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

$17,500

7515 Pelican Bay Blvd 5b, NAPLES

2 Beds 2 Baths 1,800 SqFt Rental MLS® # 226029195

Royal Shell Real Estate, Inc.

$17,500

9169 Mercato Way, NAPLES

4 Beds 5 Baths 3,256 SqFt Rental MLS® # 226027619

Premier Sotheby's Int'l Realty

$17,500

142 Colonade Cir 701, NAPLES

3 Beds 3 Baths 2,005 SqFt Rental MLS® # 226026205

Naples Vacation Properties

$17,500

↑ $1,500

8476 Mallards Pt, NAPLES

3 Beds 3 Baths 2,739 SqFt Rental MLS® # 226018240

Naples Homes and Rentals Inc

$17,500

7515 Pelican Bay Blvd 17d, NAPLES

3 Beds 3 Baths 2,500 SqFt Rental MLS® # 226006943

John R Wood Properties

$17,500

1030 3rd Ave S 417, NAPLES

2 Beds 3 Baths 1,832 SqFt Rental MLS® # 226001836

Compass Florida LLC

New New

$17,000

1135 3rd Ave S 319, NAPLES

2 Beds 3 Baths 1,883 SqFt Rental MLS® # 226031107

Coldwell Banker Realty

$17,000

6315 Serano Way, NAPLES

3 Beds 3 Baths 2,615 SqFt Rental MLS® # 226029312

ENGEL & VOELKERS NAPLES

$17,000

16328 Corsica Way 101, NAPLES

3 Beds 3 Baths 2,532 SqFt Rental MLS® # 226029620

Real Broker, LLC

$17,000

6573 Marissa Loop 1704, NAPLES

3 Beds 2 Baths 1,643 SqFt Rental MLS® # 226027834

Royal Shell Real Estate, Inc.

$17,000

995 9th Ave S 6, NAPLES

3 Beds 4 Baths 1,838 SqFt Rental MLS® # 2026029174

Gordon Pass Realty LLC

$17,000

↑ $7,000

16394 Corsica Way 101, NAPLES

3 Beds 4 Baths 2,532 SqFt Rental MLS® # 225075849

Real Broker, LLC

$17,000

6001 Pelican Bay Blvd F, NAPLES

3 Beds 3 Baths 3,133 SqFt Rental MLS® # 226019969

William Raveis Real Estate

$17,000

9375 Gulf Shore Dr 602, NAPLES

2 Beds 2 Baths 1,530 SqFt Rental MLS® # 226019710

SunStream Realty

Open House

$17,000

↑ $2,000

2728 Tiburon Blvd E Ph-503, NAPLES

3 Beds 4 Baths 2,985 SqFt Rental

Open House

Fri, Sep 18th, 2026 @ 2pm - 4pm

MLS® # 226017523

Real Estate Specialty Svcs II

$17,000

15495 Rio Ponace Ct, NAPLES

4 Beds 4 Baths 2,465 SqFt Rental MLS® # 226008948

William Raveis Real Estate

$17,000

9536 Montelanico Loop, NAPLES

3 Beds 3 Baths 2,343 SqFt Rental MLS® # 226010958

DomainRealty.com LLC

$17,000

↑ $11,500

14190 Galley Ct, NAPLES

4 Beds 3 Baths 3,015 SqFt Rental MLS® # 226008116

Coldwell Banker Realty

$17,000

↑ $1,000

6573 Marissa Loop 2005, NAPLES

3 Beds 2 Baths 1,787 SqFt Rental MLS® # 226003153

Downing Frye Realty Inc.

$17,000

↑ $5,000

4901 Gulf Shore Blvd N 604, NAPLES

2 Beds 3 Baths 2,259 SqFt Rental MLS® # 225070775

William Raveis Real Estate

$17,000

8967 Lely Island Cir, NAPLES

3 Beds 2 Baths 2,056 SqFt Rental MLS® # 225070281

Berkshire Hathaway FL Realty

$16,500

16390 Viansa Way 1-202, NAPLES

3 Beds 4 Baths 2,350 SqFt Rental MLS® # 226011206

RMC REALTY INTERNATIONAL

$16,500

1111 Central Ave 216, NAPLES

3 Beds 4 Baths 2,010 SqFt Rental MLS® # 226009578

John R Wood Properties

$16,500

9653 Gulf Shore Dr 402, NAPLES

2 Beds 3 Baths 1,579 SqFt Rental MLS® # 225077633

Downing Frye Realty Inc.

$16,500

↓ $1,000

6255 Brunello Ln, NAPLES

3 Beds 3 Baths 2,046 SqFt Rental MLS® # 225069330

Premier Sotheby's Int'l Realty

New New

$16,000

651 106th Ave N, NAPLES

4 Beds 3 Baths 2,122 SqFt Rental MLS® # 226030262

Waterfront Realty Group Inc

$16,000

9375 Gulf Shore Dr Dr 203, NAPLES

2 Beds 2 Baths 1,530 SqFt Rental MLS® # 226027731

John R Wood Properties

$16,000

9445 Caymas Ter, NAPLES

3 Beds 3 Baths 2,366 SqFt Rental MLS® # 226026293

John R Wood Properties

$16,000

60 Seagate Dr 1606, NAPLES

3 Beds 3 Baths 2,403 SqFt Rental MLS® # 226027089

Berkshire Hathaway FL Realty

$16,000

4005 Gulf Shore Blvd N 700, NAPLES

3 Beds 3 Baths 1,646 SqFt Rental MLS® # 226026907

Downing Frye Realty Inc.

Naples Vacation Rentals

Naples Vacation Rentals - Active Listings

$17,500

7515 Pelican Bay Blvd 5b, NAPLES

$17,500

9169 Mercato Way, NAPLES

$17,500

142 Colonade Cir 701, NAPLES

$17,500

8476 Mallards Pt, NAPLES

$17,500

7515 Pelican Bay Blvd 17d, NAPLES

$17,500

1030 3rd Ave S 417, NAPLES

$17,000

1135 3rd Ave S 319, NAPLES

$17,000

6315 Serano Way, NAPLES

$17,000

16328 Corsica Way 101, NAPLES

$17,000

6573 Marissa Loop 1704, NAPLES

$17,000

995 9th Ave S 6, NAPLES

$17,000

16394 Corsica Way 101, NAPLES

$17,000

6001 Pelican Bay Blvd F, NAPLES

$17,000

9375 Gulf Shore Dr 602, NAPLES

$17,000

2728 Tiburon Blvd E Ph-503, NAPLES

$17,000

15495 Rio Ponace Ct, NAPLES

$17,000

9536 Montelanico Loop, NAPLES

$17,000

14190 Galley Ct, NAPLES

$17,000

6573 Marissa Loop 2005, NAPLES

$17,000

4901 Gulf Shore Blvd N 604, NAPLES

$17,000

8967 Lely Island Cir, NAPLES

$16,500

16390 Viansa Way 1-202, NAPLES

$16,500

1111 Central Ave 216, NAPLES

$16,500

9653 Gulf Shore Dr 402, NAPLES

$16,500

6255 Brunello Ln, NAPLES

$16,000

651 106th Ave N, NAPLES

$16,000

9375 Gulf Shore Dr Dr 203, NAPLES

$16,000

9445 Caymas Ter, NAPLES

$16,000

60 Seagate Dr 1606, NAPLES

$16,000

4005 Gulf Shore Blvd N 700, NAPLES