Family-friendly rentals near Caspersen Beach

Pool & fenced-in yard in downtown edge bungalow

This 2 bed-2 bath house is a homey Florida bungalow with wood floors and lots of natural light, located in a quiet neighborhood on the downtown core edge. Enjoy a spacious and private, fenced-in backyard with pool, covered grill and eating area. The home is minutes away from the Legacy Trail, the new Bay Park, Payne Park, dining, live music, bars, theatres, opera house, performance venues, comedy club, antiquing, kayak launches, tennis and basketball courts, farmer's market, shopping and more.

Venice lakefront house, enclosed heated pool

We are good after hurricane Milton. Welcome to the Whispering Lake House located in Venice Birds Sanctuary Area. Fully equipped kitchen. Eating area, Lanai overlooking lake. Private Backyard, turquoise water pool and fresh mangoes (in season) to enjoy. Furnished, 4KUHD TV in Living Room and SMART TV in Master, Free Wi-Fi, walk in closets, 2car garage. Pets considered. No smoking. minutes to the Venice Beach, to Pelican Pointe or Jacaranda West Golf & Country Clubs. Restaurants, Bars are nearby.

Entire Standalone Villa,1.2k sf,1 block Lido Beach

Welcome to our cute, spacious, sun filled and newly renovated Beach Villa. A Happy place for sandy feet, friends, and family. The Villa is located 1 block away from world famous Lido Beach, a 7 min walk to St Armand's Circle, and a short 3 mile drive to grocery shopping & the excitement of downtown Sarasota. The 2 bdr villa comfortably sleeps up to 6 people and features a private outdoor patio, spacious dining area, in-unit washer/dryer & dedicated parking. Come enjoy a taste of paradise!

SIESTA BEACH HOUSE HEATED POOL☀️🌴3 MIN TO BEACH!!

Your "Beach Home" w/ heated pool is a private home 1 and 1/4 mile drive to Beach Access 12 on Siesta Key. 3bedroom/2bathroom. It's ideal for families/couples. Everything you need for a great vacation!Fully equip kitchen,towels/linen, laundry room . Large pool w/ gas bbq & patio area. Use our chairs, cooler,umbrella,beach cart.STRICT OCCUPANCY OF MAX 6 PEOPLE INCLUDING INFANTS/KIDS AT HOUSE. NO OUTSIDE GUESTS DAY/NIGHT. DO NOT BOOK IF YOUR GROUP IS LARGER. No Pets. Min Age 26 to book

2 Bedroom Flat: Downtown Boca Grande:#1

We’ve weathered the storms of Hurricanes Helene and Milton, and now we’re thrilled to welcome you! This beautifully renovated 2-bedroom, 1-bath flat is nestled in the heart of historic Boca Grande on stunning Gasparilla Island. The ground-floor location and a private outdoor sitting area, it’s your perfect island retreat. Steps away from The Temp Restaurant, a 3-minute stroll to the Gasparilla Inn, and only 2 minutes to the beach. Everything you need for an unforgettable vacation awaits!

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

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.

Luxury Lemon Bay 6 BR villa w/ 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.

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.