Holiday rentals with breakfast in North Naples

Private Cozy Coastal Bugalow

Welcome to our woodsy coastal getaway! Located 15 minutes from the sunny beaches. An attached studio guest suite is peaceful & relaxing. Enjoy the mini kitchenette, private bathroom and entrance w/its own patio, along with parking. Take a walk down our long driveway sprinkled with close to 100 orchids that may be in bloom. Some bloom throughout the year and others only once a year. We are a friendly couple who welcome all visitors from around the world. We hope you enjoy your visit to Naples!

Villa Cascata Mediterranean Home

Same Day Bookings-- Please Inquire First; Not guaranteed to be able to accommodate. Unique and updated, tropical oasis tucked into the ideal Vanderbilt Beach location! Villa Cascata is a Mediterranean-style home complete with a lush landscaped backyard oasis & waterfall pool. Located just 3/4 mi to popular Vanderbilt Beach. Primary: King. Guest Room Queen, Third bedroom has a twin over full bunk bed with a trundle (bunkroom has a total of 3 beds & can sleep 4). Extra Charges: Pets Pool Heat

Beach Vacation Getaway

Great for a couple with 1 -2 young kids or a getaway for 2 or a business traveler. Guesthouse is totally separate from the main house. Bedroom-king sized bed. Couch, 24 inch high twin air mattress and ottoman w/ twin sized bed. Fully screened lanai/Indoor HEATED private pool/w 8ft wall (swim at your own risk). No pets. WiFi/cable TV. 10 minute drive to the beach/shopping. Walking/biking/jogging path. 4 bikes-(ride at your own risk)/BBQ grill/continental breakfast/a variety of snacks/beverages

NEW Luxury Lakefront Villa! Heated Salt-Water Pool

Stunning, luxurious, lakeside, centrally located villa, features 4 bedroom/3 full bath, features two master suites. Located in the fully gated Briarwood community with 24-hour guard on duty. Available weekly and monthly! The community of Briarwood features Tennis, Lap Pool, Resort Pool, Basketball, Volleyball, Pickleball, Playground and Sports Field. The villa is less than 10 minutes from Naples Pier, Beach, 5th Av. Restaurants, Shopping . Less than 5 min. from grocery stores, I-75 and dining.

Briarwood Paradise - The Briarwood Rental Company

Welcome to your own private vacation paradise. Located in the private gated community of Briarwood, this tastefully decorated lake front home has a split floor plan and offers an expansive lanai with direct access from the master bedroom and the living room. Enjoy free community amenities including two pools, tennis, pickleball and basketball courts, and playground equipment. Located just 10 mins from downtown Old Naples and beautiful local beaches.

Backyard Oasis: White sand, exotic trees & plants.

3 Bed, 2 Bath - Dog Friendly and the Best Value in Naples Park! The "Hideaway" is a charming "Key West" style house with a large white sand back yard. This OASIS of exotic plants, palm & bamboo trees on 1 & 1/2 lots. A hammock, an outdoor hot/cold shower with a raindrop shower head. A Fire pit and gurgling dolphin fountain all lit up at night. We provide bicycles, pickleball rackets, fishing rods, beach chairs & towels. Also golf clubs on request.

Modern 3BR • Smart TVs • Near Downtown Naples

Welcome to your bright and modern Naples escape! This updated 3-bedroom apartment features clean interiors, smart TVs in every room, a fully equipped kitchen, and sleeping space for up to six guests. Just minutes from Downtown Naples, top dining, and Gulf beaches, it’s designed for convenience and comfort. Enjoy spacious bedrooms, stylish living areas, reliable Wi-Fi, central AC, and private parking—perfect for quick getaways or longer stays.

"Tropical Retreat"

YOUR PRIVATE PARADISE AWAITS! QUIET & SECLUDED GEM OFF THE BEATEN PATH, YET CLOSE TO EVERYTHING NAPLES HAS TO OFFER. Minutes to the Beach during the day and the Mercato Entertainment District at night. Great options for Golfing, Fishing, Dining and Shopping close by. This home is PERFECT for weekly & monthly visitors! Unwind and enjoy a true vacation atmosphere either off the grid, or plug in for a perfect remote work environment.

Luxury 3BR Ole Resort | Steps to Amenities

Experience refined Naples living in this spacious two-story retreat at Olé at Lely Resort. Just a short walk to the pool and main amenities, this 3-bedroom + large office home blends privacy with resort convenience. Enjoy open-concept living on the main floor, with all bedrooms upstairs for added comfort. Relax on the screened front porch and unwind in a beautifully furnished home designed for extended stays and effortless Florida living.

"Casa Bella" Poolside boutique style guest suite

Casa Bella is a large European home with stylish, comfortable décor. Enjoy our private pool side guest suite, bedroom with king size bed; living room 85 " TV; dining area, bathroom. Breakfast items offered. Kitchenette- sink, refrig, cooktop, micro. BBQ grill, great for dining outside. Private entrance, pool, parking, beach chairs, umbrella, towels etc. less than 1.5 miles from Bonita Beach, Walk to markets, many restaurants, shops.

Naples Hideaway

Short term rental, 2 bedrooms with private bath, private access for each. Private lanai with front and back patios, plenty of parking. Stroll to the beach or ride our bikes to the Ritz Carlton, Mercato, Whole Foods or Walmart. Arthrex University and NCH are walking distance away. Very reasonable w/4 people it can be under $50 per person per night and less than $100 per room per night. Rent as a suite. Owner on site.

Coastal Elegance: Dual Master Bedroom Retreat 3/3

This stunning single-story home is just one mile from the white sands of Vanderbilt Beach, perfect for an evening stroll or a quick bike ride. At Naples Coastal Vacations, we personally develop and manage our properties to ensure an exceptional guest experience. Every detail of this home has been thoughtfully crafted to offer luxury living that exceeds expectations, creating the ultimate coastal getaway.