Pet-friendly holiday rentals in Old Naples

A modern pool area is featured with a spacious swimming pool surrounded by a screened-in lanai. Lounge seating and vibrant cabanas are positioned nearby, providing shaded relaxation. An adjacent game room is visible, equipped with a pool table and foosball table under unique lighting.

4.96 out of 5 average rating, 116 reviews

New Home, 6 Beds, Heated POOL / Game Room

Park in the driveway and enter through the front double doors to a newly and completely updated Home with 3bedrooms and 3 full bathrooms located just 7 miles from the trendy 5th avenue south, white sanded beaches and the famous Naples pier; This private and MODERN exquisite home has everything you need to enjoy an endless summer alike stay. Heat for the Pool Available EXTRA $ October to May $40 EXTRA per each night stay May to September $30 EXTRA per each night stay. Game Room and and Gym area.

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.

4.95 out of 5 average rating, 198 reviews

Home Close To Beach & Downtown Naples

We have stellar reviews, come check us out & see for yourself. Stay at this downtown Naples relaxing 1,864 sqft, 4 BD (2-king beds & 2-queen beds+twin blow up), 2 BA home for the best of vacations. Minutes from 5th Ave beaches/shopping/food/activities. Bonus: 2 outdoor seating areas/ample entertaining space/BBQ/outdoor games (corn hole, jenga, putting green), 2 bikes & beach equipment for 8. If looking for a pool, we have resort access to 6 area resort pools (day rate fees apply). Message me!

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, 165 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!

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.

4.95 out of 5 average rating, 130 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).

5 out of 5 average rating, 18 reviews

An open-concept living area features a comfortable beige sectional sofa adorned with decorative pillows, centered around a natural wood coffee table. A ceiling fan and warm lighting complement the neutral decor, with a large wall art piece depicting palm trees enhancing the inviting ambiance.

Condo in Lake Park

Naples 2-BDRM Condo, SuperClean, Patio, Lake Park!

Enjoy a stylish experience at this centrally-located unit in desirable Lake Park! Less than a mile to the beach and 1.5 miles from 5th Avenue. This unit has everything you need to relax! The living room and kitchen is a spacious and open concept. 2 bedrooms with queen beds and a shared bathroom with a tub/shower. Great location with close proximity to restaurants, shopping and the beach. We have limited short-term rental availability, we offer discounts for periods of 30 days or more.

The exterior of a two-story house is framed by palm trees, showcasing a welcoming entry with steps leading up to a spacious deck. Lush green foliage surrounds the home, providing a tropical feel beneath a clear blue sky.

4.86 out of 5 average rating, 142 reviews

#Closest2Beach - 3BD/3BA Oasis by RITZ BEACH GOLF

CLOSEST RENTAL HOME TO BEACH in Naples Park. Sleeps 6 with possibility of up to 10 by adding the additional Private Suites if available. Great Home for Large Family Vacations located near Ritz Carlton Beach Resort in Naples. Short Stroll to soft white sands at Vanderbilt Beach-Restaurants-Shops-Boats! See other listings for options: #Closest2Beach - 4BR/4BA Lux by RITZ- BEACH & GOLF #Closest2Beach - 4BR/4BA Cabana by RITZ BEACH GOLF #Closest2Beach - Huge 5BR/5.5BA by Ritz & Beach

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, 109 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.

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, 108 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!

4.91 out of 5 average rating, 137 reviews

A bright studio features a spacious bed covered with a colorful sea-themed quilt. A kitchenette with essential appliances, including a refrigerator, coffee maker, and counter space, is visible in the background, accompanied by soft lighting from nearby windows.

Guest suite in Naples

Private Studio 5 Minutes From Beach (All New)

You can make your stay in Naples complete when you unwind in this bright and cozy studio. Features: Private entrance with flexible self-check-in Private bathroom and kitchenette with all the essentials 516 Mbps fiber optic wifi On-site washer/dryer Private patio with loveseat Complimentary coffee and wine This unit is located just minutes away from the many beaches, shopping centers, and dining options that this slice of paradise has to offer.

4.82 out of 5 average rating, 181 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 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, 123 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.

4.91 out of 5 average rating, 233 reviews

Sunny Naples Escape | Poolside + Beach Access

Welcome to your Naples escape! Just 11 minutes from the beach, this tranquil home features a private heated pool and cozy comfort for up to 9 guests. Enjoy hybrid memory foam beds, hypoallergenic pillows, and freshly updated linens and drapes. Designed for restful, easygoing stays—perfect for beach days, poolside lounging, and quality time together. Make yourself at home and unwind in sunny style!

Popular amenities for Old Naples pet-friendly home rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Pet-friendly house rentals

4.92 out of 5 average rating, 118 reviews

566 Sea Esta Palms | Private Pool & Minutes2Beach

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, 212 reviews

Last Minute Deals! Walk to beach! Jacuzzi & Pool

The large heated pool, measuring 45 feet, features descending sheer waterfalls and is surrounded by a travertine deck. Comfortable lounge chairs are positioned nearby, with lush landscaping enhancing the private outdoor space. The insulated roof of the lanai provides shade and comfort.

4.91 out of 5 average rating, 140 reviews

An Egret named Eddie

A heated pool reflects the surrounding tropical decor under a screened lanai, illuminated by soft string lights. Comfortable seating is arranged for relaxation, with a view leading into a tastefully decorated living area featuring a neutral palette and accessible pathways.

5 out of 5 average rating, 7 reviews

Private Heated Pool• Outdoor TV & Gated in Naples

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, 12 reviews

The Marquee of Naples

A screened-in outdoor area features a clear blue inground pool alongside a jacuzzi, both surrounded by stone pavers. Lush greenery is visible beyond the enclosure, providing a serene backdrop. Comfortable seating awaits for relaxation in this private oasis.

4.93 out of 5 average rating, 137 reviews

Venetian Photoshoot - La Dolce Vita

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.

4.94 out of 5 average rating, 17 reviews

Naples Bungalow-Perfectly located & Pet Friendly

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.

5 out of 5 average rating, 21 reviews

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

Pet-friendly home rentals with a pool

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.

4.9 out of 5 average rating, 79 reviews

Tropical Pool Paradise close to 5th Ave/Beaches

A charming exterior view of the property features a welcoming entrance with a vibrant blue door. Lush green hedges and palm trees frame the landscape, accented by colorful tropical plants in the flower beds. A smoothly paved driveway leads to a covered parking area.

5 out of 5 average rating, 18 reviews

Naples Oasis SwimSpa, Tiki Bar, Arcade, and Fire

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.

4.98 out of 5 average rating, 113 reviews

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

A screened-in outdoor area features a private pool and a spacious patio. Comfortable lounge chairs are positioned beside the pool. A dining table with wooden chairs is arranged on one side, providing space for gatherings. Lush greenery surrounds the enclosure, enhancing privacy.

4.98 out of 5 average rating, 55 reviews

Heated Florida Pool Home - Flamingo Times

5 out of 5 average rating, 12 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!

4.95 out of 5 average rating, 82 reviews

Luxury Private Retreat with New Pool in Naples

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, 35 reviews

Mediterranean Inspired Villa with Private MiniGolf

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, 203 reviews

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

Private, pet-friendly home rentals

5 out of 5 average rating, 12 reviews

Apartment in Naples

Tropical Dream 2BR/2BA w./ Pool, Gym, and Theater

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.

4.91 out of 5 average rating, 45 reviews

Embassy Paradise

4.99 out of 5 average rating, 98 reviews

A bright pool area features a sparkling blue swimming pool surrounded by beige stone tiles. Comfortable lounge chairs are positioned alongside the pool, with a shaded gazebo in the background. Lush greenery and palm trees create a serene atmosphere, enhancing the outdoor experience.

Cottage in Naples Park

Sugar Beach Bungalow With a Pool!

4.91 out of 5 average rating, 65 reviews

A bright bedroom features a spacious bed with a turquoise blanket and subtle accent pillows. Natural light enters through two large windows. A small nightstand with a lamp is positioned next to the bed, while a modern kitchenette and bathroom entrance are visible in the background.

Apartment in Naples

Coastal Guest Suite Near Downtown

A colorful sign displays 'The Pickleball Haven of Naples' prominently, surrounded by manicured green grass and vibrant landscaping. The modern building in the background features large windows, allowing natural light to brighten the space. Decorative elements, including icons related to pickleball, enhance the inviting entrance.

4.93 out of 5 average rating, 27 reviews

The Pickleball Haven of Naples - Gray Supreme

4.96 out of 5 average rating, 28 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!

5 out of 5 average rating, 9 reviews

The outdoor pool area is enclosed by a screened lanai, showcasing a tranquil setting with palm trees and water views. Comfortable lounge chairs line the poolside, while the surface reflects the colors of the sunset, providing a serene atmosphere.

Home in Bonita Springs

Luxurious 4-Bed Pool Home with Dock & Gulf Views,