Family-friendly holiday rentals in Old Naples

Find and book unique family-friendly homes on Airbnb

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Popular amenities for Old Naples family-friendly rentals

Family-friendly home rentals with a hot tub

Superhost
Home in Caloosahatchee
4.86 out of 5 average rating, 22 reviews

Luxury Sailboat Access Pool/Spa Home by Yacht Club

DavidRating, 5 stars3 months ago
Best house we have stayed in. We rebooked for next year! The host went above and beyond for our 3 month stay! Can’t wait to come back in December!!!
Superhost
Condo in Sanibel
4.88 out of 5 average rating, 32 reviews

Shorewood 1C

NathanRating, 5 stars2 months ago
Our family of five had a great time. The place was very nice, the pool was great and warm. We essentially had it to ourselves most of the time. From the pool it was a short walk to the beach. My kids enjoyed the tennis courts, pickle ball option as well and basketball court. The interior was very nice. We all had a great time.
Guest favourite
Apartment in Fort Myers Beach
4.75 out of 5 average rating, 56 reviews

304 Lovers Key Resort Condo

WhitneyRating, 5 stars3 months ago
We enjoyed 6 days here and were so sad to come home. We didn’t want to stay downtown in fort Myers beach area and wanted something a little more quiet, this place was perfect. It’s situated in a great location, 15 min from fort myers beach and 10 min from Bonita springs if you want to get out and explore. Also right next to lovers key state park which was a must see. The condo was just as described and the views were amazing, we saw dolphins almost every morning while eating breakfast, it was magical! Very spacious bathroom and kitchen area. Bonus points came with beach chairs and an umbrella so we didn’t have to worry about renting at the beach. We would definitely come back to this rental!
Superhost
Apartment in Fort Myers Beach
4.67 out of 5 average rating, 105 reviews

Great Resort! Large Heated Pool / Hot Tub

LaurieRating, 5 stars1 week ago
Best place ever!!! Highly recommend to everyone! Will book it again in future!! Super GREAT! Owner is lovely to work with…
Superhost
Condo in South Naples
4.91 out of 5 average rating, 11 reviews

Seagrape - Best View in Lely, Coastal Golf Villa

FranklynRating, 5 stars48 months ago
This property is literally unbelievable! If you’ve never been there, I honestly envy you simply because that first time feeling of walking in is priceless. Everything in the photos was literally as described. The condo had everything you would think a vacation home should have. The kitchen is fully stocked - you will not need to purchase anything. From beach chairs and an umbrella to laundry detergent. Outstanding decor and furnishings. Well kept property that entices you to return. The location is great and easily accessible to restaurants and shops. The golfing community property is simply priceless! The pool/gym/hot tub are clean and well maintained. We were beyond satisfied and had such a remarkable experience, we decided to extend our stay one more night. The hosts were phenomenal and kept us up to speed with all details for check in and check out all throughout the stay. We will definitely be coming back. I highly recommend this property.
Top Guest favourite
Home in Estero
4.89 out of 5 average rating, 98 reviews

SERENE & ATTRACTIVE 3BR HEATED POOL/SPA HOME

CharlieRating, 5 stars8 months ago
Enjoyed this just as much as the first time we stayed here. If we come back down this way we will definitely book Lis & Tim's place.
Guest favourite
Condo in Fort Myers
4.97 out of 5 average rating, 120 reviews

2nd Floor Beachfront Condo Sanibel Harbour

YvonneRating, 5 stars3 weeks ago
The place was exactly as described—clean, comfortable, and well-equipped with everything we needed. The check-in process was smooth. The location was peaceful, perfect for relaxing. We especially enjoyed being right on the water for the beautiful sunsets.
Superhost
Condo in Fort Myers Beach
4.94 out of 5 average rating, 50 reviews

Lover's Key Resort Unit #807

LuAnnRating, 5 stars2 months ago
We had a wonderful stay! We came to Florida for our anniversary and were happy to find Kevin's place. The Condo was beautiful and supplied with everything we needed. It was very quiet and private. We enjoyed the view of the Gulf from the balcony. The pool area was very clean and not crowded. Flippers Restaurant had exceptional food every time. We would definitely stay here again! Highly recommended.

Family- and pet-friendly home rentals

Superhost
Condo in Sanibel
4.73 out of 5 average rating, 132 reviews

Sanibel Romantic Getaway

MicheleRating, 5 stars1 month ago
We had a wonderful week at Nancy’s place! It was just right for my husband, me, and our small dog. Location is great and it’s an easy walk to the beach! While small, the apartment has all the necessities. We particularly liked that there is a bike rack and the house is beside a bike path.
Superhost
Home in Fort Myers Beach
4.89 out of 5 average rating, 233 reviews

La Casa On Mango, heated pool-5 min walk to Beach

MandyRating, 5 stars5 months ago
Location is close enough to bike into downtown FMB and to the Publix, and we did both during our stay! The kids enjoyed the pool. House was stocked with everything you'd need for a day at the beach, which was much appreciated!
Superhost
Home in Naples
4.93 out of 5 average rating, 29 reviews

Tivoli Paradise Salt Pool & Spa Villa with a Water

PeterRating, 5 stars5 months ago
We had a wonderful stay at Derek’s place. Quite frankly, it is the perfect Airbnb. It is a beautiful house in a beautiful neighborhood in beautiful condition. Everything worked perfectly, and Derek was always available within information to assist us with anything we needed. I look forward to the time where I can stay here again.
Guest favourite
Cottage in Naples Park
4.82 out of 5 average rating, 106 reviews

Cozy Cottage Near Vanderbilt Beach

ColleenRating, 5 stars2 weeks ago
It was a wonderful stay! Ben was very kind and provided wonderful service during our stay. He provided bikes so we wouldn’t have to pay for parking and it was only 10 minutes to the beach. If you’re looking for a quiet vacation, this is the place to be! The home was plenty of space to host friends family or even furry companions.
Superhost
Townhouse in Fort Myers
4.87 out of 5 average rating, 192 reviews

Hideaway at Hidden Palms Cove

DakotaRating, 5 stars1 month ago
It was very nice! It was close to Sanibel island and near by restaurants. The place was clean! We stayed here on a work trip and it worked for us
Guest favourite
Home in Fort Myers
4.95 out of 5 average rating, 124 reviews

Private Heated Pool and Spa

TimRating, 5 stars1 month ago
This was our second time at Alex's house. Gets better every year. Alex is very accommodating.
Superhost
Home in Fort Myers
5 out of 5 average rating, 11 reviews

Lovely home nestled near Sanibel & Ft. Myers Beach

LindaRating, 5 stars15 months ago
Beautiful house in convenient location! Neighborhood was quiet and the pool was great! Host was very responsive when we had a couple of minor issues (that were addressed immediately). We very much enjoyed our first snowbird experience!!
Top Guest favourite
Home in Naples Park
5 out of 5 average rating, 93 reviews

Value In Naples Grand SPA Pool Home Walk To Gulf

LesiaRating, 5 stars2 weeks ago
We had a great stay! The home is clean, cozy, and has everything you need. The beach is very close, which made our trip even better. We truly enjoyed our time here and definitely recommend this place!

Family-friendly home rentals with a pool

Superhost
Home in Naples
4.93 out of 5 average rating, 14 reviews

Modern Briarwood Naples 4 Bdr Villa with Lakeview

SandyRating, 5 stars28 months ago
Very responsive and friendly hosts. Lovely house on a pond in a gated community. House is large with attractive furnishings and decor. Great for families or friends vacationing together.Great for biking . Close to shopping , wildlife habitats, parks and beach.
Superhost
Condo in Vanderbilt Beach
4.86 out of 5 average rating, 87 reviews

Naples Beach Getaway

AndrewRating, 5 stars1 month ago
Kelly was extremely responsive with clear check i/building access instructions. Pictures don’t do the unit justice and it bugger than we realized. Beautiful view of ocean and canal. Walk to ocean is approx 5min and easily accessible through private walkway. Thank you for the wonderful stay and look forward to returning!
Condo in Naples
4.83 out of 5 average rating, 150 reviews

Top Floor, A+ Location, Club Membership Included!

RobRating, 5 stars1 month ago
Comfortable location with easy access to North Naples and a quick drive into downtown. Nice value. Comfortable beds and enough space to relax. Pool and club were pleasant and not crowded.
Home in Naples
4.78 out of 5 average rating, 101 reviews

Woodridge: Work Friendly, Pool, Near Beach

AlexanderRating, 5 stars2 months ago
A very comfortable stay! Would highly recoommend this home for traveling throug the Naples area. Was visiting the area for work and this place had everything we needed. Fully stocked kitchen, bathroom supplies, comfortable beds and thoughtful touches throughout the space. Quiet nighborhood, easy parking. Outdoor pool and seating area was everything we were looking for. Could have used a bit more outdoor lighting to enjoy the space in the evenings better but otherwise it's a great home!
Guest favourite
Apartment in South Naples
5 out of 5 average rating, 11 reviews

Minutes to 5th Ave-No steps-Lakefront-End Unit

LiseRating, 5 stars4 months ago
This was our first time using Airbnb so we were not familiar with the process. Matt was amazing and helpful from the beginning to end. Everything that could ever need is already there. House was amazing, well maintained and clean. Nice pool very clean, everyone is friendly and very secured place. Would highly recommend to anyone. We will absolutely be visiting again. Thank you Matt.
Home in East Naples
4.93 out of 5 average rating, 129 reviews

Heated Pool Home, Close to Downtown

KristonRating, 5 stars1 month ago
We stayed with our parents for a 5 day trip for pickleball US Open. short 10 to 12 minute drive. Plenty of space for seating in living room and great layout with comfortable beds. Plenty of toilet paper, toiletries, and kitchen well stocked. Communication was great and friendly. The pool was relaxing and did need a sweep for buggies with the skimmer net. Mostly updated in kitchens and baths. Some signs of age with flooring and windows but not an issue for us!! Would stay again.
Guest favourite
Home in Naples Park
4.89 out of 5 average rating, 101 reviews

"Sonset" Close to Vanderbilt Beach

DariiaRating, 5 stars10 months ago
I recommend this house for a vacation! All clean, neat. Great location. The pool is the top. The host always responds very quickly and tries to make our vacation go 100% . We will definitely come back here again
Guest favourite
Home in Bonita Springs
4.79 out of 5 average rating, 53 reviews

Canal heated pool house access to Golf and Gulf

BillRating, 5 stars1 week ago
First time we stayed at Micheline's house. It was just like the listing said. The house and pool are very private and it is in a quiet neighborhood. Check in was extremely easy. The house was very clean and had everything one would need. There are many options for any type of restaurant one would want within minutes of the house. Bonita Beach is a very short drive and there are many other beaches close by. We spent most of our time relaxing on the lanai and enjoying the pool. Had a wonderful time and are hoping to return in the fall. Bill

Quick stats about holiday rentals that are family-friendly in Old Naples

  • Total rentals

    220 properties

  • Nightly prices starting at

    $117 NZD before taxes and fees

  • Total number of reviews

    2.5K reviews

  • Pet-friendly rentals

    30 properties allow pets

  • Rentals with a pool

    170 properties have a pool

  • Rentals with dedicated workspaces

    110 properties have a dedicated workspace

Destinations to explore

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