luxury villa, or a cozy cottage, CaliFlorida Dreamin' STR is here to help you find the perfect property to suit your needs and lifestyle. Contact us today to start your real estate journey in paradise!

Somerset Ocean Villas is a luxurious beachfront resort located at 924 Whelk Court on Okaloosa Island, Florida. This stunning property offers spacious and beautifully appointed villas with breathtaking views of the ocean. Guests can enjoy a range of amenities including a private beach access, outdoor swimming pool, fitness center, and on-site dining options. Whether you're looking for a relaxing getaway or a fun-filled vacation, Somerset Ocean Villas is the perfect destination for your next trip to the Sunshine State.

The Scallop Inn is a real estate and travel agency located at 7086 Southwest Highway 358 in Steinhatchee, Florida, United States. Our beautiful condo is situated right on the Steinhatchee River, offering the perfect location for fishing, scalloping, or simply enjoying the scenic views. With a private dock and assigned boat slip, guests have easy access to the river for all their water activities. For those without a boat, nearby marinas offer rentals and services. The fully equipped condo includes amenities such as Cable TV, Wi-Fi, Memory Foam mattresses, and a stocked kitchen with essential appliances. Security cameras ensure added safety, while a fish cleaning station and gazebo provide convenience and relaxation. After a day of adventure, guests can dine at one of the many nearby restaurants or explore the town of Steinhatchee. Come experience leisure and comfort on the Stienhatchee River at The Scallop Inn. Book your stay now and discover the wonders of this charming town.

Annual Rentals. Marco Island by Horizons is a reputable real estate and travel agency located at 661 South Collier Boulevard in Marco Island, Florida. Specializing in long-term rentals, they offer a wide range of properties for those looking to make Marco Island their home. With a dedicated team of professionals, they provide excellent customer service and strive to ensure that each client finds the perfect rental to suit their needs. Whether you are looking for a beachfront condo or a luxurious villa, Annual Rentals. Marco Island by Horizons has something for everyone. Experience the beauty and tranquility of Marco Island with the help of this trusted agency.

Sea Gull Condos is a luxurious waterfront accommodation located at 200 Wrenn Street in Tavernier, Florida. Nestled in the heart of the Florida Keys, this stunning property offers spacious and beautifully appointed condominiums with breathtaking views of the crystal-clear waters of the Atlantic Ocean. Guests can relax and unwind in the on-site pool, or take a short stroll to the nearby sandy beach for a day of sunbathing and swimming. With its convenient location and top-notch amenities, Sea Gull Condos is the perfect choice for a relaxing and memorable vacation in paradise.

Ocean Pointe Suites is a charming lodging institution located at 92530 Overseas Highway in Tavernier, Florida. Situated right on the waterfront, this resort offers stunning views of the ocean and easy access to the beach. The suites are spacious and well-appointed, perfect for a relaxing getaway or a family vacation. Guests can enjoy amenities such as a swimming pool, tennis courts, and a fitness center. With its convenient location and comfortable accommodations, Ocean Pointe Suites is the perfect choice for those looking to experience the beauty of the Florida Keys.

Ocean Shore Villas is a luxurious seaside retreat located at 133 Ocean Bay Drive in Key Largo, Florida. Nestled along the stunning coastline of the United States, this institution offers unparalleled views of the ocean and a serene atmosphere for guests to relax and unwind. The villas are elegantly designed and equipped with modern amenities to ensure a comfortable stay. Whether you are looking for a romantic getaway or a family vacation, Ocean Shore Villas is the perfect destination for a memorable experience by the sea.

Manatee Bay Marina, LLC is a unique vacation experience located at 999 Morris Avenue in Key Largo, Florida. This holistic vacation destination offers comfortable self-catering accommodations with stunning views, a communal pool, and included amenities such as kayaks and stand-up paddle boards. Guests can also take advantage of on-site boat rentals and boat captain services, making it the perfect base for exploring the Florida Keys, the Everglades, and Miami. With luxury amenities, personalized service, and a convenient location, Manatee Bay Marina is the ideal choice for a memorable vacation in Key Largo.

KeysVacationHouse.com is a premier real estate and travel agency located at 88005 Overseas Highway in Islamorada, Florida. Specializing in luxurious vacation rentals in the beautiful Florida Keys, our agency offers a wide selection of stunning properties for visitors to choose from. Whether you are looking for a cozy beachfront cottage or a spacious waterfront villa, we have the perfect vacation house to suit your needs. Our team of experienced agents is dedicated to providing exceptional customer service and helping you find the ideal accommodation for your dream getaway. Book your next vacation with KeysVacationHouse.com and experience the ultimate in comfort and relaxation in the tropical paradise of the Florida Keys.

Venetian Tropics is a luxurious lodging and real estate agency located at 106 San Remo Drive in the stunning Islamorada, Florida. Nestled in the heart of the Florida Keys, this institution offers a unique blend of tropical charm and Venetian elegance. Whether you are looking for a relaxing vacation rental or seeking to invest in a piece of paradise, Venetian Tropics has a team of expert agents ready to assist you. With a prime location near the turquoise waters of the Atlantic Ocean, guests and clients alike can enjoy the ultimate tropical getaway experience. Book your stay or find your dream property with Venetian Tropics today!

Located at 209 Andros Road in Key Largo, Florida, 209Andros.com is a real estate and travel agency institution that offers a unique and luxurious experience for guests. Situated just steps away from The Inn, Buccaneer Island, Carysfort Hall, and The Marina, our guests enjoy the convenience of being in the heart of all the action at Ocean Reef. Our guests choose us again and again for three main reasons. Firstly, time matters, especially on vacation, and our guests want to maximize every minute of their precious holiday. With our modern beach house just seconds away from all the best amenities and activities, including pools, restaurants, and fitness centers, guests can easily walk everywhere without worry.

Ocean Reef Condo is a luxurious oceanfront property located at 8 Marlin Lane in Key Largo, Florida. This stunning condominium offers breathtaking views of the ocean and access to pristine beaches, making it the perfect getaway for those seeking a relaxing and rejuvenating vacation. With spacious and elegantly furnished suites, state-of-the-art amenities, and top-notch service, Ocean Reef Condo provides guests with a truly unforgettable experience. Whether you're looking to unwind by the pool, explore the nearby attractions, or simply soak in the natural beauty of the surroundings, Ocean Reef Condo is the ideal destination for your next holiday.

Mickey's Sunny Mansion is the perfect vacation home for your family in Florida. Located just minutes away from Disney, this spacious seven-bedroom house offers all the amenities you need to make your stay comfortable and enjoyable. With two washing machines, two dryers, and two dishwashers, you can spend less time on chores and more time with your loved ones. The house features a game room, large patio area, and a private pool and spa for relaxation. Each room is beautifully decorated and designed to make your family feel at home. The kitchen is fully equipped with modern appliances, and the living room offers a cozy space to relax with a 70-inch 4k TV and Amazon Alexa. The house also has two master bedrooms, each with a king-sized bed and ensuite bathroom. The other bedrooms are themed with popular Disney characters like Belle, Walt Disney, and Mickey Mouse. The house also has a second master bedroom with its own ensuite bathroom. The air-conditioned game room includes a full-size pool table, air hockey table, arcade games, and a second refrigerator. Mickey's Sunny Mansion is located in the gated community of Emerald Island, with easy access to shopping, dining, and attractions. With its convenient location and luxurious amenities, this vacation home is the perfect choice for your family getaway in Florida.

Gertrude Rentals, located at 360 Canal Road in Siesta Key, Florida, is a real estate and travel agency offering over 60 units in the Beach Village or Lagoon area. With only the best locations available, there is a perfect fit for every group and budget. The team at Gertrude Rentals consists of natives, transplants, visitors, and locals who all share a common goal of understanding the importance of your vacation time. Situated near North America's best white sand beaches, our units are within walking distance to world-famous shopping, dining, and entertainment. Each unit offers unique features such as private pools, ocean-views, lagoon front decks, lazy hammocks, tiki-huts, and rooftop sun-decks. Whether you are looking for a relaxing beach vacation or an adventure-filled getaway, Gertrude Rentals has something for everyone.

Located at 1200 Siesta Bayside Drive in Siesta Key, Florida, Gulf & Bay Club Bayside is a real estate and travel agency offering stylish accommodations and residential-style amenities for a tranquil retreat. Nestled amidst serene waterways and lush greenery, this tropical hideaway provides a haven of comfort and relaxation. Guests can unwind by two heated swimming pools, stay active in the fitness center, or enjoy friendly matches on the tennis and pickleball courts. Each individually owned residency offers convenience with a private garage and in-unit washer and dryer. Just a short stroll away from Siesta Key Village, guests can easily explore the stunning Siesta Key and Crescent Beach, with golf-cart taxis and the Siesta Key tram available for transportation. Escape to this personalized retreat in Siesta Key and indulge in the best of tropical living at Gulf & Bay Club Bayside.

Beach House on Siesta is a premier real estate and travel agency located at 669 Avenida De Mayo in the beautiful Siesta Key, Florida. Our agency specializes in providing luxurious beachfront properties for sale or rent, offering stunning views and top-notch amenities. Whether you are looking to invest in a vacation home or plan a dream getaway, our team of experienced agents is here to assist you every step of the way. Escape to paradise with Beach House on Siesta and experience the ultimate beachfront living in the United States.