Pet-friendly holiday rentals in Old Naples

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).

Royal Palm flat Bay side shoppes

Royal Palm flat first floor charming , updated , with large back porch and shared garage with beach toys, close to the beach 1 block from 5th Ave. one mile from beach 3 blocks from Naples bay. close to many restaurants and shops on 5th ave. The beach is at the end of 5th Ave. great walk down the heart of Naples down town and charming tin city shops and dinning. view 5th ave from rear porch. entire first floor. no room for car in garage, right next to the new Marriott being built very central.

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.

Rare Gem, Fast WiFi, 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. FAST WiFi at antique desk. SMALL quiet pets ok. Attached to owner's home but Studio is Completely Private! Only One Bed!

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.

Oasis Naples Condo 2BR/2Bath

Soak up the warm southwest Florida sun and enjoy a clean modern home with gorgeous views. This newly renovated condo is a short 5 minute car ride to Naples Beaches and 15 minutes to downtown. Two bedroom, two full bath home is the perfect quiet place for a couple’s retreat or for working remotely with high speed internet. The main pool IS open dawn to dusk!!! It’s a two minute walk within the community! (The smaller pool by the condo is closed and still waiting for completion.)

Coral Cottage Retreat

Enjoy a quintessential 2-bedroom, 2-bath beach cottage in the heart of central Naples! You’re just 12 minutes from Mercato’s shops and restaurants and 8 minutes from the dining and boutiques of Old Naples’ 5th Avenue. The home comfortably accommodates guests with three queen-size beds, including a sofa bed. Prefer to explore nearby? Walk or bike to great local spots—our favorites are in your guest guide. Or hop on a complimentary bicycle and reach the beach in just 9 minutes!

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.

Heated Pool + Lanai | 10 min Beach | Game Room

✨ Welcome to The Periwinkle — a family-friendly pool home 10 min to Naples Beach! 🏊 XL heated pool, fire pit, screened lanai, fenced yard & BBQ 🎮 Game room with foosball 🍽️ Fully stocked kitchen, indoor/outdoor dining & WFH desk 🛏️ 4 bedrooms, 2 full baths, memory foam mattresses & smart TVs throughout 👶 Kids gear included — pack 'n play, high chair & more 📍 Naples Pier, 5th Ave, Sugden Park (beach, sailing, water-ski) & East Naples pickleball all within 10 min

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!

Sugar Beach Bungalow With a Pool!

Come jump in the pool! Put away your wool hats, hang up your parkas, and break out the swim trunks, sunglasses and flip flops. There’s no better way to celebrate summer (or escape winter) than with a relaxing beach vacation. Bring the whole family, roll with a group of friends, or make it a romantic retreat. Whatever the trip, opt for a luxurious vacation rental with all the home amenities you’re used to at home—and some. This incredible beach home has it all!

Walk to The Ritz & Beaches, 2 Mstrs w Kings, Pets

Fabulous 500 block location. Just a short walk/bike ride to the beach. This exclusive layout w 2 master suites, large walk-in closets, and private baths. Every living space has been thoughtfully designed for large groups of 8-10 to gather and enjoy. The house is fully stocked. This includes a coffee maker, dishes, pots and pans, beach cruiser bikes, beach chairs, a wagon, etc. All you need is to pack your bags, sit back and relax...