Family-friendly vacation rentals in Englewood

4.86 out of 5 average rating, 145 reviews

A light and airy kitchen space features modern cabinetry and stainless steel appliances. A glass dining table is surrounded by four upholstered chairs. Natural light streams in through large sliding doors, revealing an outdoor patio area adorned with greenery.

Townhouse in Siesta Key

"Relax Here" -Royal Palm Suite- Siesta Key Beach

The pampering begins HERE: 3 bed/ 2.5 baths townhouse, sqft 1,850, 2 kings & 1 queen bed, an enchanting loft bedroom with it's own balcony and incredible Gulf / Beach views All 3 balconies have Gulf views!! Imagine sitting on your patio and watching people at the beach. Gumbo Limbo Rentals is a mini resort, 60 steps to the beach with only 2 duplexes sharing a black bottom lagoon pool which is heated during the colder winter months. Free: Wifi, beach chairs & sun umbrellas, 2-3 parking spaces

4.88 out of 5 average rating, 153 reviews

A cozy living area is highlighted by a soft, textured chair and a light wooden console holding a large television. A view into the adjacent bedroom is visible, featuring a spacious bed and bedside tables, while natural light cascades in through the windows.

Home in Sarasota

5 minutes to private Siesta Key Beach + 2 pools

Best getaway, beach vacation, and staycation! The luxurious condo is on the 1st. floor and located on Siesta Key in a tropical setting. It is kid-friendly and has private access to its private beach on Siesta Key Beach within 5 minutes of walking distance (the Best Beach in the U.S.A.) with crystal white sand and turquoise waters of the Gulf of Mexico. There are two heated pools, barbeque areas, lighted pickleball and tennis courts, a fishing pier, a gym, and a sauna, all for your enjoyment.

4.83 out of 5 average rating, 120 reviews

A bright yellow bungalow is surrounded by tropical landscaping, featuring palms and flowering plants. A white picket fence lines the front, complementing the pebbled driveway. The structure includes multiple windows, allowing natural light to enhance the welcoming exterior.

Apartment in Englewood

BeachBay SeaHouse (1519)

Best location/value on Manasota Key. 300 yards to pristine gulf beaches, 300 yards to boat ramp and dock on Lemon Bay if you have a boat or want to see dolphin or fish from dock. 4/10s of a mile to several great restaurants and 1 mile to Stump Pass State Park and a few more miles to walk via the park to Stump Pass. 1519 Beachway Bungalows has one bedroom with a queen bed and a pull-out sofa. There is a full kitchen and a great outside screened in patio that is shared with SeaHouse 1521.

4.96 out of 5 average rating, 236 reviews

A modern kitchen features dark wood cabinetry and a granite countertop. Stainless steel appliances, including a refrigerator and dishwasher, are included. A doorway leads to a bright living area where natural light filters through a window, illuminating a cozy seating arrangement.

Home in Sarasota

The Key Lime Cottage 2 miles from Siesta Key Beach

Great location. 2 miles from the # 1 rated Beach in America , Siesta Key . The cottage is near several other beaches as well. Close to restaurants and shopping. 1 hour from Tampa and 2 hours from Orlando. The Key Lime Cottage is totally updated with new stainless steel & granite in the kitchen . There are two new beds ..... one is a queen size and the other is a full size. (URL HIDDEN) Linens & towels are all new. New tile and wood floors throughout. Quite neighborhood for walking .

4.93 out of 5 average rating, 199 reviews

A modern living area is visible, showcasing a cozy gray sofa and a glass coffee table atop a patterned rug. The open kitchen features stainless steel appliances and a bright green accent wall. Natural light streams through a nearby window, enhancing the inviting space.

Condo in Siesta Key

Steps away from beach and village! #1 in Siesta!

The Little Sandy... Your secret hideaway Incredibly located Two bedrooms, one bath Sleeps 6 easily Bring the kids...or not Walk everywhere. 3-minutes to the beach, 8 to Siesta Village Super-fast Wi-fi! Icy A/C Lovely pool Play in the water, play on the sand, play in the village Rinse and repeat Comfy beds, soft towels A great night's sleep And the best hosts on Airbnb Tradewinds included free of charge. So book now and find your Siesta-self Just like you, only funner.

4.76 out of 5 average rating, 118 reviews

An aerial view displays a spacious home set amidst lush greenery, featuring a saltwater pool bordered by a deck. A canal runs alongside the property, and a private dock is visible, ideal for boating activities.

Home in South Gulf Cove

Pool Home on Saltwater Canal Accommodating 10

Unique opportunity to rent this gorgeous, pool home overlooking the saltwater canal. The home has accommodations for up to 10. Two homes in one connected by a common interior sitting area. Beautifully decorated and equipped with all the modern conveniences of home. With 7 bedrooms and 4.5 baths, multiple families can vacation together without feeling cramped. Dock with davits is found at the rear and can accommodate your vessel. This makes for a convenient day on the water.

5 out of 5 average rating, 140 reviews

A charming cottage is depicted with light blue wooden siding and white accents. The front yard is gravelled, surrounded by landscaping featuring mature trees and shrubs. A welcoming porch with a railing leads to the main entrance, enhancing the property's inviting look.

Home in Siesta Key

Beach, Village, Dock & Private Pool! One-of-a-kind

FULLY RESTORED POST HURRICANE! HERE IT IS! This “one of a kind” property is uniquely situated between the beach, canal, village with a private heated pool & dock, one of the best spots on Siesta Key! This charming 1,500 sq. ft. cottage beach home is being offered for the 1st time and post hurricane updates! If you want a cute, private original bungalow style beach cottage home all to yourself without the shared wall feel of a condo, then you are in the right spot!

4.88 out of 5 average rating, 205 reviews

The bathroom features a clean, functional layout with a white sink and toilet. Fresh, white towels are neatly hung on chrome holders. A glass shelf displays toiletries, while a small tissue box and toilet paper roll are positioned for convenience.

Apartment in Boca Grande

Historic Boca Grande 2 Bedroom Flat: #7 Special Rt

We made it through Milton and Helene and are ready to host you! A great, second-floor, 2-bedroom, one bath flat in the heart of historic Boca Grande on the gorgeous Gasparilla Island. Across the street from The Temp Restaurant and down the block from Hudson's Market. Going to the beach, no worries; it is just down the road. Just a 3-minute walk to the Gasparilla Inn. Guests receive a 10% discount on golf cart and bike rentals through Gasparilla Adventures.

4.85 out of 5 average rating, 169 reviews

A modern kitchen features white cabinetry and a spacious counter. Stainless steel appliances, including an oven and microwave, are visible. A decorative beach sign adorns the wall, and a bowl of fresh fruit sits on the counter, adding a pop of color to the bright space.

Condo in Siesta Key

Best Gulf Coast Condo - rarely available

Rarely Available! Beautiful, open floor plan is the perfect location vacation. Condo is stocked with everything you will need to enjoy your stay. The resort is quiet and peaceful with direct access to the most beautiful private white sand beach. Also enjoy the Intra Coastal waterway with fishing and boat dock right on the property in our backyard next to the huge pool and bbq. This is the best of both worlds!!! Individually managed by owners.

4.95 out of 5 average rating, 244 reviews

A wide view of a sandy beach features clusters of beachgoers enjoying the sun. Colorful beach chairs and umbrellas are scattered across the white sand. The gentle waves of the blue ocean can be seen in the distance, with high-rise buildings lining the shore.

Guest suite in Sarasota

2 Miles to Siesta Key

Comfortable Accommodations with Private Entrance & Quiet Surroundings. This is a Private Guest Suite in a home with a king size bed, full bathroom, and kitchenette with sink and countertop, fridge and freezer, microwave, and coffee maker. This provides ample utility to prepare simple meals but is not suitable for cooking since there is no stove or oven.

4.97 out of 5 average rating, 119 reviews

An outdoor tennis court is visible, featuring multiple fenced-in playing areas with nets in place. The court's green surface contrasts with the blue sky and white clouds, while the condominium complex can be seen in the background, surrounded by lush landscaping.

Condo in Siesta Key

Siesta Key Condo. Checkout our great rates!

Our beautiful Siesta Key condo is located a short stroll from the famous Siesta Key beach with its beautiful quartz sand and amazing sunsets. The Midnight Cove II condominium complex has private beach access with outstanding amenities and is very family friendly, come and enjoy the natural beauty this complex and all Siesta Key has to offer.