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

$3,750

↓ $200

6828 Sterling Greens Pl 4105, NAPLES

2 Beds 2 Baths 1,242 SqFt Rental MLS® # 225080858

Realty One Group MVP

$3,750

1270 Wildwood Lakes Blvd 204, NAPLES

2 Beds 2 Baths 1,042 SqFt Rental MLS® # 226025612

Realty One Group MVP

$3,750

1854 Amador Ct, NAPLES

4 Beds 3 Baths 2,127 SqFt Rental MLS® # 226012011

Sun Realty

New New

$3,700

3037 Lunar St, NAPLES

3 Beds 3 Baths 1,619 SqFt Rental MLS® # 226027325

Coldwell Banker Realty

$3,700

3032 Sandpiper Bay Cir G203, NAPLES

2 Beds 2 Baths 1,200 SqFt Rental MLS® # 226020580

Waterfront Realty Group Inc

$3,700

↓ $500

306 Emerald Bay Cir J5, NAPLES

3 Beds 2 Baths 1,490 SqFt Rental MLS® # 226017123

REMAX Affinity Mercato

$3,650

N/A, NAPLES

3 Beds 3 Baths 1,850 SqFt Rental MLS® # 225071453

Coldwell Banker Realty

$3,600

5741 Deauville Cir F108, NAPLES

3 Beds 2 Baths 1,427 SqFt Rental MLS® # 226016806

Premier Property Management

$3,600

↓ $200

9492 Casoria Ct 101, NAPLES

3 Beds 2 Baths 1,883 SqFt Rental MLS® # 225079678

Elite Home Sales & Mgmt, LLC

$3,600

1265 Wildwood Lakes Blvd 3-103, NAPLES

2 Beds 2 Baths 1,042 SqFt Rental MLS® # 225072129

Premier Sotheby's Int'l Realty

$3,600

↑ $100

4060 Ice Castle Way 10, NAPLES

2 Beds 2 Baths 1,246 SqFt Rental MLS® # 225076163

REMAX Affinity Mercato

$3,595

↓ $5

7596 Morgan Way, NAPLES

3 Beds 3 Baths 1,841 SqFt Rental MLS® # 226019976

John R Wood Properties

$3,570

7870 Mahogany Run Ln 1713, NAPLES

2 Beds 2 Baths 1,062 SqFt Rental MLS® # 226018224

Premier Property Management

$3,530

↓ $230

72 7th St S 306, NAPLES

1 Bed 1 Bath 712 SqFt Rental MLS® # 226003622

Starlink Realty, Inc

$3,500

↓ $2,000

4345 Montalvo Ct, NAPLES

3 Beds 3 Baths 1,995 SqFt Rental MLS® # 226022305

Illustrated Properties Real Estate Inc.

$3,500

↓ $4,750

7271 Mill Pond Cir, NAPLES

3 Beds 2 Baths 1,700 SqFt Rental MLS® # 226006784

Naples Luxury Real Estate Grou

$3,500

1055 Forest Lakes Dr F203, NAPLES

2 Beds 2 Baths 1,050 SqFt Rental MLS® # 225070618

Downing Frye Realty Inc.

$3,500

209 Robin Hood Cir 201, NAPLES

2 Beds 2 Baths 1,225 SqFt Rental MLS® # 225083859

Waterfront Realty Group Inc

$3,500

1056 Forest Lakes Dr A201, NAPLES

2 Beds 2 Baths 1,050 SqFt Rental MLS® # 226020707

Berkshire Hathaway FL Realty

$3,500

9366 Pocida Ct 202, NAPLES

2 Beds 2 Baths 1,528 SqFt Rental MLS® # 226020703

Realty One Group MVP

$3,500

326 Bradstrom Cir 204f, NAPLES

3 Beds 2 Baths 1,200 SqFt Rental MLS® # 226011775

William Raveis Real Estate

$3,500

9066 Albion Ln N 5106, NAPLES

3 Beds 3 Baths 1,715 SqFt Rental MLS® # 226025718

Waterfront Realty Group Inc

$3,500

1055 Forest Lakes Dr E209, NAPLES

2 Beds 2 Baths 1,050 SqFt Rental MLS® # 226004026

Berkshire Hathaway FL Realty

$3,500

↓ $250

749 105th Ave N, NAPLES

3 Beds 2 Baths 1,394 SqFt Rental MLS® # 225084243

Naples Trust Real Estate Servi

$3,500

815 Gulf Pavilion Dr 203, NAPLES

2 Beds 2 Baths 1,179 SqFt Rental MLS® # 226002844

Century 21 AllPoints Realty

$3,500

800 Golf Dr S 104, NAPLES

2 Beds 2 Baths 1,060 SqFt Rental MLS® # 226029468

Andrea Deane & Associates, Inc

$3,500

12945 Vanderbilt Dr 402, NAPLES

2 Beds 2 Baths 1,102 SqFt Rental MLS® # 226011659

Florida Home Realty, Inc.

$3,500

↑ $1,500

321 Robin Hood Cir 201, NAPLES

2 Beds 2 Baths 1,225 SqFt Rental MLS® # 225075686

WeichertRealtors-ParadiseHomes

$3,500

9107 Napoli Ct 201, NAPLES

3 Beds 2 Baths 2,099 SqFt Rental MLS® # 226012302

WeichertRealtors-ParadiseHomes

$3,500

1405 Tiffany Ln 1408, NAPLES

2 Beds 2 Baths 1,795 SqFt Rental MLS® # 226013848

Coldwell Banker Realty

Naples Vacation Rentals

Naples Vacation Rentals - Active Listings

$3,750

6828 Sterling Greens Pl 4105, NAPLES

$3,750

1270 Wildwood Lakes Blvd 204, NAPLES

$3,750

1854 Amador Ct, NAPLES

$3,700

3037 Lunar St, NAPLES

$3,700

3032 Sandpiper Bay Cir G203, NAPLES

$3,700

306 Emerald Bay Cir J5, NAPLES

$3,650

N/A, NAPLES

$3,600

5741 Deauville Cir F108, NAPLES

$3,600

9492 Casoria Ct 101, NAPLES

$3,600

1265 Wildwood Lakes Blvd 3-103, NAPLES

$3,600

4060 Ice Castle Way 10, NAPLES

$3,595

7596 Morgan Way, NAPLES

$3,570

7870 Mahogany Run Ln 1713, NAPLES

$3,530

72 7th St S 306, NAPLES

$3,500

4345 Montalvo Ct, NAPLES

$3,500

7271 Mill Pond Cir, NAPLES

$3,500

1055 Forest Lakes Dr F203, NAPLES

$3,500

209 Robin Hood Cir 201, NAPLES

$3,500

1056 Forest Lakes Dr A201, NAPLES

$3,500

9366 Pocida Ct 202, NAPLES

$3,500

326 Bradstrom Cir 204f, NAPLES

$3,500

9066 Albion Ln N 5106, NAPLES

$3,500

1055 Forest Lakes Dr E209, NAPLES

$3,500

749 105th Ave N, NAPLES

$3,500

815 Gulf Pavilion Dr 203, NAPLES

$3,500

800 Golf Dr S 104, NAPLES

$3,500

12945 Vanderbilt Dr 402, NAPLES

$3,500

321 Robin Hood Cir 201, NAPLES

$3,500

9107 Napoli Ct 201, NAPLES

$3,500

1405 Tiffany Ln 1408, NAPLES