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, 132 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, 227 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.

4.97 out of 5 average rating, 116 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.

4.94 out of 5 average rating, 144 reviews

LUXE Oasis | 10 min Beach+5th Ave• HTD Pool • 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, 142 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).

An outdoor space is shown, featuring two lounge chairs with decorative pillows, positioned beneath a blue umbrella. A sleek, modern side table sits between them, complemented by a vibrant arrangement of flowers. Water fountains gently spray into the clear pool, surrounded by lush greenery.

4.94 out of 5 average rating, 155 reviews

577 SunnyDaze | Private Heated Pool | Walk 2 Beach

Welcome to 577 Sunny Daze! Located just 4 blocks from the gorgeous, white sands of Vanderbilt Beach, this heated pool home blends easy beach living w/ inviting coastal comfort throughout. Step outside to your private, lush tropical backyard, where the heated pool, tropical palms, & lush greenery create a peaceful oasis - perfect for morning coffee, afternoon swims, or evenings under the stars! If you've come to soak up the warm Florida sunshine, Sunny Daze is the perfect place to vacation!

A heated pool area features relaxing lounge chairs partially submerged in the water, accompanied by a large white umbrella providing shade. The pool is surrounded by a spacious deck, framed by lush greenery and palm trees, with additional seating visible in the background.

4.98 out of 5 average rating, 104 reviews

Private Naples Oasis w/ Cart, Gym & Saltwater Pool

Welcome to your private slice of paradise in sunny Naples Park—just minutes from Vanderbilt Beach, Delnor-Wiggins Pass, and the shops and dining at Mercato! This bright and beachy 3-bedroom, 2-bath home has everything you need for the perfect Florida getaway. Whether you're cruising to the beach in our golf cart (optional rental), soaking up the sun by the private heated saltwater pool, or enjoying dinner on the screened lanai, this spot makes it easy to relax, recharge, and have fun.

A light blue two-story villa is shown, featuring a spacious front porch with railing supported by two ceiling fans. The ground level includes a double garage with a textured facade, set against a backdrop of palm trees and a clear blue sky.

4.86 out of 5 average rating, 296 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, 3 blocks from 5th Ave Shopping. just over one mile to beach with many beach toys in garage. right next to New Marriott being built Center of downtown near New high-rises and many restaurants

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, 309 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.

4.95 out of 5 average rating, 216 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, 340 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 spacious living area is depicted with a comfortable couch and a dining table set with two chairs. A large television is mounted on the wall, while a doorway leads to a well-equipped kitchen. Natural light fills the space through a nearby window.

4.89 out of 5 average rating, 159 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

Popular amenities for house rentals in Old Naples

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

An inviting lounge area features a spacious layout with contemporary furnishings. Natural light floods the room through large glass doors that open to a private swimming pool. Decorative plants enhance the aesthetic, while a modern kitchen is visible in the background.

4.92 out of 5 average rating, 83 reviews

The Lounge| Modern,Pool, Privacy, 10min Beach/5th

5 out of 5 average rating, 6 reviews

Beachcombers Pool Getaway

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, 35 reviews

Chic Pool Naples Beach House

5 out of 5 average rating, 16 reviews

Home in Bonita Springs

3BD 1-Acre Oasis: Private Pool Estate near Beaches

An inviting outdoor space features a saltwater pool surrounded by comfortable seating areas and lush greenery. Sun loungers with rolled towels rest beside the pool, offering a relaxing atmosphere for sunbathing. An umbrella provides shade over the seating arrangement, creating an ideal spot for outdoor gatherings.

4.97 out of 5 average rating, 65 reviews

Your Oasis in Naples! Saltwater Heated Pool!

An outdoor area features a heated pool and a hot tub surrounded by lush greenery. Lounge chairs are positioned on the patio, and a blue shade sail is draped overhead. The sky is painted in soft hues of pink and purple, creating a serene evening ambiance.

4.78 out of 5 average rating, 9 reviews

Brand New! 4 Bedroom, 4.5 Bathroom, Pool, Spa

A heated pool is enclosed by a screened patio, providing a relaxing space for guests. Lounge chairs are positioned beside the pool, while the indoor dining area and living space can be seen in the background, framed by large glass doors that invite natural light.

4.91 out of 5 average rating, 247 reviews

Heated Pool Retreat• Naples Oasis Minutes to Beach

A single-story home is set amidst a lush green lawn, featuring a tiled roof and arched windows. Palm trees and shrubs frame the entrance, which is highlighted by a welcoming front porch. The driveway leads to a spacious garage, enhancing the overall curb appeal.

5 out of 5 average rating, 49 reviews

Modern Luxury Retreat in Naples

Weekly 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, 50 reviews

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

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 out of 5 average rating, 17 reviews

Unique Charming Home 3 Min to Downtown! FAST WiFi

5 out of 5 average rating, 3 reviews

Chardonnay Beach Escape, Naples, Florida

A modern living area features a mix of comfortable seating, including a spacious blue sofa and brown leather chairs. A round wooden coffee table sits center stage, adorned with a floral arrangement. A wall-mounted TV and light streaming through large windows enhance the bright atmosphere.

4.99 out of 5 average rating, 82 reviews

Sea Grape Cottage close to everything in Naples!

4.93 out of 5 average rating, 27 reviews

1 Bedroom/ Bayshore Art District

An open living area features a comfortable white sectional sofa facing a large wall-mounted TV. Natural light flows through sliding glass doors leading to an outdoor space. A round wooden coffee table and a stylish accent chair add to the welcoming atmosphere.

4.95 out of 5 average rating, 75 reviews

Old Naples Home | Hot Tub, 5 Min Downtown & Beach

4.87 out of 5 average rating, 53 reviews

An open living area features a light-colored leather sofa, accented by patterned pillows. A coffee table with a rustic finish sits in front. The walls are painted in a calming blue hue. Visible in the background is the dining area with red chairs and a modern kitchen.

Home in Lake Park

Golf Cart to Beach! Charming Home w/ Patio

5 out of 5 average rating, 25 reviews

Home in Lake Park

Seashell Retreat, your place to relax and enjoy

Private house rentals

5 out of 5 average rating, 25 reviews

A vibrant pink inflatable flamingo floats on the clear water of the heated pool, surrounded by a screened enclosure. In the background, a shaded seating area with a large umbrella and wicker furniture is visible, framed by lush greenery and stone columns.

Home in Willoughby Acres

Blue Oasis!. The Perfect Getaway w/ Heated Pool!

4.99 out of 5 average rating, 69 reviews

Close to Everything! Stylish Home w/ Pool & Spa

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 out of 5 average rating, 26 reviews

Poolside Stay for Every Getaway

A single-story house features a neatly landscaped front yard with green grass and a variety of plants. The exterior showcases light-colored siding and blue shutters. In the center, a welcoming front door is framed by a decorative circular window. Abundant palm trees and shrubbery create a tropical ambiance.

4.89 out of 5 average rating, 56 reviews

Embassy Paradise

4.99 out of 5 average rating, 75 reviews

Home in Palm River

Charming 3BR Lake Home w/ Pool, Hot Tub & Fire Pit

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.

4.97 out of 5 average rating, 33 reviews

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

5 out of 5 average rating, 33 reviews

Sandy Cove Villa Central Naples and near the Beach