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.

4.94 out of 5 average rating, 163 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

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, 138 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.

4.99 out of 5 average rating, 101 reviews

Black Vanilla" Luxe Stay, Sauna, Cold Plunge & Spa

Welcome to " Black Vanilla, " your serene getaway in the heart of Naples. Only 3.5 miles from Downtown and the beach. Our modern and elegant space is perfectly designed for comfort and relaxation. All brand new, high-quality comfortable furniture, Tempur-Pedic mattress, Very Fast WiFi, King-size bed, TVs in all bedrooms, fully equipped kitchen, Fire pit, BBQ. Enjoy Nespresso coffee with soothing sight of the Sudgen Lake. Book " Black Vanilla " today and experience the best of Florida's charm

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, 230 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 !

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, 156 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).

A spacious living area is highlighted by a light-colored sofa adorned with turquoise cushions. An elegant chandelier hangs from the ceiling, complementing the large wall-mounted TV. Natural light fills the room through windows, with a dining area visible in the background.

4.97 out of 5 average rating, 107 reviews

Beach, Sun and Fun! *Beach House * New Listing

Location! Location! Location! 3 beautiful bedrooms, 2 baths, just 1 mile to the beach and entertainment. Peaceful and private, this home boasts an abundance of room for entertaining and outdoor space, free parking and access to private beach. Conveniently located close to the Venetian Village, Water Side mall and 5th Avenue which futures several casual and upscale dinning, shopping and multiple entertainment venues. Great for a relaxing vacation and enjoying the Florida sunshine and sunsets!

4.97 out of 5 average rating, 118 reviews

Lux Prvte Fam Home Pool Pcklbl Mins 2 Beach/Dning

🏡 THIS LUXURY PROPERTY IS IDEAL FOR FAMILIES/SMALL GROUPS (SLEEPS 8) YOU HAVE MADE IT! You are now viewing one of the most unique properties in Naples 🌴 & here is why: 🌳 This property is on 2.5 acres of land & VERY private 🏖️ Beach is only 12 minutes away 🍽️ 10 minutes from heart of the city (Dining, shopping, nightlife) 🏊‍♂️ Heated saltwater pool/spa ⛳ Golf putting green 🎾 2 Pickleball Courts 🏓 Ping Pong table W/AC in garage 🏀 Adjustable Basketball Hoop 💻⚡ Blazing fast WIFI

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.

4.95 out of 5 average rating, 108 reviews

Attention Naples Lovers! Entire Home w/Pool&HotTub

Enjoy the heart of Naples from a modern vacation home located in a quiet, safe neighborhood with a private hot tub, heated pool, and screened patio. Stay in and have a wine night in the stunning, open-space kitchen island or go out and enjoy the many fine dining and beautiful beach views that Naples has to offer - minutes away! The home is newly renovated with new appliances, new furniture, a new hot tub, and a heated pool to savor Florida right in your own fully fenced private backyard.

4.96 out of 5 average rating, 102 reviews

Luxury Private Retreat with New Pool in Naples

Welcome to The Park Villa, a serene private retreat in the heart of Naples. Nestled among nature, this peaceful haven features a brand-new salt water heated pool and is just minutes from the Gulf of Mexico's beautiful beaches and vibrant downtown Naples, with its top restaurants and shops. Situated next to a regional park with the largest freshwater lake in Collier County, enjoy stunning views of the park and spot local wildlife like iguanas and tropical birds from your backyard.

4.9 out of 5 average rating, 176 reviews

Private Pool Retreat • 5th Ave + Beach Nearby

Escape to your own private Naples pool retreat, just 1.5 miles from 5th Avenue and 2.5 miles from the beach. Spend mornings biking around Naples, afternoons floating in the pool, and evenings grilling and dining under the screened lanai. This private 2-bedroom home sleeps four and features two queen bedrooms with direct access to the pool area, a fully equipped kitchen, outdoor shower, complimentary bikes and everything you need for a beach day.

4.94 out of 5 average rating, 235 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

An inviting outdoor space features a heated pool and spa, enclosed by a fine mesh screen. Comfortable seating areas are arranged nearby, complemented by lush greenery. Sunlight streams through the enclosure, highlighting the tranquil atmosphere of this private oasis.

4.89 out of 5 average rating, 142 reviews

Private Oasis in the of Naples Heated Pool/Spa

Escape to The Private Oasis in the heart of Naples! → Welcome to 2,279 square feet of modern and elegant furnishings → Minutes to 5th Avenue, Tin City, Beach, Zoo, and Pier → Fully equipped kitchen fit for the chef at heart → Dine and unwind poolside in the enclosed lanai → Take a dip in the heated pool and spa → Grill masters will love the outdoor kitchen & bluetooth speakers → Click the ❤ to add listing to wishlist!

Popular amenities for house rentals in Old Naples

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.94 out of 5 average rating, 192 reviews

“Estey Oasis” Heated Pool! Near Beach & 5th Ave.

A screened-in pool area features a sparkling pool surrounded by a spacious deck, adorned with potted greenery. Several lounge chairs are positioned nearby, with views of lush landscaping visible through the screens. Sliding glass doors lead into the home, offering a seamless connection to indoor spaces.

4.98 out of 5 average rating, 129 reviews

Naples Retreat: Heated Pool - Minutes to Beach

4.92 out of 5 average rating, 185 reviews

An Egret named Eddie

4.78 out of 5 average rating, 147 reviews

Beautifully private homeHeated Pool/Spa and Cabana

An outdoor dining area features a table with teal accents and an umbrella, set near a glistening pool. Lounge chairs are positioned along the poolside, while a gazebo is visible in the background, surrounded by greenery and a white fence.

4.98 out of 5 average rating, 157 reviews

Cozy Vacation Home * Heated Pool*Near The Beach !

4.93 out of 5 average rating, 108 reviews

Naples Luxury 5BDRM Home/Htd Pool/SuperClean/Pets

4.95 out of 5 average rating, 99 reviews

Home in Naples Park

560 Perfectly Situated · Walk 2 Beaches & The Ritz

The spacious pool area is surrounded by a screened enclosure, with a shimmering blue pool set against a backdrop of lush greenery. Comfortable loungers are positioned near the water, inviting relaxation. A grill is visible in the background, enhancing the outdoor experience.

4.94 out of 5 average rating, 105 reviews

TERRACOTTA|Private Pool Retreat, 10 min Beach/5th

Weekly house rentals

Superhost

A spacious living area showcases a blue leather sectional couch and a marble-topped coffee table. Bright white bar stools are positioned around a light-colored kitchen island, with navy blue cabinets in the background. Natural light enters through nearby windows, enhancing the inviting environment.

4.92 out of 5 average rating, 195 reviews

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

A cozy living area features a light-colored sofa and a round, woven coffee table adorned with a small plant. Natural light filters through sheer curtains, highlighting a rattan chair positioned beside a tall mirror, creating an inviting and warm ambiance.

4.92 out of 5 average rating, 309 reviews

" The Bohemian Heaven " w/ SPA, 2miles to downtown

5.0 out of 5 average rating, 17 reviews

Home in Old Naples

Newly Restored Old Naples Estate - Best Location!

A spacious living area features a large sectional sofa in neutral tones, paired with accent pillows. A coffee table sits on a textured rug, while plants add a touch of greenery. Natural light floods in through expansive glass doors that open to a private outdoor space.

4.93 out of 5 average rating, 68 reviews

3 Bedroom Waterfront Getaway in Downtown Naples!

5.0 out of 5 average rating, 6 reviews

Luxury Resort Condo – Walk to Beach & 5th Ave

4.96 out of 5 average rating, 57 reviews

Cozy and Stylish, 2 King, Close to Beach & 5th Ave

5.0 out of 5 average rating, 13 reviews

Rainbow Retreat

The inviting outdoor area features a sparkling saltwater pool with a Baja shelf and two in-water loungers. Bright green umbrellas provide shade over the loungers, while additional stylish chairs are positioned nearby, surrounded by lush tropical landscaping.

5.0 out of 5 average rating, 27 reviews

Modern 3BR w/ Pool & Lanai | 5 Min to Downtown

Private house rentals

Superhost

An aerial view displays a spacious home surrounded by lush greenery and water, featuring a private pool on a patio. The property is bordered by calm waterways, enhancing its tropical ambiance and offering direct waterfront access.

4.88 out of 5 average rating, 51 reviews

Charming Waterfront Tropical Escape Near Downtown

The outdoor space features a glistening pool surrounded by lush tropical landscaping. Several lounge chairs are arranged nearby, inviting relaxation. The bright blue sky and vibrant greenery create a serene atmosphere, perfect for enjoying sunny days by the water.

5.0 out of 5 average rating, 43 reviews

Poolside Stay for Every Getaway

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.

5.0 out of 5 average rating, 33 reviews

Pool Home Minutes to the Beach

Superhost

A modern two-story home is featured, showcasing large glass doors that open to a serene outdoor space. A sleek pool is visible, surrounded by stone and greenery, while comfortable seating areas are arranged on the patio, enhancing the inviting atmosphere.

4.83 out of 5 average rating, 18 reviews

Luxury 5bd/5ba heated Pool, 5Min to Beach & 5th av

A stilt home is nestled among lush greenery, surrounded by tall trees and colorful potted plants. A spacious deck extends from the front, offering a shaded area. The gravel driveway leads to the house, adding to the property's natural charm and peaceful setting.

5.0 out of 5 average rating, 30 reviews

Unique Charming Home 3 Min to Downtown! FAST WiFi

5.0 out of 5 average rating, 13 reviews

Home in South Naples

Naples Retreat - w Private Heated Pool

An open living and dining area showcases stylish furnishings and a light color palette. The cozy sofa is positioned near a glass coffee table. A dining table with wooden chairs is visible, complemented by a modern kitchen area featuring bar stools and white cabinetry.

5.0 out of 5 average rating, 45 reviews

Modern 4BR Oasis Near 5th Ave & Beaches

A private outdoor area features a heated pool with inviting blue water, complemented by four lounge chairs arranged on a stone patio. A large umbrella provides shade, and a wooden bench is positioned near the entrance, surrounded by lush greenery and a sandy landscape.