Family-friendly holiday rentals in Sarasota

Coastal Farmhouse - 3/2 with heated saltwater pool

Experience relaxation at this tranquil 3BD/2BA home with a heated pool, perfect for a family retreat! Prepare meals in the fully equipped kitchen or savor local delights on the screened-in lanai. Each bedroom boasts plush bedding, ensuring a restful night's sleep. Plus, a cozy living room. Conveniently located, just under 9 miles from Siesta & Lido Key Beach, Der Dutchman 2.2 miles and 2.5 miles from Yoder's Restaurant. Shopping and dining options at University Town Center, only 7.7 miles away.

The Bradford Cottage/Heated Pool /Mins to Siesta

If you are looking for a cozy retreat in a safe and private neighborhood than look no further! From the minute you step inside this immaculate private residence you will feel right at home. With a beautiful open floor plan with plenty of room to spread out, natural light that pours in every room and a spacious back porch overlooking the heated pool this is the perfect place to unwind and relax. Minutes from the #1 rated Siesta Key beach and downtown Sarasota you are in the middle of it all!

Sun-Kissed Memories!

This sublime oceanfront studio is directly on the pristine white sands and serene blue waters of the Gulf of Mexico in Longboat Key, Florida! On the second floor, overlooking the heated pool and ocean, this dreamy studio condo is optimal for sunset viewing from a private lanai. Take a 30-second walk to the pool and secluded beach. Enjoy a relaxing vacation at our peaceful condo at The Beach at Longboat Key Resort! To see all four of our listings, click on my Host photo and scroll down...!

Luxury Villa with Pool, Game Room, Near Beach

Welcome to your tropical luxury escape! Spacious living flows to the heated pool, game room and sunny patio—perfect for family fun. • Bedrooms: 4 private suites, plush linens to ensure restful nights. • Location: Quiet neighborhood just minutes from the sandy beach, dining and shopping hotspots. • Heated pool & sun loungers • Arcade-style game room • Fast Wi-Fi & 5-star cleanliness • Pet friendly with fenced yard Have questions? We reply in under an hour—book your stay today! VR24-00060

Modern 4BR Home *Heated Pool & Spa*

Discover elegance in this centrally located Sarasota gem, featuring four bedrooms and two bathrooms to accommodate up to eight guests. Enjoy a laid-back vibe while lounging at Sarasota's beaches or immersing yourself in local attractions. Siesta Beach and Lido Beach are within easy reach at 7.6 and 6.4 miles respectively. Rest easy knowing commitment to cleanliness aligns with your travel priorities. Your serene vacation awaits in this beautifully adorned home. VR24-00265

Roselawn St | Private Pool, Fire Pit + Patio!

BNB Breeze Presents: Roselawn Street! Located in the heart of Sarasota, just 10 minutes away from Siesta Key Beach, the location of this home is everything! This stunning oasis with a private pool and basketball court includes: • Private Heated Pool - heated at NO extra cost from Nov 21 - April 1st • Miniature Basketball Court • Covered Outdoor Dining Area + Grill • Lightning Fast Wi-Fi (Perfect for Remote Work!) • Incredible Fire Pit w/ String Lights! • 2 Living Rooms

Coastal Getaway *With Bikes & NEW Saltwater Pool*

Just outside of Downtown near the Legacy Trail, this home is located in a quiet neighborhood only 15 minutes from the Siesta Key Beach. The home stands out with its bright and airy design, brand new saltwater pool in the private backyard, and its breezy living room. The large master bathroom rain shower is perfect to wash off the leftover sand from the beach. You can also spend your evenings grilling out back or playing corn hole in the patio area.

Saltwater heated pool w/ massage chair + hot tub

Welcome to Citrus & Serena Stays, your private tropical oasis perfect for large families or groups! Near Bradenton’s attractions, including Anna Maria Island, this property features a screened-in heated saltwater pool, electric massage chair, fire pit, and more. With its playful orange-fruity décor, it’s ideal for an unforgettable vacation ☀Bradenton Beach - 12 Min ☀Riverwalk - 10 Min ☀Anna Maria Island - 12 Min ☀IMG Academy - 10 Min

Beaches, Shopping, Sculling-Sarasota is calling!

Escape to this 3BR, 2BA Sarasota retreat in a quiet neighborhood, just minutes from UTC Mall, Nathan Benderson Park, and a short drive to award-winning beaches. Sleeps 6 comfortably with a bright open layout, fully equipped kitchen, and cozy living spaces. The highlight is the private heated saltwater pool, perfect for relaxing after a day of shopping, dining, or beach adventures. Your Sarasota getaway starts here!

2BR, 2BA home in the heart of downtown Sarasota

Our 2BR/2BA bungalow is fully renovated and spotlessly maintained. You can walk downtown, visit parks, explore art, dine at fine restaurants, and enjoy views of Sarasota Bay. The shops at St. Armand's Circle & beaches of Lido Key are 5 miles away. You’ll love our neighborhood and our home. A detached carriage house/garage apartment available for separate rental.

Charming Sarasota Home with Pool!

Charming 3/2 home with a pool! very safe neighborhood, 8.9 miles to Siesta Beach and 5.5 miles to Lido Beach. 15 minute walk to The quaint little village of Pinecraft and Der Dutchman Restaurant and more restaurants and shops. Very clean, private back yard, heated pool, coffee station... really everything you need for a relaxing and enjoyable stay in Sarasota.

The Sarasota Sea Turtle Cottage

Paradise found at the private Cottage in a lush and quiet area with modern amenities and decor that feels artistic and comfortable -- all at once. The location is sublime -- walking distance to vibrant downtown SRQ & short car-ride to the beach. Please see our newest luxury accommodations "The Mermaids & Corkscrew Loft". http://abnb.me/EVmg/rt4iVIO3cF.