Family-friendly vacation rentals in Caspersen Beach

Find and book unique family-friendly homes on Airbnb

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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Guest favorite

Guesthouse in Sarasota

4.93 out of 5 average rating, 477 reviews

La Casetta: "the little house" near to the beaches

La Casetta means, in Italian, little house. Set in a private, peaceful, mature Florida tropical garden, a real hideaway. I am proud of the cleanliness of our property, however in this new reality that we live in, we do carry out enhanced cleaning and sanitizing between guests. We also practice social distancing, insofar as guests have their own part of our luscious back garden as well as your own entrance. La Casetta has 1 queen sized bed, bathroom & kitchenette. Wifi & Netflix available.

Guest favorite

Guest suite in Sarasota

4.94 out of 5 average rating, 505 reviews

Studio Apartment. Priv Yard. 5 min to Siesta Key!

Self checkin. Includes kayak and bikes! You’ll love my place because of the coziness, the high ceilings, and the location. My place is good for couples, solo adventurers, and business travelers. Converted garage space. Your own private fenced back yard, kitchenette, fridge, private bathroom, Amazon Firestick with Netflix, Hulu and dock/boat ramp just 30 sec from your door and in a beautiful neighborhood. Just a 10 min bike ride to Siesta Key. The #1 beach in America! What more could you ask for!

Guest favorite

Rental unit in Sarasota

4.96 out of 5 average rating, 160 reviews

ROYS PLACE Romantic, Private, Paradise!

NAMED #1 BEST AIRBNB WITH POOL IN SARASOTA BY TRIP 101 TRAVEL GUIDE FOR THREE YEARS. "I LOVE ROYS PLACE!" Words most commonly used by guests in reviews are "quality" "clean" "cute" "sexy" "cool" "safe" . This is a restored 600 sq. ft. one bedroom apartment in an old historic home located in the heart of coveted safe Northwest Sarasota. Offered for you, a romantic boutique apartment with your own private (exclusive to you, not shared) CLOTHING OPTIONAL lanai, outdoor shower and heated pool.

Guest favorite

Guesthouse in Sarasota

4.97 out of 5 average rating, 264 reviews

Sarasota guest house only 8 miles to Siesta Key

Our Florida-themed guest house has everything you need to enjoy your vacation in beautiful Sarasota, Florida. It is a very comfortable, clean and private one bedroom and one bathroom guest house. It is a completely separate space and has it's own private entrance. It is conveniently located in a quiet, safe neighborhood near Interstate I-75, Shopping, Dining, Twin Lakes Park, Serenoa Golf Course, Myakka River State Park and just 8 miles from the #1 beach in the U.S. - Siesta Key Beach.

Guest favorite

Home in Sarasota

4.96 out of 5 average rating, 224 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 .

Guest favorite

Hotel room in Venice

4.86 out of 5 average rating, 207 reviews

Near Downtown/Beach | Tropical Villas Venice Beach

Tropical Villas of Venice Beach offers 10 Villas on the Island of Venice FL. The Villas give the Old time Florida vibe with a convenient location to the beach, stores and restaurants. - 3 blocks from the beach - 2 blocks from the downtown - Near the Legacy Bike trail - In front of the beautiful John N. Park (Picnic) - Tropical gardens & swimming pool - Smart TV : NFLX, DIS +, Hulu, Espn+ - BBQ and Bikes and beach gears provided - Shark teeth equipment - Farmer Market every Saturday

Guest favorite

Vacation home in Venice

4.83 out of 5 average rating, 125 reviews

🌟Venice Cute Pool Villa with bikes Kayaks 🌈🐬

Escape to our charming Venice pool home, where relaxation meets adventure! Perfectly located near the water, this tranquil three-bedroom retreat is nestled on a quiet, palm-lined street. Enjoy easy access to bikes and kayaks for exploring, plus all the beach essentials: cooler, umbrella, and chairs. The pool awaits for sunny days and peaceful evenings (note: a brand-new pool cage is on its way, expected in December). Book now to experience Venice’s beauty from your private oasis!

Guest favorite

Condo in Englewood

4.95 out of 5 average rating, 129 reviews

Gulf Side Condo Englewood Florida

A cozy 2 bed 2 bath condo with a full kitchen, dining area, living room, a king size master bedroom and a small 2nd bedroom. The coastal decor and furnishings create the ambiance of an island home. The condo opens onto a wide porch which has beautiful views of the Gulf of Mexico. Wander down the sandy path to a private beach and the turquoise waters of the Gulf. Enjoy sunsets from the porch or the beach. Unwind and let all of your cares float away on the Gulf breezes.

Guest favorite

Home in Sarasota

4.89 out of 5 average rating, 624 reviews

Charming Apt. in old Florida home

Cozy, charming suite in a historic 1920's home. Lots of character and charm. Amazing location. One block from the bay with beautiful sunsets. And just a few miles to the beach and downtown. Clean, comfy and a welcoming host. Great for 1 or up to 3 guests. ****Please read the full detailed description for more information before booking. This is very old home, not fully restored, old Florida house. Owner occupied Non- Smoking guests 🙏 Hope to see you soon

Guest favorite

Villa in Englewood

4.9 out of 5 average rating, 126 reviews

Great after Milton-Magnificent Waterfront-gs

Fantastic Manasota Key Location! Upstairs at Blue Island Inn, waterfront “Seaglass Villa” dazzles with spectacular Bay views! 2 cozy bedrooms; 1 bathroom, kitchen & 1 cozy family room. On-site resort pool overlooks stunning Lemon Bay. 5-minute walk to ocean-side beach or enjoy “Bay-front beach” out back. Quiet island street. low-key quiet respectful vacationers. 1 car parking spot. No visitor parking. No boats. No pets. No smoking. Free use of kayaks!

Guest favorite

Home in Englewood

4.86 out of 5 average rating, 103 reviews

Lemon Bay Luxury 6 BR Villa with Pool&Tennis Court

This beautiful house is located at the Lemon Bay and close to the Manasota Beach. The beach is just a 0.6 mile walk or 0.8 drive away. The property offers a 1/2 acre lot. This house offers, with a 34x12 feet swimming pool and own tennis court, a completely new rental experience. You will find the barbecue area outside of the pool area. The charging of EV is not allowed and an extra fee will be charged.

Guest favorite

Guesthouse in Sarasota

4.98 out of 5 average rating, 254 reviews

Casita Lantana, a 1925 cottage in a Tropical Oasis

Welcome to my original 1925 Casita, built in the heyday of the John Ringling era. We are centrally located between Sarasota, Lakewood Ranch, and Bradenton, making it an ideal place to explore all the area offers. Getting around is easy since we are located very close to the Ringling Museum of Art. Plus, it is only a short 15-minute drive to downtown Lido Beach and St. Armands Circle.