Top Naples rentals with pool or private pool - Florida

Explore Naples rentals with pools

Bellasera Resort

Sleeps 4 · 1 bedroom

Fifth Avenue Beach Club entrance from 5th Avenue South

BEACH DREAMING Luxury condo, newly renovated on 5th Ave; Steps to beach & dining

Sleeps 4 · 2 bedrooms · 2 bathrooms

Your Serene Escape Awaits Discover Paradise in Naples at Park- near beach & golf

Sleeps 4 · 2 bedrooms · 2 bathrooms

Top rated rentals with pools - Naples

Premier Host

Lovely stay at Naples Cay

We enjoyed our stay at Club 103. The apartment is spacious and very well appointed. We were pleased to find everything clean and tidy. Highly recommended for either couples or families. The Pool is very nice and whist well used. We had no issues with finding loungers. The Beach is nearby, and is indeed very nice and reasonably quiet. So ideal for a lovely holiday.

Simon W.

Stayed Apr 2025

Premier Host

Excellent Condo in upmarket resort and town

The Naples Bay Club condo we stayed in was everything we had hoped for and more. No complaints, just praise. The Club itself was clean with a lovely pool area that we used every day. The Adults only area was particularly well appreciated.

Kevin M.

Stayed Sept 2024

Premier Host

Excellent apartment and views

We had a great stay in Naples Cay. The apartment is perfectly situated for walks along the beach, for watching the sunsets over the gulf coast and we particularly liked the pool area. Checkin was straightforward and the apartment was extremely well equipped for our needs and very clean and comfortable. We would definitely recommend

Tina G.

Stayed May 2024

Large private Lanai, living room to the right, indoor-outdoor living at its best

Premier Host

Naples holiday

quiet location but only 5 minutes from beach and downtown, host responded immediately to any questions and queries we are long term visitors to Naples and would 100% stay at this home again

David B.

Stayed Jul 2023

Great property in an ideal location

This is one of the best properties we have rented in SW Florida and have been coming to the state for 40 years. Impeccable cleanliness throughout and many of the appliances seem to be brand new. The location is also superb with an excellent restaurant/bar (Hogfish Harry's) in walking distance and a Publix and other shops also in walking distance. Highly recommend T-Michaels fine dining restaurant on Venetian Bay (3 minute drive). Use of a private beach was also a plus although we prefer the beaches in Anna Maria and Marco over Naples. One small gripe was a poor electric BBQ (which was also new but very flimsy and difficult to clean) rather than a conventional gas grill. However, we had a great 2 weeks in the property and can highly recommend it. We will be back!

ian j.

Stayed Jun 2023

Beautiful condo

Really enjoyed our stay, enjoyed sitting on the balcony looking at the view. High standard of cleaning, would stay again.

Carol Y.

Stayed May 2023

Nicely Presented. Illa

Lovely home with good facilities and outside area which the whole family used a lot. Set in a quite neighbourhood close to the beach. We thoroughly enjoyed our stay.

Mark W.

Stayed Jun 2022

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Frequently asked questions

Are there any holiday rentals with a pool in Naples?

Pick from 5,120 holiday rentals with a pool in Naples that offer all the space, privacy and amenities you need for a splashing good time. Check out houses in sought-after neighbourhoods such as Old Naples, Oyster Bay and Ridge Lakes.

How much does it cost to stay in a holiday rental with a pool in Naples?

If you're hoping to save on your holiday rental with a pool, our filters can help. Once you've done your initial search, tailor your results according to your preferences, including location, total price and features and amenities. We've got properties in Naples for all types of budgets, so make the most of our filters to discover your dream stay.

When is the best time to book a holiday rental with a pool in Naples?

With temperatures ranging from 16ºC (61ºF) to 22ºC (72ºF), January is when many Vrbo guests plan their stay. Be sure to browse our holiday rentals with a pool in this part of Collier County during other months too. You may find better availability if you avoid Naples's busier months.

What holiday rentals with a pool in Naples have nice views?

After a big day out, head back to your holiday rental with a pool to kick back poolside. The icing on the cake? Some of these stays in Naples also come with gorgeous beach views.

Are there holiday rentals with a private pool in Naples?

Day or night, go swimming whenever you want when you book a holiday rental with a private pool in Naples. To search for Vrbo properties that'll boost the fun factor during your trip, use our "Private pool" filter.

What are the top things to do in Naples?

Fun times in Naples await for the family when you book a holiday home rental with a pool. On top of visiting well-known attractions like Naples Zoo at Caribbean Gardens, Barefoot Beach and Tin City, you'll be able to spend your downtime practicing cannonballs.

Why should I book my holiday rental with a pool with Vrbo?

When you choose a Vrbo holiday rental with a pool, the only people you'll share your living space with are the people you take with you. It will only be you and your nearest and dearest with the entire place to yourselves having a splashing good time. Also, with our free rewards programme, One Key™, you can collect and use OneKeyCash™* on eligible bookings made through Vrbo. Plus, our flexible cancellation policies also mean you can book your rental house with peace of mind if your plans change. *OneKeyCash disclaimer - OneKeyCash is not redeemable for cash and can only be used on Vrbo.