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

$10,000

780 Willowbrook Dr 707, NAPLES

3 Beds 2 Baths 1,910 SqFt Rental MLS® # 226028550

John R Wood Properties

$10,000

2216 Gulf Shore Blvd N R3, NAPLES

2 Beds 2 Baths 1,265 SqFt Rental MLS® # 226028178

William Raveis Real Estate

$10,000

6557 Caldecott Dr, NAPLES

3 Beds 2 Baths 1,975 SqFt Rental MLS® # 226028841

Coldwell Banker Realty

$10,000

1256 Naples Lake Dr, NAPLES

4 Beds 3 Baths 1,902 SqFt Rental MLS® # 226027900

Downing Frye Realty Inc.

$10,000

663 10th Ave S B663, NAPLES

2 Beds 2 Baths 1,241 SqFt Rental MLS® # 2026033176

Gordon Pass Realty LLC

$10,000

5555 Heron Point Drive 101, NAPLES

2 Beds 2 Baths 1,289 SqFt Rental MLS® # 226028127

Compass Florida LLC

$10,000

202 Bears Paw Trl 97, NAPLES

2 Beds 2 Baths 1,665 SqFt Rental MLS® # 226028024

Downing Frye Realty Inc.

$10,000

5601 Turtle Bay Dr 2003, NAPLES

2 Beds 2 Baths 1,733 SqFt Rental MLS® # 226027244

Berkshire Hathaway FL Realty

$10,000

↓ $4,000

7660 Cottesmore Dr, NAPLES

3 Beds 2 Baths 2,258 SqFt Rental MLS® # 226026805

Downing Frye Realty Inc.

$10,000

5637 Turtle Bay Dr Ii-22, NAPLES

3 Beds 2 Baths 1,506 SqFt Rental MLS® # 226026736

Royal Shell Real Estate, Inc.

$10,000

9512 Napoli Ln 101, NAPLES

3 Beds 2 Baths 1,741 SqFt Rental MLS® # 226026096

WeichertRealtors-ParadiseHomes

$10,000

1050 9th St S 102, NAPLES

2 Beds 2 Baths 1,680 SqFt Rental MLS® # 226024911

Naples Diamond Realty

$10,000

250 7th Ave S 207, NAPLES

2 Beds 2 Baths 1,000 SqFt Rental MLS® # 226022890

Premier Sotheby's Int'l Realty

$10,000

225 5th Ave S 104, NAPLES

2 Beds 3 Baths 1,900 SqFt Rental MLS® # 226019862

William Raveis Real Estate

$10,000

1035 3rd Ave S 411, NAPLES

3 Beds 3 Baths 2,264 SqFt Rental MLS® # 226020182

Royal Shell Real Estate, Inc.

$10,000

9248 Cormorant Dr, NAPLES

2 Beds 2 Baths 1,900 SqFt Rental MLS® # 226019745

John R Wood Properties

$10,000

1111 Wildwood Ln 1111, NAPLES

3 Beds 2 Baths 2,060 SqFt Rental MLS® # 226019721

Downing Frye Realty Inc.

$10,000

8385 Excalibur Cir G3, NAPLES

2 Beds 2 Baths 1,382 SqFt Rental MLS® # 226015036

William Raveis Real Estate

$10,000

9115 Strada Pl 5417, NAPLES

2 Beds 2 Baths 1,548 SqFt Rental MLS® # 226016917

Realty One Group MVP

$10,000

271 Southbay Dr 155, NAPLES

2 Beds 2 Baths 1,056 SqFt Rental MLS® # 226016598

Royal Shell Real Estate, Inc.

$10,000

9114 Prima Way 102, NAPLES

3 Beds 2 Baths 1,883 SqFt Rental MLS® # 226016461

WeichertRealtors-ParadiseHomes

$10,000

9476 Napoli Ln 202, NAPLES

3 Beds 2 Baths 2,099 SqFt Rental MLS® # 226016050

Waterfront Realty Group Inc

$10,000

↓ $1,000

705 10th St S 301, NAPLES

4 Beds 5 Baths 2,930 SqFt Rental MLS® # 226014692

Real Estate Specialty Svcs II

$10,000

8888 Mustang Island Cir, NAPLES

3 Beds 3 Baths 2,028 SqFt Rental MLS® # 226013310

Downing Frye Realty Inc.

$10,000

N/A, NAPLES

2 Beds 2 Baths 1,526 SqFt Rental MLS® # 226011527

Downing Frye Realty Inc.

$10,000

↑ $500

595 Serendipity Dr 595, NAPLES

3 Beds 2 Baths 1,395 SqFt Rental MLS® # 226012777

Premier Sotheby's Int'l Realty

$10,000

13441 Coronado Dr, NAPLES

3 Beds 2 Baths 1,837 SqFt Rental MLS® # 226012235

John R Wood Properties

$10,000

784 Willowbrook Dr 607, NAPLES

2 Beds 2 Baths 1,862 SqFt Rental MLS® # 226011121

Douglas Elliman Florida,LLC

$10,000

↑ $6,200

7699 Groves Rd, NAPLES

3 Beds 2 Baths 2,259 SqFt Rental MLS® # 226010422

Florida Home Realty, Inc.

$10,000

N/A, NAPLES

3 Beds 2 Baths 1,900 SqFt Rental MLS® # 226009123

Coldwell Banker Realty

Naples Vacation Rentals

Naples Vacation Rentals - Active Listings

$10,000

780 Willowbrook Dr 707, NAPLES

$10,000

2216 Gulf Shore Blvd N R3, NAPLES

$10,000

6557 Caldecott Dr, NAPLES

$10,000

1256 Naples Lake Dr, NAPLES

$10,000

663 10th Ave S B663, NAPLES

$10,000

5555 Heron Point Drive 101, NAPLES

$10,000

202 Bears Paw Trl 97, NAPLES

$10,000

5601 Turtle Bay Dr 2003, NAPLES

$10,000

7660 Cottesmore Dr, NAPLES

$10,000

5637 Turtle Bay Dr Ii-22, NAPLES

$10,000

9512 Napoli Ln 101, NAPLES

$10,000

1050 9th St S 102, NAPLES

$10,000

250 7th Ave S 207, NAPLES

$10,000

225 5th Ave S 104, NAPLES

$10,000

1035 3rd Ave S 411, NAPLES

$10,000

9248 Cormorant Dr, NAPLES

$10,000

1111 Wildwood Ln 1111, NAPLES

$10,000

8385 Excalibur Cir G3, NAPLES

$10,000

9115 Strada Pl 5417, NAPLES

$10,000

271 Southbay Dr 155, NAPLES

$10,000

9114 Prima Way 102, NAPLES

$10,000

9476 Napoli Ln 202, NAPLES

$10,000

705 10th St S 301, NAPLES

$10,000

8888 Mustang Island Cir, NAPLES

$10,000

N/A, NAPLES

$10,000

595 Serendipity Dr 595, NAPLES

$10,000

13441 Coronado Dr, NAPLES

$10,000

784 Willowbrook Dr 607, NAPLES

$10,000

7699 Groves Rd, NAPLES

$10,000

N/A, NAPLES