
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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Popular amenities for Old Naples rentals with a pool
House rentals with a pool

Briarwood Paradise - The Briarwood Rental Company
This is the second time we've stayed at this house, and the third time with Marc and Anne as hosts. They're great! The house is very complete, tidy, there are plenty of towels and the kitchen is a 10. I recommend opening the windows and letting the sun in. It's a super bright house. The patio is always our meeting place: between the pool and the barbecue. We had a problem with the dryer, and Marc was absolutely prompt, attentive and helpful. The weather didn't help, but we still had a FANTASTIC time. The house has bicycles, which we enjoyed riding around the neighborhood, which is beautiful. Thanks for having us once again. We really take care of and feel at home in your home. Because that's how you make us feel, really well taken care of. THANK YOU FOR EVERYTHING ❤️

Charming Heated Pool Villa - minutes from beach
We live in Estero, but our children & grandchildren were visiting & I needed a larger place with a pool to accommodate everyone. It was exactly as we needed. Quiet, peaceful, private & enjoyable. We brought our cornhole board & large jinga blocks, so it was perfect combo with what he already offered for our family.

Modern Home in Naples w/ Heated Pool
First time going through Airbnb and it did not disappoint. Michele made everything go as smooth as possible with check-in, recommendations for places to eat/beaches to visit, and being very responsive. House was exactly as described from the amenities to the pictures provided. We would definitely rent this house from Michele again if we are in the Naples area. Thanks Michele for providing my family and I a great place to stay and enjoy while we were in Naples.

Cathedral Heights
We had a great stay! The host is very accommodating and great communication. The home was beautiful.

Perfect 2 Bedroom House w/ Pool!
First time in Naples and 10/10 would stay here again. Everything was very clean and looked how it was in pictures. Inside and outside was beautiful, backyard was amazing pool was very clean and all amenities were a nice addition. Samuel was also very responsive and gave very clear instructions on everything as well as many recommendations for the area!

Beautifully private homeHeated Pool/Spa and Cabana
We have stayed with Karrie and Todd before and have loved their beautiful home. We have had the privilege of staying at her other space as well and loved the quality of decor, cleanliness, and friendliness of our hosts!! Will stay and recommend both places in the future

“Estey Oasis” Heated Pool! Near Beach & 5th Ave.
Jesse’s home was clean and had an easy check in process. Everything listed n description as far as amenities was accurate. The area was quiet and was a quick 8 minute drive to Naples downtown area. Check out was easy as well with clear instructions given the day before along with what needed to be done before leaving. If we ever stop by Naples again we know where to stay for an affordable and family friendly home.

Your Oasis in Naples! Saltwater Heated Pool!
Excellent stay. Well equipped, responsive hosts, so comfortable. Loved the pool area, kitchen and dining area, master bed and bath - excellent. Would highly recommend!
Apartment rentals with a pool

EBT 206C Exceptional Panoramic Gulf Views +2 Bikes
We had an incredible week at this beautiful Ft. Myers Beach condo! From the moment we booked, Caihlin was warm, responsive, and extremely thoughtful—providing clear check-in instructions, local tips, and even a care package that made us feel right at home. The location was unbeatable. Mornings spent sipping coffee on the deck while watching dolphins glide by felt like a dream. The beach, just steps away, was private and peaceful—a perfect escape from the crowds. We tried several of the recommended restaurants and weren’t disappointed once. It’s clear Caihlin truly knows and loves this area. We left feeling refreshed, grateful, and already plotting our return. Highly recommend this stay to anyone looking for a little slice of paradise!

Lely Greenlinks Golf Resort Luxury Condo
We had an amazing time. The condo was extremely clean and had everything you could need and more. I am extremely organized and felt like I was right at home. lol. We will definitely stay here on future trips to Naples!

25% OFF | Beach 3mi | 2HtPools | Tennis | Bikes | PB
Beautiful place at Naples , blocks away from the beach and the zoo, close to explore what Naples has to offer. The condo was clean well organized, we felt right at home Tamara is a great host and she was very attentive asking how we doing , making sure everything was going well with us. I would come back

Cool Condo for your Cozy Stay
Dovile's condominium was perfect for our family of four. It was just like the pictures and was very clean and well stocked. It was also very convenient to Naples, Marco and the Everglades. We loved being able to walk to tennis, pickleball and the pool and we really enjoyed the wonderful golf at Lely! Dovile's responses were always extremely timely, kind and answered any and all of our questions. We loved our stay and would definitely stay there again! Thanks so much, Dovile for being such a great host and for renting us your fantastic condominium! All the best, John and Julie

Park Shore Resort Beautiful Top Floor 2 Bed 2Bath
I have stayed in no fewer than 8 different units at PSR over the years and this was by far the most highly finished, nicest, most-well-outfitted! Will definitely stay again. Lauren has done a fabulous job and has really thought of everything!

Park Shore Resort, Top Floor BLDGH #347-Lake view
Josh’s unit is newly updated and has everything you need for your stay. It’s lovely. Josh is very responsive. Even our building’s elevator is new! The pool area is well maintained . Hog Harry’s restaurant on site was our delightful bonus. Good food and great service. We’ll be back!

Beautiful Pool 5m to the Beach Downtown & Shopping
I loved this place!! We had a really great family time. The property was very nice and clean which was super important to me because I went with my 5 months old baby. The host was super nice and gave me all the instructions that I needed before the check-in. I would highly recommend this place!!!!!

Casa Bonita - Relax @ The Beach (Newly Remodeled)
The unit was exactly as described—clean, comfortable, and well-equipped. The location was excellent, and it had everything I needed to make breakfast each morning. While the grounds are still recovering from the hurricane, with some visible damage, the pools are open and fully functional. Overall, it didn’t detract from an enjoyable stay.
Quick stats about holiday rentals with a pool in Old Naples
Total rentals
230 properties
Nightly prices starting at
₹6,018 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
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- Naples Beach
- Captiva Island
- Lovers Key Beach
- Clam Pass Park
- Barefoot beach Bonita Springs,FL
- Tigertail Beach
- The Club at The Strand
- Worthington Country Club
- Seagate Beach Club
- Delnor-Wiggins Pass State Park
- Heritage Bay Golf & Country Club
- Panther Run Golf Club
- Bonita National Golf & Country Club
- LaPlaya Golf Club
- Morgan Beach
- Cypress Woods Golf & Country Club
- The Quarry Golf Club Naples
- Talis Park Golf Club
- Gasparilla Island State Park
- Esplanade Golf & Country Club of Naples
- Park Shore Beach Park
- Sanibel Island Northern Beach
- Boca Beach
- Manatee Park