Holiday rentals with a pool in Old Naples

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Old Naples

Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

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Top guest favourite

Home in Caloosahatchee

4.98 out of 5 average rating, 128 reviews

Heated Pool | Pet-friendly | Near Beach | Stocked

Catch your beach vibes at this newly renovated airy oasis with water views, relaxing lanai and huge heated pool in Cape Coral's desired Yacht Club community! Our coastal escape is pet and family friendly and is fully stocked with everything you need for an amazing vacation! We just renovated the entire house after Hurricane Ian so you'll get to enjoy a brand new kitchen (and huge island), new bathroom and new luxurious memory foam beds. Our pet fee is $75 per stay. 2 dogs max. NO cats please.

Top guest favourite

Home in Naples Park

5 out of 5 average rating, 6 reviews

Sunset Splash Luxe, Epic Pool, Hot Tub, Beaches

Sunset Splash is a luxury 3-bed, 2-bath (Sleeps 8) vacation rental in Naples, Florida. This gem offers quick access to the world's top beaches, fabulous restaurants, shopping (luxury shopping, too), and more. The property features a brand-new sizeable heated pool, hot tub, BBQ, outdoor shower, hammock, Wi-Fi, TVs in all rooms, dedicated work space, parking, and laundry room. Whether you're looking to relax by the pool or explore the nearby coastal gems, this home offers the best of both worlds

Guest favourite

Home in Caloosahatchee

5 out of 5 average rating, 12 reviews

Spacious Relaxing & Pet Friendly Home With Pool

Staying with Southern Raised is the perfect plan for all your travels ✈️ Our place in Cape Coral is a completely remodeled four-bedroom, two-and-a-half-bath home that boasts a spacious living room, brand-new kitchen, two completely updated full bathrooms, one fantastic powder and pool bath, and a panoramic sliding patio door that opens up the home to the gorgeous lanai and pool area. This space is perfect for larger groups that are traveling together. Did we mention we're pet-friendly?! 🐾

Superhost

Home in Caloosahatchee

4.84 out of 5 average rating, 118 reviews

Amazing Location! Walk to Downtown, Heated Pool!

Book this incredible tropical pool home just 2 mins from Downtown. King Bed, lush garden, heated lagoon saltwater pool, fenced yard, amazing resort-style waterfall feature provides a relaxing oasis. This modern, open-concept kitchen and living room home is a short 25 min drive to Fort Myers Beach, and a bike ride to the Cape Coral Yacht Club Beach. INCLUDED FOR FREE: • Fast WiFi, Peacock, Netflix • All Kitchen Utensils • Beach Towels, Chairs • Soap, Shampoo & Conditioner • and much more!

Guest favourite

Home in Fort Myers

4.91 out of 5 average rating, 34 reviews

Why rent a hotel when you can have a pool home?

Relax with the whole family at this peaceful place to stay. Heated pool with propane BBQ in the pool area. Super spacious kitchen with inside dining for 6 and outside dining for 4 (total seating for 10 persons). No additional fee for pool heating or bbq. Fully fenced private back yard. Some pets allowed at additional cost with approval. Please text through app for animal approval prior to reservation. Please make sure the proper number of persons are on your initial reservation. Piano also.

Guest favourite

Home in Naples

4.95 out of 5 average rating, 63 reviews

Attention Naples Lovers! Entire Home w/Pool&HotTub

Enjoy the heart of Naples from a modern vacation home located in a quiet, safe neighborhood with a private hot tub, heated pool, and screened patio. Stay in and have a wine night in the stunning, open-space kitchen island or go out and enjoy the many fine dining and beautiful beach views that Naples has to offer - minutes away! The home is newly renovated with new appliances, new furniture, a new hot tub, and a heated pool to savor Florida right in your own fully fenced private backyard.

Guest favourite

Home in Bonita Springs

4.83 out of 5 average rating, 18 reviews

Stunning Lakefront Heated Pool & Spa House!

Your perfect getaway awaits! Escape to tranquility in our beautifully updated 3/2 lakefront retreat with a heated (optional for a fee) pool and spa! This remodeled peaceful gem is nestled on a serene, private lot with breathtaking lake views. Just 7 miles to the pristine Bonita Beach and minutes from, shopping, and dining. Don’t miss out on this extraordinary retreat where comfort meets nature. Book your stay today and experience the ultimate in relaxation and luxury!

Top guest favourite

Home in Naples Park

4.96 out of 5 average rating, 24 reviews

South Exposure Heated Pool Home

Southern Exposure Heated Pool Home Look no further, this beach bungalow has the most amazing heated pool you will find, surrounded by tropical landscaping that is completely fenced in and private. Enjoy days grilling out by the pool and nights by the fire pit, this home has it all. This beach bungalow has been recently remodeled. The home features premium foam mattresses in every room and beautiful beachy chic decor.

Guest favourite

Home in Fort Myers

5 out of 5 average rating, 8 reviews

Coastal Oasis 52

Discover luxury between Sanibel and Fort Myers Beach! Our 3-bed, 2-bath rental features granite counters, large TVs, and high-grade linens. Outside, enjoy a screened lanai with a saltwater pool, jacuzzi, and gas fire pit. Entertain with a grill, pool table, and keg cooler. Perfect for groups with three attached units. Book now for an unforgettable getaway!

Guest favourite

Home in Pelican

4.89 out of 5 average rating, 232 reviews

Modern Oasis pool paradise

Location! Location! The entire place. This is a brand new Condo with gorgeous pool located next to supermarkets, restaurants including famous seafood restaurant, very close to Captiva, Fort Myers and Sanibel beaches Beautiful modern decor quiet secluded amazing!!! Great pool. No pets no service dogs no comfort pets allowed owner is allergic.

Superhost

Home in Fort Myers Beach

4.95 out of 5 average rating, 126 reviews

Blue Lagoon w/ heated pool-2 min walk to beach

FMB Reg 19-1212 . Hurricane Ian caused damage to the island but the home is back fully operational as it was prior to the storm & beaches look great! Come be part of #FMBStrong! Check the Town of FMB or Chamber Websites for more info. No refunds outside our cancelation policy. TRAVEL INSURANCE IS HIGHLY RECOMMENDED FOR TRAVEL DISRUPTION.

Superhost

Home in Naples Park

4.79 out of 5 average rating, 38 reviews

Poolside Paradise Tre

Welcome to Poolside Paradise Tres!! Our three properties are consistently in the top 5 rented in Naples. With our private heated pools, about 1 mile from 2 beach heads, a mile or so from many outstanding restaurants and food stores you can’t go wrong this immaculately clean house that has 50+ 5-star reviews on VRBO.