Family-friendly vacation rentals in Caspersen Beach

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Top-rated family-friendly rentals in Caspersen Beach

Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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Superhost

Home in Bradenton

4.87 out of 5 average rating, 127 reviews

IMG golf & close to AMI- Ocean View | Slt Wtr Pool

**Welcome to The Beachview @ Bayside** Your private slice of paradise in beautiful Bradenton, Florida! With breathtaking views of the inner coastal waterway, Longboat Key, and Anna Maria Island, this spacious retreat is the ultimate destination for families or groups looking for relaxation, adventure, and everything in between. **Spacious Comfort for Everyone** The Beachview @ Bayside features 3 main-level bedrooms, each with a private deck for sipping morning coffee or unwinding with sun

Superhost

Townhouse in Siesta Key

4.86 out of 5 average rating, 145 reviews

"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

Guest favorite

Home in Sarasota

4.96 out of 5 average rating, 124 reviews

5 Star! Walk/Bike DTN ~ 5 mi to Lido Beach Pets Ok

Bright & Comfy Downtown Home | Walk to Main St, Near Trolley to Lido Beach! Centrally located in a quiet downtown neighborhood along the Legacy Bike Trail & Payne Park, this updated 3BR/2BA home is clean, cozy, and filled with coastal charm. Enjoy a screened-in lanai, a large fenced backyard, WiFi, Smart TV, BBQ, beach gear, washer/dryer and carport. Pets welcome! Prime Location: 1 mi to Main St dining. 2 mi to waterfront dining and boat tours. 5 mi to Lido Beach. Take the nearby free Trolley

Guest favorite

Home in Sarasota

4.93 out of 5 average rating, 110 reviews

Sunny Sarasota Vacation Home - VR2400236

Quiet Neighborhood - Single Private Home, Great Location! This beautiful home includes 3 bedrooms, 2 bathrooms and sleeps up to 10 people. Near #1 Rated SIESTA KEY BEACH & LIDO KEY BEACH. Come and relax in this newly renovated home. Large living room, dining room and lanai to accommodate your friends & family. 5 TV's, DVD players, Cable, Internet. Fully equipped kitchen & laundry. Bus stops, grocery stores & restaurants are near by. Base rate covers 6 guests; $20.00/night/additional guest.

Guest favorite

Home in Sarasota

4.88 out of 5 average rating, 153 reviews

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.

Superhost

Apartment in Englewood

4.83 out of 5 average rating, 120 reviews

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.

Top guest favorite

Home in Sarasota

4.96 out of 5 average rating, 235 reviews

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 .

Top guest favorite

Home in Sarasota

4.92 out of 5 average rating, 294 reviews

❤ Villa & Garden in Downtown ~ 5 Min to Beaches

Our bright and contemporary Heart Villa offers the quintessential Sarasota downtown and beach experience. It is nestled among tropical trees in a charming cul-de-sac in historic Laurel Park – right in the heart of downtown with loads of restaurants, boutiques, and sights on offer. Several fantastic beaches are just 5-mins ride away! And the villa's private garden is the perfect place to enjoy alfresco dining! We’ve poured our hearts & souls into this villa, it's our family business.

Guest favorite

Cottage in Sarasota

4.76 out of 5 average rating, 126 reviews

Siesta Key Cottages Crescent 1B Beach/Pool/Hot Tub

4 separate BRAND NEW inside (renovated 12/24) 2 bedroom/2 bath (+Queen Sofa Bed+ Chair/Bed) pool homes (Each sleeps 7) ONLY A 4 MINUTE WALK TO SIESTA KEY BEACH #1 in USA (no major streets to cross): First Class! 2 Heated Pools, 2 hot tubs,2 gyms, Smart TV’s in all rooms, fine linens, towels, bikes, beach equipment, private porch, grill, fire pit, outdoor shower, private parking: Great restaurants / nightlife in walking distance. Running/Walking: You have miles of beach to take in!

Top guest favorite

Home in Siesta Key

5 out of 5 average rating, 140 reviews

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!

Guest favorite

Apartment in Boca Grande

4.88 out of 5 average rating, 202 reviews

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.

Guest favorite

Guest suite in Sarasota

4.95 out of 5 average rating, 243 reviews

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.

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What guests are saying

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

4.93 out of 5 average rating, 198 reviews2 weeks ago

Whenever needed to get in contact, they were very responsive and would follow up. Had a slight issue that they quickly resolved. Communicated things in advance so we knew what to expect. Recommend their place for people who want easy walking access to the beach and downtown areas.

Condo in Siesta Key

What guests are saying

Lido Beach Cottage 1 Block To Beach

4.95 out of 5 average rating, 93 reviews10 months ago

What a perfect location! It’s charming and comfortable with everything we needed to enjoy our stay. The location is an easy walk to the beautiful beach, the kayak rentals through the amazing mangroves, and also to St. Armand’s Circle and all the shops and restaurants. The house is very relaxing and had plenty of space for our family. Everything was very comfortable. (The only challenge we had was finding a convenient store or grocery store close by, so plan to shop in Sarasota on the way in.) I highly recommend this location!

Home in Sarasota

What guests are saying

Family friendly with large pool

5 out of 5 average rating, 31 reviews3 weeks ago

Overall, this is a wonderful place to stay. The house provided plenty of room for our family of six adults and two kids. There are several nice features in the home including multiple deck spaces to relax in and a large pool and hot tub. The house was very well equipped and organized. Also, the location was away from traffic noise and advantageously situated on the north end of the Key avoiding the heavy traffic that occurs on the south end. Better advanced communication and more prompt responses to a few issues we discovered upon arrival would have made the experience more enjoyable. In the course of our month long stay we were able to address most of the issues and the host accommodated our concerns. We are planning on staying again next year.

Home in Sarasota

What guests are saying

LUX VILLAs close to sparkling Siesta Beach.

4.86 out of 5 average rating, 29 reviews5 months ago

My two boys and I truly enjoyed the condo. It was clean, tidy, roomy, well-equipped, and conveniently located. The community was quiet and peaceful. My boys loved the pool and I loved the hot tub. We were extremely pleased. While we were given a unit that differed from our original request, we understood the reason given and we were in no way disappointed with the new arrangement. The unit was perfect for us and we would definitely return. Bea and her assistant were quick to respond to my questions prior to arrival. We had no issues during our stay, so we never needed to communicate while we were there. Check-in and check-out were both extremely easy.

Apartment in Sarasota

What guests are saying

Florida Bella Rosa-2 spas & pools near IMG/beaches

4.86 out of 5 average rating, 112 reviews3 months ago

We are already looking to see when we can come back to Florida and stay in Daniel's rental again! It has everything you need, it is well-kept, and it is close to everything you want/need (the beach, Detwiler's, Publix, stores, restaurants). It is in a safe location. The Shorewalk ammenities (pools and hot tubs) are nice as well. Even though one pool's heater was broken, there was another pool to choose from and two hot tubs. He checked-in with us to make sure check-in went well and to make sure that our stay was going well. Daniel provided thorough instructions and recommendations for everything you could possibly need. He was a great host with a great home away from home!

Condo in Bradenton

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