Family-friendly vacation rentals in Englewood

Find and book unique family-friendly homes on Airbnb

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Popular amenities for Englewood family-friendly rentals

Family-friendly home rentals with a hot tub

Top guest favorite
A screened-in pool area features a sparkling pool surrounded by a spacious patio. Lounge chairs provide seating options, while colorful floaties rest on the water's surface. The backyard is lined with lush greenery, offering a sense of privacy and relaxation.
Home in Sarasota
4.98 out of 5 average rating, 136 reviews

Gorgeous Home / Heated Pool and Spa

CristianRating, 5 stars1 week ago
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!
Superhost
A large heated pool is surrounded by a spacious limestone deck, furnished with lounging chairs and tropical plant arrangements. Sunlight reflects off the clear water, creating a serene atmosphere. The pool area is designed for relaxation and enjoyment in a private outdoor setting.
Home in Siesta Key
5 out of 5 average rating, 26 reviews

Canal home short walk to Beach & Village, Heated P

CarlyRating, 5 stars23 months ago
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!!
Guest favorite
A patio area features several chairs positioned beside large windows, inviting relaxation. Colorful pink flowers and green shrubs enhance the outdoor space, creating a vibrant atmosphere. The setting offers views of the surrounding courtyard and lends itself to enjoying the fresh air.
Condo in Siesta Key
4.92 out of 5 average rating, 146 reviews

Siesta Key Serenity At The Palm Bay Club

DeborahRating, 5 stars5 months ago
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.
Superhost
The living area is furnished with two large sofas and a coffee table, set upon a blue and white area rug. A painting with a serene landscape hangs on the wall, while a ceiling fan adds comfort. Natural light enters through large windows, enhancing the open layout.
Home in Cape Coral
4.87 out of 5 average rating, 149 reviews

Villa Scottsdale -Waterfront Home with Pool

DavidRating, 5 stars2 weeks ago
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
Guest favorite
A wooden pathway leads through lush greenery to a sandy beach. The gentle ocean waves are visible in the distance under a partly cloudy sky. Colorful paddleboards and kayaking equipment are positioned along the shoreline, inviting outdoor activities.
Island in Sarasota
4.97 out of 5 average rating, 323 reviews

Now NEW AUG Openings! Sarasota #1 Lux BEACH Villa

CarolRating, 5 stars1 week ago
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!
Superhost
A private pool area is surrounded by tropical greenery, featuring a wooden deck with smooth steps leading down to the water. Bright lounge chairs sit nearby, and pool floats are casually draped over the railing, inviting relaxation and enjoyment.
Home in Sarasota
4.76 out of 5 average rating, 112 reviews

5min to Siesta, Heated Pool & Jacuzzi, Grill, WiFi

TiffanyRating, 5 stars3 weeks ago
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!
Top guest favorite
The charming exterior of the home is framed by lush greenery and palm trees, featuring a well-maintained front yard. A paved driveway provides access to the garage, while bicycles are visible in the driveway, suggesting outdoor activity options.
Home in Rotonda West
4.92 out of 5 average rating, 39 reviews

Amazing Lagoon | Rock Grotto Swimming Pool | Spa

MarkRating, 5 stars8 months ago
Amazing, clean place. Great pool
Top guest favorite
A spacious living area features a sectional sofa adorned with patterned cushions. Dual accent chairs complement a central coffee table, with light streaming in through the windows. A decorative fireplace with artworks above adds character to the warm, neutral palette.
Home in Fort Myers
4.98 out of 5 average rating, 120 reviews

The Parsonage-Private Villa-Heated Pool & Spa.

RachelRating, 5 stars2 weeks ago
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

Superhost
A ranch-style vacation home exterior is showcased, featuring a landscaped yard with several lounge chairs arranged on the patio. Sunlight illuminates the area, and a clock is mounted on the wall near the entrance, adding a functional detail to the inviting space.
Villa in Cape Coral
4.73 out of 5 average rating, 63 reviews

3 Bed 2 Bath Heated Pool Home with Privacy Fence!

JoshuaRating, 5 stars5 months ago
The place was perfect for us and our pups. We will definitely be back!!
Top guest favorite
The image features a cozy living area with a dark sofa and a round coffee table, accompanied by a remote control. A modern kitchen is visible in the background, showcasing dark cabinets, a black refrigerator, and bar stools, creating a functional and inviting space.
Apartment in Punta Gorda
4.95 out of 5 average rating, 20 reviews

The Cottages at Punta Villas - Historic District

TeresaRating, 5 stars2 weeks ago
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.
Superhost
The bathroom features a clean and modern design, with a white bathtub/shower combination and a white vanity. A large mirror reflects natural light, while a turquoise shower curtain adds a pop of color. Soft, luxury bath towels hang nearby.
Villa in Sarasota
4.75 out of 5 average rating, 126 reviews

Aloha Villa Pet Friendly 3 miles to Siesta Key #2

AwildaRating, 5 stars3 weeks ago
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.
Guest favorite
A screened-in pool area features a crystal-clear heated pool with lounge chairs positioned nearby. An umbrella provides shade over a seating area, surrounded by lush greenery and fencing that enhances privacy.
Home in Sarasota
4.95 out of 5 average rating, 206 reviews

2bed/2bath with POOL house, close by SIESTA KEY!!!

JoelRating, 5 stars1 month ago
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.
Guest favorite
A bright bathroom is presented with light green walls and a spacious vanity featuring dual sinks. Natural light filters through a window, illuminating the white tiled walk-in shower. Fresh greenery decorates the countertop, enhancing the clean and tranquil atmosphere.
Bungalow in Sarasota
4.82 out of 5 average rating, 151 reviews

Pink Flamingo: 4 Beds/3 Baths Screened Pool Oasis

MiriamRating, 5 stars4 months ago
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.
Superhost
A single-story house is framed by lush greenery and palm trees, showcasing a well-maintained front yard with grass and shrubs. A driveway leads to a parked vehicle, while the exterior features a covered porch and large windows that contribute to the home's inviting presence.
Home in Grove City
4.81 out of 5 average rating, 37 reviews

Comfortable cottage only 5 min. to the beach

FranzRating, 5 stars2 weeks ago
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
Superhost
A spacious backyard features a heated pool surrounded by palm trees and lush plants. A patio area with seating is visible, along with a fire pit placed on the grass. The outdoor space is well-maintained and offers a serene atmosphere.
Home in Sarasota
4.82 out of 5 average rating, 249 reviews

Private Siesta Beach House Oasis with Heated Pool.

AnaRating, 5 stars1 week ago
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!
Top guest favorite
A two-story duplex is framed by lush palm trees and landscaping. The property features a welcoming front porch with white railings and ample outdoor seating. A gravel driveway leads to two designated parking spaces in front, enhancing accessibility to the entrance.
Home in Englewood
4.87 out of 5 average rating, 62 reviews

Turtle Nest Retreat - Manasota Key (upper unit)

BenjaminRating, 5 stars1 week ago
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

Superhost
The screened lanai features a heated pool surrounded by four lounge chairs. Lush greenery and open views of the landscape are visible beyond the pool area, creating a serene outdoor setting.
Villa in Rotonda West
4.97 out of 5 average rating, 37 reviews

Riverview Villa, full refund*, pool heat, sleeps 6

AbelRating, 5 stars1 month ago
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.
Top guest favorite
A screened lanai surrounds a serene swimming pool, featuring a bright pink inflatable flamingo. Comfortable loungers and a sitting area are positioned near the water, while lush greenery is visible beyond the enclosure, creating a tranquil outdoor space.
Home in Cape Coral
4.99 out of 5 average rating, 89 reviews

5 Star Paradise Plus/Canal/Pool/Spa/Kayaks

KarenRating, 5 stars2 months ago
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!!
Superhost
A bright sunroom features comfortable seating in uplifting blue tones, arranged around a coffee table. Large windows provide views of the surrounding greenery, while decorative elements, such as an art piece on the wall and a patterned rug, add character to the space.
Home in Punta Gorda
4.92 out of 5 average rating, 12 reviews

Waterfront PGI Heated Pool! Near Fishermen's!

MikeRating, 5 stars2 months ago
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.
Guest favorite
The front exterior of the home features a welcoming entrance with two prominent blue doors. Lush landscaping, including palm trees and flowering shrubs, is visible in the yard, complemented by a generous concrete walkway leading up to the entrance.
Home in Rotonda West
4.91 out of 5 average rating, 185 reviews

❤ROTONDA RETREAT❤*Spacious*Fully Furnished*Pool*

ToniRating, 5 stars1 week ago
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!!!
Superhost
The image displays a private pool area illuminated in purple tones. Six colorful drinks are placed along the pool's edge. A large screen is visible in the background, suggesting a movie or entertainment feature in the area.
Home in Fort Myers
4.97 out of 5 average rating, 34 reviews

Your Dream Home Away From Home

KayRating, 5 stars21 months ago
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 !!!!
Superhost
A heated pool is enclosed by a screened patio, featuring clear blue water reflecting natural light. The surrounding greenery offers a serene backdrop, enhancing the tranquil atmosphere of the space.
Home in North Port
4.81 out of 5 average rating, 105 reviews

Well Appointed and relaxing Pool Home

DonnaRating, 5 stars3 months ago
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.
Superhost
Home in Venice
4.8 out of 5 average rating, 99 reviews

Venice lakefront house, enclosed heated pool

ChristinaRating, 5 stars10 months ago
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
Superhost
A well-lit living area features a light-colored sectional sofa paired with a decorative coffee table on a patterned rug. A tall lamp provides ambient lighting, while dining chairs can be seen in the adjacent area. Large windows offer natural light and views outside.
Home in South Gulf Cove
5 out of 5 average rating, 4 reviews

Sunset Paradise: Book your Christmas and New Years

Margaret AnnRating, 5 stars2 months ago
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

Destinations to explore