As the temperatures drop across the northern United States and Canada, Florida becomes the go-to destination for snowbirds—travelers seeking a warm, sunny escape from the cold. Florida’s mild winters, beautiful beaches, and diverse attractions make it an ideal spot for long-term winter stays. Whether you’re looking for a quiet retreat, an active social scene, or proximity to the ocean, Florida has plenty of vacation rental options that cater to snowbirds.
In this guide, we’ll highlight some of the top winter escape destinations in Florida and recommend the best long-term vacation rentals for snowbirds looking to soak up the sunshine.
Interested in booking a long-term rental this winter? Contact Grimaldi & Weiss Management for expert assistance in finding the perfect winter retreat in Florida.
1. Naples: Luxury Living on the Gulf Coast
Naples is known for its upscale living, pristine beaches, and world-class golf courses, making it a top choice for snowbirds who want to enjoy the finer things in life. Located on Florida’s Gulf Coast, Naples offers a relaxed atmosphere with plenty of outdoor activities, including boating, tennis, and birdwatching. It’s also home to high-end shopping, dining, and cultural experiences, perfect for those looking for both luxury and leisure during their winter escape.
Why Naples Is Ideal for Snowbirds:
- Mild Winters: With average winter temperatures ranging from the mid-60s to 70s°F (18-24°C), Naples provides a perfect climate for outdoor activities.
- Luxury Amenities: Upscale dining, shopping, and golf courses abound in Naples, catering to snowbirds who want to indulge in the finer things.
- Nature and Outdoor Activities: Naples offers beautiful beaches and nature preserves, including the Naples Pier and the Corkscrew Swamp Sanctuary, where snowbirds can enjoy walking trails and wildlife.
Best Long-Term Rentals in Naples:
1. Golf Course Condo with Pool Access
- Description: This two-bedroom, two-bath condo is located within a gated golf community, offering access to world-class golfing, swimming pools, and tennis courts. With a fully equipped kitchen and spacious living area, it’s ideal for snowbirds looking for a quiet, comfortable stay.
- Why Snowbirds Love It: The condo offers easy access to golf courses and walking trails, plus it’s just a short drive from Naples’ white sandy beaches.
- Amenities: Access to golf courses, pools, fitness center, and club dining.
2. Beachfront Villa with Private Patio
- Description: This luxury beachfront villa offers stunning ocean views, a private patio, and direct beach access. With three bedrooms, it’s perfect for snowbirds looking to spend their winter months by the sea.
- Why Snowbirds Love It: The location is unbeatable, with immediate beach access and proximity to downtown Naples for shopping and dining.
- Amenities: Private beach access, outdoor dining area, and fully equipped kitchen.
Naples Tip:
- Book early to secure prime rentals, as Naples is a highly sought-after winter destination for snowbirds. Look for properties that include access to community amenities like pools, tennis courts, and golf courses.
2. Fort Myers: Affordable Waterfront Escapes
For snowbirds looking for a more budget-friendly option without sacrificing beach access and outdoor activities, Fort Myers is a fantastic choice. Located on the Gulf Coast, Fort Myers offers beautiful beaches, historical sites, and a laid-back atmosphere. It’s particularly popular among retirees, with numerous waterfront properties, nature reserves, and easy access to nearby Sanibel and Captiva Islands.
Why Fort Myers Is Ideal for Snowbirds:
- Affordable Long-Term Rentals: Fort Myers offers a wide range of affordable condos and waterfront homes that are perfect for extended stays.
- Beaches and Nature: The area is home to stunning beaches like Fort Myers Beach and wildlife-rich parks such as Lovers Key State Park, perfect for kayaking, fishing, or birdwatching.
- Community Atmosphere: Fort Myers is known for its welcoming and active snowbird community, making it easy to meet new friends and engage in social activities.
Best Long-Term Rentals in Fort Myers:
1. Waterfront Condo Near Sanibel Island
- Description: This one-bedroom condo offers stunning water views and is just minutes from Sanibel Island. The property is part of a resort-style complex with access to pools, a fitness center, and boat rentals.
- Why Snowbirds Love It: The condo’s proximity to the beaches and nature of Sanibel Island, combined with its budget-friendly pricing, makes it ideal for long-term winter stays.
- Amenities: Resort-style pool, gym, and marina access.
2. Cozy Cottage Near Fort Myers Beach
- Description: This charming two-bedroom cottage is located a short drive from Fort Myers Beach and offers a quiet, homey atmosphere. With a spacious backyard and patio, it’s perfect for snowbirds looking to enjoy Florida’s mild winter climate.
- Why Snowbirds Love It: The cottage offers peace and privacy, while still being close to the beach and local attractions.
- Amenities: Private patio, grill, and fully equipped kitchen.
Fort Myers Tip:
- Take advantage of Fort Myers’ proximity to Sanibel and Captiva Islands for day trips, where you can enjoy shelling, cycling, and kayaking in a serene natural environment.
3. Boca Raton: Upscale Beachside Living on the Atlantic
Boca Raton is an upscale city on Florida’s Atlantic Coast that offers snowbirds a perfect blend of beautiful beaches, high-end shopping, and cultural attractions. Known for its stunning architecture, luxury lifestyle, and exclusive golf communities, Boca Raton is a popular destination for snowbirds seeking an active and refined winter escape.
Why Boca Raton Is Ideal for Snowbirds:
- Luxury Living: Boca Raton is home to numerous luxury condos, waterfront homes, and golf communities, perfect for snowbirds who want to enjoy a high-end lifestyle.
- Cultural and Outdoor Activities: From Mizner Park to the Boca Raton Museum of Art, there’s no shortage of cultural attractions. Snowbirds can also enjoy golfing, tennis, and water sports at Red Reef Park.
- Beach Access: Boca Raton’s beaches are known for their cleanliness and tranquility, offering a more relaxed beach experience compared to busier tourist spots.
Best Long-Term Rentals in Boca Raton:
1. Luxury Condo with Ocean Views
- Description: This two-bedroom luxury condo offers ocean views, modern amenities, and access to a private beach. Located in a high-end building with a pool and gym, it’s perfect for snowbirds seeking a premium experience.
- Why Snowbirds Love It: The condo’s location offers both beach access and proximity to downtown Boca Raton’s shopping and dining.
- Amenities: Private beach access, pool, gym, and parking.
2. Golf Community Home with Pool
- Description: This spacious three-bedroom home is located in one of Boca Raton’s prestigious golf communities. With a private pool, outdoor patio, and modern kitchen, it’s perfect for snowbirds looking to relax and play golf throughout the winter months.
- Why Snowbirds Love It: The private pool and golf course access make this property a top choice for active retirees.
- Amenities: Private pool, golf course access, and outdoor lounge area.
Boca Raton Tip:
- Boca Raton offers excellent options for long-term rentals, but many communities have HOA restrictions. Be sure to verify long-term rental policies in gated or golf communities before booking.
4. Sarasota: Arts and Culture on the Gulf Coast
Sarasota is a cultural hub on Florida’s Gulf Coast, known for its vibrant arts scene, beautiful beaches, and laid-back atmosphere. With attractions like The Ringling Museum, the Sarasota Opera, and the nearby beaches of Siesta Key, Sarasota is a perfect destination for snowbirds who enjoy art, culture, and outdoor activities.
Why Sarasota Is Ideal for Snowbirds:
- Rich Cultural Offerings: Sarasota boasts a thriving arts and culture scene, with theaters, galleries, and museums to explore during the winter months.
- Beautiful Beaches: Siesta Key Beach is consistently ranked as one of the best beaches in the U.S., offering powdery white sand and crystal-clear waters.
- Walkable City: Sarasota’s downtown is walkable and filled with charming shops, cafes, and restaurants, making it an easy city to explore on foot.
Best Long-Term Rentals in Sarasota:
1. Siesta Key Beach House with Private Pool
- Description: This charming beach house is located just steps from Siesta Key Beach and offers a private pool and spacious patio for outdoor dining. With three bedrooms and modern amenities, it’s perfect for snowbirds looking to relax near the water.
- Why Snowbirds Love It: The home’s proximity to the beach, combined with its private pool, makes it a top choice for long-term stays.
- Amenities: Private pool, patio, and beach access.
2. Downtown Sarasota Condo with Arts District Access
- Description: This modern one-bedroom condo is located in downtown Sarasota, within walking distance of theaters, galleries, and restaurants. It’s ideal for snowbirds who want to immerse themselves in the city’s cultural scene.
- Why Snowbirds Love It: The condo’s central location allows easy access to Sarasota’s arts district and the waterfront.
- Amenities: Walkable location, modern kitchen, and parking.
Sarasota Tip:
- Take advantage of Sarasota’s vibrant arts scene by attending winter performances at the Sarasota Opera or catching a show at the historic Van Wezel Performing Arts Hall.
Final Thoughts: Finding the Perfect Winter Escape in Florida
Florida offers a wide range of vacation rental options for snowbirds seeking a warm winter retreat. From the luxury living in Naples and Boca Raton to the affordable waterfront escapes in Fort Myers, there’s a destination for every type of snowbird. Whether you’re looking for beachfront living, access to golf courses, or a vibrant arts scene, Florida’s long-term vacation rentals cater to every taste and budget.
Ready to book your winter escape? Contact Grimaldi & Weiss Management today to secure the perfect long-term rental and enjoy a warm, sunny winter in Florida. Let us help you find the ideal property for your snowbird retreat!
