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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 Fort Myers Beach
5 out of 5 average rating, 7 reviews

NEW! Across from BEACH! Private Heated Pool!

EricRating, 5 stars2 weeks ago
It's a nice, new, house. Location is great. About a mile south of the busy area on Ft. Myers Beach. About a block to the beach. The pics show the beach entrance under a condo, but the condo has a ton of signs prohibiting beach access. We used it without a problem and there is public beach access 1/2 block south. The island is still recovering from IAN, be prepared for some construction noise.
Top guest favourite
Home in Bonita Springs
5 out of 5 average rating, 31 reviews

Modern spacious home with private heated pool

BenRating, 5 stars1 month ago
Had a great stay at this home. Home has everything you could need for the stay and loved the location between Fort Myers and Naples. Easy drive to everything the area has to offer. Will definitely look to stay again.
Guest favourite
Home in Fort Myers
4.88 out of 5 average rating, 40 reviews

Welcome Ft Myers 3br/2ba pool vacation- dogs ok

JessicaRating, 5 stars2 weeks ago
The place was a nice getaway for our family. It was close to some of our favorite beaches. The area was peaceful. The neighbors were friendly. Our host was fast to respond to any questions. Thanks for the fun stay.
Superhost
Home in Fort Myers
4.85 out of 5 average rating, 108 reviews

Casa Las Palmas 3BD/2BH/Heated Pool Home

SammyRating, 5 stars1 month ago
We stayed here for a wedding with a group of friends. It was conveniently located and the pool table, ping pong table and pool were great amenities to have! Quiet neighborhood, with a private backyard. There were limited items in the kitchen (like pans, glasses), but we made it work and found that we overall had what we needed. The rooms were clean and cozy. The couch was very comfortable. The soaps in the shower were not full, but we brought our own anyways. Lidiana was very responsive to messages whenever we had a question. Thanks for hosting us!
Guest favourite
Home in Fort Myers
4.95 out of 5 average rating, 122 reviews

Private Heated Pool and Spa

ChristineRating, 5 stars2 months ago
Great place! Very clean and dog friendly. Alex was responsive within minutes of any questions. Would definitely stay again
Superhost
Home in Pelican
4.85 out of 5 average rating, 34 reviews

Tropical House with Pool

NormaJeanRating, 5 stars1 week ago
Awesome place to stay! There were plenty of beds for everyone, and the pool was super nice to hang out by. The host was very nice and made everything easy for us. Would definitely come back!
Superhost
Home in South Naples
4.6 out of 5 average rating, 10 reviews

Naples Home with Private pool + Lely Resort access

PaulRating, 5 stars1 month ago
Walking into the house was great. The Handbook outlined all the essentials on house operation & had great suggestions of local hotspots. The pictures lived up to reality & the beds were very comfortable, great water pressure & extra ice in the freezer. We said if you think of something you needed Adele had it. The screened in heated pool area was spacious, comfortable and the water temp was great. We used the spa tub bubbles to rejuvenate on the last day and should have used it everyday…yes the bubbles are that good. Would we rent again, YES!
Guest favourite
Home in Fort Myers
4.91 out of 5 average rating, 23 reviews

Family Villa w/ private pool and hot tub!

DanielleRating, 5 stars1 week ago
Caleb's place was beautifull, spacious, and clean. The community center amenities were fantastic! Our family had a wonderful time and would definitely stay there again.

Apartment rentals with a pool

Guest favourite
Apartment in South Naples
4.93 out of 5 average rating, 161 reviews

Lely Resort Luxury Condo-2 Spectacular Pool/Golf

MellanieRating, 5 stars6 days ago
We really enjoyed our stay at this condo. Everyone at the tennis/pickleball courts were friendly, and we got in good practice and games. The pool and hot tub were a great way to end the day. Ken was responsive to any of my questions. Close to grocery stores and shopping. Ken gave great recommendation for visiting the beach.
Guest favourite
Apartment in Fort Myers
4.76 out of 5 average rating, 84 reviews

Sunny Florida condo!

JesseRating, 5 stars3 weeks ago
One of my favorite Airbnb rentals to date. The condo was clean, quiet and had everything we needed/wanted. On top of the space being great, Ken and Becky were amazing hosts. I usually stay in different places each time, but I'll be staying here anytime I'm in or near Fort Myers it's that good. 100% recommend booking with them !!
Top guest favourite
Apartment in South Naples
5 out of 5 average rating, 29 reviews

Gorgeous Condo with 2 Bedroom, 2 Bath, Pool

RonRating, 5 stars4 days ago
This place exceeded our expectations. The condo was very clean with many amenities. The pool was heated to a perfect temperature. Having restrooms at pool was nice. Beds were comfortable. Having a wagon and beach chairs were so helpful to have. Even enjoyed the games left by host. Having grocery within walking distance was a bonus. We were there for US Open pickleball tournament only 5 miles away, very convenient. Highly recommend this place.
Top guest favourite
Apartment in South Naples
4.95 out of 5 average rating, 106 reviews

Cool Condo for your Cozy Stay

SandraRating, 5 stars5 days ago
We absolutely loved our stay at Dovile’s condo!! It truly exceeded our expectations. We felt so at home and comfortable. It is everything the description states and more. We loved the beautiful pool just steps away and met some very nice people there. I took a few morning walks and really enjoyed taking in the beautiful grounds at Green Links and Lely. Naples Beach, Isle of Capri, Marco Island, Bayfront, Tin City, and the Naples Zoo are a few of the places we visited just a short drive from the condo. I would definitely love to stay there again!!
Top guest favourite
Apartment in South Naples
5 out of 5 average rating, 33 reviews

Lovely 2-bedroom condo with pool

EliRating, 5 stars2 weeks ago
The place is perfect and as advertised -- the pictures do it justice. It was great for our family stay and I would highly recommend it. Lidia is wonderful to deal with and a great host. The pool was warm and perfect -- we just loved it there.
Top guest favourite
Apartment in Fort Myers Beach
5 out of 5 average rating, 7 reviews

Beach condo on yachat marina

SheriRating, 5 stars2 weeks ago
Karley’s place exceeded our expectations. Very peaceful neighborhood. Very friendly people in the neighborhood. The condo had everything that we needed. The lanai was my favorite spot! We even got to fish just a few steps from the door. Very comfortable and super clean condo. We rented e-bikes just a 5 minute walk away. They were great for passing backed up traffic going towards Times Square at the beach. We also rode them all the way back on the shoreline. It was awesome! We would definitely not hesitate to stay there again. Any questions that we had were answered super quick. Great host and co-host! Thanks again Karley and Kelly for letting us stay at your place!
Guest favourite
Apartment in East Naples
4.89 out of 5 average rating, 36 reviews

Casa Di Napoli: 2/2 Chic Retreat/Private Pool

JazlynRating, 5 stars3 weeks ago
We LOVED this bnb from the moment we arrived! Anthony went above and beyond to make us feel like we were on vacation, but still at home. The house is beautifully decorated which we loved. This air bnb is a main reason we would come back to Naples to visit, and I would recommend it to all of my friends !
Top guest favourite
Apartment in Park Shore
4.91 out of 5 average rating, 159 reviews

Park Shore Resort Modern Top Floor 2 Bed 2 Bath

MohitRating, 5 stars4 months ago
Lauren has done up the place very well and having beach towels and beach chairs really helped us. The place is clean and the view from the balcony overlooking the water body is gorgeous. Having a pull out sofa in the living area is an added bonus. The best part is that good eateries and a grocery store are walking distance from the apartment. Lauren is extremely responsive and helped us whenever we needed it. We would certainly like to stay here again if we visit Naples.

Quick stats about holiday rentals with a pool in Old Naples

  • Total rentals

    230 properties

  • Nightly prices starting at

    £53 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