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

$7,000

1 Bluebill Ave 703, NAPLES

1 Bed 1 Bath 800 SqFt Rental MLS® # 225077740

Serhant-Naples

$7,000

↑ $500

14796 Canton Ct, NAPLES

3 Beds 2 Baths 1,677 SqFt Rental MLS® # 225077549

Premier Sotheby's Int'l Realty

$7,000

↑ $500

7138 Cayo Coco Ln, NAPLES

2 Beds 2 Baths 1,205 SqFt Rental MLS® # 225076738

Berkshire Hathaway FL Realty

$7,000

↓ $500

9393 Pocida Ct 104, NAPLES

2 Beds 2 Baths 1,625 SqFt Rental MLS® # 225071561

William Raveis Real Estate

$7,000

9731 Acqua Ct 541, NAPLES

2 Beds 2 Baths 1,232 SqFt Rental MLS® # 225071834

WeichertRealtors-ParadiseHomes

$7,000

↑ $1,500

7302 Acorn Way, NAPLES

3 Beds 3 Baths 2,300 SqFt Rental MLS® # 225071425

Florida Home Realty, Inc.

$7,000

5892 Three Iron Dr 1504, NAPLES

2 Beds 2 Baths 1,793 SqFt Rental MLS® # 225070664

John R Wood Properties

$7,000

6520 Valen Way C 503, NAPLES

2 Beds 2 Baths 1,436 SqFt Rental MLS® # 225070288

Downing Frye Realty Inc.

$7,000

9554 Trevi Ct 4723, NAPLES

2 Beds 2 Baths 1,232 SqFt Rental MLS® # 225069549

Safe Harbor Real Estate Servic

$6,950

589 Lambton Ln, NAPLES

3 Beds 2 Baths 1,823 SqFt Rental MLS® # 226030327

Premier Sotheby's Int'l Realty

$6,900

840 Meadowland Dr H, NAPLES

3 Beds 3 Baths 1,748 SqFt Rental MLS® # 226018192

William Raveis Real Estate

$6,900

10330 Heritage Bay Blvd 2626, NAPLES

2 Beds 2 Baths 1,414 SqFt Rental MLS® # 225076552

Bluewater Signature Realty LLC

$6,850

↑ $3,750

9092 Chula Vista St 11003, NAPLES

2 Beds 2 Baths 1,404 SqFt Rental MLS® # 225081982

Napoli Realty Services, LLC

$6,800

5886 Paradise Cir, NAPLES

3 Beds 3 Baths 1,922 SqFt Rental MLS® # 226027542

Premier Property Management

$6,800

950 7th Ave S 23, NAPLES

1 Bed 1 Bath 631 SqFt Rental MLS® # 226023297

Waterfront Realty Group Inc

$6,800

9552 Caymas Ter, NAPLES

3 Beds 3 Baths 2,366 SqFt Rental MLS® # 226015978

John R Wood Properties

$6,800

5693 Heron Ln 502, NAPLES

2 Beds 2 Baths 1,490 SqFt Rental MLS® # 225069800

Royal Shell Real Estate, Inc.

$6,800

1334 Crayton Rd 1, NAPLES

2 Beds 2 Baths 1,100 SqFt Rental MLS® # 225069304

Premier Sotheby's Int'l Realty

$6,750

7778 Emerald Cir 204, NAPLES

3 Beds 2 Baths 1,199 SqFt Rental MLS® # 226023597

Berkshire Hathaway FL Realty

$6,750

↓ $1,000

8260 Laurel Lakes Blvd, NAPLES

3 Beds 2 Baths 2,100 SqFt Rental MLS® # 226022102

Waterfront Realty Group Inc

$6,700

451 Bayfront Pl 5206, NAPLES

1 Bed 2 Baths 1,325 SqFt Rental MLS® # 226017997

Berkshire Hathaway FL Realty

$6,700

1 Bluebill Ave 803, NAPLES

1 Bed 2 Baths 1,147 SqFt Rental MLS® # 225070123

William Raveis Real Estate

New New

$6,500

9066 Albion Ln N 5104, NAPLES

3 Beds 2 Baths 1,771 SqFt Rental MLS® # 226031467

Realty One Group MVP

New New

$6,500

9532 Avellino Way 2722, NAPLES

2 Beds 3 Baths 1,414 SqFt Rental MLS® # 226031380

Parkline Realty

New New

$6,500

14523 Topsail Dr, NAPLES

4 Beds 2 Baths 2,046 SqFt Rental MLS® # 226031291

Compass Florida LLC

$6,500

774 Wiggins Lake Dr 106, NAPLES

3 Beds 2 Baths 1,374 SqFt Rental MLS® # 226030638

WeichertRealtors-ParadiseHomes

$6,500

5660 Northboro Dr 202, NAPLES

3 Beds 2 Baths 2,144 SqFt Rental MLS® # 226030626

Royal Shell Real Estate, Inc.

$6,500

9596 Trevi Ct 5446, NAPLES

2 Beds 2 Baths 1,232 SqFt Rental MLS® # 226029267

WeichertRealtors-ParadiseHomes

$6,500

1313 Solana Rd W A3, NAPLES

2 Beds 2 Baths 1,728 SqFt Rental MLS® # 226028919

Downing Frye Realty Inc.

$6,500

3917 Isla Ciudad Ct, NAPLES

3 Beds 3 Baths 1,983 SqFt Rental MLS® # 226028545

REMAX Affinity Mercato

Naples Vacation Rentals

Naples Vacation Rentals - Active Listings

$7,000

1 Bluebill Ave 703, NAPLES

$7,000

14796 Canton Ct, NAPLES

$7,000

7138 Cayo Coco Ln, NAPLES

$7,000

9393 Pocida Ct 104, NAPLES

$7,000

9731 Acqua Ct 541, NAPLES

$7,000

7302 Acorn Way, NAPLES

$7,000

5892 Three Iron Dr 1504, NAPLES

$7,000

6520 Valen Way C 503, NAPLES

$7,000

9554 Trevi Ct 4723, NAPLES

$6,950

589 Lambton Ln, NAPLES

$6,900

840 Meadowland Dr H, NAPLES

$6,900

10330 Heritage Bay Blvd 2626, NAPLES

$6,850

9092 Chula Vista St 11003, NAPLES

$6,800

5886 Paradise Cir, NAPLES

$6,800

950 7th Ave S 23, NAPLES

$6,800

9552 Caymas Ter, NAPLES

$6,800

5693 Heron Ln 502, NAPLES

$6,800

1334 Crayton Rd 1, NAPLES

$6,750

7778 Emerald Cir 204, NAPLES

$6,750

8260 Laurel Lakes Blvd, NAPLES

$6,700

451 Bayfront Pl 5206, NAPLES

$6,700

1 Bluebill Ave 803, NAPLES

$6,500

9066 Albion Ln N 5104, NAPLES

$6,500

9532 Avellino Way 2722, NAPLES

$6,500

14523 Topsail Dr, NAPLES

$6,500

774 Wiggins Lake Dr 106, NAPLES

$6,500

5660 Northboro Dr 202, NAPLES

$6,500

9596 Trevi Ct 5446, NAPLES

$6,500

1313 Solana Rd W A3, NAPLES

$6,500

3917 Isla Ciudad Ct, NAPLES