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Vacation rentals with a pool in Naples

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Naples

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

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Condo in Naples

4.87 out of 5 average rating, 115 reviews

Top Floor, A+ Location, Club Membership Included!

Lakeside, top 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, Publix, dining, CVS and Walgreens etc very close. Four miles to the beautiful Naples beach which extends for many miles. Tennis Club membership included at no cost, including larger swimming pool, hot tub, 16 tennis courts, gym, seasonal cafe, pro-shop, match making through proshop, bocce ball, pickle ball, sauna

Jul. 18 – 25

$193 CAD per night

Guest favourite

Guest suite in Naples

5.0 out of 5 average rating, 134 reviews

By the Beach and 5th - Studio Guest Home & Pool

Great location! Newly renovated! A studio guest home with your own private entrance & your own full kitchen & bath! A non-smoking home only 1 mile from the beach, 5th Ave dining and shops, the mall, the zoo, beautiful Baker Park, and that's not all- Only steps away are local restaurants and shops! Bikes and beach equipment included! Did we mention the pool? Or that you can sing along to your fave tunes in the shower via a Bluetooth shower speaker? This home is 350 square feet of clean cuteness!

Oct. 21 – 28

$288 CAD per night

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!

Jun. 11 – 18

$673 CAD per night

Apartment in Naples

4.78 out of 5 average rating, 27 reviews

Modern Comfort l Biking. Gym. Beach Nearby

Welcome to the Hampton Inn Naples-Central, where modern comfort and exceptional hospitality converge in the heart of the vibrant Naples community. ✔ Relax and Enjoy the hotel amenities such as outdoor pool and fitness center. ✔ Explore Naples Beaches. ✔ Enjoy a leisurely stroll or fish off the Naples Pier while taking in stunning views of the Gulf of Mexico. ✔ Go biking or hiking in nearby parks. ✔ Naples is a golfing paradise with numerous golf courses catering to different skill levels

Jun. 16 – 23

$191 CAD per night

Guest favourite

Condo in Naples

4.95 out of 5 average rating, 283 reviews

Lely Greenlinks Golf Resort Luxury Condo

This beautiful and spacious 2-bedroom, 2 bath condo is luxurious, impeccably clean, well-stocked - and perfect for your next vacation getaway! Greenlinks Golf Resort is situated within the prestigious Lely Resort Golf & Country Club in Naples. It is just a two minute walk over to the clubhouse where you can tee off on the Lely Flamingo or Mustang golf courses. Ideal central location between downtown Naples and Marco Island, you are just 15 minutes from downtown or beaches in either location.

Jul. 20 – 27

$262 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.

Sep. 26 – Oct. 3

$538 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

Jul. 4 – 11

$202 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.

Dec. 7 – 14

$1,144 CAD per night

Guest favourite

Guesthouse in Naples

4.93 out of 5 average rating, 113 reviews

Private & Spacious Studio 1 mile fr 5th Ave w/Pool

Welcome to Kevin's Newly Renovated Air BNB in Naples, featuring a private swimming pool, patio w/sun shade, parking, luxury sheets, fully stocked kitchen, full size W/D, and more! This uber-quiet and private space is located just over 1 mile from 5th Avenue/downtown Naples, & 2 miles from the beach. 5 minute walk to Naples Bay Resort, coffee shops & restaurants. Walk or use complimentary bikes to check out nearby Celebration Park, a brewery, Market 360, & pickleball courts!

Jul. 25 – Aug. 1

$234 CAD per night

Guest favourite

Condo in Naples

4.97 out of 5 average rating, 61 reviews

Gulfside Sleeper in the ❤ of Historic Old Naples

Bright, clean 2nd floor studio is ideal for 1 or 2 travellers. Minimalist design with an emphasis on comfort and relaxation is perfect for executive business travellers or sun seeking beachgoers. No car necessary. The small space is hard flooring of wood and tile. There is an open closet with hanging rod. The shower access is a bit tight, and may not be suitable for big and tall or plus sized individuals. The westward view from the window is one block from the beach sunsets.

Aug. 12 – 19

$253 CAD per night

Guest favourite

Condo in Naples

4.94 out of 5 average rating, 97 reviews

Sea Shell Villa 1

Your will be close to everything when you stay at this centrally-located villa. Our villa is fully upgraded. Has a full kitchen, 1 bedroom with a queen bed and laundry room with a full size washer and dryer. There is a great variety of restaurants and shopping just minutes away. In just 15 minutes you can be at the famous Naples pier for a fun day at the beach. We also have Marco Island, which is one of the top beaches in the world, just 20 minutes away.

Jan. 8 – 15

$215 CAD per night

Guest favourite

Guest suite in Naples

4.91 out of 5 average rating, 56 reviews

839 GulfShore Studio | Walk 2 Mercato & Beaches

Welcome to 839 GulfShore Studio! Bask in the Florida sunshine, practice your golf swing, & explore the Gulf Coast in style when you choose this completely remodeled vacation rental! This 1BD/1BA Studio is just a block away from Mercato Shopping Center, where you'll unique shops, eateries, live entertainment & more. With a fully equipped kitchen, Smart TV, free WiFi, modern decor, & a peaceful location, this studio invites you to kick back, relax, & enjoy!

Jul. 9 – 16

$251 CAD per night

Vacation rentals for every style

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Popular amenities for Naples rentals with a pool

Free parking on premises

Air conditioning

House rentals with a pool

Guest favourite

Home in Naples

4.97 out of 5 average rating, 119 reviews

Vandy Beach Retreat (Walk to Beach!)

Nov. 2 – 9

$659 CAD per night

Guest favourite

Home in Naples

4.98 out of 5 average rating, 161 reviews

Unique Waterfront Naples Experience

Mar. 23 – 30

$886 CAD per night

Guest favourite

Home in Naples

4.95 out of 5 average rating, 111 reviews

☀ 1mi to Beach ☀ Heated Pool ☀ Custom Kitchen ☀

Dec. 2 – 9

$826 CAD per night

Guest favourite

Home in Naples

4.98 out of 5 average rating, 208 reviews

Island lifestyle family vacation home (Salt Pool)

Oct. 5 – 12

$367 CAD per night

Guest favourite

Home in Naples

4.98 out of 5 average rating, 117 reviews

Luxury Abounds at Vanderbilt Beach, Pool & Spa

Jun. 20 – 27

$813 CAD per night

Guest favourite

Home in Naples

4.94 out of 5 average rating, 36 reviews

Zen Beach Retreat * the ultimate luxury getaway

Dec. 8 – 15

$575 CAD per night

Guest favourite

Home in Naples

4.97 out of 5 average rating, 31 reviews

The Sun-kissed Retreat •Vanderbilt Beach• Pool&Spa

Jun. 12 – 19

$556 CAD per night

Guest favourite

Home in Naples

5.0 out of 5 average rating, 9 reviews

Perfect 2 Bedroom House w/ Pool!

Jun. 5 – 12

$317 CAD per night

Condo rentals with a pool

Guest favourite

Condo in Naples

4.93 out of 5 average rating, 144 reviews

Lely Resort Luxury Condo-2 Spectacular Pool/Golf

May 27 – Jun. 3

$300 CAD per night

Guest favourite

Condo in Marco Island

4.95 out of 5 average rating, 126 reviews

Amazing New Seaside Condo-5 fl View -Best Building

Sep. 14 – 21

$347 CAD per night

Guest favourite

Condo in Naples

4.91 out of 5 average rating, 110 reviews

Beautiful Pool 5m to the Beach Downtown & Shopping

Apr. 14 – 21

$689 CAD per night

Guest favourite

Condo in Marco Island

4.93 out of 5 average rating, 122 reviews

Marco Beach Ocean Resort 707

Aug. 11 – 18

$558 CAD per night

Guest favourite

Condo in Naples

4.89 out of 5 average rating, 107 reviews

Top Loc, Best Views, Park Shore 258

Sep. 3 – 10

$254 CAD per night

Guest favourite

Condo in Naples

4.91 out of 5 average rating, 146 reviews

Park Shore Resort Modern Top Floor 2 Bed 2 Bath

Dec. 18 – 25

$607 CAD per night

Guest favourite

Condo in Marco Island

4.92 out of 5 average rating, 250 reviews

Elegant Beach Vacation Condo, Unbeatable Location

Jun. 9 – 16

$364 CAD per night

Guest favourite

Condo in Naples

4.87 out of 5 average rating, 218 reviews

Park Shore Walk to Beach!

Apr. 3 – 10

$525 CAD per night

Home rentals with a private pool

Home in Marco Island

4.83 out of 5 average rating, 6 reviews

Lighthouse 1124

Apr. 20 – 27

$976 CAD per night

Guest favourite

Home in Cape Coral

4.92 out of 5 average rating, 72 reviews

Luxury Waterfront Home with Pool

Jul. 16 – 23

$489 CAD per night

Guest favourite

Home in Cape Coral

5.0 out of 5 average rating, 16 reviews

Awesome Location W/boat Dock, Pool, & Kayaks!

Apr. 24 – May 1

$588 CAD per night

Home in Cape Coral

5.0 out of 5 average rating, 4 reviews

Blue Oasis

Apr. 28 – May 5

$407 CAD per night

Home in Marco Island

4.86 out of 5 average rating, 7 reviews

Sandcastle of Marco Island Waterfront Private Pool

Aug. 13 – 20

$511 CAD per night

Home in Fort Myers Beach

147 Curlew St

May 10 – 17

$809 CAD per night

Home in Bonita Springs

New place to stay

Coastal Waterfront Home W/pool-Tiki-Dock

Mar. 2 – 9

$1,228 CAD per night

Quick stats about vacation rentals with a pool in Naples

Total rentals
870 properties
Rentals with dedicated workspaces
500 properties have a dedicated workspace
Pet-friendly rentals
240 properties allow pets
Family-friendly rentals
730 properties are a good fit for families
Total number of reviews
13K reviews
Nightly prices starting at
$41 CAD before taxes and fees

Destinations to explore