Holiday rentals in Naples Bay

4.96 out of 5 average rating, 115 reviews

New Home, 6 Beds, Heated POOL / Game Room

Park in the driveway and enter through the front double doors to a newly and completely updated Home with 3bedrooms and 3 full bathrooms located just 7 miles from the trendy 5th avenue south, white sanded beaches and the famous Naples pier; This private and MODERN exquisite home has everything you need to enjoy an endless summer alike stay. Heat for the Pool Available EXTRA $ October to May $40 EXTRA per each night stay May to September $30 EXTRA per each night stay. Game Room and and Gym area.

4.95 out of 5 average rating, 194 reviews

Home Close To Beach & Downtown Naples

We have stellar reviews, come check us out & see for yourself. Stay at this downtown Naples relaxing 1,864 sqft, 4 BD (2-king beds & 2-queen beds+twin blow up), 2 BA home for the best of vacations. Minutes from 5th Ave beaches/shopping/food/activities. Bonus: 2 outdoor seating areas/ample entertaining space/BBQ/outdoor games (corn hole, jenga, putting green), 2 bikes & beach equipment for 8. If looking for a pool, we have resort access to 6 area resort pools (day rate fees apply). Message me!

4.96 out of 5 average rating, 116 reviews

Parks Place - Ocean, Beach and Pickleball Haven

This stunning new home is surrounded by 4 beautiful Naples Parks and is ideal for ocean & beach lovers, nature enthusiasts, and pickleball. The US Open Pickleball Park is across the street. Bayview Park & Boat Ramp, with gorgeous views & access to Naples Bay is just down the street. Walk or bike around Lake Avalon/Sugden Park - 2 blocks away. Just .8 miles to Naples Botanical Gardens. Near the Bayshore Arts District, and a short drive to the gorgeous beaches, Naples Pier, and infamous 5th Ave.

4.98 out of 5 average rating, 182 reviews

Cottage in Naples

Sandy Cove Cottage/Sandy Cove Villa near the beach

Sandy Cove is one bedroom, one bathroom Cottage located only 10 minutes from Downtown Naples, beaches, 5th Ave, fine dining and world-class art galleries. Sandy Cove Cottage is next to the Hamilton Harbor Yacht club, & within walking distance to beautiful Naples Bay. Only a short bike ride to the Naples Botanical Gardens, Sudgen Park, & East Naples Park- Home of the Pickleball Championship! Sandy Cove Cottage is fully furnished, just bring your clothes and settle in for some fun in the sun!

4.93 out of 5 average rating, 125 reviews

Apartment in 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, 114 reviews

Apartment in Naples

2.5 miles to Beaches & 5th Ave

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.

4.95 out of 5 average rating, 170 reviews

Modern Loft Just minutes to Naples Beach

Unplug and recharge in our treetop loft. Perfect for remote workers seeking inspiration or travelers craving tranquility, this stylish and cozy retreat offers the best of both worlds. Immerse yourself in the art-infused ambiance while enjoying the peace and privacy of your own space. Just 10 minutes away from Naples' sunny beaches and vibrant downtown, you're never far from adventure. Experience the ultimate work-life balance. Book your escape today!

4.98 out of 5 average rating, 134 reviews

Pool Home! Near Beach, Walk to Coffee & Dining!

Your Perfect Naples Getaway! This modern 3-bed, 2.5-bath pool home offers the perfect mix of comfort and convenience. Just 4 miles from Naples Beach and Downtown 5th Ave, you'll be close to world-class shopping, dining, and entertainment. Enjoy a walkable neighborhood with restaurants, a coffee house, a brewery, and fishing nearby. After a day of exploring, relax by your private pool and soak in the Naples lifestyle!

4.98 out of 5 average rating, 282 reviews

Garden House-2 Bedroom/2 Bath-Naples / Park Shore

WHOLE HOUSE RENTAL-Intimate quiet setting just ten minutes (4 miles) from downtown Naples, within easy walking distance of restaurants and bars, and 2 miles from the beach. Outdoor hot tub, fire-pit and lush green gardens for a tranquil stay. There are no hidden cleaning fees on this listing which is a huge plus. There are also no hidden cameras or sensors of any kind at the house—your privacy is respected.

4.98 out of 5 average rating, 119 reviews

Sunside House, 3/2 Pool Home in Gated Community

Prepare to be impressed as you enter this beautiful home in the sought-after Community of Briarwood. It certainly has the 'WOW' factor. The open aspect of this great-room floor plan, which flows out to a large, very private SW facing Patio and Pool area, makes this a perfect home for entertaining, family time or your golf time. You will love how light, bright and spotless this gorgeous home is. So much NEW.

4.93 out of 5 average rating, 106 reviews

Jony’s Paradise

Only 1 parking available 1 Room- Kitchen- Bathroom located 3 miles from Beach and Downtown Naples with private entrance and free parking. 350 sqft Do not to bring AC bellow 20* 70* because it might get frozen Turn off AC before getting out since it might be frozen once you get back Please do not trow paper towels or anything into the toilet. No smoking Thanks