Vacation rentals with a pool in North Naples

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in North Naples

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

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Guest favourite

Home in Naples

4.99 out of 5 average rating, 103 reviews

POOL HOUSE, CLOSE TO THE BEACH & DOWN TOWN NAPLES!

HEATED Pool home - Completely renovated home that comfortably sleeps 6 Only 5 minutes to the most desirable Beaches in the USA! Also very close to incredible restaurants, Publix, Target, Shopping, Parks and only 10 minutes to Downtown Naples. Flat-Screen TVs, Hi-Speed Internet, Comfy beds, modern and fully-stocked Kitchen. Very private and large pool with outside grill and patio furniture. Perfect for relaxing after a long day at the beach, we look forward to welcoming you to our HAPPY PLACE!

Aug. 26 – Sep. 2

$789 CAD per night

Superhost

Home in Naples Park

4.92 out of 5 average rating, 71 reviews

POOL, BEACH 1 MILE: Sandbank Cottage @Vanderbilt B

Enjoy a "stay"cation at Sandbank Cottage, the perfect location, 1-mile walking distance to beach, malls, art museums, and parks...all the attractions of Vanderbilt Beach! Family-friendly beach cottage with private 86 degree-heated pool and lanai screened-in porch. Open concept living, spacious bedrooms, Master en suite with king bed , and lots of amenities make this the perfect getaway for a short or long term stay! Bikes and beach equipment provided! NEW & IMPROVED WIFI (Aug 2020) No Pet Prope

Oct. 31 – Nov. 7

$363 CAD per night

Guest favourite

Home in Naples

4.98 out of 5 average rating, 172 reviews

3 bdrm up to 6 guest pool walk to Vanderbilt Beach

Our home is located in the heart of North Naples. It is less than 1mi. to the beautiful white sand Vanderbilt Beach. Our brand new remolded non-smoking, 3 bedroom 2 bath home is surrounded by numerous local restaurants, entertainment and shopping centers. It's less than 1mi to the newest Naples hot spot "The Mercato". It's 10 min to downtown Naples, 15mi to Miromar Outlets SWFL top place to shop. You can relax in our open floor plan that leads out to the deck of private Pool and hot tub.

Oct. 13 – 20

$542 CAD per night

Guest favourite

Home in Naples

4.96 out of 5 average rating, 153 reviews

Luxe Beach Home! Perfect for the Whole Family

This 2,000-square foot stunner has a saltwater pool, hot tub, two-car garage, three bedrooms and four bathrooms. There are bikes and beach accessories on site to take to the beach. Guest who is booking the reservation must be 26 years or older. There is a fee of $100/night per person for any guest over 7 in total up to a maximum of 9 guests. For example, if you have 8 guests, then the extra charge will be $100 per night. Please enter the exact number of guests before completing your booking.

Jul. 17 – 24

$725 CAD per night

Guest favourite

Apartment in Naples

4.99 out of 5 average rating, 121 reviews

Beach Vacation Getaway

Great for a couple with 1 -2 young kids or a getaway for 2 or a business traveler. Guesthouse is totally separate from the main house. Bedroom-king sized bed. Couch, 24 inch high twin air mattress and ottoman w/ twin sized bed. Fully screened lanai/Indoor HEATED private pool/w 8ft wall (swim at your own risk). No pets. WiFi/cable TV. 10 minute drive to the beach/shopping. Walking/biking/jogging path. 4 bikes-(ride at your own risk)/BBQ grill/continental breakfast/a variety of snacks/beverages

Jun. 27 – Jul. 4

$202 CAD per night

Guest favourite

Apartment in Naples

4.97 out of 5 average rating, 75 reviews

Lovely Beach Bungalow pool/spa 1.5 mile bch Naples

Lovely Pool/Spa bungalow, located in Naples Park, 1.5 miles from Vanderbilt Beach. Across the street from Marcato shopping center, Whole Foods, Cinema, restaurants and clubs. The unit is in pristine shape and features elegant furnishings and decor, tile floors throughout, granite counters in the kitchen, stainless steel appliances, impact windows and all white linens. Private screened in patio at the front and shared backyard area with pool/spa and BBQ. King Bed and Queen Sleeper Sofa.

Sep. 9 – 16

$253 CAD per night

Guest favourite

Cottage in Naples Park

5.0 out of 5 average rating, 15 reviews

*Megs Beach Cottage is Back On The Market!

Cottage back in market..taking reservations! Pictures were just taken. WALK OR BIKE RIDE TO BEAUTIFUL VANDERBILT BEACH. Enjoy a glass of wine in our front patio with fire pit or relax by the pool or tiki hut. Close to amazing restaurants and LESS THAN A MILE TO MERCATO AND VERY TO WATERSIDE SHOPPES, VANDERBILT BEACH, WIGGINS PASS and everything Naples has to offer. Don't miss out on this amazing opportunity to stay a few blocks from the beach. This home will not disappoint!

Jul. 21 – 28

$798 CAD per night

Guest favourite

Home in Naples

4.98 out of 5 average rating, 90 reviews

The WaterSun Oasis - Luxury Private Pool & Spa

The WaterSun Oasis is a 3 bedroom, 2 1/2 bath home, perfect for family or friends to get away. Less than one mile from Vanderbilt Beach, this high-quality private house, equipped with a top-notch outdoor pool area, is packed with best-in-class amenities to set your experience apart from others. Located just 30-minutes from RSW International Airport and surrounded by multiple beaches, restaurants, shopping centers, night life and more. Book your stay today!

Aug. 1 – 8

$597 CAD per night

Superhost

Condo in Bonita Springs

4.95 out of 5 average rating, 85 reviews

Ken & Gina's Beach Condo (#2301)

***Due to hurricane Ian, no amenities are available (pool, tennis, etc)*** 1 pool ready on 8/1/24 Studio condo across the street from Bonita Beach. 3rd floor unit offering partial views of the gulf. Being able to walk to the beach (2 mins) and 2 restaurants while centrally located between Ft. Myers and Naples makes this a great location. Local bike rental shops offer delivery of bicycles. Bonita beach offers jet ski, paddle board and catamaran rental.

Jun. 2 – 9

$172 CAD per night

Superhost

Condo in Naples

4.85 out of 5 average rating, 156 reviews

Ground Floor, A+ Location Club Membership Included

Lakeside, ground floor condo, located in the prestigious World Tennis Club, with 50 acres devoted solely to beautiful landscaping and lakes. Great location in Naples with box stores, dining, Publix, CVS and Walgreens etc very close. Four miles to the beautiful Naples beach which extends for many miles. Membership is included, giving access to the larger swimming pool, hot tub, 16 tennis courts, gym, seasonal cafe, pro-shop tennis match making, etc.

Aug. 2 – 9

$185 CAD per night

Guest favourite

Guesthouse in Naples

4.93 out of 5 average rating, 95 reviews

Manatees

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, Manatees 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.

Aug. 10 – 17

$179 CAD per night

Guest favourite

Home in Naples Park

4.96 out of 5 average rating, 52 reviews

664 Naples Beach Paradise Private Pool & Spa

Welcome to 664 Naples Beach Paradise! A luxurious 2BD/2BA newly remodeled pool home; a short ride/walk to the famously soft, white sands of SWFL beaches. Perfect location in North Naples; just minutes to shopping, dining & entertainment. Bring your loved ones and enjoy a care free luxurious vacation on our welcoming property. Our staff is dedicated to provide and ensure a wonderful experience throughout your stay.

Aug. 12 – 19

$490 CAD per night