House holiday rentals in Old Naples

A spacious deck extends over the canal, surrounded by lush palm trees. Comfortable seating is arranged around a fire pit, with a paddleboard propped nearby. A BBQ grill is visible, inviting outdoor dining in a serene waterfront setting.

4.95 out of 5 average rating, 131 reviews

Boaters Bayshore Bungalow w/HOT TUB view of water.

BRING YOUR BOAT! This ranch home is located on a canal with direct access to the Gulf/Naples Bay(no bridges). Amazing water sports access. In the cool/hip Bayshore Arts district! Great restaurants, Naples Botanical Gardens, boating, 3 miles to DT Naples and 4 to the best beaches. This is a perfect family/friends vacation spot. We have all the gear to enjoy this location. Quiet neighborhood/newly renovated/great views. Coffee on the deck with sunrise in front of you or drinks at sunset. Serenity

The living area showcases a modern design with a white leather sofa and a stylish ottoman. A large television is mounted on a sleek wall unit. Colorful bar stools surround a kitchen island, providing a lively contrast to the white cabinetry and stainless-steel appliances.

4.96 out of 5 average rating, 224 reviews

The Paradise

Welcome to The Paradise !! We are Joe and Emma , your friendly and attentive hosts . Our home offers a warm, safe, and relaxing atmosphere — perfect for couples, families, or anyone looking to unwind and enjoy a calm getaway. You will find everything you need for a pleasant and refreshing stay, surrounded by tranquility and good energy. We speak English, Spanish, French and Russian , and we are always happy to help. “The Paradise” is the perfect place to enjoy the best of Naples. Thank you !

A serene beach scene captures a vibrant sunset, with hues of pink and orange reflected on the water's surface. Gentle waves lap at the shoreline, while soft sand stretches along the beach, interspersed with small scattered shells.

4.96 out of 5 average rating, 114 reviews

Magical Gateway in Naples FL

You'll fall in love with this tinny but magical place in the heart of Naples, modern open concept,high end finishes, a lot light, 2 BR queens beds, fine blinens, full bathroom with marble, enclosed pool, spacious back yard and a wood burning fire pit, 2 parking spaces just few steps from your front door. This place is near to all Naples has to offer, beautiful beaches, dining & nightlife, it is only 3km from the beach, 3 km from 5th ave in Old Naples and less than a mile from shopping centers.

A spacious screened-in lanai features a heated pool with a shallow area for children. Luxury chaise lounges are positioned near the pool, offering comfortable seating. The outdoor space is designed for relaxation and enjoyment, with clear views of the surrounding greenery.

4.95 out of 5 average rating, 142 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!

The image showcases a bright, inviting pool area featuring clear blue water illuminated by string lights above, creating a relaxed atmosphere. Surrounding spaces include a cozy living room with comfortable seating and a spacious kitchen area with modern fixtures and finishes.

4.96 out of 5 average rating, 139 reviews

Coastal Getaway *Heated Pool *3 King Rooms

Tropical Oasis Downtown Naples 3 BD/2 BA full house w/ a HEATED pool, outdoor entertaining, BBQ grill, lanai seating/dining for 8, outdoor games, 2 living rooms w/ large TVs (main room has a 75" screen TV), master suite w/ ensuite bathroom & flatscreen TV, all 3 bedrooms have king beds. Close to downtown restaurants/shopping (9 min), beaches/Naples Pier (14 min). DOG POLICY: Only after owner's approval, a non-shedding small dog is allowed with $100 per dog non-refundable fee (2 dog maximum).

4.97 out of 5 average rating, 188 reviews

A single-level traditional home is showcased with a bright green garage door and welcoming front entrance. The circular driveway is paved, surrounded by neatly manicured grass. Mature trees and shrubs are positioned around the property, providing a touch of greenery under a clear blue sky.

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.

A sun setting over the horizon casts a warm glow on the water, creating a serene scene. The beach is lined with soft white sand, and a pier extends into the sea in the distance, framed by a clear sky above.

4.95 out of 5 average rating, 150 reviews

Naples Retreat with Pool Near Beaches and 5th Ave

Modern 3BR/2.5BA Naples pool home, sleeps 8. Perfect for families, sports tournaments, boaters, golfers. King suite, queen room, queen bunks, plus air mattresses. Garage, boat parking, washer/dryer. Walk to restaurants, coffee shops, Ankrolab Brewing, Naples Botanical Gardens. Close to Paradise Coast Sports Complex, Bayview Marina, downtown Naples, beaches. Naples Zoo 4 miles. High-speed WiFi, Smart TVs. Fully equipped kitchen, beach gear, coolers and grill. Your Naples adventure awaits.

A light-filled living room features a comfortable seating arrangement with soft sofas and an armchair, complemented by a decorative area rug. Large windows invite views of lush greenery, while a painting enhances the tranquil atmosphere. A ceiling fan is mounted for added comfort.

4.98 out of 5 average rating, 304 reviews

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

WHOLE HOUSE RENTAL-Intimate quiet setting. 2 miles from the beach and 4 miles from (a 10 minute drive) Downtown / 5th Avenue Naples. The house is within easy walking distance of the Park Shore Area / US41 / Tamiami Trail restaurants and bars. 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.

4.92 out of 5 average rating, 160 reviews

A refreshing pool area features a heated pool surrounded by lounge chairs and a dining table. An inflatable pink flamingo floats in the water, while colorful umbrellas provide shade. Lush greenery frames the outdoor space, creating a bright and inviting atmosphere.

Home in Naples Park

675 FantaSea | New Heated Resort Pool & Fire Pit

Spend the day outside morning, noon & night and live out your FantaSea vacation! Lounge on the deck or in the heated pool on the sun shelf. On a cool night sit by the fire and relax in the Adirondack chairs. Desirable designer interior with coastal decor has the comfort of home with the feel of the sea. We are just a few minutes away from white sandy beaches with beautiful sunsets, amazing restaurants and upscale shopping centers.

4.95 out of 5 average rating, 213 reviews

4BR Near Downtown Naples |Beach, Bikes, BBQ& Games

Relax in this spacious 4-bedroom Naples home minutes from the beach, 5th Ave shopping, and downtown dining. Ideal for families and groups, this 1,864 sq ft retreat offers king beds, bikes, beach gear for 8, outdoor games, BBQ, and two outdoor lounge areas everything needed for an easy Southwest Florida getaway. We have stellar reviews, come check us out & see for yourself. ⭐ Consistently 5-star rated | Superhost owned & operated

A spacious backyard is highlighted by a hot tub under a wooden gazebo. Sun loungers are arranged on the manicured lawn, while a sandy area offers relaxation. Greenery surrounds the space, providing a private atmosphere, with a putting green featuring a small flag for recreational activities.

4.94 out of 5 average rating, 336 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!

A serene outdoor space features a pool surrounded by a spacious paved area, complemented by lounge chairs and umbrellas. Lush palm trees and vibrant greenery create a natural border, while a sunset sky casts warm tones over the setting, enhancing the tranquil atmosphere.

4.93 out of 5 average rating, 136 reviews

Brookside Bungalow- Perfect 2 Bedroom House & Pool

Perfect 2 Bedroom House with a Pool only 2.5 Miles to the Beach and 1.5 Miles to Beautiful 5th Ave in Naples, FL! This House is perfect for those coming to Naples on Vacation, for work, or seasonally! Enjoy a completely private backyard with a pool, outdoor shower, and lanai! Relax in your very own private oasis within a short driving distance of all of the most popular Naples spots! This house is perfect for 1-4 guests.

Popular amenities for house rentals in Old Naples

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

An outdoor pool area is presented within a screened enclosure, featuring a clear blue pool. Two chaise lounges with towels sit alongside the pool, and lush greenery frames the space, providing a serene backdrop under a partly cloudy sky.

4.93 out of 5 average rating, 107 reviews

Elegant house w/heated Private Pool

The outdoor space features a heated pool surrounded by sun loungers and lush greenery. A cozy sectional seating area with vibrant blue cushions is positioned near a fire pit. The screened-in lanai offers a glimpse of outdoor dining and a grill, creating an inviting atmosphere.

5 out of 5 average rating, 31 reviews

*New*5minto5th|Heatedpool|privateyard|10mintobeach

A spacious and brightly colored outdoor living area features a screened-in pool surrounded by lush greenery. Comfortable seating and lounge chairs are set on a striped rug, creating an inviting atmosphere for relaxation. A ceiling fan provides additional comfort in this tranquil setting.

4.95 out of 5 average rating, 138 reviews

1 Mile to Beach! Pool, King Bed, BBQ, Games

An expansive lanai features a shimmering pool with a waterfall-edge spa and in-pool loungers. The outdoor space is surrounded by a screened enclosure, providing views of well-kept greenery. A comfortable seating area and dining space are visible in the background, enhancing the outdoor living experience.

5 out of 5 average rating, 26 reviews

Pool Home Minutes to the Beach

A tranquil pool scene is captured at sunset, featuring vibrant orange and pink hues in the sky. A pink inflatable flamingo floats on the water, surrounded by a well-kept pool deck with lounge chairs and umbrellas nearby, framed by lush greenery and palm trees.

4.96 out of 5 average rating, 26 reviews

Hidden Gem-Central Naples-3 Miles to Town & Beach

5 out of 5 average rating, 10 reviews

MarAzul, heated saltwater pool home 8 min to beach

4.94 out of 5 average rating, 89 reviews

Naples Oasis: Heated Pool 85F & 10 Min to Beach

A heated swimming pool is surrounded by a spacious patio and lush greenery. Inviting lounge chairs in a mix of vibrant colors are positioned around the pool, while soft lighting illuminates the area, enhancing the tranquil evening ambiance.

4.82 out of 5 average rating, 156 reviews

Palm Breeze

Weekly house rentals

A spacious outdoor area is featured, showcasing a heated pool surrounded by a textured stone patio. Multiple loungers are arranged along the poolside, each adorned with soft cushions. A tiki bar with a television is visible in the background, along with lush greenery and a white privacy fence.

4.94 out of 5 average rating, 48 reviews

Naples 3 BDRM/Big Htd Pool/Tiki Bar/BBQ

5 out of 5 average rating, 5 reviews

Great area super close to beach and shops

An inviting outdoor area features a heated pool surrounded by a screened enclosure. A floating pool toy is present in the water, while lounge chairs are positioned nearby. Sliding doors lead to the interior living space, enhancing the seamless indoor-outdoor connection.

4.95 out of 5 average rating, 21 reviews

Families-private heated pool & hot tub-pickle ball

4.96 out of 5 average rating, 24 reviews

1 Bedroom/ Bayshore Art District

5 out of 5 average rating, 29 reviews

Lakefront Oasis with Heated Pool

A serene pool area is surrounded by lush greenery and palm trees, featuring a tiled patio that leads to the pool. Comfortable lounge chairs with colorful towels are positioned for relaxation. The outdoor space is complemented by a Tiki hut, adding charm and shade.

4.97 out of 5 average rating, 33 reviews

Chic Pool Naples Beach House

Superhost

Cozy bungalow 1 - 1.5 miles from 5th Ave & Beach!

An open concept living area is showcased, featuring a round glass coffee table surrounded by tropical-themed chairs. A wall-mounted Smart TV is visible, with a dining table set for four nearby. The kitchen area, furnished with essential appliances, complements the light, airy atmosphere.

4.92 out of 5 average rating, 66 reviews

Prime Location & Screened Patio

Private house rentals

A modern living area features a spacious gray sofa adorned with textured blue and a warm yellow pillow. Framed botanical artwork decorates the walls, complemented by wall-mounted planters. A sleek white coffee table sits in the center, with a decorative bowl and a wood accent piece on its surface.

5 out of 5 average rating, 47 reviews

“Taormina House” 5th ave and beaches 2 Miles away!

A modern kitchen with light cabinetry and granite countertops is visible, featuring stainless steel appliances and a seating area. Three pendant lights hang above a spacious island with bar stools. A gray leather couch is in the foreground, creating a comfortable living space.

4.95 out of 5 average rating, 86 reviews

New, Upscale Home with Pool , Close to Downtown

A light-filled living area features a comfortable sectional sofa, surrounded by large windows that provide views of the lush greenery outside. An open kitchen showcases modern appliances and a clean, white design, enhancing the spacious feel of the area. A cozy sleeping area with two beds is decorated with colorful bedding, and a private outdoor space includes a hot tub set among tropical plants.

4.85 out of 5 average rating, 26 reviews

Naples Bungalow-Perfectly located & Pet Friendly

4.97 out of 5 average rating, 93 reviews

Lux Prvte Fam Home Pool Pcklbl Mins 2 Beach/Dning

A serene outdoor area features a clear pool, surrounded by a screened enclosure. A decorative rock waterfall flows gently into the water, and lounge chairs provide space for relaxation. Lush greenery and a wooden fence frame the setting, offering privacy and a tranquil atmosphere.

4.95 out of 5 average rating, 81 reviews

Waterfall/Seasonally Heated Private Pool In Naples

5 out of 5 average rating, 5 reviews

Luxury Retreat with Heated Pool

The serene backyard features a heated in-ground pool surrounded by lush landscaping and a hot tub. A screened patio offers a dining table and lounge area with inviting cushions. The open concept kitchen and living space are visible, showcasing modern appliances and ample seating for relaxation.

4.97 out of 5 average rating, 90 reviews

Attention Naples Lovers! Entire Home w/Pool&HotTub

A private outdoor area features a rectangular pool surrounded by a tiled deck. Two lounge chairs are positioned nearby, while lush green foliage provides privacy. The space is bathed in natural light under a clear blue sky, enhancing the serene atmosphere.