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

$16,000

3340 Kumamoto Lane, NAPLES

4 Beds 4 Baths 3,119 SqFt Rental MLS® # 226024291

Waterfront Realty Group Inc

$16,000

1400 Gulf Shore Blvd N 310, NAPLES

3 Beds 4 Baths 2,472 SqFt Rental MLS® # 226023697

Berkshire Hathaway FL Realty

$16,000

1490 5th Ave S 200a, NAPLES

2 Beds 2 Baths 1,797 SqFt Rental MLS® # 226022307

John R Wood Properties

$16,000

1130 3rd Ave S 109, NAPLES

3 Beds 4 Baths 2,853 SqFt Rental MLS® # 226019330

Serhant-Naples

$16,000

1155 6th St S, NAPLES

3 Beds 2 Baths 1,384 SqFt Rental MLS® # 226019623

John R Wood Properties

$16,000

410 Flagship Dr 605, NAPLES

3 Beds 3 Baths 1,860 SqFt Rental MLS® # 226017343

William Raveis Real Estate

$16,000

16382 Viansa Way 3-102, NAPLES

3 Beds 4 Baths 2,400 SqFt Rental MLS® # 225077714

Real Estate Specialty Svcs II

$16,000

9634 Firenze Cir, NAPLES

3 Beds 3 Baths 2,799 SqFt Rental MLS® # 226011661

WeichertRealtors-ParadiseHomes

$16,000

9375 Gulf Shore Dr 401, NAPLES

2 Beds 2 Baths 1,600 SqFt Rental MLS® # 226009385

John R Wood Properties

$16,000

1437 Sandpiper St, NAPLES

3 Beds 2 Baths 1,200 SqFt Rental MLS® # 226009337

William Raveis Real Estate

$16,000

900 5th Ave S 303, NAPLES

3 Beds 3 Baths 1,905 SqFt Rental MLS® # 226001313

William Raveis Real Estate

$16,000

↑ $7,500

16382 Viansa Way 201, NAPLES

3 Beds 4 Baths 2,350 SqFt Rental MLS® # 225084680

Real Broker, LLC

$16,000

361 1st Ave N, NAPLES

3 Beds 3 Baths 1,500 SqFt Rental MLS® # 225084714

Royal Shell Real Estate, Inc.

$16,000

↓ $2,000

564 109th Ave N, NAPLES

2 Beds 2 Baths 1,080 SqFt Rental MLS® # 225080483

All In Property Management LLC

$16,000

3443 Gulf Shore Blvd N 710, NAPLES

2 Beds 2 Baths 1,215 SqFt Rental MLS® # 225078461

John R Wood Properties

$16,000

↑ $8,000

16352 Viansa Way 101, NAPLES

3 Beds 2 Baths 1,710 SqFt Rental MLS® # 225076162

Real Broker, LLC

$16,000

↑ $500

275 Indies Way 403, NAPLES

3 Beds 3 Baths 2,748 SqFt Rental MLS® # 225075280

Royal Shell Real Estate, Inc.

$15,900

↑ $9,000

7864 Valencia Ct, NAPLES

3 Beds 2 Baths 2,190 SqFt Rental MLS® # 225081215

Downing Frye Realty Inc.

$15,400

410 Flagship Dr 806, NAPLES

3 Beds 3 Baths 1,979 SqFt Rental MLS® # 226013624

William Raveis Real Estate

$15,300

N/A, NAPLES

2 Beds 2 Baths 1,489 SqFt Rental MLS® # 226029796

William Raveis Real Estate

New New

$15,000

9103 Vanderbilt Dr 208, NAPLES

3 Beds 2 Baths 1,468 SqFt Rental MLS® # 226030538

Naples Vibe Realty, LLC

New New

$15,000

9799 Everglades Dr, NAPLES

3 Beds 3 Baths 2,100 SqFt Rental MLS® # 226030530

Naples Vibe Realty, LLC

$15,000

795 Bentwater Cir 204, NAPLES

3 Beds 2 Baths 1,831 SqFt Rental MLS® # 226030287

William Raveis Real Estate

$15,000

6361 Pelican Bay Blvd 402, NAPLES

2 Beds 2 Baths 1,456 SqFt Rental MLS® # 226030005

William Raveis Real Estate

$15,000

400 Flagship Dr 1207, NAPLES

3 Beds 3 Baths 2,035 SqFt Rental MLS® # 226029543

William Raveis Real Estate

$15,000

400 Flagship Dr 705, NAPLES

3 Beds 3 Baths 1,750 SqFt Rental MLS® # 226029539

William Raveis Real Estate

$15,000

1115 Central Ave 445, NAPLES

2 Beds 3 Baths 1,692 SqFt Rental MLS® # 226027908

John R Wood Properties

$15,000

↓ $2,000

15710 Triesta Ln, NAPLES

3 Beds 3 Baths 2,550 SqFt Rental MLS® # 226026599

Waterfront Realty Group Inc

$15,000

544 10th Ave S 202n, NAPLES

3 Beds 2 Baths 1,365 SqFt Rental MLS® # 226026403

John R Wood Properties

$15,000

6020 Pelican Bay Blvd E402, NAPLES

2 Beds 2 Baths 1,550 SqFt Rental MLS® # 226025893

Carolyn Weinand Properties

Naples Vacation Rentals

Naples Vacation Rentals - Active Listings

$16,000

3340 Kumamoto Lane, NAPLES

$16,000

1400 Gulf Shore Blvd N 310, NAPLES

$16,000

1490 5th Ave S 200a, NAPLES

$16,000

1130 3rd Ave S 109, NAPLES

$16,000

1155 6th St S, NAPLES

$16,000

410 Flagship Dr 605, NAPLES

$16,000

16382 Viansa Way 3-102, NAPLES

$16,000

9634 Firenze Cir, NAPLES

$16,000

9375 Gulf Shore Dr 401, NAPLES

$16,000

1437 Sandpiper St, NAPLES

$16,000

900 5th Ave S 303, NAPLES

$16,000

16382 Viansa Way 201, NAPLES

$16,000

361 1st Ave N, NAPLES

$16,000

564 109th Ave N, NAPLES

$16,000

3443 Gulf Shore Blvd N 710, NAPLES

$16,000

16352 Viansa Way 101, NAPLES

$16,000

275 Indies Way 403, NAPLES

$15,900

7864 Valencia Ct, NAPLES

$15,400

410 Flagship Dr 806, NAPLES

$15,300

N/A, NAPLES

$15,000

9103 Vanderbilt Dr 208, NAPLES

$15,000

9799 Everglades Dr, NAPLES

$15,000

795 Bentwater Cir 204, NAPLES

$15,000

6361 Pelican Bay Blvd 402, NAPLES

$15,000

400 Flagship Dr 1207, NAPLES

$15,000

400 Flagship Dr 705, NAPLES

$15,000

1115 Central Ave 445, NAPLES

$15,000

15710 Triesta Ln, NAPLES

$15,000

544 10th Ave S 202n, NAPLES

$15,000

6020 Pelican Bay Blvd E402, NAPLES