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

Spacious and private home in prime Naples location

Spacious and clean 3 bedroom, 2 bathroom house fully furnished in Naples with lots of land and a lake view! Central to everything! Less than 10 minutes to the beach and 5 minutes to Mercato! Enjoy fishing, manicured lawn and landscaping, privacy, and a beautiful view from your back porch! Perfect for families, adults in need of relaxation, or a business trip! Family friendly neighborhood great for walking or biking. Plenty of seating for dining, including an outdoor table on lanai. 2 king beds!

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.

Resort Style Tropical Oasis

Location, location, location! This beautiful 3 bed 3 bath waterfront modern home, which offers the perfect blend of comfort, convenience and entertainment. Ideal for families and friends. Just a short walk to the beach and minutes away you can enjoy easy access to fine dinning, shops and lively nightlife. Relax in luxury at this waterfront retreat featuring a pool, hot tub, fire pit, 6 smart TVs, full outdoor kitchen, bar, and private dock. Perfect for entertaining or unwinding in style.

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.

Naples Oasis – Perfect Getaway!

This serene 4-bed, 2-bath home offers a fully equipped kitchen and outdoor BBQ area for relaxing dinners. Beach chairs, umbrellas, and golf clubs are included. Just 7 minutes from Clam Pass and Seagate beaches, you can bike or drive to the best beach spots. Walking distance to Publix, Target, and more. Bedrooms include a king, queen, twin beds, and bunk beds (queen and full). Perfect for a relaxing stay near shops, restaurants, and the beach!

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.