Family-friendly holiday rentals in Old Naples

4.98 out of 5 average rating, 425 reviews

Guest suite in Naples

Naples Loft-private-18 min to the beach

Beautiful newer construction loft that offers 640 square feet of open floor plan! This unit sits above our two car garage , 130 feet from the main house. Full kitchen, microwave, coffeemaker, toaster, iron, and washer/dryer! Our home sits on 1.14 acres with a circular driveway in a very quiet neighborhood. Enjoy organic farm fresh eggs when the hens are laying. If you have children, your welcome to play in the "island" (our kids play area) with a playhouse and climbing dome. Very relaxing place!

4.95 out of 5 average rating, 132 reviews

LUXE Oasis | HTD Pool• 10 min Beach +5th Ave •Crib

Welcome to Your Naples Getaway! Why our home is perfect for your vacation: 🏖️ Beaches Nearby – Just a quick 10–15 minute drive to Via Miramar and Lowdermilk Beach. 📍Prime Location – Nestled on a peaceful street only 7 minutes from the iconic 5th Avenue. 🏡 Resort-Style Comfort – Relax in our fully screened lanai featuring: • Heated private pool • Luxury chaise loungers • Outdoor TV • Gas grill for BBQ nights Unwind with a cocktail, take a sunset dip, or simply kick back under the stars!

4.95 out of 5 average rating, 162 reviews

Apartment in Naples

Sea Shell Villa 1

Your will be close to everything when you stay at this centrally-located villa. Our villa is fully upgraded. Has a full kitchen, 1 bedroom with a queen bed and laundry room with a full size washer and dryer. There is a great variety of restaurants and shopping just minutes away. In just 15 minutes you can be at the famous Naples pier for a fun day at the beach. We also have Marco Island, which is one of the top beaches in the world, just 20 minutes away. We do not offer snorkeling gear.

4.97 out of 5 average rating, 186 reviews

Home in Lake Park

Relaxing Naples Home close to beach and downtown.

Enjoy this single level "just renovated" traditional Naples home, just blocks from beautiful beaches, the Naples Zoo, Naples Preserve, the Conservancy of Southwest Florida, the Gordon River Greenway Park, Coastland Mall, and 5th Avenue's abundant restaurants and shopping. Features include 3 bedrooms (including 1 bedroom with bunk beds (double and twin), a 2 car garage, covered lanai and laundry. It is located in the Lake Park neighborhood known for its quiet charm and mature canopy trees.

4.93 out of 5 average rating, 126 reviews

Apartment in Old Naples

NEW! ONE BLOCK to the Beach, Restaurants & Shops!

Welcome to your newly renovated condo in the heart of Olde Naples! Just ONE BLOCK to the beautiful Naples beaches and all of the shops and dining on 3rd Street! Your first floor condo suite is ideally situated just steps from the oversized heated pool. And with large windows you can let that warm Florida sunshine in. The studio also has a designated parking space, common laundry, kitchen, bathroom, dining table, king size bed, pull out single trundle bed and can sleep up to 3 people.

4.95 out of 5 average rating, 128 reviews

Home in Naples Park

Lovely Beach Bungalow pool/spa 1.5 mile bch Naples

Lovely Pool/Spa bungalow, located in Naples Park, 1.5 miles from Vanderbilt Beach. Across the street from Marcato shopping center, Whole Foods, Cinema, restaurants and clubs. The unit is in pristine shape and features elegant furnishings and decor, tile floors throughout, granite counters in the kitchen, stainless steel appliances, impact windows and all white linens. Private screened in patio at the front and shared backyard area with pool/spa and BBQ. King Bed and Queen Sleeper Sofa.

4.96 out of 5 average rating, 113 reviews

Apartment in Naples

Beaches & 5th Ave 2.5 miles away!

Bring your family and friends to our Southwest Florida paradise! This stylish space is the newest addition to our profile. Located in Naples Florida and within a 7 min drive to 5th Ave shops, restaurants, and beaches. Enjoy a 10 min walk to Celebration Park and local restaurants. Guests can enjoy this newly remodeled condo that has everything you will need for your Naples getaway. **If you have a larger party, inquire and view our profile about the 3 other condos on this property.

4.9 out of 5 average rating, 136 reviews

Guest suite in Naples

Private Studio 5 Minutes From Beach (All New)

You can make your stay in Naples complete when you unwind in this bright and cozy studio. Features: Private entrance with flexible self-check-in Private bathroom and kitchenette with all the essentials 516 Mbps fiber optic wifi On-site washer/dryer Private patio with loveseat Complimentary coffee and wine This unit is located just minutes away from the many beaches, shopping centers, and dining options that this slice of paradise has to offer.

4.95 out of 5 average rating, 142 reviews

Three Palms Oasis - 2 Miles to Beach and 5th Ave

We invite you to stay at this stylish, yet affordable luxury home with a gourmet kitchen right in the heart of central Naples. Three Palms Oasis is located in a quiet coastal neighborhood under two miles from the best that downtown Naples has to offer including the sugar white sand beaches, Naples Design District, dining and shopping on 5th Ave, Naples Zoo, Olde Naples, and so much more! You won’t find a better value in the prestigious 34102.

4.95 out of 5 average rating, 131 reviews

Guest house in Naples

Manatees

Wake up to a chorus of singing birds under the splendid South Florida weather. Brew a coffee in the privacy of your bungalow, and get ready to seize the day. After a fun day at the beach or a productive working session, Manatees Bungalow will be perfect for the relaxation you need. Sit outside and enjoy the peaceful backyard view, pool, and the sweet afternoon breeze. The sun is warm, flowers are blooming… I wouldn’t wait.

Superhost

4.87 out of 5 average rating, 285 reviews

Charming Keys Style house

Unique Key West Style Villa on a friendly private Pave stone street. You will have the entire second floor which consist of an open kitchen/living area plus two bedrooms and two bathrooms. There is a private front porch and a shared rear patio with grill . Queen bed master all quality mattress, all items are new sofa bed also. 3 blocks from 5th Ave Shopping. just over one mile to beach with many beach toys in garage.