Pet-friendly holiday rentals in Old Naples

A spacious covered porch offers a view of a tranquil lagoon surrounded by tropical foliage. Comfortable outdoor seating is complemented by a small table, while vibrant flowers are arranged in a vase. Sunlight reflects off the water, enhancing the outdoor ambiance.

4.96 out of 5 average rating, 173 reviews

Tropical Cottage by the Sea- your own private home

Welcome to your own private waterfront home on private lot close to Naples beaches! This small cottage comes with a big view of a tropical, peaceful lagoon. Fish and kayak right from the back yard! Two Kayaks & bikes provided! Lush, tropical setting and lots of wild life to see too! 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! Short drive to famous 5th Ave & Naples beaches! Lots of fun things to do close by!

A private outdoor space features a saltwater pool and hot tub, surrounded by lush greenery. Comfortable seating arrangements include a fire pit and outdoor dining area, all sheltered under a screened enclosure, providing a tranquil setting for relaxation.

4.97 out of 5 average rating, 208 reviews

LUXE: Beach Home w/ Screened Pool & Spa, BBQ

This 2,000-square foot stunner has a saltwater pool, hot tub, two-car garage, three bedrooms and four bathrooms. There are bikes and beach accessories on site to take to the beach. Guest who is booking the reservation must be 26 years or older. There is a fee of $100/night per person for any guest over 7 in total up to a maximum of 9 guests. For example, if you have 8 guests, then the extra charge will be $100 per night. Please enter the exact number of guests before completing your booking.

4.91 out of 5 average rating, 143 reviews

An Egret named Eddie

Home has 3 bedroom and 2 full baths, entire home and pool deck has travertine. Nice landscaping around the home. All bedrooms have good tv package. Furnishings are very good. Home has very comfortable feel. Large screen lanai has insulated roof, stays cool. The heated pool is large, 45 feet long, 3 sheer descending falls and has 6 led colored lights. Home is very tranquil and in a quiet area, just down the street to 5th ave shops and restaurants. New Publics food store just across street.

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, 148 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!

4.99 out of 5 average rating, 100 reviews

A bright bedroom features a spacious bed with a soft yellow coverlet. A small dining table with two chairs is positioned nearby. A painting adorns the wall, with light entering through the window. A laundry area is visible, providing added convenience.

Apartment in Naples

Aesthetic Lush Landscape, 3 Min to Town, King Bed

For Guests Who Love Privacy! Sunny Studio where Art is highlighted. French Doors to Lg Screened Porch for Outside Dining/Working. Peaceful. Stilt home (8 steps) in Safe, Quiet area w parking right outside. Backyard is yours w BBQ grill, table & chairs. Charmingly Furnished w Recliner, Heavenly King Bed, Convection/Microwave oven, Kitchen Aid stove top & Full Fridge. 624/34 Mbps at antique desk. SMALL quiet pets ok. Attached to owner's home but Studio is Completely Private! Only One Bed!

4.94 out of 5 average rating, 120 reviews

A bright living room is highlighted by a blue sectional sofa adorned with colorful cushions. A round, glass coffee table sits on a patterned rug, while a white armchair complements the space. Windows with blinds allow natural light to fill the room.

Condo in Naples

Beaches & 5th Ave 2.5 miles away!

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.

A modern kitchen is showcased with white cabinetry, stainless steel appliances, and a large island featuring a marble countertop. Ample natural light enters through windows, illuminating the space. A dining area with wooden chairs is visible in the background, complementing the warm tones of the flooring.

4.98 out of 5 average rating, 111 reviews

Naples Retreat: Heated Pool - Minutes to Beach

We know that you’ll love it here – whether you spend your time lounging by our pool, or at Naples’ world-renowned beautiful beaches. The home is only 10 minutes away from downtown Naples, which features some of the very best restaurants in Florida. If dining-in is more your thing, you will have a fully stocked kitchen with every amenity you could wish for. As this is our own vacation home, we’ve made every effort to make it as comfortable and convenient as possible.

4.93 out of 5 average rating, 149 reviews

A light-filled living area features a comfortable beige sofa adorned with blue and green cushions. A white coffee table sits on a textured rug, while soft curtains frame the glass door leading to the private deck. A ceiling fan enhances the airy feel of the space.

Cottage in Naples

Coral Cottage Retreat

A quintessential 2-bedroom / 2-bath beach cottage experience in fantastic central Naples! Just 12 minutes to all the trendy Mercado shops and restaurants in N. Naples, or just 8 minutes to all the luxury offerings of Old Naples’ 5th Avenue! Want to walk or bike to some great local spots?...We provide some of our favorite recommendations on your guest welcome guide! Also, take one of the complementary bicycles to the ocean, just a 9-minute ride to the Beach!

A spacious outdoor area features a rectangular pool surrounded by lounge chairs. A covered seating area is visible to the left, with a shaded structure supported by wooden beams. Lush greenery and palm trees add a tropical ambiance, complementing the exterior of the home.

4.92 out of 5 average rating, 115 reviews

Private Heated Pool | Playset | Near the Beach!

Just minutes from the beach, Flamingo Feliz is a cheerful 3-bedroom getaway with a brand-new pool, cozy tiki lounge, and family-friendly extras. Enjoy smart TVs in every room, a fully stocked kitchen, beach gear, bikes, and plenty of space to relax. The heated pool (heating avail. Oct–May) and outdoor living areas make it perfect for a sunny Florida escape. Located near 5th Ave dining, shops, and Naples' best beaches—everything you need for a laid-back vacation!

4.83 out of 5 average rating, 184 reviews

The kitchen features modern white cabinetry and sleek countertops with a subtle grey pattern. Appliances include a refrigerator, microwave, and oven. Under-cabinet lighting enhances the space, while glass pendant lights provide illumination above the bar area with seating for two.

Guest suite in Naples

Charming cottage bay area

Key west style stilt home Newly remodeled 2018, offering entire first floor bungalow, my place is 2 blocks to 5th Ave district, restaurants and dining, the beach is about 1 mile west, family-friendly activities, nightlife. close in, the location Naples Bay area. tin city -and bay front shops are 4 blocks west . roll away bed available if needed in garage. many beach toys available in garage. coolers beach towels everything you can think of.

An inviting collage showcases various areas of the Naples Holiday House. Bright outdoor seating is paired with an umbrella, while the living space features comfortable seating and coastal decor. A cozy dining area invites meals al fresco, and serene beach views complete the relaxing atmosphere.

4.96 out of 5 average rating, 203 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 outdoor living space features a screened lanai overlooking a pool. Comfortable loungers are positioned around the pool. A dining table with multiple chairs is set under a ceiling fan, complemented by a large area rug. The scene is bathed in natural light.

4.98 out of 5 average rating, 126 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.

Popular amenities for Old Naples pet-friendly home rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Pet-friendly house rentals

An inviting outdoor space features a heated pool beside a hot tub, while comfortable seating arrangements are visible. A dining area is adorned with modern green chairs, and sliding doors provide access to the interior. A pink inflatable flamingo adds a playful touch to the pool area.

4.96 out of 5 average rating, 118 reviews

2 Mstrs w Kings, Pets, Queen ensuite, hot tub, htd

A welcoming living area features a white sectional sofa adorned with neutral pillows. A glass-top coffee table sits at the center, showcasing a decorative centerpiece. Large windows provide a view of the lush garden and private pool area through bright, natural light.

5 out of 5 average rating, 9 reviews

Paradise in the Park - Heated Pool

A clear blue pool features a spa area, bordered by decorative stone. Two lounge chairs are positioned alongside the water, offering a relaxing area. A dining table with multiple chairs is visible in the background, with a privacy fence and lush greenery completing the serene outdoor setting.

4.97 out of 5 average rating, 220 reviews

Last Minute Deals! Walk to beach! Jacuzzi & Pool

A spacious outdoor area features a large heated pool surrounded by a screened enclosure. Two lounge chairs sit along the poolside, while a dining table with chairs is positioned nearby. Lush greenery and a clear blue sky create a serene setting.

5 out of 5 average rating, 13 reviews

The Marquee of Naples

A cozy outdoor space features two lounge chairs with vibrant cushions, positioned beside a sparkling pool. A large umbrella provides shade. Colorful pool floats and towels enhance the scene, while lush greenery and palm trees create a relaxing atmosphere.

5 out of 5 average rating, 29 reviews

Custom Naples 3BDRM Luxe Home/Htd Pool/SuperClean

A charming turquoise home is surrounded by lush landscaping featuring palm trees and colorful flowers. In the foreground, a heated swimming pool is nestled within a paved area, accompanied by several lounge chairs positioned for relaxation and sunbathing.

5 out of 5 average rating, 24 reviews

Walk To Beach & Shops! New 4 Bdr Pool Heated

A spacious pool area is highlighted by a large swimming pool with a built-in hot tub. Modern outdoor furniture is arranged around the pool, and a whimsical float is visible in the water. Lush greenery and palm trees frame the scene, enhancing the relaxed atmosphere.

4.94 out of 5 average rating, 65 reviews

Your Dream House -Steps to 5th Ave

The living area features a light-toned tile floor, accompanied by a spacious couch and a sofa bed against a white wall. A ceiling fan adds to the comfort, while a TV unit and a decorative shelf with items are visible. Natural light filters through the sliding glass doors, enhancing the bright atmosphere.

4.86 out of 5 average rating, 28 reviews

Blue Oasis in Downtown Naples

Pet-friendly home rentals with a pool

5 out of 5 average rating, 54 reviews

A spacious screened pool area is shown, featuring a heated saltwater pool with built-in bench seating. Lounge chairs are positioned along the edge, and a hammock is visible nearby. The outdoor dining area and sectional seating are included, with a 55" Smart TV situated to provide entertainment.

Home in Bonita Springs

Private Palm Oasis - Close to Beach

A refreshing swimming pool features floating inflatable items, including a unicorn and colorful loungers. Water fountains gently spray into the pool, surrounded by a spacious deck. Lush greenery and a privacy hedge create a serene environment, while inviting lounge chairs are positioned nearby for relaxation.

4.87 out of 5 average rating, 84 reviews

Tropical Pool Paradise close to 5th Ave/Beaches

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.

4.92 out of 5 average rating, 105 reviews

Elegant house w/heated Private Pool

4.97 out of 5 average rating, 31 reviews

An airy living room features a light-colored leather sofa set arranged around a glass coffee table on a blue area rug. A wooden entertainment unit holds a television, while large glass doors provide a view of an outdoor patio and pool area.

Villa in Naples

Lovely 3-bed villa, Briarwood neighborhood, Naples

An outdoor dining area is featured, enclosed within a screened patio. A round table is surrounded by four comfortable chairs, set with blue plates and napkins. The pool is visible nearby, framed by lush greenery and tropical plants, adding to the serene environment.

4.94 out of 5 average rating, 67 reviews

Sunshine days! Stunning pool home. Gated community

5 out of 5 average rating, 16 reviews

The sleeping area features a queen-sized bed adorned with decorative pillows and a textured blanket. Two bedside tables hold glass lamps, providing soft lighting. A decorative piece is displayed above the bed, and a woven storage chest is positioned at the foot, complementing the room's tranquil color scheme.

Guesthouse in Naples

Downtown Naples Oasis – 5 Mins to the Beach!

An outdoor dining area is visible beside a pool, equipped with a table and several chairs. The pool area is enclosed with a screen, providing a view of the surrounding landscape. Inside, two arcade machines can be seen, featuring classic games like Pac-Man and Fast and Furious, along with a television above.

4.94 out of 5 average rating, 141 reviews

1mi to Beach | Arcade | Heated Pool

A modern villa exterior is presented, featuring a spacious driveway and a neatly landscaped yard. The entrance is adorned with two chairs beside a front porch. A large garage door complements the sleek, neutral facade of the home, creating an inviting approach.

4.96 out of 5 average rating, 25 reviews

Heaven on earth in the heart of Naples 30

Private, pet-friendly home rentals

4.91 out of 5 average rating, 46 reviews

A hot tub is situated beneath a wooden pergola, surrounded by softly glowing string lights. Clear glasses and a bottle sit nearby, reflecting the warm ambiance. Palm trees can be seen in the background, adding a tropical touch to the evening setting.

Villa in Old Naples

4.97 out of 5 average rating, 31 reviews

A bright living area showcases comfortable seating arranged around a coffee table. Large windows allow natural light to fill the space, complemented by a bold floral accent wall. The fully equipped kitchen features a generous countertop with seating for four.

Apartment in Naples

Beachy Escape: 2BR/2BA w./ Pool, Gym, and Theater

4.97 out of 5 average rating, 32 reviews

A spacious two-story home showcases a large outdoor deck and a well-maintained landscape featuring various tropical plants. The exterior features light-colored siding, a brown shingled roof, and ample windows that allow natural light. Pathways lead through the surrounding greenery.

Home in Bonita Beach

Elegant Beachside Luxury Home Awaits!

An aerial view showcases a spacious home nestled in a lush, tropical landscape. A private pool can be seen adjacent to a large deck, surrounded by vibrant greenery and trees, with water visible nearby, enhancing the property's outdoor appeal.

4.86 out of 5 average rating, 37 reviews

Charming Waterfront Tropical Escape Near Downtown

An outdoor dining area is highlighted by a large wooden table surrounded by woven chairs. Pendant lights hang above, casting soft illumination. A swimming pool with clear water is visible through a screened enclosure, complemented by lush greenery in the background.

5 out of 5 average rating, 43 reviews

Mediterranean Inspired Villa with Private MiniGolf

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.

4.86 out of 5 average rating, 21 reviews

Naples Bungalow-Perfectly located & Pet Friendly

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, 61 reviews

Your Oasis in Naples! Saltwater Heated Pool!

A heated pool is surrounded by a screened lanai, featuring lounge chairs and lush greenery in the background. Sunlight reflects off the water, where an inflatable float is visible. A dining space with a large table can be seen in the shaded area nearby.