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

$6,000

790 Meadowland Dr 29-2, NAPLES

2 Beds 3 Baths 1,432 SqFt Rental MLS® # 226016690

Royal Shell Real Estate, Inc.

$6,000

1 Bluebill Ave 709, NAPLES

1 Bed 1 Bath 800 SqFt Rental MLS® # 226015801

Serhant-Naples

$6,000

6276 Shadowood Cir 1503, NAPLES

3 Beds 2 Baths 1,350 SqFt Rental MLS® # 226008944

eXp Realty LLC

$6,000

2561 Seychelles Dr 308, NAPLES

3 Beds 2 Baths 1,660 SqFt Rental MLS® # 226014842

John R Wood Properties

$6,000

↓ $1,000

2307 Queens Way, NAPLES

3 Beds 2 Baths 2,993 SqFt Rental MLS® # 226014374

Downing Frye Realty Inc.

$6,000

N/A, NAPLES

2 Beds 2 Baths 1,138 SqFt Rental MLS® # 226014633

Premier Sotheby's Int'l Realty

$6,000

3035 Horizon Ln 2206, NAPLES

2 Beds 2 Baths 1,246 SqFt Rental MLS® # 226012617

Downing Frye Realty Inc.

$6,000

9055 Capistrano St N 4206, NAPLES

2 Beds 3 Baths 1,441 SqFt Rental MLS® # 226011698

Realty One Group MVP

$6,000

9250 Veneto Pl, NAPLES

2 Beds 3 Baths 1,854 SqFt Rental MLS® # 226010116

Downing Frye Realty Inc.

$6,000

5945 Sand Wedge Ln 1003, NAPLES

2 Beds 2 Baths 1,490 SqFt Rental MLS® # 226009944

William Raveis Real Estate

$6,000

5928 Sand Wedge Ln 1808, NAPLES

2 Beds 2 Baths 1,478 SqFt Rental MLS® # 226002972

Realty One Group MVP

$6,000

↓ $500

651 Wiggins Lake Dr 102, NAPLES

2 Beds 2 Baths 1,487 SqFt Rental MLS® # 226008721

Premier Sotheby's Int'l Realty

$6,000

9723 Acqua Ct 332, NAPLES

2 Beds 2 Baths 1,100 SqFt Rental MLS® # 226008536

Waterfront Realty Group Inc

$6,000

9578 Trevi Ct 5142, NAPLES

2 Beds 2 Baths 1,232 SqFt Rental MLS® # 226005563

Achieve Realty LLC

$6,000

8039 Tauren Ct S, NAPLES

3 Beds 2 Baths 1,861 SqFt Rental MLS® # 226003452

REMAX Affinity Mercato

$6,000

3035 Horizon Ln 2203, NAPLES

2 Beds 2 Baths 1,248 SqFt Rental MLS® # 226001158

LPT Realty, LLC

$6,000

163 Indies Dr E 206, NAPLES

3 Beds 2 Baths 1,698 SqFt Rental MLS® # 226000216

Realty One Group MVP

$6,000

↑ $1,000

15400 Cedarwood Ln 1-201, NAPLES

2 Beds 2 Baths 1,286 SqFt Rental MLS® # 225084837

William Raveis Real Estate

$6,000

9054 Capistrano St N 4002, NAPLES

3 Beds 2 Baths 1,674 SqFt Rental MLS® # 225082568

John R Wood Properties

$6,000

519 Roma Ct 3-301, NAPLES

3 Beds 2 Baths 1,308 SqFt Rental MLS® # 225082578

William Raveis Real Estate

$6,000

↑ $3,000

3435 Laurel Greens Ln S 201, NAPLES

3 Beds 2 Baths 1,708 SqFt Rental MLS® # 225081129

Premier Property Management

$6,000

964 8th Ave S B-2, NAPLES

3 Beds 2 Baths 1,707 SqFt Rental MLS® # 225078599

Naples Flat Fee Realty LLC

$6,000

410 Bayfront Pl 2509, NAPLES

1 Bed 1 Bath 852 SqFt Rental MLS® # 225075298

Compass Florida LLC

$6,000

577 98th Ave N, NAPLES

3 Beds 2 Baths 1,322 SqFt Rental MLS® # 225076967

Epique Realty, INC

$5,995

↓ $255

468 12th Ave S 468, NAPLES

2 Beds 1 Bath 848 SqFt Rental MLS® # 226024136

Daane Properties LLC

$5,995

↓ $1,000

15 Bluebill Ave 103s, NAPLES

2 Beds 2 Baths 1,569 SqFt Rental MLS® # 225077359

REMAX Affinity Mercato

$5,950

643 Beachwalk Cir D-202, NAPLES

2 Beds 2 Baths 1,350 SqFt Rental MLS® # 226007345

Star Rental & Property Mngt

$5,900

3450 Gulf Shore Blvd N 210, NAPLES

3 Beds 2 Baths 1,886 SqFt Rental MLS® # 226028001

DomainRealty.com LLC

$5,900

1165 Clam Ct 7, NAPLES

2 Beds 3 Baths 1,449 SqFt Rental MLS® # 226024487

Naples Flat Fee Realty LLC

$5,900

2462 Hidden Lake Dr 208, NAPLES

2 Beds 2 Baths 1,271 SqFt Rental MLS® # 226024627

Achieve Realty LLC

Naples Vacation Rentals

Naples Vacation Rentals - Active Listings

$6,000

790 Meadowland Dr 29-2, NAPLES

$6,000

1 Bluebill Ave 709, NAPLES

$6,000

6276 Shadowood Cir 1503, NAPLES

$6,000

2561 Seychelles Dr 308, NAPLES

$6,000

2307 Queens Way, NAPLES

$6,000

N/A, NAPLES

$6,000

3035 Horizon Ln 2206, NAPLES

$6,000

9055 Capistrano St N 4206, NAPLES

$6,000

9250 Veneto Pl, NAPLES

$6,000

5945 Sand Wedge Ln 1003, NAPLES

$6,000

5928 Sand Wedge Ln 1808, NAPLES

$6,000

651 Wiggins Lake Dr 102, NAPLES

$6,000

9723 Acqua Ct 332, NAPLES

$6,000

9578 Trevi Ct 5142, NAPLES

$6,000

8039 Tauren Ct S, NAPLES

$6,000

3035 Horizon Ln 2203, NAPLES

$6,000

163 Indies Dr E 206, NAPLES

$6,000

15400 Cedarwood Ln 1-201, NAPLES

$6,000

9054 Capistrano St N 4002, NAPLES

$6,000

519 Roma Ct 3-301, NAPLES

$6,000

3435 Laurel Greens Ln S 201, NAPLES

$6,000

964 8th Ave S B-2, NAPLES

$6,000

410 Bayfront Pl 2509, NAPLES

$6,000

577 98th Ave N, NAPLES

$5,995

468 12th Ave S 468, NAPLES

$5,995

15 Bluebill Ave 103s, NAPLES

$5,950

643 Beachwalk Cir D-202, NAPLES

$5,900

3450 Gulf Shore Blvd N 210, NAPLES

$5,900

1165 Clam Ct 7, NAPLES

$5,900

2462 Hidden Lake Dr 208, NAPLES