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

$21,500

9577 Gulf Shore Dr W 504, NAPLES

3 Beds 3 Baths 1,582 SqFt Rental MLS® # 225075380

Downing Frye Realty Inc.

$21,500

1080 5th St S 1080, NAPLES

3 Beds 3 Baths 2,310 SqFt Rental MLS® # 225069820

Royal Shell Real Estate, Inc.

$21,000

15394 Turin Dr, NAPLES

3 Beds 4 Baths 2,885 SqFt Rental MLS® # 226029060

Naples Homes and Rentals Inc

$21,000

4041 Gulf Shore Blvd N 606, NAPLES

3 Beds 3 Baths 2,550 SqFt Rental MLS® # 226028630

Royal Shell Real Estate, Inc.

$21,000

295 Grande Way 1202, NAPLES

3 Beds 4 Baths 2,609 SqFt Rental MLS® # 226019069

William Raveis Real Estate

New New

$20,000

8902 Shenendoah Cir, NAPLES

3 Beds 3 Baths 4,200 SqFt Rental MLS® # 226030953

Premier Sotheby's Int'l Realty

New New

$20,000

4651 Gulf Shore Blvd N 1106, NAPLES

2 Beds 2 Baths 1,531 SqFt Rental MLS® # 226030950

Premier Sotheby's Int'l Realty

New New

$20,000

692 10th Ave S A2, NAPLES

3 Beds 3 Baths 2,321 SqFt Rental MLS® # 2026035984

Gordon Pass Realty LLC

$20,000

482 Tradewinds Ave, NAPLES

4 Beds 3 Baths 2,467 SqFt Rental MLS® # 226030489

Naples Vibe Realty, LLC

$20,000

9280 Cormorant Dr, NAPLES

3 Beds 3 Baths 2,000 SqFt Rental MLS® # 226030485

Naples Vibe Realty, LLC

$20,000

6501 Crown Colony Pl 4-201, NAPLES

3 Beds 4 Baths 3,952 SqFt Rental MLS® # 226030403

Downing Frye Realty Inc.

$20,000

2826 Tiburon Blvd E 103, NAPLES

3 Beds 2 Baths 2,502 SqFt Rental MLS® # 226027068

William Raveis Real Estate

$20,000

↓ $5,000

600 5th Ave S A-212, NAPLES

3 Beds 2 Baths 2,700 SqFt Rental MLS® # 225074205

Premier Sotheby's Int'l Realty

$20,000

967 Tivoli Dr, NAPLES

3 Beds 3 Baths 2,823 SqFt Rental MLS® # 226029700

Waterfront Realty Group Inc

$20,000

707 Port Side Dr, NAPLES

4 Beds 3 Baths 2,490 SqFt Rental MLS® # 226027571

Premier Sotheby's Int'l Realty

$20,000

4000 Gulf Shore Blvd N 1400, NAPLES

2 Beds 2 Baths 1,753 SqFt Rental MLS® # 226026675

John R Wood Properties

$20,000

740 5th Ave N, NAPLES

3 Beds 3 Baths 2,051 SqFt Rental MLS® # 225079434

Naples Trust Real Estate Servi

$20,000

10475 Gulf Shore Dr 115, NAPLES

3 Beds 2 Baths 1,594 SqFt Rental MLS® # 226025793

Downing Frye Realty Inc.

$20,000

8963 Gustavia Ct, NAPLES

4 Beds 4 Baths 2,847 SqFt Rental MLS® # 226025240

Berkshire Hathaway FL Realty

$20,000

975 Tivoli Ct, NAPLES

4 Beds 3 Baths 2,340 SqFt Rental MLS® # 226023096

Waterfront Realty Group Inc

$20,000

2658 Bolero Dr 9-2, NAPLES

3 Beds 2 Baths 2,450 SqFt Rental MLS® # 226014435

Real Estate Specialty Svcs II

$20,000

2736 Gulfview Dr, NAPLES

3 Beds 3 Baths 1,732 SqFt Rental MLS® # 226022311

John R Wood Properties

$20,000

16366 Corsica Way 201, NAPLES

3 Beds 4 Baths 3,382 SqFt Rental MLS® # 226019781

Real Broker, LLC

$20,000

374 14th Ave S, NAPLES

3 Beds 4 Baths 2,369 SqFt Rental MLS® # 226020309

Downing Frye Realty Inc.

$20,000

13925 Old Coast Rd 1104, NAPLES

3 Beds 5 Baths 3,287 SqFt Rental MLS® # 226020230

Premier Sotheby's Int'l Realty

$20,000

1130 3rd Ave S 109, NAPLES

3 Beds 4 Baths 2,853 SqFt Rental MLS® # 226019315

Serhant-Naples

$20,000

739 7th Ave N, NAPLES

3 Beds 3 Baths 2,253 SqFt Rental MLS® # 226019054

William Raveis Real Estate

$20,000

3971 Gulf Shore Blvd N 401, NAPLES

2 Beds 3 Baths 2,522 SqFt Rental MLS® # 226012079

Premier Sotheby's Int'l Realty

$20,000

9155 Torrefino Ct, NAPLES

4 Beds 5 Baths 4,534 SqFt Rental MLS® # 226005995

Premier Sotheby's Int'l Realty

$20,000

2654 Bolero Dr 8-1, NAPLES

3 Beds 2 Baths 1,768 SqFt Rental MLS® # 225029512

Real Estate Specialty Svcs II

Naples Vacation Rentals

Naples Vacation Rentals - Active Listings

$21,500

9577 Gulf Shore Dr W 504, NAPLES

$21,500

1080 5th St S 1080, NAPLES

$21,000

15394 Turin Dr, NAPLES

$21,000

4041 Gulf Shore Blvd N 606, NAPLES

$21,000

295 Grande Way 1202, NAPLES

$20,000

8902 Shenendoah Cir, NAPLES

$20,000

4651 Gulf Shore Blvd N 1106, NAPLES

$20,000

692 10th Ave S A2, NAPLES

$20,000

482 Tradewinds Ave, NAPLES

$20,000

9280 Cormorant Dr, NAPLES

$20,000

6501 Crown Colony Pl 4-201, NAPLES

$20,000

2826 Tiburon Blvd E 103, NAPLES

$20,000

600 5th Ave S A-212, NAPLES

$20,000

967 Tivoli Dr, NAPLES

$20,000

707 Port Side Dr, NAPLES

$20,000

4000 Gulf Shore Blvd N 1400, NAPLES

$20,000

740 5th Ave N, NAPLES

$20,000

10475 Gulf Shore Dr 115, NAPLES

$20,000

8963 Gustavia Ct, NAPLES

$20,000

975 Tivoli Ct, NAPLES

$20,000

2658 Bolero Dr 9-2, NAPLES

$20,000

2736 Gulfview Dr, NAPLES

$20,000

16366 Corsica Way 201, NAPLES

$20,000

374 14th Ave S, NAPLES

$20,000

13925 Old Coast Rd 1104, NAPLES

$20,000

1130 3rd Ave S 109, NAPLES

$20,000

739 7th Ave N, NAPLES

$20,000

3971 Gulf Shore Blvd N 401, NAPLES

$20,000

9155 Torrefino Ct, NAPLES

$20,000

2654 Bolero Dr 8-1, NAPLES