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

$12,000

451 Bayfront Pl 5311, NAPLES

3 Beds 2 Baths 1,869 SqFt Rental MLS® # 226020693

Premiere Plus Realty Company

$12,000

9218 Veneto Ln 43, NAPLES

3 Beds 2 Baths 1,854 SqFt Rental MLS® # 226030036

Safe Harbor Real Estate Servic

$12,000

4005 Gulf Shore Blvd N 603, NAPLES

2 Beds 2 Baths 1,267 SqFt Rental MLS® # 226027362

Downing Frye Realty Inc.

$12,000

8906 Lely Island Cir, NAPLES

4 Beds 3 Baths 2,291 SqFt Rental MLS® # 226028907

Alfred Robbins Realty Group

$12,000

672 100th Ave, NAPLES

3 Beds 2 Baths 1,600 SqFt Rental MLS® # 226028705

Gulf Breeze Real Estate LC

$12,000

760 106th Ave, NAPLES

3 Beds 2 Baths 1,968 SqFt Rental MLS® # 226028701

Gulf Breeze Real Estate LC

$12,000

5549 Foxhunt Way, NAPLES

3 Beds 2 Baths 1,881 SqFt Rental MLS® # 226028428

Realty One Group MVP

$12,000

9432 Purple Martin Ct, NAPLES

3 Beds 2 Baths 2,000 SqFt Rental MLS® # 226028493

John R Wood Properties

$12,000

1032 Tivoli Ln, NAPLES

3 Beds 3 Baths 2,296 SqFt Rental MLS® # 226026944

Waterfront Realty Group Inc

$12,000

14715 Kelson Cir, NAPLES

3 Beds 4 Baths 2,225 SqFt Rental MLS® # 226027870

Berkshire Hathaway FL Realty

$12,000

789 Coldstream Ct, NAPLES

3 Beds 2 Baths 1,715 SqFt Rental MLS® # 226027599

Downing Frye Realty Inc.

$12,000

651 10th Ave S C651, NAPLES

2 Beds 2 Baths 1,241 SqFt Rental MLS® # 226026514

Diversified Real Estate Group

$12,000

4001 Gulf Shore Blvd N 105, NAPLES

2 Beds 2 Baths 1,247 SqFt Rental MLS® # 226025861

RE/MAX Hallmark Realty

$12,000

9530 Piacere Way, NAPLES

2 Beds 3 Baths 1,850 SqFt Rental MLS® # 226022785

Compass Florida LLC

$12,000

↑ $5,000

N/A, NAPLES

2 Beds 2 Baths 2,159 SqFt Rental MLS® # 226021981

Luxe Naples Real Estate

$12,000

5069 Tortola Ct, NAPLES

3 Beds 3 Baths 2,390 SqFt Rental MLS® # 226023219

WeichertRealtors-ParadiseHomes

$12,000

6773 Southern Oak Ct, NAPLES

3 Beds 2 Baths 2,090 SqFt Rental MLS® # 226022922

KW Elevate Luxury

$12,000

800 Breakaway Ln 203, NAPLES

2 Beds 2 Baths 1,703 SqFt Rental MLS® # 226021228

William Raveis Real Estate

$12,000

16356 Viansa Way 101, NAPLES

3 Beds 2 Baths 1,710 SqFt Rental MLS® # 226021683

Downing Frye Realty Inc.

$12,000

9380 Gulf Shore Dr 102, NAPLES

3 Beds 2 Baths 1,800 SqFt Rental MLS® # 226020317

William Raveis Real Estate

$12,000

↑ $1,000

230 3rd Ave S 4, NAPLES

2 Beds 3 Baths 978 SqFt Rental MLS® # 226018533

Compass Florida LLC

$12,000

315 Dunes Blvd 505, NAPLES

3 Beds 2 Baths 1,893 SqFt Rental MLS® # 226018463

William Raveis Real Estate

$12,000

5550 Heron Point Dr 802, NAPLES

2 Beds 2 Baths 1,263 SqFt Rental MLS® # 226018227

Premier Sotheby's Int'l Realty

$12,000

↓ $1,500

1111 Central 417s, NAPLES

2 Beds 2 Baths 1,265 SqFt Rental MLS® # 226015543

REMAX Affinity Mercato

$12,000

4051 Gulf Shore Blvd N 700, NAPLES

2 Beds 2 Baths 2,074 SqFt Rental MLS® # 226015416

William Raveis Real Estate

$12,000

2850 Aviamar Cir, NAPLES

3 Beds 2 Baths 2,246 SqFt Rental MLS® # 226014824

WeichertRealtors-ParadiseHomes

$12,000

10701 Gulf Shore Dr 702, NAPLES

2 Beds 2 Baths 1,560 SqFt Rental MLS® # 226014810

WeichertRealtors-ParadiseHomes

$12,000

9415 Piacere Way, NAPLES

2 Beds 3 Baths 1,850 SqFt Rental MLS® # 226014187

WeichertRealtors-ParadiseHomes

$12,000

731 104th Ave N, NAPLES

2 Beds 2 Baths 1,388 SqFt Rental MLS® # 226013876

Realty One Group MVP

$12,000

3860 Cotton Green Path Dr, NAPLES

4 Beds 3 Baths 2,300 SqFt Rental MLS® # 226013900

Premier Sotheby's Int'l Realty

Naples Vacation Rentals

Naples Vacation Rentals - Active Listings

$12,000

451 Bayfront Pl 5311, NAPLES

$12,000

9218 Veneto Ln 43, NAPLES

$12,000

4005 Gulf Shore Blvd N 603, NAPLES

$12,000

8906 Lely Island Cir, NAPLES

$12,000

672 100th Ave, NAPLES

$12,000

760 106th Ave, NAPLES

$12,000

5549 Foxhunt Way, NAPLES

$12,000

9432 Purple Martin Ct, NAPLES

$12,000

1032 Tivoli Ln, NAPLES

$12,000

14715 Kelson Cir, NAPLES

$12,000

789 Coldstream Ct, NAPLES

$12,000

651 10th Ave S C651, NAPLES

$12,000

4001 Gulf Shore Blvd N 105, NAPLES

$12,000

9530 Piacere Way, NAPLES

$12,000

N/A, NAPLES

$12,000

5069 Tortola Ct, NAPLES

$12,000

6773 Southern Oak Ct, NAPLES

$12,000

800 Breakaway Ln 203, NAPLES

$12,000

16356 Viansa Way 101, NAPLES

$12,000

9380 Gulf Shore Dr 102, NAPLES

$12,000

230 3rd Ave S 4, NAPLES

$12,000

315 Dunes Blvd 505, NAPLES

$12,000

5550 Heron Point Dr 802, NAPLES

$12,000

1111 Central 417s, NAPLES

$12,000

4051 Gulf Shore Blvd N 700, NAPLES

$12,000

2850 Aviamar Cir, NAPLES

$12,000

10701 Gulf Shore Dr 702, NAPLES

$12,000

9415 Piacere Way, NAPLES

$12,000

731 104th Ave N, NAPLES

$12,000

3860 Cotton Green Path Dr, NAPLES