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

* When in Naples *Heated Pool Villa, 2mil downtown
Very clean and beautiful property always a very comfortable stay. Top notch host, very responsive and will take care of anything that may come up highly recommend.

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 ❤️

Waterfront w/Pool & Patio - Close to Everything
This place is just what our family was looking for. The home was clean, with comfortable beds and nice linens. The pool area had privacy, which was nice. The neighborhood was quiet and we liked being right next to the pickleball courts. We did a lot of fishing off the back dock catching catfish and snapper. Only a few miles from the beach. Some great local restaurants nearby. Dara was responsive and helpful with any questions I sent her way. Overall, would highly recommend this stay for a family or friends getaway.

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
We had a really great vacation at Michele’s house. The pool area is huge and very well furnished with a variety of seating areas. Very relaxing! The pool has a lake view and excellent privacy. We had everything we needed and Michele was extremely responsive and informative throughout our time there. Highly recommended!

Private Pool, Spa, Minutes to the Beach &King Bed
We had an incredible stay at this beautiful Airbnb in Naples, Florida. The home was absolutely immaculate — spotlessly clean, modern, and equipped with all the appliances and comforts you could need. It was incredibly family-friendly, with thoughtful touches throughout that made us feel right at home. The swimming pool was a highlight — pristine and perfect for relaxing or playing with the kids. Even on the couple of rainy days we had, the hosts went above and beyond by sending thoughtful gifts for our children, which really made the experience extra special. We truly appreciated the attention to detail and warm hospitality. We couldn’t have asked for a better place to stay and would highly recommend this home to any families visiting Naples. We’d come back in a heartbeat!

“Estey Oasis” Heated Pool! Near Beach & 5th Ave.
This was a great place to stay for our family. The young kids especially enjoyed the splash pad in the pool. It was great for the littles who couldn’t quit swim by themselves. I appreciate that they thought of their guests and had all the extra amenities for us to use during our vacation, especially for the beach. We would absolutely stay again!

Attention Naples Lovers! Entire Home w/Pool&HotTub
Had cozy stay at liliyas. I enjoyed the utensils provided. Most items were new and clean. Really enjoyed cooking breakfast in the kitchen and most items we needed were provided. Beds and rooms were cozy, each with their own AC unit as described. everything was clean overall. Host was responsive and helpful when I needed help getting Hulu onto TV. Would stay again.
Condo rentals with a pool

Westshore Naples Cay #202- Stunning Ocean view
Condo is located in a very beautiful setting that includes 24 hour security. The area is stunning and only a short walk to the beach. View from the balcony is gorgeous! Ocean view and view of the shared pool. Well maintained grounds and very clean! Grills for common use could use some maintenance and a good cleaning but they are centrally located for easy use. Kevin is a great owner! Very responsive and helpful. Condo itself is very nice and comfortable! Some updates would be nice however it offers so many great amenities! Beach wagon, chairs and umbrella are provided however again could be updated. Overall our family believes we found a gem of a condo on a great beach in beautiful Naples! Well done Kevin!

EBT 206C Exceptional Panoramic Gulf Views +2 Bikes
Caihlin was a fantastic host. Very responsive to our questions/concerns. The place was just as beautiful as the pictures showed and we enjoyed everything about it. There were plenty of beach items to use, so we didn't need to purchase anything to enjoy the beach. There were plenty of games to play, books to read and even a drawer full of extra batteries for the TV remote if needed. We even had access to their 2 bikes and took an enjoyable morning bike ride into Fort Myers beach. You will not be disappointed at all with your stay.

Lely Greenlinks Golf Resort Luxury Condo
Justin’s condo had everything we needed for our stay, and then some. Would stay again for sure.

25% OFF | Beach 3mi | 2HtPools | Tennis | Bikes | PB
I stayed with my husband, parents and our 6 month old baby. The apartment was super clean, newly renovated and it had everything we needed for our baby including crib and pack and play. Host was very responsive, friendly and attentive, a true professional. The location is very close to Publix and other shops, overall a great stay.

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

The Club at Naples Cay 501 - Gulf Views
We had a fantastic stay! The condo was immaculate and well-equipped. The beach locker made trips to the uncrowded beach easy, and the pool and landscaping were well-maintained. It was stocked with 10+ beach towels, 5–6 chairs, boogie boards, sand toys and a beach umbrella (the umbrella was broken, but we purchased a new one and left it, along with some extra sand toys). The kitchen had everything, including kids’ cups/utensils, making it very family-friendly. There were even small toys and games for the kids too. The master closet was spacious enough for a pack-n-play. To help future guests pack wisely: the condo has plenty of essentials, so you can pack lighter! This was the first rental that I didn't need to buy laundry soap or dishwasher soap. A few minor issues: the bathroom shower light was out, the laundry door was tricky, and the bathtub had drainage problems that resolved itself out after a couple days. Highly recommend this condo and we are looking forward to returning!

Renovated Beautiful Condo In Tropical Paradise
We had a wonderful stay at Nataliya’s place! She was an amazing host : very responsive, kind, and helpful throughout our stay. The apartment is spacious, very well equipped, and comfortable. The location is great, just a few minutes’ drive from the beach, and the residence itself has great amenities like a pool and a BBQ area. Everything was perfect for a relaxing holiday. We already want to come back, thank you again, Nataliya!

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
$117 NZD 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
- The Quarry Golf Club Naples
- Cypress Woods Golf & Country Club
- Talis Park Golf Club
- Gasparilla Island State Park
- Esplanade Golf & Country Club of Naples
- Park Shore Beach Park
- Sanibel Island Northern Beach
- Boca Beach
- The National Golf & Country Club Ave Maria