What is downtown Naples like for vacation visitors?

Downtown Naples — centered on Olde Naples and 5th Avenue South and 3rd Street South — offers award-winning dining, art galleries, boutique shopping, and proximity to the beach in a compact, pedestrian-friendly setting. For visitors who want to experience Naples as a place rather than just a beach destination, downtown is the ideal base.

How close are downtown Naples vacation rentals to the beach?

Olde Naples sits directly adjacent to the Gulf Coast — the beach is accessible from virtually any downtown rental in under ten minutes on foot. The Naples Pier at 12th Avenue South is the neighborhood's iconic beach landmark, and the stretch of beach nearby is among Naples' most beautiful.

What types of vacation rentals are available in downtown Naples?

Downtown Naples vacation rentals range from luxury condominiums within walking distance of 5th Avenue South to private estate homes in Olde Naples and the Moorings. Many Olde Naples estates offer private pools and spacious outdoor living. Condominiums along Gulf Shore Blvd offer Gulf views and direct beach access.

What is the price range for downtown Naples vacation rentals?

Condominiums near 5th Avenue South range from $6,000 to $15,000 per month during peak season. Estate homes in Olde Naples range from approximately $15,000 to $50,000 per month. Off-season rates are typically 30-50% lower than peak season pricing.

What are the best restaurants on 5th Avenue South in Naples?

Fifth Avenue South standouts include Campiello for Mediterranean cuisine, Barbatella for American bistro cooking, The English Room for continental fine dining, and Bayside Seafood Grill and Bar for waterfront dining. Third Street South adds Ridgway Bar & Grill, Osteria Tulia, and numerous others.

How do I find and book a downtown Naples vacation rental?

Browse listings above or contact Alpizar & Company at (239) 438-1102. Share your preferred downtown location, group size, dates, and budget — we will identify matching properties. Complimentary assistance with no pressure. Our real estate team also specializes in Olde Naples ownership if your stay inspires that conversation.

Downtown Naples Vacations | Walk to 5th Avenue South & the Beach

$10,479

↑ $2,979

1295 Gulf Shore Blvd S 218, NAPLES

2 Beds 2 Baths 662 SqFt Rental MLS® # 226010595

John R Wood Properties

$10,000

1050 9th St S 102, NAPLES

2 Beds 2 Baths 1,680 SqFt Rental MLS® # 226024911

Naples Diamond Realty

$10,000

663 10th Ave S B663, NAPLES

2 Beds 2 Baths 1,241 SqFt Rental MLS® # 2026033176

Gordon Pass Realty LLC

$10,000

802 10th Ave S 802, NAPLES

2 Beds 2 Baths 1,480 SqFt Rental MLS® # 225079052

Naples Diamond Realty

$10,000

↓ $1,000

705 10th St S 301, NAPLES

4 Beds 5 Baths 2,930 SqFt Rental MLS® # 226014692

Real Estate Specialty Svcs II

$10,000

250 7th Ave S 207, NAPLES

2 Beds 2 Baths 1,000 SqFt Rental MLS® # 226022890

Premier Sotheby's Int'l Realty

$10,000

↑ $9,000

280 4th St S 104, NAPLES

2 Beds 2 Baths 1,058 SqFt Rental MLS® # 226030277

John R Wood Properties

$10,000

250 7th Ave S 202, NAPLES

2 Beds 2 Baths 1,000 SqFt Rental MLS® # 225068976

Coldwell Banker Realty

$10,000

250 7th Ave S 301, NAPLES

2 Beds 2 Baths 1,000 SqFt Rental MLS® # 225068977

Coldwell Banker Realty

$9,500

↓ $1,000

964 8th Ave S B-2, NAPLES

3 Beds 2 Baths 1,707 SqFt Rental MLS® # 225078596

Naples Flat Fee Realty LLC

$9,500

↑ $500

284 4th St S 103, NAPLES

2 Beds 2 Baths 979 SqFt Rental MLS® # 225082881

John R Wood Properties

New New

$9,500

1100 8th Ave S 328h, NAPLES

2 Beds 2 Baths 1,350 SqFt Rental MLS® # 226030877

Premier Sotheby's Int'l Realty

$9,000

↑ $2,000

1140 5th St S A, NAPLES

3 Beds 3 Baths 1,140 SqFt Rental MLS® # 226025604

Naples Flat Fee Realty LLC

$8,500

980 7th Ave S 201, NAPLES

1 Bed 1 Bath 540 SqFt Rental MLS® # 226017785

Grice Realty Inc

$8,000

1100 8th Ave S H227, NAPLES

2 Beds 2 Baths 1,350 SqFt Rental MLS® # 226028740

William Raveis Real Estate

$8,000

↓ $500

286 4th St S 203, NAPLES

2 Beds 2 Baths 1,058 SqFt Rental MLS® # 226014845

Naples Vacation Properties

$8,000

↑ $1,000

666 3rd St S 201, NAPLES

2 Beds 2 Baths 1,115 SqFt Rental MLS® # 225069944

Coldwell Banker Realty

$7,500

341 3rd Ave S 341, NAPLES

2 Beds 2 Baths 1,300 SqFt Rental MLS® # 226019412

Royal Shell Real Estate, Inc.

$7,500

271 Broad Ave S 203, NAPLES

2 Beds 2 Baths 1,400 SqFt Rental MLS® # 225074670

Coldwell Banker Realty

$7,500

271 Broad Ave S 202, NAPLES

2 Beds 2 Baths 1,500 SqFt Rental MLS® # 225074679

Coldwell Banker Realty

$7,500

250 7th Ave S 305, NAPLES

2 Beds 2 Baths 1,000 SqFt Rental MLS® # 226026745

Waterfront Realty Group Inc

$7,000

980 7th Ave S 109, NAPLES

1 Bed 1 Bath 540 SqFt Rental MLS® # 226001386

Re/Max Alliance Group

$7,000

1051 3rd St S 301, NAPLES

2 Beds 2 Baths 1,256 SqFt Rental MLS® # 226017342

Downing Frye Realty Inc.

$7,000

975 9th Ave S 5, NAPLES

1 Bed 1 Bath 523 SqFt Rental MLS® # 225084378

Realty One Group MVP

$6,800

950 7th Ave S 23, NAPLES

1 Bed 1 Bath 631 SqFt Rental MLS® # 226023297

Waterfront Realty Group Inc

$6,500

375 8th Ave S D, NAPLES

3 Beds 3 Baths 1,915 SqFt Rental MLS® # 226011746

Premier Sotheby's Int'l Realty

$6,500

766 Central Ave 112, NAPLES

2 Beds 2 Baths 855 SqFt Rental MLS® # 226027476

Royal Shell Real Estate, Inc.

$6,500

↓ $500

1100 8th Ave S 226g, NAPLES

2 Beds 2 Baths 1,350 SqFt Rental MLS® # 226018673

Premier Sotheby's Int'l Realty

$6,500

480 5th St S 102, NAPLES

1 Bed 1 Bath 600 SqFt Rental MLS® # 226024912

Berkshire Hathaway FL Realty

$6,500

980 7th Ave S 204, NAPLES

1 Bed 1 Bath 540 SqFt Rental MLS® # 225082879

John R Wood Properties

Downtown Naples Vacations

Seasonal Rentals in Olde Naples

$10,479

1295 Gulf Shore Blvd S 218, NAPLES

$10,000

1050 9th St S 102, NAPLES

$10,000

663 10th Ave S B663, NAPLES

$10,000

802 10th Ave S 802, NAPLES

$10,000

705 10th St S 301, NAPLES

$10,000

250 7th Ave S 207, NAPLES

$10,000

280 4th St S 104, NAPLES

$10,000

250 7th Ave S 202, NAPLES

$10,000

250 7th Ave S 301, NAPLES

$9,500

964 8th Ave S B-2, NAPLES

$9,500

284 4th St S 103, NAPLES

$9,500

1100 8th Ave S 328h, NAPLES

$9,000

1140 5th St S A, NAPLES

$8,500

980 7th Ave S 201, NAPLES

$8,000

1100 8th Ave S H227, NAPLES

$8,000

286 4th St S 203, NAPLES

$8,000

666 3rd St S 201, NAPLES

$7,500

341 3rd Ave S 341, NAPLES

$7,500

271 Broad Ave S 203, NAPLES

$7,500

271 Broad Ave S 202, NAPLES

$7,500

250 7th Ave S 305, NAPLES

$7,000

980 7th Ave S 109, NAPLES

$7,000

1051 3rd St S 301, NAPLES

$7,000

975 9th Ave S 5, NAPLES

$6,800

950 7th Ave S 23, NAPLES

$6,500

375 8th Ave S D, NAPLES

$6,500

766 Central Ave 112, NAPLES

$6,500

1100 8th Ave S 226g, NAPLES

$6,500

480 5th St S 102, NAPLES

$6,500

980 7th Ave S 204, NAPLES