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

$7,500

9518 Avellino Way 2313, NAPLES

2 Beds 2 Baths 1,454 SqFt Rental MLS® # 225070619

Safe Harbor Real Estate Servic

$7,500

↓ $999

3960 Deer Crossing Ct 6-204, NAPLES

3 Beds 2 Baths 2,329 SqFt Rental MLS® # 225069019

Bluewater Signature Realty LLC

$7,500

9389 Pocida Ct 202, NAPLES

2 Beds 2 Baths 1,625 SqFt Rental MLS® # 225068978

Coldwell Banker Realty

$7,500

↑ $1,500

9081 Albion Ln S 6505, NAPLES

2 Beds 2 Baths 1,225 SqFt Rental MLS® # 225068373

Realty One Group MVP

$7,400

↓ $600

8982 Gustavia Ct, NAPLES

4 Beds 5 Baths 2,824 SqFt Rental MLS® # 225081585

Berkshire Hathaway FL Realty

$7,300

853 Tanbark Dr 203, NAPLES

2 Beds 2 Baths 1,200 SqFt Rental MLS® # 226016892

Downing Frye Realty Inc.

$7,300

9715 Acqua Ct 127, NAPLES

2 Beds 2 Baths 1,137 SqFt Rental MLS® # 226014060

Downing Frye Realty Inc.

$7,300

565 Beachwalk Cir T-102, NAPLES

2 Beds 2 Baths 1,350 SqFt Rental MLS® # 226013419

Sun Realty

$7,250

15543 Monterosso Ln 101, NAPLES

3 Beds 3 Baths 2,503 SqFt Rental MLS® # 226005322

Downing Frye Realty Inc.

$7,200

262 Indies Dr 101, NAPLES

3 Beds 2 Baths 1,537 SqFt Rental MLS® # 226026916

Realty One Group MVP

$7,200

9509 Avellino Way 1822, NAPLES

2 Beds 2 Baths 1,414 SqFt Rental MLS® # 226021462

KW Elevate Luxury

$7,200

2748 Tiburon Blvd E C-301, NAPLES

1 Bed 2 Baths 1,160 SqFt Rental MLS® # 225054830

Real Estate Specialty Svcs II

$7,200

14940 Edgewater Cir, NAPLES

2 Beds 2 Baths 1,519 SqFt Rental MLS® # 225070451

Real Estate Specialty Svcs II

$7,200

↑ $200

473 12th Ave S B11, NAPLES

2 Beds 2 Baths 800 SqFt Rental MLS® # 225078297

Alfred Robbins Realty Group

New New

$7,000

10020 Siesta Bay Dr 9026, NAPLES

3 Beds 2 Baths 1,661 SqFt Rental MLS® # 226031174

Your Naples Realty LLC

New New

$7,000

12945 Vanderbilt Dr 306, NAPLES

2 Beds 2 Baths 1,200 SqFt Rental MLS® # 226030648

Florida Home Realty, Inc.

New New

$7,000

14670 Catamaran Pl, NAPLES

3 Beds 2 Baths 1,816 SqFt Rental MLS® # 226030833

Premier Property Management

$7,000

4339 Bismark Way, NAPLES

3 Beds 3 Baths 2,000 SqFt Rental MLS® # 226029428

Florida Home Realty, Inc.

$7,000

9097 Cherry Oaks Trl 102, NAPLES

3 Beds 2 Baths 2,408 SqFt Rental MLS® # 226029133

Bluewater Signature Realty LLC

$7,000

9596 Trevi Ct 5413, NAPLES

2 Beds 2 Baths 1,232 SqFt Rental MLS® # 226029105

Naples Vacation Properties

$7,000

1281 10th St N, NAPLES

4 Beds 2 Baths 1,580 SqFt Rental MLS® # 226027863

Staton Properties, LLC

$7,000

9063 Capistrano St N 4405, NAPLES

2 Beds 2 Baths 1,225 SqFt Rental MLS® # 226024549

Waterfront Realty Group Inc

$7,000

9572 Trevi Ct 5017, NAPLES

2 Beds 2 Baths 1,137 SqFt Rental MLS® # 226027127

Safe Harbor Real Estate Servic

$7,000

7631 Jacaranda Ln, NAPLES

2 Beds 2 Baths 1,542 SqFt Rental MLS® # 226026924

Grice Realty Inc

$7,000

3722 Rachel Ln, NAPLES

3 Beds 3 Baths 2,141 SqFt Rental MLS® # 226026624

John R Wood Properties

$7,000

6065 Pinnacle Ln 1001, NAPLES

2 Beds 2 Baths 1,700 SqFt Rental MLS® # 226026191

Coldwell Banker Realty

$7,000

7184 Cayo Coco Ln, NAPLES

2 Beds 2 Baths 1,204 SqFt Rental MLS® # 226025280

Berkshire Hathaway FL Realty

$7,000

5550 Heron Point Dr 105, NAPLES

3 Beds 2 Baths 1,514 SqFt Rental MLS® # 226024292

Waterfront Realty Group Inc

$7,000

14644 Edgewater Cir, NAPLES

2 Beds 2 Baths 1,519 SqFt Rental MLS® # 226024374

Coldwell Banker Realty

$7,000

178 Indies Dr E 201, NAPLES

3 Beds 2 Baths 2,444 SqFt Rental MLS® # 226024447

Realty One Group MVP

Naples Vacation Rentals

Naples Vacation Rentals - Active Listings

$7,500

9518 Avellino Way 2313, NAPLES

$7,500

3960 Deer Crossing Ct 6-204, NAPLES

$7,500

9389 Pocida Ct 202, NAPLES

$7,500

9081 Albion Ln S 6505, NAPLES

$7,400

8982 Gustavia Ct, NAPLES

$7,300

853 Tanbark Dr 203, NAPLES

$7,300

9715 Acqua Ct 127, NAPLES

$7,300

565 Beachwalk Cir T-102, NAPLES

$7,250

15543 Monterosso Ln 101, NAPLES

$7,200

262 Indies Dr 101, NAPLES

$7,200

9509 Avellino Way 1822, NAPLES

$7,200

2748 Tiburon Blvd E C-301, NAPLES

$7,200

14940 Edgewater Cir, NAPLES

$7,200

473 12th Ave S B11, NAPLES

$7,000

10020 Siesta Bay Dr 9026, NAPLES

$7,000

12945 Vanderbilt Dr 306, NAPLES

$7,000

14670 Catamaran Pl, NAPLES

$7,000

4339 Bismark Way, NAPLES

$7,000

9097 Cherry Oaks Trl 102, NAPLES

$7,000

9596 Trevi Ct 5413, NAPLES

$7,000

1281 10th St N, NAPLES

$7,000

9063 Capistrano St N 4405, NAPLES

$7,000

9572 Trevi Ct 5017, NAPLES

$7,000

7631 Jacaranda Ln, NAPLES

$7,000

3722 Rachel Ln, NAPLES

$7,000

6065 Pinnacle Ln 1001, NAPLES

$7,000

7184 Cayo Coco Ln, NAPLES

$7,000

5550 Heron Point Dr 105, NAPLES

$7,000

14644 Edgewater Cir, NAPLES

$7,000

178 Indies Dr E 201, NAPLES