Pet-friendly holiday rentals in Old Naples

Sea Grape Cottage close to everything in Naples!

Charming, updated, and spacious Sea Grape cottage is located within 2 miles of sandy white beaches which are easily accessible by car or bike. Sea Grape is also located just a mile from Naples downtown area filled with shopping and restaurants. This two bedroom sleeps 4 and includes a study, dining room, and living room. Enjoy this quiet neighborhood by sitting outside on the screened in deck overlooking a tropical garden or enjoy nearby Tin City, 5th Avenue, and the Gordon River Greenway Park.

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).

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!

Amazing Old Naples Property!

Indulge in this beautifully appointed two-bedroom, two-bath retreat nestled in the heart of Old Naples. Soaring ceilings and an open-concept layout create an airy, welcoming ambiance, complemented by a sleek modern kitchen, in-unit laundry, and a private balcony perfect for al fresco dining or sunset cocktails. Retreat to plush hotel-quality linens and premium mattresses in the primary king suite and secondary full bedroom—each featuring an ensuite bathroom for privacy and convenience.

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.

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!

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!

Beachside Haven | Family 3BR Near Vanderbilt Beach

We’re so excited to share our beautiful home with YOU! Located in the heart of Naples Park . Our 3-bedroom, 2-bath home is perfect for families, friends, or anyone looking for a blend of relaxation and quiet. The home is designed the home for maximum comfort and fun! The house is FULL of amenities, games for adults and kids - if you find something we don't have - message us :-) Let us host you in Naples Park, a few minutes from beautiful Vanderbilt beach.

Beautifully private homeHeated Pool/Spa and Cabana

WELCOME PICKBALLERS! We are close to Naples Community Park and downtown Naples and beaches, perfect location. Unique one of a kind property, This house has been beautifully remodeled with Stunning Carrera marble floors, upgraded 4 bedroom 2 bath home with a separate pool house suite with its own kitchen and full bath that sleeps 4 guests. Beautiful landscaped yards with amazing pool. Only minutes to the beach. Private outdoor shower.

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

Royal Palm House Tin City shops

Large house updated.. second floor unit with large back deck porch and garage with beach toys, other toys. close to the beach 2 blocks from 5th Ave. one mile from beach 3 blocks from Tin city shops and Naples bay. close to many restaurants on 5th Ave. to walk or bike to beach, right next to the new Marriott being built downtown in the center of downtown and large high-rises close to everything. no room for car in garage. roku

566 Sea Esta Palms | Private Pool & Minutes2Beach

Welcome to 566 SeaEsta Palms! Channel the brilliance & serenity of the shore at SeaEsta Palms with shades of sky & sea. Life will feel like a permanent vacation in this beautifully decorated pool home. SeaEsta Palms is freshly updated & fully equipped with all of the comforts of home. Located in the heart of the Vanderbilt Beach area, just minutes to the beaches & the Mercato Shopping & Dining District.