Old Naples vacation rentals

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Top-rated vacation rentals in Old Naples

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

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Guest favorite

Guest suite in Naples

5.0 out of 5 average rating, 133 reviews

By the Beach and 5th - Studio Guest Home & Pool

Great location! Newly renovated! A studio guest home with your own private entrance & your own full kitchen & bath! A non-smoking home only 1 mile from the beach, 5th Ave dining and shops, the mall, the zoo, beautiful Baker Park, and that's not all- Only steps away are local restaurants and shops! Bikes and beach equipment included! Did we mention the pool? Or that you can sing along to your fave tunes in the shower via a Bluetooth shower speaker? This home is 350 square feet of clean cuteness!

Dec 5 – 12

R4,406 ZAR per night

Guest favorite

Guest suite in Naples

4.98 out of 5 average rating, 337 reviews

Naples Loft

Beautiful new 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 from our backyard chickens! If you have children, your welcome to play in the "island" (our kids play area) with a playhouse and climbing dome. Very relaxing place!

Jun 7 – 14

R1,978 ZAR per night

Superhost

Guesthouse in Old Naples

4.8 out of 5 average rating, 296 reviews

Waterfront Sea Cottage

*Newly rebuilt after Hurricane Ian. Expect some construction within the main home. Enjoy Naples in this private waterfront tiny cottage conveniently located on the Gordon River with gulf access near the heart of Downtown 5th Avenue. Our cottage is only 1.5 miles (2.4 km) from the beach and is located within walking distance to parks, shopping, bars, restaurants, and many outdoor activities. Located in a safe, vibrant, and transitioning community full of life and the true flavor of old Naples.

Dec 21 – 28

R1,815 ZAR per night

Guest favorite

Cottage in East Naples

4.99 out of 5 average rating, 164 reviews

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!

Jul 25 – Aug 1

R3,197 ZAR per night

Guest favorite

Guest suite in Naples

4.97 out of 5 average rating, 301 reviews

Tropical Garden Studio Cottage (2 miles to beach)

Studio beach cottage experience in North Naples. Take one of the complementary bicycles on an easy 15 min bike ride to the beautiful Wiggins Pass State Park or Vanderbilt beach. Just 3 miles from the popular Mercado shops, restaurants and theater. Prefer to walk? It's less than 10 mins walking to multiple great restaurants, grocery stores, and even paddle board/boat rentals, fishing trips, dolphin eco sunset & tours. Feeling adventurous? Take one of double kayaks from the dock to the beach.

Aug 23 – 30

R2,264 ZAR per night

Guest favorite

Tiny home in Pelican Bay

5.0 out of 5 average rating, 143 reviews

BEACHYVibes TINY House Pickleball Ct Mile to Beach

From the minute you step inside our “Tiny House" the beachy vibe gently reminds you of why you came! The 12' living room makes the 400 sq ft space feel more expansive. Sailor’s knot rope tied around anchored cleats create a banister/railing to the 6’2” spacious loft bedroom. Nestled below an eat-in kitchen and full bath. Located less than one mile from the beach in the center of the city hustle, the stand alone new construction has a private entrance and luscious outdoor private patio.

Aug 8 – 15

R2,862 ZAR per night

Guest favorite

Cottage in Old Naples

4.95 out of 5 average rating, 133 reviews

Historic Coral Cottage in the Heart of Old Naples

Charming, historic cottage in Old Naples. 2 bedrooms/1 bath, 950 sf. The artist owners have decorated with colorful paintings and vintage furniture. A unique oasis in the heart of downtown Naples it appeals to those who appreciate history and enjoy the convenience of a village lifestyle but not appropriate for those seeking new and modern housing. Extremely convenient to the restaurants and shops of the 3rd Street shopping area and to the Pier and beach. No pets or children, please.

Nov 17 – 24

R4,974 ZAR per night

Guest favorite

Guest suite in East Naples

4.92 out of 5 average rating, 258 reviews

Garden Studio Just minutes to Naples Sandy Beaches

Discover a serene escape just 4 miles from Naples' beaches. Ideal for the modern solo or couple traveler, our space seamlessly blends relaxation with rejuvenation. Savor wine in our lush garden and enjoy the convenience of an upgraded micro-kitchenette. While tucked away for tranquility, you're near the lively Bayshore Arts District, Botanical Gardens, Celebration Park, and Pickleball Courts. With the iconic 5th Ave S close by, our newly renovated haven is your perfect Naples gateway.

Aug 21 – 28

R2,717 ZAR per night

Guest favorite

Home in East Naples

4.94 out of 5 average rating, 104 reviews

Tropical Cottage by the Sea

Welcome to your own private home on private lot! This 1 bedroom/1 bath cottage comes with a million dollar view & is perfectly located in the beautiful Bayshore Arts District in Naples. Quiet neighborhood but close to beaches & lots of fun things to do! Beautiful wild life and tropical plants abound. Fish and kayak right in the back yard. Relax on the back porch where there's always a breeze! Bike over to the Botanical Gardens or one of the many restaurants close by! This is the one!

Sep 19 – 26

R3,103 ZAR per night

Guest favorite

Guesthouse in East Naples

4.93 out of 5 average rating, 112 reviews

Private & Spacious Studio 1 mile fr 5th Ave w/Pool

Welcome to Kevin's Newly Renovated Air BNB in Naples, featuring a private swimming pool, patio w/sun shade, parking, luxury sheets, fully stocked kitchen, full size W/D, and more! This uber-quiet and private space is located just over 1 mile from 5th Avenue/downtown Naples, & 2 miles from the beach. 5 minute walk to Naples Bay Resort, coffee shops & restaurants. Walk or use complimentary bikes to check out nearby Celebration Park, a brewery, Market 360, & pickleball courts!

Jul 30 – Aug 6

R2,766 ZAR per night

Guest favorite

Home in Naples

4.96 out of 5 average rating, 207 reviews

Coastal Farmhouse w/ mini Golf, Private Beach &Spa

We welcome you to our high end, next level, brand new Farmhouse, which is conveniently located in the heart of Naples. Only 1.5 miles away from the beach, minutes away from the nearby plaza, which offers dining experience, shops, supermarkets, gas stations, etc. The well-known downtown district is only four miles away and Mercato, if you are looking for nighttime activities. Brand new High-end furniture and beds. Welcome, Home!

Jul 10 – 17

R3,842 ZAR per night

Guest favorite

Cottage in East Naples

4.94 out of 5 average rating, 140 reviews

Mango Tree Cottage close to Beach

Charming cottage with a touch of luxury close to beach and old Naples. Compleately remodled and newly furnished 2023. Originally built in 1946 the cottage is nestled in a tropical garden very close to old Naples and 5th Ave. with its many restaurants and shops. Enjoy the nearby beaches, boat tours from Tin City, sightseeing tours to the Everglades, Marco Island, Fort Myers, Sanibel Island, etc.

Jun 10 – 17

R2,801 ZAR per night