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

$8,000

410 Bayfront Pl 2208, NAPLES

1 Bed 2 Baths 1,126 SqFt Rental MLS® # 226000791

Compass Florida LLC

$8,000

↓ $1,000

6535 Valen Way E-202, NAPLES

2 Beds 2 Baths 1,350 SqFt Rental MLS® # 225082015

Naples Trust Real Estate Servi

$8,000

5899 Chanteclair Dr 222, NAPLES

2 Beds 2 Baths 1,481 SqFt Rental MLS® # 225079531

Royal Shell Real Estate, Inc.

$8,000

2276 Heritage Greens Dr, NAPLES

3 Beds 2 Baths 1,632 SqFt Rental MLS® # 225076705

Royal Shell Real Estate, Inc.

$8,000

1878 Mustique St, NAPLES

3 Beds 2 Baths 2,064 SqFt Rental MLS® # 225074450

The Real Estate Connection LLC

$8,000

724 100th Ave N, NAPLES

3 Beds 2 Baths 1,424 SqFt Rental MLS® # 225073640

Compass Florida LLC

$8,000

1 Bluebill Ave 410, NAPLES

2 Beds 2 Baths 1,040 SqFt Rental MLS® # 225073630

Serhant-Naples

$8,000

10686 Gulf Shore Dr A302, NAPLES

2 Beds 2 Baths 1,500 SqFt Rental MLS® # 225072146

Premier Sotheby's Int'l Realty

$8,000

9596 Trevi Ct 5425, NAPLES

2 Beds 2 Baths 1,250 SqFt Rental MLS® # 225071052

Naples Vacation Properties

$8,000

6669 Alden Woods Cir 7-201, NAPLES

2 Beds 2 Baths 2,040 SqFt Rental MLS® # 225070654

Premier Sotheby's Int'l Realty

$8,000

8177 Saratoga Dr 1001, NAPLES

2 Beds 2 Baths 1,880 SqFt Rental MLS® # 225070650

Premier Sotheby's Int'l Realty

$8,000

500 L'ambiance Cir 5-104, NAPLES

2 Beds 2 Baths 1,349 SqFt Rental MLS® # 225068974

Coldwell Banker Realty

$8,000

3105 Riviera Dr A-201, NAPLES

2 Beds 2 Baths 1,625 SqFt Rental MLS® # 225068979

Coldwell Banker Realty

$7,995

↓ $5

450 Bayfront Pl 4502, NAPLES

1 Bed 2 Baths 1,126 SqFt Rental MLS® # 225081488

Orlando Regional Realty Inc

$7,950

9572 Trevi Ct 5033, NAPLES

2 Beds 2 Baths 1,232 SqFt Rental MLS® # 226030487

Naples Vibe Realty, LLC

$7,950

↓ $1,050

4082 Belair Ln 9, NAPLES

3 Beds 2 Baths 1,525 SqFt Rental MLS® # 226026653

DomainRealty.com LLC

$7,800

↓ $700

5633 Turtle Bay Dr 37, NAPLES

2 Beds 2 Baths 1,423 SqFt Rental MLS® # 226023625

Naples Realty & Property Mgmt

$7,800

586 Beachwalk Cir O-205, NAPLES

2 Beds 2 Baths 1,350 SqFt Rental MLS® # 226021501

Realty One Group MVP

$7,800

430 Cove Tower Dr 1202, NAPLES

3 Beds 2 Baths 1,519 SqFt Rental MLS® # 226018214

Premier Property Management

$7,800

2165 Arielle Dr 1602, NAPLES

2 Beds 2 Baths 1,633 SqFt Rental MLS® # 226016767

Coldwell Banker Realty

$7,800

↑ $100

8225 Danbury Blvd E 1-102, NAPLES

2 Beds 2 Baths 1,558 SqFt Rental MLS® # 225066222

Sun Realty

$7,800

↑ $800

2110 Arielle Dr 103, NAPLES

2 Beds 2 Baths 1,560 SqFt Rental MLS® # 225069804

Royal Shell Real Estate, Inc.

$7,700

2230 Arielle Dr 1902, NAPLES

2 Beds 2 Baths 1,633 SqFt Rental MLS® # 226015482

Premier Sotheby's Int'l Realty

$7,500

526 Lake Louise Cir 4-403, NAPLES

3 Beds 2 Baths 1,740 SqFt Rental MLS® # 226029390

Premier Sotheby's Int'l Realty

$7,500

↑ $2,500

9727 Acqua Ct 423, NAPLES

2 Beds 2 Baths 1,137 SqFt Rental MLS® # 225084284

WeichertRealtors-ParadiseHomes

$7,500

586 Beachwalk Cir O-305, NAPLES

2 Beds 2 Baths 1,350 SqFt Rental MLS® # 226028870

Realty One Group MVP

$7,500

4551 Gulf Shore Blvd N 306, NAPLES

2 Beds 2 Baths 1,671 SqFt Rental MLS® # 226028476

Real Estate Specialty Svcs II

$7,500

7111 Cayo Coco Ln, NAPLES

2 Beds 2 Baths 1,387 SqFt Rental MLS® # 226028399

Berkshire Hathaway FL Realty

$7,500

583 Beachwalk Cir Q-203, NAPLES

2 Beds 2 Baths 1,350 SqFt Rental MLS® # 226027986

Realty One Group MVP

$7,500

10572 Smokehouse Bay Dr 101, NAPLES

3 Beds 2 Baths 1,883 SqFt Rental MLS® # 226027554

SunStream Realty

Naples Vacation Rentals

Naples Vacation Rentals - Active Listings

$8,000

410 Bayfront Pl 2208, NAPLES

$8,000

6535 Valen Way E-202, NAPLES

$8,000

5899 Chanteclair Dr 222, NAPLES

$8,000

2276 Heritage Greens Dr, NAPLES

$8,000

1878 Mustique St, NAPLES

$8,000

724 100th Ave N, NAPLES

$8,000

1 Bluebill Ave 410, NAPLES

$8,000

10686 Gulf Shore Dr A302, NAPLES

$8,000

9596 Trevi Ct 5425, NAPLES

$8,000

6669 Alden Woods Cir 7-201, NAPLES

$8,000

8177 Saratoga Dr 1001, NAPLES

$8,000

500 L'ambiance Cir 5-104, NAPLES

$8,000

3105 Riviera Dr A-201, NAPLES

$7,995

450 Bayfront Pl 4502, NAPLES

$7,950

9572 Trevi Ct 5033, NAPLES

$7,950

4082 Belair Ln 9, NAPLES

$7,800

5633 Turtle Bay Dr 37, NAPLES

$7,800

586 Beachwalk Cir O-205, NAPLES

$7,800

430 Cove Tower Dr 1202, NAPLES

$7,800

2165 Arielle Dr 1602, NAPLES

$7,800

8225 Danbury Blvd E 1-102, NAPLES

$7,800

2110 Arielle Dr 103, NAPLES

$7,700

2230 Arielle Dr 1902, NAPLES

$7,500

526 Lake Louise Cir 4-403, NAPLES

$7,500

9727 Acqua Ct 423, NAPLES

$7,500

586 Beachwalk Cir O-305, NAPLES

$7,500

4551 Gulf Shore Blvd N 306, NAPLES

$7,500

7111 Cayo Coco Ln, NAPLES

$7,500

583 Beachwalk Cir Q-203, NAPLES

$7,500

10572 Smokehouse Bay Dr 101, NAPLES