The 30 Best Florida keys vacation homes in Florida

Siesta Beach Rentals is a premier real estate and travel agency located at 333 Canal Road in Sarasota, Florida. We specialize in offering vacation rentals in the beautiful Siesta Key area, known for its stunning white sand beaches and crystal-clear waters. Our experienced team is dedicated to helping you find the perfect rental property for your next beach getaway, whether you're looking for a cozy condo or a luxurious beachfront villa. With our personalized service and attention to detail, we strive to make your vacation experience unforgettable. Contact Siesta Beach Rentals today to start planning your dream beach vacation in Sarasota, Florida.

CCVS - Villa Tropical Dream is a premier real estate and travel agency located in Cape Coral, Florida. Situated at 5011 Southwest 17th Avenue, our institution offers luxurious vacation rentals in the tropical paradise of Cape Coral. Our team of experienced professionals is dedicated to providing top-notch service to ensure a dream vacation experience for our clients. Whether you are looking to buy a vacation home or book a rental property for your next getaway, CCVS - Villa Tropical Dream has the expertise and resources to make it happen. Contact us today to start planning your tropical dream vacation!

The Coconut Cabana is a unique vacation rental located at 3597 San Carlos Drive in Saint James City, Florida. Following the devastation caused by Hurricane Ian on Pine Island, the property has undergone renovations and is now ready for guests to enjoy. The main house, Villa Key West, exudes the charm and style of a Key West home, with plenty of space and privacy. The Coconut Cabana is a separate guesthouse adjacent to the main house, offering accommodation for up to 2 people. The property boasts stunning grounds filled with exotic flowers, trees, and plants from around the world, as well as native Florida flora. Guests can enjoy swimming, boating, fishing, kayaking, and shelling right at their doorstep. Nearby attractions such as Ft Myers Beach, Sanibel Island, Cayo Costa State Park, and Boca Grande are just a short boat or ferry ride away. Villa Key West features one of the largest private pools on Pine Island, providing a relaxing oasis for guests to enjoy.

Old Wooden Bridge Guest Cottages & Marina is a charming lodging institution located at 1791 Bogie Drive in Big Pine Key, Florida, United States. Nestled in a picturesque setting, this establishment offers cozy and rustic cottages for guests to relax in. The marina provides easy access to the beautiful waters surrounding the Florida Keys, perfect for those looking to enjoy water activities such as boating and fishing. With its old-world charm and tranquil atmosphere, Old Wooden Bridge Guest Cottages & Marina is the ideal destination for a peaceful getaway.

Hillsboro Recreational Cottages is a charming lodging institution located on the picturesque Hillsboro Mile in Hillsboro Beach, Florida. Nestled along the stunning coastline of the United States, this quaint retreat offers cozy cottages for guests looking to unwind and relax in a peaceful setting. Each cottage is tastefully decorated and equipped with modern amenities to ensure a comfortable stay. With its convenient location near the beach, guests can enjoy a variety of recreational activities such as swimming, sunbathing, and water sports. Whether you're seeking a romantic getaway or a fun-filled family vacation, Hillsboro Recreational Cottages provides the perfect accommodation for a memorable stay in Florida.

Escape to Sweet Retreat is a luxurious real estate and travel agency located on Sweet Retreat Lane in the beautiful coastal town of Perdido Key, Florida, United States. Our agency specializes in providing the perfect vacation rentals and real estate properties for those looking to escape the hustle and bustle of everyday life and unwind in a peaceful and serene environment. Whether you're in search of a beachfront condo, a cozy cottage, or a spacious vacation home, our team of experts is dedicated to helping you find the perfect retreat for your getaway. Let us help you make your dream vacation a reality at Escape to Sweet Retreat.

Perdido Retreat is a premier real estate and travel agency located at 7927 Sweet Retreat Lane in Pensacola, Florida. Our agency specializes in providing luxurious vacation rentals and real estate properties in the beautiful coastal area of Perdido Key. Whether you are looking for a relaxing beachfront retreat or a stunning waterfront property, our experienced team is dedicated to helping you find the perfect getaway. With a wide range of options to choose from, Perdido Retreat is your go-to destination for an unforgettable vacation experience. Contact us today to start planning your dream retreat in paradise.

Emerald Coast Realty Pros is a reputable real estate agency located at 125 West Romana Street in Pensacola, Florida. Situated in a city with a rich history and diverse cultural influences, Pensacola offers a unique blend of architecture and attractions. Known for its temperate climate and beautiful beaches, Pensacola is a sought-after destination for retirees and those seeking a coastal lifestyle. The Greater Pensacola area includes several cities and towns, each with its own charm and appeal. From Gulf Breeze to Perdido Key, there are a variety of properties available for investors and vacationers alike. Our experienced Realtors have extensive knowledge of the local market and can help you find the perfect home or condo to suit your needs.

Destiny Beach Villas is a premier real estate and travel agency located at 3551 Scenic Highway 98 in Destin, Florida. We specialize in offering short and long term rental properties that are fully furnished and include all utilities in most properties. Our homes are available for weekly and monthly rentals, as well as six and twelve month leases. We manage only the finest properties in Orange Beach, Alabama, Perdido, Pensacola Beach, Destin, and Santa Rosa Beach in Florida. Our sister company, Emerald Gulf Coast Properties, is a full service Real Estate Company that serves the Gulf Coast of Florida and Alabama.

Splash - Sleeps 32 is a luxurious 8 bedroom home located at 3463 Scenic Highway 98 in Destin, Florida. This stunning property features 7 King Beds, 6 Queen Beds, and 6 Twin Beds, as well as 9 bathrooms and 2 laundry rooms with 3 sets of washers and dryers. As a real estate and travel agency, Splash offers a range of amenities to ensure a comfortable and enjoyable stay for guests. These include a game room with pool table and foosball table, 30 TVs throughout the home, pool towels, an elevator (with fee), a garage, and easy access to restaurants. The highlight of the property is the resort-style pool with a swim-up pool bar, perfect for relaxing and enjoying the Florida sunshine.

VillaKey is a real estate and travel agency located at 1420 Celebration Boulevard in Celebration, Florida, United States. Specializing in Orlando vacation rentals for all types of families, VillaKey offers a wide selection of affordable homes with private pools, townhomes, and condos just minutes away from popular attractions like Disney World, Universal Studios, and SeaWorld Orlando. Their vacation rental homes feature game rooms, themed rooms with favorite characters, and resort amenities like resort-style pools and clubhouses. With a focus on providing clean, comfortable, and well-equipped rental homes, VillaKey ensures that families have a special place to bond and relax while on vacation. Their team is available 24/7 for assistance and questions, and they also offer a unique vacation rental management program for homeowners.

Emerald Island Resort Orlando is a luxurious real estate and travel agency located at 8532 Sunrise Key Drive in Kissimmee, Florida. Our resort offers a range of stunning vacation homes and villas for rent, perfect for families and groups looking to experience the magic of Orlando. With top-notch amenities such as a clubhouse, swimming pools, and sports facilities, guests can enjoy a relaxing and unforgettable stay just minutes away from the world-famous theme parks and attractions. Come experience the beauty and convenience of Emerald Island Resort Orlando for your next vacation getaway.

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.

Disney World House Rental is a luxurious real estate and travel agency located at 8578 Sunrise Key Drive in Kissimmee, Florida, United States. This stunning property offers guests a truly magical vacation experience, with top-notch amenities and a prime location just a 4-mile drive from Disney World's Animal Kingdom Theme Park. The house features beautiful vinyl plank flooring, high-quality pool and spa heating, and a private pool deck surrounded by lush flowering plants. Guests can enjoy the spa/Jacuzzi, high-speed Wi-Fi, and over 100 TV channels on the 7 LED HD Smart TVs. The 6-bedroom, 5 ½ bathroom house can accommodate up to 18 guests, with 4 master suites and 2 children's bedrooms. The upscale furnishings and elegant decor create a warm and inviting atmosphere throughout the 2900 square foot property. The fully stocked kitchen and spacious family room with vaulted ceilings provide the perfect space for relaxing and entertaining. Outside, guests can enjoy the South-facing pool and lanai, with comfortable loungers and a safety fence for young children. The Emerald Island Resort Clubhouse offers additional amenities, including a heated pool and spa, fitness room, Tiki Bar, and nature walking trail. With 24/7 security and a range of entertainment options, Disney World House Rental is the perfect choice for a magical vacation in Florida.

Real Property Management Verita, located at 1401 Town Plaza Court in Winter Springs, Florida, is dedicated to providing quality residential property management services to property owners and residents. With over 30 years of nationwide experience, Real Property Management Verita offers affordable solutions for managing real estate in Seminole County, Florida. The institution's Wealth Optimizer tool allows property owners to easily access important metrics and compare multiple properties to determine the best investment for their portfolio. Backed by Real Property Management's 35 years of experience, Wealth Optimizer helps users analyze financial assumptions and key performance indicators to maximize their property's return.

Wish Upon A Starfish is a real estate and travel agency located at 411 80th Street in Holmes Beach, Florida, United States. This Key West style 3 bedroom home offers a peaceful and relaxing retreat on Anna Maria Island. With vaulted ceilings, an open floor plan, and a private heated pool, this paradise found is perfect for families looking for a beach getaway. The fully equipped kitchen, spacious front deck, and cozy living room provide all the comforts of home. The home is family-friendly, with amenities such as a pack n' play, high chair, and baby gates provided. Children will love the bunk bed room with its own private bathroom, while adults can relax in the Queen size guest bedroom with an adjustable bed.

Claudia Centesimo, LionHeart Brokers is a top-notch real estate agency located at 941 West Morse Boulevard in Winter Park, Florida, United States. With a focus on bringing your real estate goals to fruition, Claudia Centesimo, the lead real estate agent, has a wealth of experience and a passion for helping clients navigate the buying and selling process. Growing up in Illinois and Indiana, Claudia learned the values of hard work, family, and community. With a background in sports and a strong work ethic, she graduated with top honors from West Virginia University before embarking on a successful career at Disney. Her dedication to guest service and commitment to excellence are evident in her work as a real estate agent.

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.

Sunset Royale is a premier real estate and travel agency located at 711 Beach Road in the beautiful Siesta Key, Florida. Our team of dedicated professionals is committed to helping clients find their dream vacation rental or forever home in this stunning beachfront community. With a wide range of properties to choose from, including luxurious condos and beachfront villas, Sunset Royale is your go-to destination for all your real estate and travel needs in Siesta Key. Contact us today to start planning your next getaway or to find your perfect piece of paradise in this idyllic coastal town.

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.

Siesta By The Sea is a charming lodging establishment located at 1138 Windsong Lane, Siesta Key, Florida. As a real estate and travel agency, we offer a range of accommodations for travelers looking to experience the beauty of Siesta Key. Our cozy rooms and beachfront properties provide the perfect setting for a relaxing getaway by the sea. Whether you're looking for a weekend escape or a longer stay, Siesta By The Sea is your home away from home on the stunning shores of Florida. Contact us today to book your stay and start planning your dream vacation.

Coldwell Banker Realty is a premier real estate agency located at 100 North Tamiami Trail in Sarasota, Florida. Our office is conveniently situated near the Ritz and Westin, making it easily accessible for all of Sarasota. With over 150 agents, we have a strong customer service reputation and make a significant impact on the real estate market in Sarasota and Manatee Counties. Our office serves a wide range of areas including Sarasota, Bradenton, Bradenton Beach, Lakewood Ranch, Longboat Key, Siesta Key, Venice, Nokomis, Osprey, Anna Maria, and Holmes Beach. We offer a variety of properties including luxury homes, condominiums, new construction, resales, commercial properties, condo-hotels, and fractional ownership. Our experienced agents have received national recognition for their dedication and production.

Siesta Dunes is a reputable real estate agency located at 6200 Midnight Pass Road in the beautiful Siesta Key, Florida. Our experienced team of professionals is dedicated to helping clients find their dream homes or investment properties in this stunning coastal area. With a focus on personalized service and attention to detail, Siesta Dunes is committed to making the buying or selling process as smooth and stress-free as possible. Whether you are looking for a beachfront condo, a luxurious estate, or a cozy vacation rental, Siesta Dunes has the expertise and resources to meet your real estate needs. Contact us today to start your journey towards owning a piece of paradise in Siesta Key.

Charlotte House is a charming lodging option located at 302 East Charlotte Avenue in Punta Gorda, Florida. This small bungalow has an open floor plan that makes it feel larger than its 750 square feet. With 2 bedrooms, Charlotte House can comfortably sleep 5 guests in beds - one room with a queen bed, another with two twin beds, and a bonus room with a daybed. Situated in the historic town of Punta Gorda on Charlotte Harbor, where the Peace River meets the Gulf of Mexico, Charlotte House offers easy access to wonderful restaurants, cocktails, and stunning sunsets. The town is centrally located between two famous beaches - Siesta Key in Sarasota to the north and Sanibel Island to the south. Outdoor enthusiasts will enjoy activities such as boating and fishing, as well as beautiful parks and pickleball courts along the Harbor. Punta Gorda also hosts a variety of events throughout the year, including block parties, wine and jazz festivals, and dragon boat races.

Villa Ferienspatz / Villa Mango is a luxurious real estate and travel agency located in the beautiful city of Cape Coral, Florida. Our stunning villas offer the perfect blend of comfort and sophistication, making them the ideal choice for your next vacation or investment property. With a prime location just minutes away from the beach and other popular attractions, Villa Ferienspatz / Villa Mango ensures a memorable and relaxing stay for all guests. Whether you're looking for a dream vacation rental or a lucrative real estate investment, our dedicated team is here to help you every step of the way. Experience the ultimate in luxury living with Villa Ferienspatz / Villa Mango.

The Eberly Team is a reputable real estate agency located at 1675 West Marion Avenue in Punta Gorda, Florida. With a team of experienced and dedicated professionals, The Eberly Team specializes in helping clients buy and sell properties in the Punta Gorda area. Their personalized approach and attention to detail ensure that each client receives top-notch service and achieves their real estate goals. Whether you are looking to purchase your dream home or sell your current property, The Eberly Team is committed to providing exceptional service and expertise every step of the way.

Salty Air Retreat Beach House, located at 127 Miramar Street in Fort Myers Beach, Florida, is a charming and cozy retreat right by the sea. This real estate and travel agency offers a selection of beautiful beach houses for rent, perfect for a relaxing vacation getaway. With stunning ocean views, easy access to the beach, and a peaceful atmosphere, Salty Air Retreat Beach House is the ideal destination for those looking to unwind and rejuvenate by the sea. Experience the beauty of Fort Myers Beach and create unforgettable memories at this lovely retreat.

Villa Lazy River - with Pool & Hot Tub in Bonita Springs The Villa Lazy River will immediately impress you upon arrival. Park in your long driveway or in your double garage. Step inside and be enchanted by the ambiance of this brightly furnished villa with a large pool. Enjoy your vacation with us, you deserve it.

City2Shore Real Estate - Southern Palm is a premier real estate agency located in Fort Myers, Florida. Situated at 5294 Summerlin Commons Way, this institution specializes in helping clients buy and sell properties in the Southern Palm area. With a team of experienced and knowledgeable real estate agents, City2Shore Real Estate - Southern Palm provides top-notch service and guidance to ensure a smooth and successful real estate transaction. Whether you are looking to find your dream home or sell your current property, City2Shore Real Estate - Southern Palm is dedicated to helping you achieve your real estate goals.