What is the best time of year to visit Naples, Florida?

Naples' peak season runs December through April when snowbirds arrive for warm weather and Naples' full social calendar. Shoulder seasons — November and May through early June — offer excellent weather at more accessible prices. Summer offers significantly lower rates with less crowded beaches. Golfers particularly benefit from summer visits with reduced course rates and exceptional course conditions.

What types of vacation rentals are available in Naples?

Naples vacation rentals range from studio condominiums to six-bedroom Gulf-front estates in Olde Naples and Port Royal. Options include 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, and estate homes near 5th Avenue South.

What is the price range for Naples vacation rentals?

Naples vacation rental prices range from approximately $5,000 to $15,000 per month for condominiums during peak season, $8,000 to $30,000 for single-family homes, and $50,000 to over $125,000 per month for Gulf-front estates in Olde Naples and Port Royal. Off-season rates are typically 30-50% lower than peak season pricing.

Are pets allowed in Naples vacation rentals?

Pet policies vary by individual property. Some Naples vacation rentals are fully pet-friendly, others allow small dogs only, and others do not permit pets. Contact Alpizar & Company directly to identify which properties accommodate your specific pet. 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. Our waterfront vacation category features properties with private dock access. Canal depths, bridge clearances, and Gulf access routes vary by location. Contact us with your vessel specifications and we can match you to properties that accommodate your boat.

How do I book a Naples vacation rental with Alpizar & Company?

Browse available listings on this page or use the experience category tiles to search by vacation type. Contact us at (239) 438-1102 or use the contact form to confirm availability and book. We offer complimentary, pressure-free assistance finding the right rental — and if you fall in love with Naples, our real estate team is ready to help you explore ownership options.

Naples Vacation Rentals | Beach, Golf, Waterfront & More

$50,000

21 Casa Mar Ln 21, NAPLES

3 Beds 6 Baths 4,049 SqFt Rental MLS® # 226020778

Ivanova Realty LLC

$50,000

↓ $10,000

↑ $10,000

2700 Treasure Ln, NAPLES

4 Beds 5 Baths 3,797 SqFt Rental MLS® # 225072204

Naples Homes and Rentals Inc

$49,500

↑ $25,500

362 2nd Ave N, NAPLES

6 Beds 6 Baths 3,811 SqFt Rental MLS® # 226025169

John R Wood Properties

$49,000

883 Galleon Dr, NAPLES

5 Beds 5 Baths 4,400 SqFt Rental MLS® # 226019253

Brand And Associates Inc

$48,000

942 9th Ave S, NAPLES

4 Beds 5 Baths 3,156 SqFt Rental MLS® # 226029666

John R Wood Properties

$48,000

687 9th Ave S, NAPLES

5 Beds 4 Baths 3,277 SqFt Rental MLS® # 226029663

John R Wood Properties

336 Oak Ave, NAPLES

4 Beds 4 Baths 2,700 SqFt Rental MLS® # 226025126

Current Property Management

$45,000

760 Park Shore Dr, NAPLES

3 Beds 5 Baths 3,431 SqFt Rental MLS® # 226019015

William Raveis Real Estate

$45,000

377 Pirates Bight, NAPLES

5 Beds 6 Baths 5,106 SqFt Rental MLS® # 225079001

William Raveis Real Estate

$45,000

195 2nd Ave N, NAPLES

5 Beds 6 Baths 4,434 SqFt Rental MLS® # 225075483

John R Wood Properties

$43,500

255 2nd Ave N, NAPLES

6 Beds 7 Baths 4,351 SqFt Rental MLS® # 225083529

William Raveis Real Estate

$42,750

$36,000

225 Egret Ave, NAPLES

3 Beds 4 Baths 3,395 SqFt Rental MLS® # 226002653

London Foster Realty

Naples Vacation Rentals

Naples Vacation Rentals - Active Listings

$50,000

21 Casa Mar Ln 21, NAPLES

$50,000

111 Caribbean Rd, NAPLES

$50,000

13935 Old Coast Rd 1703, NAPLES

$50,000

700 Wedge Dr, NAPLES

$50,000

2700 Treasure Ln, NAPLES

$49,500

362 2nd Ave N, NAPLES

$49,000

883 Galleon Dr, NAPLES

$48,000

942 9th Ave S, NAPLES

$48,000

687 9th Ave S, NAPLES

$48,000

270 5th Ave S H-2, NAPLES

$48,000

8665 Bay Colony Dr 2001, NAPLES

$48,000

194 4th Ave N, NAPLES

$45,000

2750 Treasure Ln, NAPLES

$45,000

215 Mooring Line Dr, NAPLES

$45,000

336 Oak Ave, NAPLES

$45,000

760 Park Shore Dr, NAPLES

$45,000

377 Pirates Bight, NAPLES

$45,000

195 2nd Ave N, NAPLES

$43,500

255 2nd Ave N, NAPLES

$42,750

354 1st Ave N, NAPLES

$42,500

431 1st Ave N, NAPLES

$42,000

206 1st Ave N, NAPLES

$40,000

3123 Crayton Rd, NAPLES

$40,000

13945 Old Coast Rd 1202, NAPLES

$40,000

428 Rudder Rd, NAPLES

$40,000

481 21st Ave S, NAPLES

$40,000

4646 Crayton Rd, NAPLES

$38,000

13945 Old Coast Rd 301, NAPLES

$38,000

3377 Gulf Shore Blvd N 1b, NAPLES

$36,000

225 Egret Ave, NAPLES