
Family-friendly holiday rentals in Englewood
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Top-rated family-friendly rentals in Englewood
Guests agree: these family-friendly homes are highly rated for location, cleanliness and more.
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Popular amenities for Englewood family-friendly rentals
Family-friendly home rentals with a hot tub

Paradise, full refund*, heated pool, sleeps 6
only thing is there was like 1 laundry tab 1 dish tab 2 trash bags they want ya 2 clean up but nothing 2 do it with .....so it wasnt provided an it was waterer down this dish soap an laundry soap had water in them as someone had refilled the bottles an its was only $1 tree items 2 began with so make sure you have extra or go shopping otherwise everything was WONDERFUL peaceful spacious it was a great time had 2 weird times someone i think the owner came an stopped by 2 xs. an was watching us on the Camaras was a lil weird if i must say please let people know your stopping by before you peep your head around the corner even if your staying a few houses down

Burnt Store Marina- Harbor Towers, 2bdrm, GulfView
A perfect retreat located in the Burnt Store Marina development. We enjoyed a week at this condo which was centrally located between Cape Coral and Punta Gorda. The condo was extremely clean and very well organized. Beds were very comfortable and we loved the little extras, such as an insulated beach bag, and beach towels. Kitchen was well supplied with pots, pans, dishes, wine glasses, and even a small supply of spices as we often eat in while on vacation and it was very nice not to have to buy. As boating people, this is a great neighborhood. Definitely research boat rentals, tours, fishing charters if you’re thinking of fun things to do. The highlight was traveling to Boca Grande beaches (3 times!) which was just stunning. We really enjoyed the pool in the afternoons and going over to the Cass Cay restaurant in the evenings. Bill was very responsive with any questions we had!

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.

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!

Secluded paradise with pool and SPA! 37PVR
Great vacation at Mikes! (Again!) Very nice home in a very nice neighborhood with a very nice pool and hot tub. We have rented from Mike a few times and honestly, I would never rent in Florida from anyone else. The property is as advertised and anything you might need is one text message away. I Highly recommend this house as well as any of Mike’s other properties. The peace of mind, knowing that if you have a question, it will be answered, if you have a glitch, it will be fixed, and that the house will be spotless, is priceless.

Amazing Lagoon | Rock Grotto Swimming Pool | Spa
Amazing, clean place. Great pool
Family- and pet-friendly home rentals

Gulf Side Condo Englewood Florida
A very peaceful condo with a great view. Easy walk to the beach or sit on the comfy balcony and enjoy the view. The condo was very cute but spacious. It’s also a short walk to the nearest restaurant with entertainment. The island is still working to recover from the devastating hurricanes but this place was a slice of heaven. Also very good communication.

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.

The Pineapple Suite.Teal tropical home in Sarasota
The house was spacious and very comfortable! Quiet neighborhood. Easy check-in, close to everything. Looking forward to our next stay!

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.

Sarasota Pool House
This was our second time staying at Lubos pool house. We really enjoyed our stay and are already looking far time to escape back. Great location near restaurants, stores and beaches. Back yard and pool are a dream and very peaceful.

Pink Flamingo: 4 Beds/3 Baths Screened Pool Oasis
Yvonne couldn't have been more responsive, helpful and accommodating for our group of 5. She had great recommendations for things to do. The pool was wonderful and was used every day. It was great to have 3 bathrooms for 5 women. Would definitely book again with her!

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

HTD Salt Water Pool house monthly or long term
We enjoyed our stay as we transitioned from one home to another. The host was responsive and fixed any issues immediately. We made it through 2 hurricanes safely, and it was a great location. The pool was a nice addition to enjoy as well.

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!!!

Low Rates Serene Lake Frt-Pool Home 3Bd/2Ba/Lr/Kt
Well laid out home. Kitchen well stocked with dinnerware, glasses, pots, coffee pot and Keurig. Very clean home. Neighborhood was very quiet.

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.

Luxury Lemon Bay 4 BR villa w/ pool
Great place! Very clean, responsive with any issues. The only huge bummer was there was nothing except towels for the beach (chairs, umbrella, softer, etc) as we’ve had in every other place we have stayed in.
Quick stats about holiday rentals that are family-friendly in Englewood
Total rentals
740 properties
Nightly prices starting at
£38 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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- Anna Maria Island
- Siesta Beach
- Captiva Island
- Anna Maria Public Beach
- Crescent Beach
- Turtle Beach
- Caspersen Beach
- Bean Point Beach
- Cortez Beach
- Lido Key Beach
- Coquina Beach
- Manasota Key Beach
- River Strand Golf and Country Club
- Myakka River State Park
- Lovers Key Beach
- Tara Golf & Country Club
- Lakewood National Golf Club
- South Jetty Beach
- Van Wezel Performing Arts Hall
- Englewood Beach
- Tarpon Bay Beach
- Boca Beach
- North Jetty Beach
- Del Tura Golf & Country Club