Enjoy a relaxing vacation in a Southwest Florida vacation rental. With its long, shell-studded beaches and beautiful wilderness areas, this section of Florida satisfies thrill-seekers and relaxation pros. Spend your days kayaking through wild inland waterways, or bring a stack of books for lazy days at the beach. Whether you’re visiting with your best friends or your children, Southwest Florida offers the sunshine and warm weather you need for the perfect getaway. With vacation rentals in the area’s most popular towns, you can create a cozy home base for any adventure.

1. Fort Myers

Combine your beach vacation with city conveniences in Fort Myers. Start the day with a sunrise fishing trip, and spend the afternoon paddling on the Caloosahatchee River. When you need a break from the water, head to the Thomas Edison and Henry Ford winter estates, where you can tour expansive gardens, check out the onsite museum, and explore Edison’s Botanic Research Laboratory. Vacation rentals downtown place you within walking distance of the best local restaurants, while waterfront condos offer the best views.

2. Sanibel Island

Immerse yourself in the welcoming community of Sanibel Island. When you arrive, head straight for the beach; this compact island boasts miles of pristine white-sand beaches and shimmering blue water. Choose an oceanside rental for walk-out water access, or if you’re bringing a kayak or stand-up-paddleboard, look for a rental with a boat slip. The best way to see the island is by bike; rent a cruiser from a local company to check out Bowman’s Beach, and be sure to watch the flamingos at the J.N. Ding Darling National Wildlife Refuge.

3. Captiva Island

Book your own piece of paradise with a seaside cottage or a modern condo on tiny Captiva Island. Here, brilliant blue waters meet sunny skies, and visitors kick back on postcard-perfect shores. While you’re in town, enjoy a walk down the beach to pick up the shells that wash in from the Gulf of Mexico. Pack your fishing rods and try your luck at Turner Beach, and make a point to head to the water for some of Southwestern Florida’s most spectacular sunsets.

4. Naples

With its excellent shopping and family-friendly atmosphere, Naples offers something for every traveler. Bring the kids to the Naples Zoo at Caribbean Gardens, or spend an afternoon marveling at the exotic plants in the Naples Botanical Garden. Find the perfect new dress or work of art in the historic downtown area, which is known for its galleries and upscale boutiques. When you’re ready to soak up the sun, head for the Naples Pier for fishing and beautiful sunset views.


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5. Marco Island

Enjoy a luxurious escape on Marco Island, a sprawling area south of Naples. Here, it’s a breeze to find a waterfront vacation rental; opt for a beach condo on the western side of the island for the best sunsets, or choose a canal rental with a private dock for fast boat launching. If you’re feeling active, rent a kayak and paddle around the Ten Thousand Islands National Wildlife Refuge to explore hidden beaches and search for playful manatees.

6. Everglades City

Establish the perfect base for your Everglades adventure in Everglades City. After watching the sunrise from your vacation rental, book a paddle tour to the legendary Wilderness Waterway. Feel the adrenaline rise on an airboat tour through the nearby Everglades National Park, or walk the boardwalks of the Big Cypress National Preserve in search of the mysterious Florida panther. If you’re visiting in February, don’t miss the mouth-watering dishes at the Everglades Seafood Festival.

7. Sarasota

Spend your vacation soaking up the sun in fun, relaxed Sarasota. Known for its stunning beaches and vibrant social scene, this friendly city is a great choice for couples, families, and large groups. On a hot day, bring the kids to Bayfront Park to play in the water features and test out the large playground. Cool off at the John and Mable Ringling Museum of Art and the nearby Circus Museum, enjoy an evening performance at the Sarasota Operaor watch Indie films at the annual Sarasota Film Festival.

8. Siesta Key

Relax and rejuvenate with a vacation rental on beautiful Siesta Key. Spend lazy days sunbathing and swimming at Siesta Beach, which has been named the best in America by TripAdvisor. When you’re ready for adventure, rent a Jet Ski or a boogie board from one of many local vendors. Enjoy excellent snorkeling at Point of Rocks, or head to Turtle Beach for a quiet, peaceful beach escape. Vacation rentals near Siesta Village place you a short walk from the area’s best restaurants and bars.

9. Venice

Whether you’re in Southwest Florida for a girls’ weekend or a romantic getaway, Venice is the perfect choice. With its year-round sunshine, lovely beaches, and walkable downtown, this charming city has something for everyone. Spend an afternoon wandering through shops and cafes in the Italian-inspired downtown, and cool down in the splash fountain at Centennial Park. For a unique local experience, search for fossilized shark teeth along the beach by the Venice Fishing Pier.

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