
Family-friendly holiday 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

Rowan's Retreat
Beautiful historic home ! Loved the wrap around porch and the hot tub. Great shower ! Loved the coffee and wine and cozy blankets on the couch . Wish we could have stayed longer . Lots of space ! Close to downtown fort Myers

Gorgeous Home / Heated Pool and Spa
Another great stay at this house! Love the location, very clean throughout, has everything you would need and more. We spent most of our time in covered outdoor area which has lots of seating options, the pool/hot tub is perfect! The only small issue we had was the door to the pool does not lock securely, therefore adding a safety risk if you have young children. It needs to have an added safety lock on top or something to that nature.

Siesta Key Serenity At The Palm Bay Club
Super clean, quiet, comfy bed. We enjoyed the bayside pool. Nice views. Palm Bay club nice benefit as after a short walk over to the beach we enjoyed the chaises delivered and set up close to the water and hole drilled for our beach umbrella. Amazing sand is not over rated. Warm gulf waters and easy entry and exit. Breeze Trolley with their app made getting around without driving convenient . Lots of fun food and shops minutes away. This bayside spot a was a delight.

Private View Villa/Heated Pool/Pickleball/7883
Spacious home with all the amenities you need, well equipped kitchen. We loved the lanai and had all our meals outside. Green and silent surrounding, nice neighbors. A lot of beautiful beaches within 45min (AMI) or just 15min (Siesta). Good shopping possibilities. We had a great time and will be back!

5min to Siesta, Heated Pool & Jacuzzi, Grill, WiFi
Our stay was amazing, Ven was a great host, unfortunately there are always minor issue that come about when staying in properties but their communication was so great it over shadowed all of our concerns! Thank you for the stay!

Siesta Key Cottages Crescent 1B Beach/Pool/Hot Tub
This cottage was perfect for me, my husband, and our baby girl. We had the pool to ourselves the whole time, which isn’t guaranteed but was great. Weather was perfect. The beach is so close and so nice. The area has beautiful, large homes, which made for nice scenery when we walked. I really liked the location of this place vs the north end of Siesta Key. It was less crowded and very easy to navigate places. Dave, the property manager, was amazing. He was very informative, friendly, responsive, and helpful.

The Parsonage-Private Villa-Heated Pool & Spa.
This was a great “home base” for our event at the Heitman House. It was nearby and walkable, with plenty of space for all our guests. The house and backyard were excellent for hosting meals and hangouts, and the place was really well-stocked, making it feel like home and not a random rental. The beds were comfy and there were plenty of linens, including lots of extras so despite being at full capacity for days we didn’t need to go without. I really appreciated the amount of bath and pool towels that were provided! The hosts were responsive and had anticipated many of our questions and needs. Details like the kitchen having multiple coffee makers, and extra bug spray & beach chairs were nice touches.

"Seahorse Villa" by the water Pool & Spa +Tiki Hut
Overall we were very happy with our stay. We loved having access to 2 kayaks to enjoy the canals. The pool and hot tub were awesome, and the house was amazing. The only things that were slightly annoying was having a member from the rental stop by bright and early on our first and last day to go over the status of the rental. When traveling it's a bit annoying to be woken up super early on your first day. I would also suggest changing the timer on the sprinklers. They would go off about 930 at night when we were trying to enjoy the hot tub. While they wouldn't always hit us, the water had a very strong smell of rotten eggs which made us not want to stay outside anymore. Thankfully they didn't come on every night.
Family- and pet-friendly home rentals

Waterfront Pool and Dock! Great Family Retreat
Beautiful spot, not far from numerous restaurants and things to do. Not far from the Charlotte Event Center. Good amenities, stocked cupboards (coffee filters, seasonings, etc). Definitely would stay here again if we visit.

Villa Coral with boat dock & waterview- own pool
We spent the month of March at this home and enjoyed the experience. With only solar heat we were afraid we wouldn’t use the pool but it was great and enjoyed lots of floats. We thoroughly enjoyed the outdoor area and beautiful canal views. Everything looked like the pictures. We loved the quiet neighborhood too

Vacation Paradise Close to Beach!
What a beautiful home! It had all the comforts and convenience of being home. Jane was very responsive to any questions we had.

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
From reservation to check-out this experience was easy, and delightful

Low Rates Serene Lake Frt-Pool Home 3Bd/2Ba/Lr/Kt
Great location with lovely views. Home is very comfortable and super clean with perfect location with all the amenities you need. The host is very kind and she has excellent communication.

Siesta Key, FL - Casa Berano
We thoroughly enjoyed our stay. The house was a private and calm place to come home to after our long beach days. We enjoyed spending our nights out by the pool. The pool lights we a nice touch. Would recommend to those who enjoy being in a quiet area.

Home away from home mins to Siesta Beach!
Melissa has a beautiful place and is a wonderful host. Extended our stay one day due to a last-minute change. Very responsive and helpful! Cannot recommend the location more - quiet, close to everything you need. Stay here while in Sarasota...unless we're there!!
Family-friendly home rentals with a pool

Beachfront Getaway in Siesta Key
Our stay was so easy and enjoyable! Dior’s place is so cute and very clean. We were able to walk to multiple shops, bars, and restaurants. It was so nice to have our private beach access right down the sidewalk, and right beside the pool! We were also so glad that she was able to accommodate us on such short notice. Everything was perfect! This will definitely be our go-to place to stay when we visit Siesta!

Good after Milton - Kayaks & Steps to Beach-pc
Amy is a terrific host and always on hand with local suggestions, additionally to the comprehensive package at the property. The property itself is in an amazing location, with just a 60 second walk to the beach and bath like sea! To help, Amy provides all the kit needed for the beach with chairs, parasols and towels easily to hand. The kitchen is great with all cooking implements you need and the living room has a massive TV with all the required streaming services logged in. I would definitely recommend Amy as a host!

Manasota Key Condo Bay side Beach Access
Great place, great stay.

SIESTA BEACH HOUSE HEATED POOL☀️🌴3 MIN TO BEACH!!
Great place, very clean and had everything we needed. Instructions very clear and the pie waiting for us in the fridge was much appreciated! The beach gear was a nice touch, just a pity the weather wasn’t kind to us.

Little Piece of Paradise
Thank you Judy! We really enjoyed our stay it was delightful sitting out looking at the Marina watching the boats and the Sunset! Cass Cay is a great place to get dinner, drinks and listen to great music! Met your neighbor Mark and his friends Jim and Debby very nice to meet and talk with them. If we come to the area again we would definitely stay with you again! Thank you!

Tropical Island Getaway with Ferry & Parking Incl.
Lisa & Chris’s condo on Little Gasparilla Island is such a peaceful vacation. The condo is spotless. The beach is a wonderful place for long uncrowded walks. Sights of Manatees in the surf, fossilized sharks teeth in the sand & fresh turtle nesting tracks heading into the dunes. Bring lots of groceries over on the ferry when you first arrive. Then, It’s an easy ferry ride to the mainland for groceries to replenish your stocks after 3-4 days. The owners are very responsive and go out of their way to make their guests feel welcomed.

Sunset Paradise: Book your Summer Vacation
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.

On Manasota Key with Direct access to our Beach B)
Great place to stay on the Bay. The golf was a short walk and was beautiful. Walking distance to several restaurants. My husband was able to catch fish off the dock. Our host, Dave had excellent communication. Thank you for the great time!
Quick stats about holiday rentals that are family-friendly in Englewood
Total rentals
740 properties
Nightly prices starting at
₹4,327 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
- Lovers Key Beach
- River Strand Golf and Country Club
- Myakka River State Park
- North Jetty Beach
- South Jetty Beach
- Marie Selby Botanical Gardens
- Englewood Beach
- Tara Golf & Country Club
- Van Wezel Performing Arts Hall
- Lakewood National Golf Club
- Gasparilla Island State Park
- Stump Pass Beach State Park