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Holiday 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

Guest favourite
Home in East Naples
4.93 out of 5 average rating, 58 reviews

* When in Naples *Heated Pool Villa, 2mil downtown

JustinRating, 5 stars3 weeks ago
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.
Top Guest favourite
Home in Naples
5 out of 5 average rating, 27 reviews

Briarwood Paradise - The Briarwood Rental Company

GuadalupeRating, 5 stars4 months ago
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 ❤️
Guest favourite
Home in Naples
5 out of 5 average rating, 10 reviews

Waterfront w/Pool & Patio - Close to Everything

JulieRating, 5 stars6 days ago
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.
Guest favourite
Home in Naples
4.9 out of 5 average rating, 110 reviews

Charming Heated Pool Villa - minutes from beach

LauraRating, 5 stars5 days ago
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.
Top Guest favourite
Home in Naples
5 out of 5 average rating, 15 reviews

Modern Home in Naples w/ Heated Pool

JeffreyRating, 5 stars1 month ago
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!
Top Guest favourite
Home in Naples
5 out of 5 average rating, 46 reviews

Private Pool, Spa, Minutes to the Beach &King Bed

PatrickRating, 5 stars1 week ago
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!
Guest favourite
Home in East Naples
4.93 out of 5 average rating, 151 reviews

“Estey Oasis” Heated Pool! Near Beach & 5th Ave.

Miranda KateRating, 5 stars1 week ago
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!
Guest favourite
Home in Naples
4.96 out of 5 average rating, 69 reviews

Attention Naples Lovers! Entire Home w/Pool&HotTub

AlondraRating, 5 stars2 weeks ago
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

Top Guest favourite
Condo in Pelican Bay
4.97 out of 5 average rating, 33 reviews

Westshore Naples Cay #202- Stunning Ocean view

KimRating, 5 starstoday
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!
Guest favourite
Condo in Fort Myers Beach
4.81 out of 5 average rating, 107 reviews

EBT 206C Exceptional Panoramic Gulf Views +2 Bikes

JeffRating, 5 stars1 month ago
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.
Top Guest favourite
Condo in South Naples
4.96 out of 5 average rating, 313 reviews

Lely Greenlinks Golf Resort Luxury Condo

KristenRating, 5 stars2 months ago
Justin’s condo had everything we needed for our stay, and then some. Would stay again for sure.
Guest favourite
Condo in Naples
4.95 out of 5 average rating, 22 reviews

25% OFF | Beach 3mi | 2HtPools | Tennis | Bikes | PB

JennieseRating, 5 stars5 days ago
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.
Top Guest favourite
Condo in South Naples
4.95 out of 5 average rating, 107 reviews

Cool Condo for your Cozy Stay

JohnRating, 5 stars3 weeks ago
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
Guest favourite
Condo in Park Shore
4.98 out of 5 average rating, 48 reviews

The Club at Naples Cay 501 - Gulf Views

NatalieRating, 5 stars1 week ago
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!
Top Guest favourite
Condo in Park Shore
4.86 out of 5 average rating, 49 reviews

Renovated Beautiful Condo In Tropical Paradise

CamilleRating, 5 stars4 weeks ago
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!
Top Guest favourite
Condo in Bonita Springs
4.98 out of 5 average rating, 129 reviews

Casa Bonita - Relax @ The Beach (Newly Remodeled)

EmilyRating, 5 stars1 week ago
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

Destinations to explore

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