Pet-friendly holiday rentals in Old Naples

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.

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!

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!

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).

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.

#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

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.

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!

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

The perfect home for a beach vacation just a 6 min bike ride to the beach and 2 master suites with king beds, walk-in closets, TVs, and private baths, 1 ensuite with a Queen bed, and the 4th bedroom with twin beds. Even a pool bath and outdoor shower! A large chef's kitchen with all Bosch appliances. Every space is designed for a group of 8-10 to gather. Bikes, towels, beach chairs, toys are all included! Great for large groups of 8-10 to gather and enjoy.

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, all items are new sofa bed also. 3 blocks from 5th Ave Shopping. just over one mile to beach with many beach toys in garage.

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.

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!