Holiday rentals with a pool in Lakewood Ranch

Guest House with Hot tub & Heated Pool

Welcome to your serene retreat in sunny Florida! This beautifully finished 1-bedroom, 2-bathroom mother-in-law suite offers luxury, comfort, and privacy. With a heated pool and hot tub, we offer year round outdoor relaxation. Step into your own private oasis with a separate entrance and secluded patio, ideal for morning coffee or evening relaxation. Located in a quiet neighborhood backing up to a protected preserve, offering peace and natural beauty. Beach gear provided for easy beach days.

Pool, Hot Tub, Fun Games Near Downtown/River/Beach

Beach! River! Heated Saltwater Pool! Hot Tub! Your tropical beach vacation awaits! Prime location in proximity to local restaurants, attractions & sparkling waters. Nathan Hejl Interior Designer has updated this spacious 5BR/3.5BA vacation oasis to blend luxurious furniture & finishes w/ a barefoot, tropical vibe. Located in Historic River District in W Bradenton, walking distance to Manatee River, 2mi to Bradenton Convention & only 8mi to the famous Anna Maria Island beaches, 20mi to #1 Siesta

Serenity Lake

Keep it simple at this peaceful and centrally-located place. 15 minutes from beaches this lovely apartment sits on a pond full of fish with a dock. Large pool ready for swimming and sunning. Charcoal and gas grill available. Beautiful upper deck to sit and enjoy the large mango tree and view over the lake. Golf cart available for evening rides. There is a large driveway for a boat. Swim and fishing accessories available. Minutes from I-75 - also near the famous Lakewood Ranch downtown.

Heated 3BR Pool Home Glen Oaks | Close to Downtown

Family-friendly pool home near Bobby Jones Golf Club, perfectly located in the heart of Sarasota. You’re less than 10 minutes from top attractions, dining, and shopping, Downton Sarasota and just a short drive to the world-famous Siesta Beach or Lido Beach. This private home features its own entrance, a heated pool, and a fully fenced backyard—ideal for families and added privacy. We’re pet-friendly too! Comfortable, central, and close to everything—perfect for your Sarasota getaway VR24-00164

Serenity at Sabal Key - Renovated Relaxing Comfort

Relax in this newly renovated, sparkling clean, end-unit 2 bed / 2.5 bath townhome. Perfect for snowbirds escaping winter, families with athletes at IMG/Premier, or anyone who wants more than just the beach. Whether you're here for a season, a tournament, an extended stay, or a week, this home offers the perfect balance of resort-style living, central convenience, and long stay comfort. Enjoy the resort-style pool, pickleball, tennis, shaded walks - close to beaches, shopping and golf.

Secluded 5-Acre Escape

Welcome to your private oasis in the heart of Bradenton, Florida! Nestled on a sprawling 5-acre estate, this charming retreat offers the perfect blend of tranquility and convenience. Whether you’re seeking a peaceful getaway or an adventure-filled vacation, our property provides the ideal setting for your stay. Prepare delicious meals in the fully equipped kitchen, or your perfect outdoor BBQ on the patio overlooking the lush grounds. Unwind your evenings by the fire pit or pool. YOUR CHOICE.

Coastal Manor | Heated Pool · Dogs Welcome · LWR

Welcome to Coastal Manor, a refined coastal retreat in Bradenton, FL. This elegant 3BR, 2.5BA home offers a serene escape with a private heated pool, spacious fenced yard, and pet-friendly amenities. Located in Lakewood Ranch just minutes from UTC, Nathan Benderson Park, Premier Sports, IMG Academy and Gulf Coast beaches. It’s the perfect blend of charm and convenience. Designed with a muted coastal cottage vibe, this getaway invites you to relax, unwind, and explore the best of Florida.

New Luxury Villa W/ Resort Amenities

Brand-New Villa in Lorraine Lakes – Lakewood Ranch Be the first to live in this stunning brand-new villa. 🛏 3 Bedrooms | 2 Bathrooms 🛋 Furnished with Gorgeous Brand-New Furniture – Move-In Ready! Enjoy access to Lorraine Lakes’ gorgeous amenity center, featuring: ✅ Fitness center ✅ Resort-style pool & splash pad ✅ Pickleball, tennis, and basketball courts ✅ Clubhouse with cafe, social spaces & more 🏖 Only a short drive to world-famous Siesta Key, Lido Beach, and Anna Maria Island.

New unit! Luxury 1st floor condo @ Lakewood Ntnl

Welcome to Piper View at LWN! A modern, two bathroom condo located in Lakewood National Golf and Country Club. It’s a beautiful gated golf club community with lake and green view. The unit overlooks one of two Arnold Palmer golf courses. Enjoy resort style living with access to golf, tennis, pools, spa/salon, gym and outdoor Tiki Bar and restaurant with monthly stays! (See other details) Located by Sarasota near beautiful beaches within 40 minutes, including #1 rated Siesta Key.

Lakefront Pool Home, Pickleball +Tennis Near Beach

Escape to this lakeside haven with a private heated pool, just minutes from the pristine beaches of Siesta Key, Anna Maria Island, Bradenton Beach & Lido Key. Relax in the serene setting or explore the nearby sandy shores. Whether you're looking for a peaceful retreat or coastal adventure, this stunning getaway has it all for an unforgettable stay! Perfect for families, friends, or couples seeking both tranquility and excitement. Book your slice of paradise today!

Useppa Villa

"STOP scrolling—you've found your paradise. Come relax by the beautiful pool with a drink or head to the beach. Our mission is to ensure you have an unforgettable experience. This tastefully decorated and updated home has everything you need, from kitchen essentials to toiletries. Just pack your clothes and leave the rest to us.” We've priced this home at a two person daily rate to make it accessible to everyone, so please enter the correct number of guests.

The Seashell Cottage with peaceful water views!

Hello and welcome to my beautiful Seashell Cottage! I have completely renovated and remodeled this townhome for you! It has a new kitchen and bathroom, new vinyl plank flooring upstairs, new furniture and bedding throughout, and is freshly painted. Decorated in a turquoise beachy decor, it gives you a sense of peace and tranquility the moment you step inside! There are gorgeous water views of the lake from both the first and second floor.