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Vacation rentals with a pool in Old Naples

Find and book unique homes with a pool on Airbnb

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Popular amenities for Old Naples rentals with a pool

House rentals with a pool

Top guest favourite
Home in South Naples
4.96 out of 5 average rating, 107 reviews

New Home, 6 Beds, Heated POOL / Game Room

PollyanneRating, 5 stars5 days ago
We had a great stay and are already dreaming of our next visit to Sivys’s. The house was full of essentials, nothing was overlooked. Located in a quiet neighborhood but close to so many local attractions. Beautiful outdoor area where we spent most of our time. Bedrooms and bathrooms were all great sizes. The house was extremely clean and welcoming. No detail was forgotten, a true gem!
Guest favourite
Home in Naples Park
4.89 out of 5 average rating, 18 reviews

Casa Del Mar - Golf Lover's Dream!

Mary KateRating, 5 stars1 month ago
Our stay at this beach house was nothing short of exceptional! From the moment we arrived, we were impressed by how well-appointed and immaculately clean the home was. Every detail was thoughtfully curated, making it feel both luxurious and comfortable. The outdoor space was truly the highlight— a beautiful pool, relaxing spa, and a fun putting green that kept everyone entertained. Whether we were soaking up the sun by the pool or unwinding in the spa under the stars, it felt like our private oasis. The beach was just a short walk away, making it easy to enjoy the ocean whenever we wanted. Inside, the home was stylishly furnished with high-end touches and had everything we needed for a stress-free vacation. The kitchen was fully stocked, the bedrooms were cozy, and the living areas were perfect for gathering.
Top guest favourite
Home in Naples Park
4.97 out of 5 average rating, 74 reviews

Walk to beach New pool & baths w/ Cabana Oasis

LaurenRating, 5 stars1 week ago
We had a wonderful time! Jamie and Christine’s place was perfectly equipped for our trip with two little ones. The kitchen was stocked, the pool was pristine and there were amenities above and beyond- games, cozy blankets, shower, baths and cleaning supplies and beach gear (chairs, towels and sand toys). We loved the unique artwork in the house as well. Jamie and Christine were incredible responsive and thoughtful hosts- They provided great recommendations for the area and easy instructions for entry and checkout. The place was also in a perfect location. We were close to two lovely beaches, grocery stores - Seed to Table is quite the experience- and lots of shopping and restaurants. We would definitely recommend this place to anyone!
Guest favourite
Home in Fort Myers
4.95 out of 5 average rating, 121 reviews

Private Heated Pool and Spa

SherriRating, 5 stars2 months ago
the house was updated and very accommodating. we felt right at home. the outside amenities had the pool, jacuzzi, and an amazing area to sit outside and relax. beds were very comfortable. Alex had great communication and responded quickly. would not only recommend this house, but would stay here again.
Superhost
Home in South Naples
4.6 out of 5 average rating, 10 reviews

Naples Home with Private pool + Lely Resort access

PaulRating, 5 stars3 weeks ago
Walking into the house was great. The Handbook outlined all the essentials on house operation & had great suggestions of local hotspots. The pictures lived up to reality & the beds were very comfortable, great water pressure & extra ice in the freezer. We said if you think of something you needed Adele had it. The screened in heated pool area was spacious, comfortable and the water temp was great. We used the spa tub bubbles to rejuvenate on the last day and should have used it everyday…yes the bubbles are that good. Would we rent again, YES!
Guest favourite
Home in Bonita Springs
4.93 out of 5 average rating, 29 reviews

Beautiful 3 Bedroom house with private pool

DayanaRating, 5 stars1 month ago
Super clean place, very easy to get to the location, there’s every kind of amenity available as listed in the description and most importantly it’s exactly as pictured. Beautiful place and peaceful area. Thank you so much
Guest favourite
Home in Naples
4.9 out of 5 average rating, 31 reviews

Naples Oasis: Heated Pool, Gazebo, Grill Retreat

ValeriaRating, 5 stars1 week ago
Very nice place! Clean, nice area. Very lovely. Only thing I wish the shower heads were better they were a little old but just a little detail that will not ruin the experience. Nice place to stay!
Guest favourite
Home in South Naples
4.91 out of 5 average rating, 34 reviews

Exclusive Luxury Retreat! Stunning Outdoor Space

NatalieRating, 5 stars3 months ago
I would highly recommend Guy and his property! We stayed here with our 4 young children, including an infant. This home is SUPER kid friendly! They have an abundance of pool toys, beach towels, beach toys, a single stroller and even a pack n play! They also have different size coolers to use on outings! We had a few issues pop up during our stay but Guy was on top of all of them. He was super responsive and great to work with! We would recommend this house to any families with young children. Can’t thank him enough for his hospitality!

Condo rentals with a pool

Guest favourite
Condo in South Naples
4.93 out of 5 average rating, 159 reviews

Lely Resort Luxury Condo-2 Spectacular Pool/Golf

NancyRating, 5 stars1 week ago
We had a wonderful stay, loved the pool, restaurant at the golf club, and convienent location. Would come back😎
Top guest favourite
Condo in South Naples
5 out of 5 average rating, 28 reviews

Gorgeous Condo with 2 Bedroom, 2 Bath, Pool

JessicaRating, 5 stars4 months ago
Jenifer and Wally were great hosts. Communication was proactive and very helpful. The condo was great. It had everything we needed and more including all kitchen essentials and beach essentials. The location is perfect being 15 minutes from either Marco Island or downtown Naples. I would highly recommend staying here and would definitely come back. Thank you Jenifer and Wally for having us!
Superhost
Condo in Fort Myers
5 out of 5 average rating, 3 reviews

Sanibel Harbour Resort - 216: Colorful condo

EmmaRating, 5 stars9 months ago
Everything was perfect, the place, the atmosphere, the spacious Apartment, very crean, perfect. I Would return
Top guest favourite
Condo in South Naples
4.95 out of 5 average rating, 105 reviews

Cool Condo for your Cozy Stay

ElizabethRating, 5 stars1 month ago
We enjoyed our stay at Doville’s condo. The location within the Lely Resort was great! We walked to workout every morning then went for a swim. The bike and walking trails were beautiful! All the extra amenities she had in the condo was an added bonus. We used the beach umbrella and chairs to visit a beach in Marco Island one day. So much to do in the area! We already booked for next March!
Top guest favourite
Condo in South Naples
5 out of 5 average rating, 32 reviews

Lovely 2-bedroom condo with pool

EliRating, 5 stars1 week ago
The place is perfect and as advertised -- the pictures do it justice. It was great for our family stay and I would highly recommend it. Lidia is wonderful to deal with and a great host. The pool was warm and perfect -- we just loved it there.
Top guest favourite
Condo in Fort Myers Beach
5 out of 5 average rating, 6 reviews

Beach condo on yachat marina

SheriRating, 5 stars1 week ago
Karley’s place exceeded our expectations. Very peaceful neighborhood. Very friendly people in the neighborhood. The condo had everything that we needed. The lanai was my favorite spot! We even got to fish just a few steps from the door. Very comfortable and super clean condo. We rented e-bikes just a 5 minute walk away. They were great for passing backed up traffic going towards Times Square at the beach. We also rode them all the way back on the shoreline. It was awesome! We would definitely not hesitate to stay there again. Any questions that we had were answered super quick. Great host and co-host! Thanks again Karley and Kelly for letting us stay at your place!
Guest favourite
Condo in East Naples
4.89 out of 5 average rating, 36 reviews

Casa Di Napoli: 2/2 Chic Retreat/Private Pool

JazlynRating, 5 stars1 week ago
We LOVED this bnb from the moment we arrived! Anthony went above and beyond to make us feel like we were on vacation, but still at home. The house is beautifully decorated which we loved. This air bnb is a main reason we would come back to Naples to visit, and I would recommend it to all of my friends !
Top guest favourite
Condo in Park Shore
4.91 out of 5 average rating, 158 reviews

Park Shore Resort Modern Top Floor 2 Bed 2 Bath

MohitRating, 5 stars3 months ago
Lauren has done up the place very well and having beach towels and beach chairs really helped us. The place is clean and the view from the balcony overlooking the water body is gorgeous. Having a pull out sofa in the living area is an added bonus. The best part is that good eateries and a grocery store are walking distance from the apartment. Lauren is extremely responsive and helped us whenever we needed it. We would certainly like to stay here again if we visit Naples.

Quick stats about vacation rentals with a pool in Old Naples

  • Total rentals

    230 properties

  • Nightly prices starting at

    $97 CAD before taxes and fees

  • Total number of reviews

    2.5K reviews

  • Family-friendly rentals

    170 properties are a good fit for families

  • Pet-friendly rentals

    30 properties allow pets

  • Rentals with dedicated workspaces

    110 properties have a dedicated workspace

Destinations to explore

  1. Airbnb
  2. United States
  3. Florida
  4. Collier County
  5. Naples
  6. Old Naples
  7. Rentals with pools