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

$6,500

10275 Heritage Bay Blvd 726, NAPLES

2 Beds 2 Baths 1,232 SqFt Rental MLS® # 226028129

ENGEL & VOELKERS NAPLES

$6,500

10321 Heritage Bay Blvd 1527, NAPLES

2 Beds 2 Baths 1,232 SqFt Rental MLS® # 226027596

Downing Frye Realty Inc.

$6,500

5944 Sand Wedge Ln 1108, NAPLES

2 Beds 2 Baths 1,478 SqFt Rental MLS® # 226025099

SunStream Realty

$6,500

191 Torrey Pines Pt, NAPLES

3 Beds 2 Baths 2,267 SqFt Rental MLS® # 226025762

Century 21 AllPoints Realty

$6,500

576 Retreat Dr 201, NAPLES

3 Beds 2 Baths 1,585 SqFt Rental MLS® # 226027425

Opyt Realty Inc

$6,500

3400 Gulf Shore Blvd N B4, NAPLES

2 Beds 2 Baths 1,450 SqFt Rental MLS® # 226023388

William Raveis Real Estate

$6,500

1150 Sweetwater Ln 1207, NAPLES

2 Beds 2 Baths 1,703 SqFt Rental MLS® # 226024846

Premier Sotheby's Int'l Realty

$6,500

5 Bluebill Ave 505/605, NAPLES

2 Beds 3 Baths 1,035 SqFt Rental MLS® # 226023690

William Raveis Real Estate

$6,500

480 5th St S 102, NAPLES

1 Bed 1 Bath 600 SqFt Rental MLS® # 226024912

Berkshire Hathaway FL Realty

$6,500

↓ $500

8578 Veronawalk Cir, NAPLES

3 Beds 3 Baths 1,901 SqFt Rental MLS® # 226024837

Keller Williams Elite Realty

$6,500

↓ $700

9209 Museo Cir 102, NAPLES

3 Beds 3 Baths 2,502 SqFt Rental MLS® # 226024107

William Raveis Real Estate

$6,500

2100 Gulf Shore Blvd N 120, NAPLES

2 Beds 2 Baths 1,200 SqFt Rental MLS® # 226023192

Sky Coastal Realty LLC

$6,500

1326 Kendari Ter, NAPLES

3 Beds 4 Baths 2,100 SqFt Rental MLS® # 226021777

Berkshire Hathaway FL Realty

$6,500

10353 Heritage Bay Blvd 2226, NAPLES

2 Beds 2 Baths 1,232 SqFt Rental MLS® # 226020043

SunStream Realty

$6,500

↓ $500

5 Bluebill Ave 504, NAPLES

1 Bed 1 Bath 896 SqFt Rental MLS® # 226018983

Serhant-Naples

$6,500

3425 Grand Cypress Dr 102, NAPLES

3 Beds 2 Baths 1,763 SqFt Rental MLS® # 226019324

Keller Williams Realty Naples

$6,500

400 L Ambiance Cir 104, NAPLES

2 Beds 2 Baths 1,349 SqFt Rental MLS® # 226012446

William Raveis Real Estate

$6,500

519 Roma Ct 306, NAPLES

3 Beds 2 Baths 1,308 SqFt Rental MLS® # 226017216

William Raveis Real Estate

$6,500

↑ $500

1111 Central 417a, NAPLES

2 Beds 2 Baths 1,265 SqFt Rental MLS® # 226015550

REMAX Affinity Mercato

$6,500

1 Bluebill Ave 707, NAPLES

1 Bed 1 Bath 1,040 SqFt Rental MLS® # 226017062

Liberty Real Estate Services

$6,500

7299 Cayo Coco Ln, NAPLES

2 Beds 2 Baths 1,476 SqFt Rental MLS® # 226013999

Bluewater Signature Realty LLC

$6,500

5928 Sand Wedge Ln 1805, NAPLES

2 Beds 2 Baths 1,478 SqFt Rental MLS® # 226013763

Realty One Group MVP

$6,500

9735 Acqua Ct 622, NAPLES

2 Beds 2 Baths 1,137 SqFt Rental MLS® # 226013131

WeichertRealtors-ParadiseHomes

$6,500

10345 Heritage Bay Blvd 2046, NAPLES

2 Beds 2 Baths 1,232 SqFt Rental MLS® # 226013032

Downing Frye Realty Inc.

$6,500

3538 Haldeman Creek Dr 113, NAPLES

2 Beds 2 Baths 1,414 SqFt Rental MLS® # 226012976

Diversified Real Estate Group

$6,500

1117 Sweetwater Ln 2201, NAPLES

2 Beds 2 Baths 1,193 SqFt Rental MLS® # 226011501

Coldwell Banker Realty

$6,500

9102 Capistrano St S 72-3, NAPLES

2 Beds 3 Baths 1,520 SqFt Rental MLS® # 226010924

Premier Sotheby's Int'l Realty

$6,500

14715 Kelson Cir, NAPLES

3 Beds 4 Baths 2,225 SqFt Rental MLS® # 226010894

Berkshire Hathaway FL Realty

$6,500

5360 Andover Dr 202, NAPLES

3 Beds 2 Baths 1,928 SqFt Rental MLS® # 226009538

William Raveis Real Estate

$6,500

10270 Heritage Bay Blvd 3422, NAPLES

2 Beds 2 Baths 1,414 SqFt Rental MLS® # 225077854

Bluewater Signature Realty LLC

Naples Vacation Rentals

Naples Vacation Rentals - Active Listings

$6,500

10275 Heritage Bay Blvd 726, NAPLES

$6,500

10321 Heritage Bay Blvd 1527, NAPLES

$6,500

5944 Sand Wedge Ln 1108, NAPLES

$6,500

191 Torrey Pines Pt, NAPLES

$6,500

576 Retreat Dr 201, NAPLES

$6,500

3400 Gulf Shore Blvd N B4, NAPLES

$6,500

1150 Sweetwater Ln 1207, NAPLES

$6,500

5 Bluebill Ave 505/605, NAPLES

$6,500

480 5th St S 102, NAPLES

$6,500

8578 Veronawalk Cir, NAPLES

$6,500

9209 Museo Cir 102, NAPLES

$6,500

2100 Gulf Shore Blvd N 120, NAPLES

$6,500

1326 Kendari Ter, NAPLES

$6,500

10353 Heritage Bay Blvd 2226, NAPLES

$6,500

5 Bluebill Ave 504, NAPLES

$6,500

3425 Grand Cypress Dr 102, NAPLES

$6,500

400 L Ambiance Cir 104, NAPLES

$6,500

519 Roma Ct 306, NAPLES

$6,500

1111 Central 417a, NAPLES

$6,500

1 Bluebill Ave 707, NAPLES

$6,500

7299 Cayo Coco Ln, NAPLES

$6,500

5928 Sand Wedge Ln 1805, NAPLES

$6,500

9735 Acqua Ct 622, NAPLES

$6,500

10345 Heritage Bay Blvd 2046, NAPLES

$6,500

3538 Haldeman Creek Dr 113, NAPLES

$6,500

1117 Sweetwater Ln 2201, NAPLES

$6,500

9102 Capistrano St S 72-3, NAPLES

$6,500

14715 Kelson Cir, NAPLES

$6,500

5360 Andover Dr 202, NAPLES

$6,500

10270 Heritage Bay Blvd 3422, NAPLES