Discover Naples, Florida — Vacation Rentals Curated for Every Experience
Naples, Florida is one of the Gulf Coast's most celebrated destinations — a city of white sand beaches, world-class golf, vibrant waterfront dining, and a coastal lifestyle that draws visitors from across the country year after year. Alpizar & Company curates a portfolio of vacation rentals across Naples and the surrounding communities, from Gulf-front beach estates and private waterfront homes with boat docks to residences within Naples' most prestigious golf communities and properties steps from 5th Avenue South. Whether you are planning a week on the beach, a golf holiday, a boating escape, or a family retreat — Naples has the perfect rental waiting for you.
Browse by Vacation Experience
Every Naples vacation is different. Choose the experience that fits your vision — each category links to a curated selection of rentals matched to that lifestyle.
Naples Vacation Rentals - Active Listings
Why Naples for Your Next Vacation?
Naples consistently ranks among Florida's most sought-after vacation destinations — and for good reason. The Gulf of Mexico here is exceptionally calm and clear, the beaches are wide and uncrowded by Florida standards, and the city itself offers a level of dining, shopping, and cultural sophistication that few coastal destinations can match. Fifth Avenue South and Third Street South bring award-winning restaurants, art galleries, and boutique shopping within steps of the water. The Naples Pier is one of the most iconic sunset destinations in the state.
Beyond the obvious, Naples rewards visitors who explore. Delnor-Wiggins Pass State Park offers one of the most pristine natural beach experiences in Southwest Florida. The Baker Museum at Artis-Naples brings world-class exhibitions to a city that takes culture seriously. The Conservancy of Southwest Florida and the Naples Zoo connect families with the remarkable natural environment that defines this corner of the coast. And for golfers, Naples' extraordinary density of championship courses — more golf holes per capita than anywhere in the United States — makes it a destination in a class of its own.
Our vacation rental portfolio spans the full range of the Naples experience — from Gulf-front estates in Olde Naples and Port Royal to condominiums in Pelican Bay, golf community homes in Grey Oaks and Mediterra, and waterfront properties with private docks throughout the canal system. Every property in our curated portfolio is managed to the same standard we apply to our luxury real estate listings — presented professionally, maintained meticulously, and matched thoughtfully to the guests who will enjoy it most.
Own a Naples Property? List it as a Vacation Rental.
Alpizar Property Management manages a carefully curated portfolio of vacation rentals across Naples and surrounding communities. We treat every rental listing with the same care and presentation we bring to our luxury real estate listings — professional photography, strategic pricing, and active marketing to the right guests. As a division of Alpizar & Company, our property management team has the backing of a top-producing Naples real estate brokerage whenever you're ready to sell or expand your portfolio.
Learn About Vacation Rental Management
Frequently Asked Questions — Naples Vacation Rentals
What is the best time of year to visit Naples, Florida?
Naples' peak season runs from December through April, when snowbirds and seasonal visitors arrive to enjoy warm weather, low humidity, and Naples' full social and cultural calendar. This is when rental inventory is most competitive and prices are highest. The shoulder seasons — November and May through early June — offer excellent weather at more accessible price points. Summer months are warm and humid with occasional afternoon storms, but rental rates drop significantly and the beaches are less crowded. For golfers specifically, summer is actually an excellent time to visit — many courses offer reduced rates and the greens are in exceptional condition.
What types of vacation rentals are available in Naples?
Naples vacation rentals span one of the widest ranges of any Gulf Coast market — from studio condominiums near the beach to six-bedroom estate homes on private Gulf-front lots in Olde Naples and Port Royal. Our curated portfolio includes Gulf-front condominiums in Pelican Bay and Vanderbilt Beach, waterfront homes with private boat docks in Aqualane Shores and Royal Harbor, golf community residences in Grey Oaks and Mediterra, estate homes steps from 5th Avenue South, and pet-friendly rentals throughout the Naples area. Whether you are looking for a romantic couples getaway, a family reunion, a serious golf holiday, or a retreat where your pets are welcome — Naples has a rental property that matches your vision.
What is the price range for Naples vacation rentals?
Naples vacation rental prices vary significantly by property type, location, season, and duration. Condominiums in established communities typically range from $5,000 to $15,000 per month during peak season. Single-family homes range from approximately $8,000 to $30,000 per month for standard properties. Luxury estate homes in Olde Naples, Port Royal, and Aqualane Shores can range from $50,000 to over $125,000 per month for Gulf-front properties during peak season. Off-season rates are typically 30-50% lower than peak season pricing.
Are pets allowed in Naples vacation rentals?
Yes — many Naples vacation rentals welcome pets, and we maintain a dedicated pet-friendly vacation rental category for exactly this reason. Pet policies vary by individual property — some are fully pet-friendly, others allow small dogs only, and others do not permit pets. Our pet-friendly vacation rental category features properties that specifically welcome pets. Contact us directly and we can identify which properties accommodate your specific pet, breed, and size. Pet deposits and fees are common even in pet-friendly properties.
Can I bring my boat to a Naples vacation rental?
Yes — many Naples vacation rentals include private boat docks, and Naples' extensive canal and waterway system provides excellent Gulf access for boaters of all vessel sizes. Our waterfront vacation category specifically features properties with private dock access. Canal depths, bridge clearances, and Gulf access routes vary by location — if you have a specific vessel, contact us and we can match you to properties that accommodate your boat's requirements.
How do I book a Naples vacation rental with Alpizar & Company?
Browse available listings above or use the experience category tiles to narrow your search by vacation type. When you find a property that interests you, contact us directly at (239) 438-1102 or use the contact form below. Our team will confirm availability, answer any questions about the property, and guide you through the booking process. We offer complimentary, pressure-free assistance finding the right rental for your Naples getaway — and if you fall in love with Naples during your stay, our real estate team is ready to help you explore ownership options.
How can we Help?
Meet the Team
Connect with Real Estate Advisors... not Salespeople.
Alpizar & Company is a family-owned independent brokerage specializing in luxury waterfront real estate across Naples' most sought-after neighborhoods. Led by Robert Alpizar (CLHMS, GRI, SRS, PSA) and Marlene Alpizar, our team operates as advisors — not salespeople — guiding buyers and sellers with firsthand local expertise and no corporate quotas.
We offer complimentary, pressure-free consultations without any commitment.
Over 250 closed transactions. $100 million in Naples luxury waterfront sales. Read what our buyers and sellers say about working with an advisor-driven independent brokerage — and why they come back.
What's it like working with Alpizar & Company?