Holiday rentals with a pool in Manatee River

4.96 out of 5 average rating, 106 reviews

A fenced-in outdoor area features a swimming pool surrounded by a red brick patio. Sun loungers are positioned beside the pool, and a pool house is visible in the background, complemented by lush greenery and large trees draped with moss.

Cottage in Palmetto

1930s Cottage + Pool 12 miles to Beach

Located in the heart of historic Palmetto FL, you will find this adorable cottage. This home has 2 bedrooms & 1 bath in the main home with a pull out sofa, as well as, a pool house with a full bath & daybed. You will love the southern charm of this home while relaxing by the pool or having morning coffee on the front porch. There are many restaurants & shops w/in walking distance as well as local parks & preserves. If you love the beach, this home is just a short drive to FL's beautiful beaches.

4.94 out of 5 average rating, 145 reviews

A sparkling pool reflects sunlight, set against a backdrop of lush greenery. Two blue chairs are positioned near a small table on grass, offering a serene view of the adjacent canal. A decorative fence surrounds the backyard, enhancing the outdoor space's privacy.

Cottage in Bradenton

Waterfront Escape•PingPong•Relax & Recharge•Pool

Your peaceful waterfront escape awaits. This cozy 2BR/2BA cottage offers two living areas. The bright Florida room overlooks the canal. It includes areas for a game of ping pong, a life‑size Jenga set, watching tv, having a bite at the table, and a sleeper sofa. Enjoy morning coffee at the dock watching the fish jump or grab your pole. Relax by the sunny pool or practice on the putting green ⛳. Fast WiFi, a dedicated workspace, beach gear, and a full kitchen make winter stays easy and relaxing.

A serene outdoor space showcases a sparkling pool framed by lush tropical landscaping. Palms and vibrant plants surround the area, with a flamingo statue in the foreground. Soft lighting from string lights enhances the tranquil atmosphere as the sky transitions to dusk.

5 out of 5 average rating, 61 reviews

Flamingo Royale — Beach Luxury Resort

Welcome to the Flamingo Royale — Your luxury sanctuary! This exquisite escape gives tropical elegance perfect for indulgent relaxation and unforgettable memories. Experience the charm of old Florida with a modern twist in a stylish setting. Step outside to your personal paradise—a shimmering pool surrounded by lush landscaping & palms galore. W/ beautiful Anna Maria Island just moments away, relish pristine beaches, boutique shopping, and fine dining. Experience paradise at the Flamingo Royale!

4.99 out of 5 average rating, 248 reviews

A private stock tank pool is surrounded by a wooden deck and lounge chairs. An umbrella provides shade over the pool area. Colorful towels and a stylish table with refreshments are visible, set amidst a landscaped courtyard with lush greenery.

Guest house in Sarasota

Magical Guesthouse 1 mi from SRQ airport

@Aloe_Stranger Dreamy + fresh! This 1-bedroom guesthouse has a king bed, full bath, kitchen, washer/dryer, daybed + sleeper sofa. NEW STOCK TANK POOL! Full of style - it feels like you're in your own art installation. 1 mile from SRQ Airport, it boasts a great location as well cushy comforts. 1/2 mile from Sarasota Bay, 15 min from Lido Beach, 15 min from Siesta Key and many beaches around the Sarasota/Bradenton area. 10 min from downtown Sarasota, 1 mile from the historic Ringling Museum

A serene outdoor area features a well-maintained lawn with stone pathways and tropical landscaping. Palm trees provide shade around a bar area, overlooking the water. A private dock is visible in the background, with the gentle bayou waters reflecting the blue sky.

5 out of 5 average rating, 59 reviews

Waterfront Bungalow• Dock•Heated Swim Spa•Near AMI

Watch for dolphins and manatees from your private dock and unwind under the stars in the heated swim spa. This peaceful waterfront bungalow near Anna Maria Island is a five-star favorite; perfect for couples or families craving calm, comfort, and coastal charm. Enjoy direct water access for boating or paddling, stunning bayou views, and quick access to beaches, shops, and dining. 🚤 Bring your boat or jet skis • 🌴 5 min to Robinson Preserve • 🏖️ 10 min to AMI • 📶 Fast Wi-Fi | Smart TV

4.94 out of 5 average rating, 120 reviews

Home in Holmes Beach

The Peachy Beach House, steps to the gulf

The perfect place for a combination family vacation and some romance-when the kids are in bed, turn on the spa and music. June, July and August, Saturday to Saturday only. If custom trip length is wanted- ask Two bedroom, 2 full bathroom, new heated private pool/spa Steps to semi-private gulf beach, on quiet street in N. HB Well-stocked kitchen, 2 TVs, large primary suite and amazing gulf views from bedrooms. Crib, high chair, beach chairs, wagon, umbrella, beach toys and towels

5 out of 5 average rating, 39 reviews

A private heated pool is surrounded by a spacious patio with lounge chairs and an umbrella for shade. The modern two-story home features large glass doors that brighten the living spaces, and vibrant greenery enhances the outdoor area.

Home in Sarasota

Sarasota Escape | Minutes to Beaches + Downtown

HEATED POOL + ECO FRIENDLY. Relax with the whole family or bring that group chat trip to life at this peaceful retreat in the heart of Sarasota. Boasting a spacious and nature-inspired design, this home is a short drive to several world class beaches, the downtown Sarasota arts district, 5 star dining, shopping and more. The home is also located within walking distance of a park complete with playground, public pool, tennis + basketball courts, workout area and walking trails.

A serene outdoor space features a sparkling pool surrounded by lush greenery and tropical plants. Comfortable lounge chairs are placed along the poolside, and string lights cast a warm glow overhead. A shaded seating area with a gazebo can be seen in the background.

4.91 out of 5 average rating, 394 reviews

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.

A sunny backyard features a refreshing saltwater pool surrounded by a smooth deck. Blue and white lounge chairs create a comfortable lounging area, while a vibrant yellow bungalow is seen in the background. Lush green turf offers a spacious setting for relaxation.

4.95 out of 5 average rating, 204 reviews

Private Heated Pool, Turfed Putting Green Retreat

Imagine life in a tropical oasis-surrounded by palms trees, turfed lawn and putting green while enjoying the Florida sun relaxing your private saltwater heated pool with extended sun shelf. This 3 bedroom/2 bath 1940s bungalow is a great place to relax and unwind with your own resort style backyard. The fully equipped home, located between downtown Bradenton and Anna Maria Island offers fun in every direction. We guarantee you'll want to stay awhile!

An aerial view captures a heated saltwater pool accompanied by a spa hot tub, surrounded by a stone patio and tropical landscaping. Loungers and Adirondack chairs are positioned for relaxation under a shaded umbrella. A serene pond and lush greenery create a tranquil backdrop.

5 out of 5 average rating, 118 reviews

Relaxing 3BR Retreat+ Hot Tub + Pool +Beaches +IMG

🌴Welcome to Beachway Haven! This 5-Star ⭐️ hideaway is just mins from Anna Maria Island's Pristine Beaches & the Gulf of Mexico. Dive into relaxation with your own Heated Saltwater Pool & Spa Hot Tub, nestled in a tropical oasis. Only a skip away from Golf Courses, Nature Parks, IMG Academy, & Palma Sola Causeway's Beach Access – your gateway to Horseback Riding, Kayaking, & endless sandy adventures. Shopping & dining are only a few mins away too!

A spacious screened-in pool area features a private heated saltwater pool surrounded by lush greenery. Lounge chairs are positioned beside the pool, and a small waterfall adds a tranquil touch. The clear blue sky is visible overhead, enhancing the bright and inviting atmosphere.

4.91 out of 5 average rating, 102 reviews

Relax @ Elegant Retreat w/ Pool Near Gulf Beaches

Welcome to this beautifully renovated open concept home located on a large corner lot. You’ll love the open bright space. Outside you’ll find a large screened in area with a private heated salt pool, grill, dining for 6, outdoor seating as well as a fenced in yard with deck and lounge chairs. Located in a quiet and safe neighborhood that is just minutes away from some of the most desired beaches, great dining options and amazing shopping.