Holiday rentals with a pool in Cortez

4.99 out of 5 average rating, 163 reviews

Home in West Bradenton

Suncoast Beach Getaway - 10 Minutes to Gulf & IMG

Enjoy some of Florida's finest white sandy beaches. Only 4 miles/10 minutes to the shimmering Gulf of Mexico or IMG Academy. This Luxurious 4 bedroom 2 bath pool home has an additional queen futon & 2 sets of bunkbeds. 100% remodeled by builder/owner. Over 2300 square ft. of A/C space (3 zones) all on one level with a huge private HEATED POOL. Featuring a fully stocked gourmet chef kitchen & stunning granite counters! The very large rear lanai also may also serve as a 4th bedroom. Come & relax!

5 out of 5 average rating, 27 reviews

Home in Bradenton

Blessed Haven Peaceful Getaway 3 Miles to Beach

Our peaceful, elegant home offers the perfect blend of luxury and comfort near multiple beaches and IMG Academy. Luxurious Amenities: Heated Pool for an add'l fee, Smart Home Features, a modern and fully equipped kitchen w/full oven air fryer for cooking, a Comfortable King-sized bed w/premium linens, Game Room w/arcade tabletop, 1GB Highspeed WiFi, 2 Dedicated Office Desks Relax & unwind in our Peaceful Getaway with morning coffee by the waterfall spa and beautiful sunset walks on the beach.

4.89 out of 5 average rating, 9 reviews

Home in Longboat Key

Beautiful Island Beach House

Beautiful Island Beach House with pool/hot tub and private beach access on Longboat Key. The large light-filled spacious home is close to everything that you want for a fun, yet relaxing beach vacation: restaurants, bars, shopping, nature walks, and sandy white private beaches. Due to island restrictions, a 28-day stay is the shortest rental period allowed. Please note that this property is not available for young children given the surrounding water. Ages over 6 are welcome with supervision.

4.99 out of 5 average rating, 139 reviews

Condo in Holmes Beach

Beach Escape - Make Memories on Anna Maria Island

Nestled in a charming, quiet community of just 8 units, this beautifully updated beach condo offers the perfect blend of relaxation and convenience. The condo is just a short stroll (about 150 steps!) to the pristine white sand beach, where you can soak up the sun and enjoy the coastal views. Wonderful family getaway or couples escape. Private, covered 2 car parking. Laundry in unit. Beach wagon, chairs and gear available. A hidden gem close to everything you need for a relaxing island stay.

Bungalow in Bradenton Beach

4.9 out of 5 average rating, 101 reviews

Bougie Bungalow at the Beach

This newly renovated, completely private, comfortable Anna Maria Island bungalow is super clean & very comfortable. It has an open, split floor plan, 2 king bedrooms, each with private baths, separate dining and Florida room & is only 3 houses from the amazing white sand beach, the bay & Pier. Only 1 block over is Historic Bridge Street with cool restaurants, mini golf, quaint shops & bars with live music. Once here, you never need to drive -everything is within a block walking distance!

5 out of 5 average rating, 12 reviews

Boater's Waterfront Retreat

Welcome to Boaters' Waterfront Retreat! Experience comfort and adventure at our canal-front home. This 2-bedroom + bunk room, 2-bath retreat includes an open floor plan, screened patio, and pool. There's 40-foot dock with direct ocean access so bring your boat and store the trailer, too. We're 3 miles from the beach and 1 mile from shops and restaurants. Beach chairs, cooler, and beach cart provided. Optional bike rentals available. As locals, we're here to ensure you have a fantastic stay!

5 out of 5 average rating, 32 reviews

Canal front, dock, heated Pool, near AMI+IMG

Fall in Love with the Gulf Coast Lifestyle! This inviting and charming canal-front home located in the boating community of San Remo Shores with a beautiful pool area offers a perfect blend of indoor and outdoor coastal living to enjoy a relaxing vacation. Enjoy the convenience of docking your boat right in your backyard, making it easy to explore the beautiful crystal-clear water of the Gulf of Mexico. Its just a short drive away from the wonderful white sandy beaches of Anna Maria Island.

4.93 out of 5 average rating, 151 reviews

2.5mi -> beach, Dogs OK, Pvt Pool, Grill, Tropical

Enjoy your own private tropical oasis with enough space for your entire family! ⭐️ AMI Beaches - 5 mins ⭐️ IMG Academy - 9 mins ⭐️ Robinson Preserve - 13 mins ⭐️ Outdoor Kitchen w/ propane grill ⭐️ Heated pool ⭐️ Sun deck in mango tree ⭐️ Split floor plan - 1 King & 2 Queen beds ⭐️ Fully equipped kitchen ⭐️ Washer & dryer One of our ⭐️⭐️⭐️⭐️⭐️ reviews: “This place was absolutely magical! We have stayed at several Airbnb’s around Florida and this was by far our favorite.” – Cory

5 out of 5 average rating, 8 reviews

Luxurious Canal Home~Pool~Dock~Games~Mins to Beach

Plan your next escape to Bradenton, Florida and experience both fresh and saltwater attractions, visit natural and cultural exhibits in museums, stroll along the Riverwalk, and peruse galleries, studios, and shops. When you stay at this 3-bedroom, 2-bathroom vacation rental home, you’ll be treated to a fully equipped kitchen, private pool, and a prime spot right on the water. Rent kayaks from local businesses to explore the canal, or simply unwind at the home with your companions.

5 out of 5 average rating, 43 reviews

5 min to IMG + AMI Beaches + Hot Tub/Pool

🌊🌴Welcome to Kingston’s Hideaway, a beautiful waterfront oasis just 2 miles from the pristine Gulf beaches of Anna Maria Island! Whether you're seeking relaxation, adventure, or a bit of both, this home offers a tranquil and luxurious escape for your next vacation! Waterfront Canal: Direct access for boating and paddleboarding-(2 paddleboards available for use) Private Dock: Conveniently dock your boat right at the house (27 ft max) Pool & Hot Tub: Relax and rejuvenate.

4.91 out of 5 average rating, 373 reviews

Home in Bradenton

Palm Retreat: #1 Top Rated Rental of Bradenton/AMI

Enjoy Florida sun in a stunning, newly renovated 4/2 pool home! We have provided almost everything we could think of including five 4k TVs w/ Netflix and cable, wifi, heated (optional) salt water pool w/ 7' privacy fencing, adult bikes, beach gear, Pack & Play, office, board games, relaxing lounge chairs, stocked kitchen, washer & dryer, garage parking, dog crate, all in a quiet and safe neighborhood. Oh, and of course it's just 5 miles to world renowned beaches.