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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

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
4.95 out of 5 average rating, 120 reviews

1 Mile to Beach! Pool, King Bed, BBQ, Games

SonjaRating, 5 stars1 month ago
We loved this location. Everything was as the pictures showed. Dara is absolutely the most helpful host I have ever had the privilege of guesting with. The pool was lovely. The house is set up nicely. There was a nice area to walk the dogs. Everything worked well. The beds were comfy. I would love to stay here again.
Superhost
Home in East Naples
4.89 out of 5 average rating, 28 reviews

Charming Waterfront Tropical Escape Near Downtown

SharonRating, 5 stars2 months ago
An Unforgettable Tropical Getaway! This Airbnb is truly a hidden gem! Nestled right on a serene lake, the property offers a perfect blend of luxury and natural beauty. From the moment we arrived, we were blown away by the stunning landscape—lush tropical greenery, swaying palms, and a peaceful water view that made every morning feel like a dream. The home itself is absolutely gorgeous. Every room is stylishly decorated with antique high-end touches that still manage to feel cozy and inviting. You can tell a lot of thought went into every detail—from the plush furnishings to the vibrant artwork and elegant lighting. We spent our days lounging by the crystal-clear pool and our evenings by the fire pit, watching the sun set over the lake. Whether we were sipping coffee on the patio or enjoying a relaxing swim, every moment here felt like pure bliss. This home is everything you need for a luxurious vacation, relaxing escape or peaceful retreat. Thanks Marco!
Guest favourite
Home in Bonita Springs
4.98 out of 5 average rating, 123 reviews

Luxe Unique: Close to Beach, Hot Tub, Heated Pool

TammyRating, 5 stars1 month ago
We had an amazing stay! The property is just a short drive from the beach and located on a quiet, safe street. Andrew was a fantastic host, super responsive and helpful throughout our stay. The home was spotless and clearly well maintained. The highlight was definitely the beautiful pool and hot tub area, it truly felt like our own private resort oasis. We felt relaxed and right at home the entire time. We’ll definitely be back and highly recommend this place to anyone looking for a peaceful, beachside getaway!
Top guest favourite
Home in South Naples
5 out of 5 average rating, 24 reviews

Mediterranean Inspired Villa with Private MiniGolf

SamRating, 5 stars2 weeks ago
This place was absolutely amazing! The outdoor area and pool were the highlights — beautifully maintained and perfect for relaxing. It truly felt like a private resort. The home itself was tastefully decorated with great attention to detail, creating a cozy yet luxurious atmosphere. We were a big group and the house had plenty of room for everyone. It was stocked with so many essentials, which made the stay super convenient. They even had everything needed for a day at the beach with the whole family. The location was also perfect — close to everything but still peaceful and private. We couldn’t have asked for a better stay and would 100% book again. Highly recommend!
Guest favourite
Home in Naples
5 out of 5 average rating, 19 reviews

Custom Naples 3BDRM Luxe Home/Htd Pool/SuperClean

HunnerRating, 5 stars1 month ago
We didn’t spend a ton of time at the house because we come from out of state; however, our mornings and evenings were so relaxing lounging by the pool, chatting with each other in the open concept living area, and the kitchen table & outdoor patio table was convenient for all of us to enjoy a meal together. The pool was very clean and warm! The back yard (grass area) was A LOT larger than what the pictures portray which we loved for our dog to have space to run! The back yard was very private so we didn’t have to worry about any of the neighbors. Overall, we were very impressed and wish we would have booked for a longer time frame! 10/10 recommend!
Guest favourite
Home in Naples
4.96 out of 5 average rating, 70 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.
Guest favourite
Home in Naples
4.93 out of 5 average rating, 75 reviews

Cozy 2B/2BA Home w/ Heated Pool, 10 Min to Beach

MaryRating, 5 stars3 weeks ago
Clean and uncluttered space. Pool was our favorite place. There were several pool floats available and plenty of seating outside, both in the sun and under cover. Well appointed kitchen. Check in before you go shopping to see what useful items are already included. Plenty of towels are available and the washer and dryer onsite was a great way to wash our clothes during our visit. Next time I will definitely pack less clothing. The huge TV allowed us to utilize our Amazon Prime to watch movies in the evening. Beds were comfortable and all the lights were labeled. Lots of ceiling fans and lighting with places to plug your devices. We will definitely return to rent this house if Tatiana will host us again.😁

Apartment rentals with a pool

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

Westshore Naples Cay #202- Stunning Ocean view

KimRating, 5 stars2 days ago
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!
Top guest favourite
Apartment in South Naples
4.96 out of 5 average rating, 314 reviews

Lely Greenlinks Golf Resort Luxury Condo

BarbaraRating, 5 stars2 weeks ago
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!
Top guest favourite
Apartment 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
Superhost
Apartment in Park Shore
4.92 out of 5 average rating, 104 reviews

Park Shore Resort Beautiful Top Floor 2 Bed 2Bath

KarlRating, 5 stars5 months ago
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!
Top guest favourite
Apartment in Naples
4.92 out of 5 average rating, 127 reviews

Beautiful Pool 5m to the Beach Downtown & Shopping

TanyaRating, 5 stars4 weeks ago
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!!!!!
Top guest favourite
Apartment 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.
Guest favourite
Apartment in Park Shore
4.87 out of 5 average rating, 241 reviews

Park Shore Walk to Beach!

JeannineRating, 5 stars3 weeks ago
Great proximity to Fifth Avenue and Mercato as well as the beach. Was great having a fun restaurant inside at the pool. Good space for two people. Lots of closet space. Host was very responsive and helpful.
Superhost
Apartment in Vanderbilt Beach
4.81 out of 5 average rating, 115 reviews

800' from the beach - Frank & Kim's

BrinRating, 5 stars1 day ago
What a beautiful location! Loved having the pool in the roof when we didn’t want to walk the 8 minutes to the beach. Frank and Kimberly were amazing hosts, and made sure the space was incredibly clean for us. Highly recommend for any amount of time, whether it be a few nights or a few weeks. If you’re looking for a place in Naples, this is the spot.

Quick stats about holiday rentals with a pool in Old Naples

  • Total rentals

    230 properties

  • Nightly prices starting at

    ₹6,058 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