
Family-friendly vacation rentals in Englewood
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Top-rated family-friendly rentals in Englewood
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Popular amenities for Englewood family-friendly rentals
Family-friendly home rentals with a hot tub

Gorgeous Home / Heated Pool and Spa
Kayla’s listing exceeded all my expectations. From the moment I booked, communication was seamless and welcoming. The space itself is beautifully decorated, spotless, and thoughtfully equipped with everything you might need for a comfortable stay. The highlight was definitely the pool — it’s great! Perfectly maintained and a fantastic spot to relax and unwind. The heated jacuzzi is also awesome — it’s perfectly functional, warm, and incredibly relaxing, making it a true standout feature of the property. The location is superb — just a few minutes’ drive to the most amazing beach in the USA! It’s the perfect base for exploring and enjoying the beautiful surroundings. Kayla was a wonderful host—friendly, attentive, and genuinely eager to ensure we had a great experience. She provided helpful local tips and made us feel right at home. I highly recommend Kayla’s listing to anyone looking for a cozy, convenient, and memorable stay with fantastic amenities. I can't wait to return!

Canal home short walk to Beach & Village, Heated P
Can’t say enough good things about the house and Steven. The house was beautiful, it was everything we could’ve wanted and to have the additional beach supplies readily available was amazing! Steven answered so quickly and was happy to help however he could. 10/10 for us!!

Siesta Key Serenity At The Palm Bay Club
This is our second year of staying here. Our hosts were very helpful and even left us little treats to welcome us. We arrived on November 8th, 2024. Weeks prior to arrival, they kept us updated on the progress of Hurricane cleanup. Their home is the perfect location. You can enjoy the ocean just across the street or the pool and hot tub with a view of the channel. Their home is clean and includes so many items that would need on this vacation. They were always willing to answer our questions as well as suggestions to make our trip even better. We feel perfectly at home here and can't wait to return next year.

Villa Scottsdale -Waterfront Home with Pool
Very nice place we stayed there while doing some night work for Lee county utility. Place was clean and cozy beds were comfortable over all would not hesitate to use again

Now NEW AUG Openings! Sarasota #1 Lux BEACH Villa
We had a wonderful visit to Casey Key while staying at Christopher and Michelle's place. The pool and hot tub are great amenities and the house was perfect for our needs. Everything was clean and comfortable and the hosts were quick to respond to any questions we had. We hope to return soon!

5min to Siesta, Heated Pool & Jacuzzi, Grill, WiFi
We loved the pool and hot tub. Ben was very responsive when I asked about if there was a speaker we could use and he dropped one off at the front door within minutes. Great location and price was reasonable. We would Definately stay again!

Amazing Lagoon | Rock Grotto Swimming Pool | Spa
Amazing, clean place. Great pool

The Parsonage-Private Villa-Heated Pool & Spa.
This place was perfect for our bachelorette party! Plenty of space and beds for everyone and a short 10-15 min walk from the restaurants and bars in downtown Fort Myers. We loved relaxing by the pool during the day. It felt private, secluded, and safe. Michelle was very helpful and friendly and we greatly appreciated her flexibility during the check in process. Highly recommend this place for large groups!
Family- and pet-friendly home rentals

3 Bed 2 Bath Heated Pool Home with Privacy Fence!
The place was perfect for us and our pups. We will definitely be back!!

The Cottages at Punta Villas - Historic District
Very niece location with easy walk to great restaurants. This home was private and well taken care of. Very kind hosts who were accommodating. Loved the private patio area.

Aloha Villa Pet Friendly 3 miles to Siesta Key #2
I visited Sarasota with my family from the state of Rhode Island from April 4 to April 7 and we stayed at Jason’s & Laura house and it was an amazing experience. The house was very clean and organized. The house is located on a great neighborhood, super safe and great amenities. The house was stocked with beach supplies like beach chairs, beach towels, a boogie board and a beach cooler that was so nice. The house was exactly what we were expecting, I would recommended to everyone. Thank you Josh and laura.

2bed/2bath with POOL house, close by SIESTA KEY!!!
Romualda’s home was very clean, beautiful, and modern. She was very communicated from the time we booked the AirBnb, to the time we checked in, and the time we checked out. We felt right at home as she had many ameneties that were offered and more. We will definately book again next time we are in town.

Pink Flamingo: 4 Beds/3 Baths Screened Pool Oasis
We enjoyed our stay at the Pink Flamingo house. The house was well supplied, and clean. I would definitely recommend this house for any one that has a bigger family to accommodate for. The children enjoyed the heated swimming pool. Yvonne was very easy to work with and always responded when we had questions.

Comfortable cottage only 5 min. to the beach
We spend two happy and relaxed weeks in Angelika‘s house. The location is perfectly located among nature, parks, beaches and great shopping opportunities though a own car is highly recommended. Thank you Angelika! Dita & Franz, Switzerland

Private Siesta Beach House Oasis with Heated Pool.
We had a wonderful time at Andrew's house! The backyard was the highlight for us; the pool area surrounded by beautiful tropical plants. I really wish there was a hammock so I could take a nap under the palm trees! The house is a short drive to the famous Siesta Key Beach, and it also even comes with beach chairs, which was super convenient. I definitely recommend it!

Turtle Nest Retreat - Manasota Key (upper unit)
Dana was an amazing host. The space was beautiful and magical. We can’t wait to return again. Thank you for everything.
Family-friendly home rentals with a pool

Riverview Villa, full refund*, pool heat, sleeps 6
Lisa and Robert not only are great host but very nice and communicative as well!. The place it’s very nice cozy and quiet for a good time to rest.

5 Star Paradise Plus/Canal/Pool/Spa/Kayaks
We had an incredible week in this lovely, inviting, relaxing slice of paradise!! Responsive and friendly hosts, lovely landscaping, private lanai with nice chaise lounge chairs and waterfall hot tub and pool! We were outside enjoying it every day. Comfortable sitting areas, beds, kitchen was stocked with all the dishes and pans we needed to make several meals. Location was great for walks. It exceeded expectations each day! Look forward to returning someday! Thanks again Connie and Dale!!

Waterfront PGI Heated Pool! Near Fishermen's!
This is an incredible house. The location is perfect and private. We had our little pug with us and it was exactly what we needed. The pool is warm and clean and very enjoyable as the sun goes down. The bed was super comfy and the kitchen well appointed. I’ve stayed at a lot of rentals and this is one of the best. If you’re looking for a rental just book this one. You won’t be disappointed.

❤ROTONDA RETREAT❤*Spacious*Fully Furnished*Pool*
Lovely quiet neighborhood, extremely clean. The decor is a little out dated & probably needs a little brighting up. But we have no complaints about our stay. Very happy!!!

Your Dream Home Away From Home
This house was perfect for our family vacation, it had everything in it, that you could possibly need especially the kitchen and the pool area I have never seen such a well-stocked kitchen, and the grandkids loved all the pool toys and accessories We are definitely going to make this our yearly vacation designation !!!!

Well Appointed and relaxing Pool Home
Paul’s house is in a very quiet neighborhood. We found the house clean, the kitchen was well stocked, there were nice beach chairs and beach towels to use and the pool was well heated. The beds were comfortable with nice linens. Paul was quick to respond to our question we had. It’s definitely a place we will stay again.

Venice lakefront house, enclosed heated pool
I had a few questions at the beginning and Gregg responded promptly. The house was neat and tidy, loved the quietness of the neighborhood. We enjoyed the wildlife I even brought my binoculars lol, The kids & I got to see a baby gator. We enjoyed the pool and the weather was great. Definitely will be back… Thank you

Sunset Paradise: Book your Christmas and New Years
Tom's place is beautifully furnished, comfortable, and spacious. It has everything you need to prepare meals. We used the pool everyday. Living on the canal was peaceful and relaxing. Tom is a great host and very responsive. We had a wonderful vacation and look forward to returning next year.
Quick stats about vacation rentals that are family-friendly in Englewood
Total rentals
740 properties
Nightly prices starting at
ﺩ.ﺇ184 before taxes and fees
Total number of reviews
13K reviews
Pet-friendly rentals
260 properties allow pets
Rentals with a pool
410 properties have a pool
Rentals with dedicated workspaces
330 properties have a dedicated workspace
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- Crescent Beach
- Bean Point Beach
- Cortez Beach
- Lido Key Beach
- Coquina Beach
- Manasota Key Beach
- Myakka River State Park
- River Strand Golf and Country Club
- Englewood Beach
- Lovers Key Beach
- Lakewood National Golf Club
- Van Wezel Performing Arts Hall
- South Jetty Beach
- Tarpon Bay Beach
- Boca Beach
- Tara Golf & Country Club
- Del Tura Golf & Country Club
- Bonita Beach Dog Park
- Gasparilla Island State Park
- Manatee Park
- Stump Pass Beach State Park
- North Jetty Beach
- Point Of Rocks
- Public Beach - 100 Broadway