Bayfront Seasonal Rentals Moments from Vanderbilt Beach
Regatta is one of the few gated communities in Vanderbilt Beach where a seasonal stay comes with resort-style pools, a marina on Vanderbilt Lagoon and the beach a short distance away. Every residence is a three-bedroom condominium with a screened lanai over the water, and many carry weekly-rental rights that most North Naples buildings never allowed. Alpizar & Company manages residences at Regatta directly — those appear first in the listings below as Exclusive Listings.
Renting at Regatta at a Glance
| Location | Vanderbilt Beach Road at Vanderbilt Drive, North Naples 34108 — on Vanderbilt Lagoon, a short distance from Vanderbilt Beach |
| Residences | Three-bedroom condominiums, approximately 1,475 to 2,320 square feet, screened lanais facing the water |
| Buildings | Two 12-story towers (400 & 410 Flagship Drive) with Gulf views from the upper floors; three 6-story buildings (450, 460 & 470 Launch Circle) beside the marina |
| Minimum Stay | 30 days in most residences; weekly stays available in residences with grandfathered rental rights |
| Amenities | Gated entry, two pools including a lagoon-style pool with waterfall, spa, fitness center, clubhouse, fishing pier, picnic and grilling area |
| Parking | One assigned under-building space per residence |
| Pets | Varies by residence and owner — ask before booking |
| Nearby | Vanderbilt Beach, The Ritz-Carlton, Naples, LaPlaya, The Turtle Club, Mercato, Delnor-Wiggins Pass State Park |
Regatta Vacation Rentals - Active Listings
Don't See Your Dates?
Availability changes weekly and the best season weeks are often spoken for before they reach the listings. Tell us your dates, how many guests, and whether a Gulf view or a marina-side building matters to you, and we'll reply with what's open across Regatta and the rest of Vanderbilt Beach.
Why Regatta for a Naples Season
Most Vanderbilt Beach rentals are either on the beach with limited amenities or inland with a pool and a drive to the sand. Regatta is the rare middle: a gated, resort-style community on the lagoon with the beach access at the end of Vanderbilt Beach Road a short distance away. Mornings start on the lanai over the water, afternoons at the waterfall pool or on the sand, and evenings at The Turtle Club, LaPlaya or Mercato without getting on the interstate. Boaters can inquire about slip leases in the on-site marina for the length of a stay.
What to Expect in a Regatta Residence
Every home is a three-bedroom plan — unusual for a rental community, and the reason Regatta suits families and couples traveling together. Expect a full kitchen, in-residence laundry, a screened lanai facing the lagoon, and one covered parking space under the building. Tower residences on higher floors add Gulf views across the barrier island; the Launch Circle buildings put you a few steps from the pool deck and marina. Furnishings and finishes vary by owner, which is why we describe each residence individually rather than as a type.
Annual Rentals at Regatta
Unfurnished and furnished annual leases at Regatta come up occasionally and are rarely advertised widely. If you're relocating or want a full-year base in Vanderbilt Beach, ask us for the current list or browse Naples annual rentals.
Own at Regatta? Put It to Work
Regatta's rental policy, amenity package and beach proximity make it one of the most bookable seasonal communities in North Naples — and residences with weekly-rental rights command a premium. Alpizar Property Management already manages homes here: marketing, guest screening, turnover, maintenance coordination and owner reporting, with an in-house team rather than a call center. Tell us about your residence and we'll outline what it could earn and how we'd manage it.
Explore Regatta
Regatta Overview | 400 Flagship Drive | 410 Flagship Drive | 450 Launch Circle | 460 Launch Circle | 470 Launch Circle
Regatta Vacation Rentals | Vanderbilt Beach Guide | Property Management
Frequently Asked Questions About Regatta Vacation Rentals
What is the minimum stay at Regatta?
Most residences at Regatta require a 30-day minimum stay. A significant number of residences are grandfathered to permit weekly rentals, which is unusual in Vanderbilt Beach. Each listing states its minimum; if you need a shorter stay, ask us and we will point you to the residences that allow it.
How far is Regatta from the beach?
Regatta sits on Vanderbilt Lagoon at the corner of Vanderbilt Beach Road and Vanderbilt Drive. The public beach access at the end of Vanderbilt Beach Road is a short distance west, and Delnor-Wiggins Pass State Park is a few minutes north. Most guests go back and forth to the sand several times a day.
When should I book a season rental at Regatta?
Peak season in Naples runs roughly January through April, and Regatta's best weeks are often reserved a year ahead by returning guests. For a January to March stay, inquire the previous spring or summer. Shoulder months — November, December and April into May — offer more availability and the same amenities.
Are pets allowed in Regatta rentals?
The community permits owners to keep pets, but whether a specific rental accepts them is the owner's decision and varies by residence. Tell us about your pet when you inquire and we will match you with residences that welcome them.
Is parking included?
Yes. Each Regatta residence comes with one assigned under-building parking space, and guest parking is available on the grounds. The community is gated, so arrival instructions and access are provided before check-in.
Does Alpizar & Company manage vacation rentals at Regatta?
Yes. Alpizar Property Management manages residences at Regatta for their owners, which is why some listings above are marked Exclusive. If you own a residence at Regatta and want to rent it seasonally, complete the owner form on this page or call (239) 438-1102.
Rental availability, rates, minimum stays and pet policies are set by each residence's owner and change frequently. Community rules and amenities are subject to change by the association.
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