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

$13,000

4923 Cerromar Dr, NAPLES

3 Beds 3 Baths 2,422 SqFt Rental MLS® # 225077906

John R Wood Properties

$13,000

5550 Heron Point Dr 1201, NAPLES

3 Beds 2 Baths 1,818 SqFt Rental MLS® # 225072184

Premier Sotheby's Int'l Realty

$13,000

↓ $500

831 Sailaway Ln 203, NAPLES

3 Beds 2 Baths 1,862 SqFt Rental MLS® # 225071273

William Raveis Real Estate

$13,000

↓ $2,000

16889 Fairgrove Way 5-201, NAPLES

3 Beds 2 Baths 2,376 SqFt Rental MLS® # 225072081

Naples Homes and Rentals Inc

$13,000

9584 Caymas Ter, NAPLES

3 Beds 5 Baths 2,703 SqFt Rental MLS® # 225070229

John R Wood Properties

$12,995

6075 Pelican Bay Blvd 1204, NAPLES

2 Beds 3 Baths 1,800 SqFt Rental MLS® # 226021244

Premier Property Management

$12,750

737 91st Ave N, NAPLES

3 Beds 2 Baths 1,566 SqFt Rental MLS® # 226030308

Gulf Breeze Real Estate LC

$12,750

575 101st Ave N, NAPLES

4 Beds 2 Baths 1,800 SqFt Rental MLS® # 226028706

Gulf Breeze Real Estate LC

New New

$12,500

N/A, NAPLES

3 Beds 3 Baths 1,813 SqFt Rental MLS® # 226030915

Premier Sotheby's Int'l Realty

$12,500

6585 Nicholas Blvd 1702, NAPLES

2 Beds 2 Baths 1,341 SqFt Rental MLS® # 226030070

John R Wood Properties

$12,500

660 Regatta Rd, NAPLES

4 Beds 3 Baths 3,000 SqFt Rental MLS® # 226029601

Realty One Group MVP

$12,500

5550 Heron Point Dr 304, NAPLES

3 Beds 2 Baths 1,514 SqFt Rental MLS® # 226024180

William Raveis Real Estate

$12,500

712 108th Ave N, NAPLES

3 Beds 3 Baths 1,997 SqFt Rental MLS® # 226028708

Gulf Breeze Real Estate LC

$12,500

690 100th Ave N, NAPLES

3 Beds 2 Baths 1,800 SqFt Rental MLS® # 226028703

Gulf Breeze Real Estate LC

$12,500

682 95th Ave N, NAPLES

3 Beds 2 Baths 1,600 SqFt Rental MLS® # 226028691

Gulf Breeze Real Estate LC

$12,500

2728 Tiburon Blvd E A-104, NAPLES

2 Beds 2 Baths 1,465 SqFt Rental MLS® # 226026763

Real Estate Specialty Svcs II

$12,500

3443 Gulf Shore Blvd N 707, NAPLES

2 Beds 2 Baths 1,164 SqFt Rental MLS® # 226023790

Premier Sotheby's Int'l Realty

$12,500

N/A, NAPLES

2 Beds 2 Baths 1,138 SqFt Rental MLS® # 226019585

Premier Sotheby's Int'l Realty

$12,500

4255 Gulf Shore Blvd N 1403, NAPLES

2 Beds 2 Baths 1,536 SqFt Rental MLS® # 226017816

Premier Sotheby's Int'l Realty

$12,500

6574 Amarone Ln, NAPLES

3 Beds 2 Baths 2,376 SqFt Rental MLS® # 226012173

Berkshire Hathaway FL Realty

$12,500

↓ $1,000

6131 Pelican Bay Blvd 7, NAPLES

3 Beds 2 Baths 1,458 SqFt Rental MLS® # 226009176

Premier Sotheby's Int'l Realty

$12,500

4001 Gulf Shore Blvd N 1106, NAPLES

3 Beds 3 Baths 1,667 SqFt Rental MLS® # 226006542

Downing Frye Realty Inc.

$12,500

271 Broad Ave S 202, NAPLES

2 Beds 2 Baths 1,500 SqFt Rental MLS® # 225080624

Coldwell Banker Realty

$12,500

↑ $600

4751 Gulf Shore Blvd N 602, NAPLES

2 Beds 2 Baths 1,424 SqFt Rental MLS® # 225079521

Downing Frye Realty Inc.

$12,500

↑ $2,500

6361 Pelican Bay Blvd 802, NAPLES

2 Beds 2 Baths 1,456 SqFt Rental MLS® # 225076426

Royal Shell Real Estate, Inc.

$12,450

↓ $50

4551 Gulf Shore Blvd N 306, NAPLES

2 Beds 2 Baths 1,671 SqFt Rental MLS® # 226022492

Real Estate Specialty Svcs II

$12,090

↑ $5,921

239 Torrey Pines Pt, NAPLES

3 Beds 3 Baths 1,907 SqFt Rental MLS® # 226019961

Posh International Properties

New New

$12,000

3443 Gulf Shore Blvd N 804, NAPLES

2 Beds 2 Baths 1,162 SqFt Rental MLS® # 226030925

Royal Shell Real Estate, Inc.

New New

$12,000

776 Willowbrook Dr 808, NAPLES

3 Beds 2 Baths 1,760 SqFt Rental MLS® # 226028947

Premier Sotheby's Int'l Realty

$12,000

1742 Marsh Run, NAPLES

2 Beds 2 Baths 1,618 SqFt Rental MLS® # 225078723

Coldwell Banker Realty

Naples Vacation Rentals

Naples Vacation Rentals - Active Listings

$13,000

4923 Cerromar Dr, NAPLES

$13,000

5550 Heron Point Dr 1201, NAPLES

$13,000

831 Sailaway Ln 203, NAPLES

$13,000

16889 Fairgrove Way 5-201, NAPLES

$13,000

9584 Caymas Ter, NAPLES

$12,995

6075 Pelican Bay Blvd 1204, NAPLES

$12,750

737 91st Ave N, NAPLES

$12,750

575 101st Ave N, NAPLES

$12,500

N/A, NAPLES

$12,500

6585 Nicholas Blvd 1702, NAPLES

$12,500

660 Regatta Rd, NAPLES

$12,500

5550 Heron Point Dr 304, NAPLES

$12,500

712 108th Ave N, NAPLES

$12,500

690 100th Ave N, NAPLES

$12,500

682 95th Ave N, NAPLES

$12,500

2728 Tiburon Blvd E A-104, NAPLES

$12,500

3443 Gulf Shore Blvd N 707, NAPLES

$12,500

N/A, NAPLES

$12,500

4255 Gulf Shore Blvd N 1403, NAPLES

$12,500

6574 Amarone Ln, NAPLES

$12,500

6131 Pelican Bay Blvd 7, NAPLES

$12,500

4001 Gulf Shore Blvd N 1106, NAPLES

$12,500

271 Broad Ave S 202, NAPLES

$12,500

4751 Gulf Shore Blvd N 602, NAPLES

$12,500

6361 Pelican Bay Blvd 802, NAPLES

$12,450

4551 Gulf Shore Blvd N 306, NAPLES

$12,090

239 Torrey Pines Pt, NAPLES

$12,000

3443 Gulf Shore Blvd N 804, NAPLES

$12,000

776 Willowbrook Dr 808, NAPLES

$12,000

1742 Marsh Run, NAPLES