
Holiday rentals with a pool in Collier County
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Collier County
Guests agree: These homes with a pool are highly rated for location, cleanliness and more.

Lush tropical 1st floor getaway in Naples
Whether you're looking for a family-oriented or quiet, romantic vacation, we've got you covered! Our unit is tucked away at the south end of our complex where the trickle of the waterfall outside your lanai is the perfect backdrop to enjoying your morning coffee or perhaps a vacation cocktail! Our unit is completely remodeled in an updated coastal-chinoiserie style that is a combo of classic and contemporary, but also livable (we have two young children). Perfect backdrop to your time in SW FL!

Beach Across the Street! Balcony in the ❤️of Marco
A modern 1 bed 1 bath condo nestled in the heart of Marco Island and packed with everything you need for an unforgettable and effortless trip. Enjoy the convenience of beach access right across the street and JW Marriott a block away! Perfectly located on the main strip with popular restaurants like Da Vinci's and Marco Prime, shops, grocery stores, and major convention centers just down the road. Wind down your day watching breathtaking western exposure sunsets from your own private balcony...

LUXE Oasis | HTD Pool• 10 min Beach +5th Ave •Crib
Welcome to Your Naples Getaway! Why our home is perfect for your vacation: 🏖️ Beaches Nearby – Just a quick 10–15 minute drive to Via Miramar and Lowdermilk Beach. 📍Prime Location – Nestled on a peaceful street only 7 minutes from the iconic 5th Avenue. 🏡 Resort-Style Comfort – Relax in our fully screened lanai featuring: • Heated private pool • Luxury chaise loungers • Outdoor TV • Gas grill for BBQ nights Unwind with a cocktail, take a sunset dip, or simply kick back under the stars!

NEW! ONE BLOCK to the Beach, Restaurants & Shops!
Welcome to your newly renovated condo in the heart of Olde Naples! Just ONE BLOCK to the beautiful Naples beaches and all of the shops and dining on 3rd Street! Your first floor condo suite is ideally situated just steps from the oversized heated pool. And with large windows you can let that warm Florida sunshine in. The studio also has a designated parking space, common laundry, kitchen, bathroom, dining table, king size bed, pull out single trundle bed and can sleep up to 3 people.

Cozy, private two-room suite
A cozy, modern space in a family-friendly town. This two-room apartment with private entrance is in walking distance of the University, restaurants, shops and a Publix grocery store. Equipped with kitchenette. Smart tv in living area. A queen-sized bed with a full bathroom and a walk-in closet. Twin air mattress and Pack ‘n play available. Amenities in town include a waterpark with waterslides and swimming lanes, playgrounds, walking and bike trails, tennis and pickleball courts.

Pool Bikes & Beach | Paddle Board Included
We welcome your family of up to 2 adults & 3 children. You will be close to sandy beaches, great restaurants and shopping at this great North Naples Location. Just a few minutes from Vanderbilt Beach and Wiggins Pass Park. You will love all the great amenities and be able to relax in this brand new clean apartment. Amenities, Bikes, paddle board, beach wagon and beach towels. Very easy to check-in, you will have your own private entrance and private one car parking available.

Venetian Photoshoot - La Dolce Vita
Escape to our charming single-family home, where comfort meets luxury in a serene setting. This delightful retreat features three spacious bedrooms, perfect for families or groups seeking a relaxing vacation. Step outside to discover your private oasis: an inground heated pool complete with a rejuvenating hot tub, ideal for unwinding after a day of exploration, enjoy al fresco dining, with ample seating to savor meals together while soaking in the beautiful Florida sunsets.

Bonita 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 beautiful Barefoot Beach, less than 3 miles away. Our home is close to everything, so many beautiful beaches, great shopping and world class restaurants. If dining-in is more your thing, you will have a fully stocked kitchen with every amenity you could wish for. This is our own vacation home, so we’ve made every effort to make it as comfortable and convenient as possible.

675 FantaSea | New Heated Resort Pool & Fire Pit
Spend the day outside morning, noon & night and live out your FantaSea vacation! Lounge on the deck or in the heated pool on the sun shelf. On a cool night sit by the fire and relax in the Adirondack chairs. Desirable designer interior with coastal decor has the comfort of home with the feel of the sea. We are just a few minutes away from white sandy beaches with beautiful sunsets, amazing restaurants and upscale shopping centers.

Turtle Bungalow
Wake up to a chorus of singing birds under the splendid South Florida weather. Brew a coffee in the privacy of your bungalow, and get ready to seize the day. After a fun day at the beach or a productive working session, Turtle Bungalow will be perfect for the relaxation you need. Sit outside and enjoy the peaceful backyard view, pool, and the sweet afternoon breeze. The sun is warm, flowers are blooming… I wouldn’t wait.

Naples Tyme Retreat
Naples Tyme Retreat is an elegant, newly renovated, 2-bedroom, 2-bath condo that sleeps 6. Enjoy luxurious resort amenities, including 5 pools, a spa, gym, tennis, and world-class dining. Just steps from vibrant 5th Avenue and Naples' stunning beaches, this serene retreat offers a private lanai, modern kitchen, and sophisticated decor. Perfect for families or mature travelers seeking a blend of relaxation and upscale living.

Beach & Pool Escape – Walk to Naples Hotspots
Modern 3BR/2.5BA Naples home with private pool, perfect for adults seeking comfort and fun. Sleeps 6 with king suite, queen room, and queen-over-queen bunks. Relax poolside or head to the beach with provided chairs, umbrellas, blankets, and coolers. Walk to Botanical Garden, breweries, and dining. High-speed WiFi, Smart TVs, and desks keep you connected if needed. Kid-ready with Pack ’n Play, high chair, and toys.
Popular amenities for Collier County rentals with a pool
House rentals with a pool

Gulf Haven Hideaway: Naples 4BD Oasis - Pool + Spa

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

Top-rated luxury pool home in prime location

3BR w/HUGE 2k sq ft Lanai & Seasonally Heated Pool

Mediterranean Inspired Villa with Private MiniGolf

Coastal Getaway *Heated Pool *3 King Rooms

Luxurious "Villa in the Hills"

Sunny Naples | Poolside Paradise + Beach Access
Condo rentals with a pool

Riverside Paradise!

Amazing New Seaside Condo-5 fl View -Best Building

Oceanfront Views + Balcony Sunsets Bikes Included

Studio- Olde Naples, 2 blocks to beach Studio unit

Lely Greenlinks Golf Resort Luxury Condo

Ft Myers Beach & Lovers Key State Park- FANTASTIC!

Park Shore Resort Modern Top Floor 2 Bed 2 Bath

Waterfront View, Boat Dock, Pool Wildlife &Fishing
Other holiday rentals with a pool

$150 (no pool Sep-Oct): Beachfront w/amazing views

Charming 3BR Lake Home w/ Pool, Hot Tub & Fire Pit

Modern Coastal Retreat / heated pool and hot tub

Spacious and private pool home

Luxury Golf Penthouse

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

The Club at Naples Cay 501 - Gulf Views

Brigth Spacios Villa w/Pool & Jacuzzi, Near Beach.
Destinations to explore
- Rentals with a washing machine and dryer Collier County
- Rentals with lake access Collier County
- Loft rentals Collier County
- Rentals with a sauna Collier County
- Rentals with an accessible height toilet Collier County
- Boutique hotel rentals Collier County
- Rentals with a hot tub Collier County
- Rentals with outdoor seating Collier County
- Tiny house rentals Collier County
- Guesthouse rentals Collier County
- Waterfront rentals Collier County
- Villa rentals Collier County
- Rentals with beach access Collier County
- Townhouse rentals Collier County
- Smoking-friendly rentals Collier County
- Rentals with a fireplace Collier County
- Rentals with a fire pit Collier County
- Fitness-friendly rentals Collier County
- Hotel rentals Collier County
- Pet-friendly rentals Collier County
- Luxury rentals Collier County
- House rentals Collier County
- RV rentals Collier County
- Apartment rentals Collier County
- Rentals with a kayak Collier County
- Rentals with an EV charger Collier County
- Rentals with breakfast Collier County
- Rentals with a patio Collier County
- Condo rentals Collier County
- Cottage rentals Collier County
- Rentals with a home theatre Collier County
- Beachfront rentals Collier County
- Family-friendly rentals Collier County
- Rentals with pools Florida
- Rentals with pools United States
- Naples Beach
- Lovers Key Beach
- Barefoot beach Bonita Springs,FL
- Clam Pass Park
- The Club at The Strand
- Tigertail Beach
- Heritage Bay Golf & Country Club
- Panther Run Golf Club
- Bonita National Golf & Country Club
- LaPlaya Golf Club
- Morgan Beach
- Seagate Beach Club
- Worthington Country Club
- The Quarry Golf Club Naples
- Spanish Wells Country Club
- Cypress Woods Golf & Country Club
- The National Golf & Country Club Ave Maria
- Sanibel Island Northern Beach
- Talis Park Golf Club
- Via Miramar Beach
- Bunche Beach
- Residents' Beach
- Park Shore Beach Park
- Esplanade Golf & Country Club of Naples