Family-friendly holiday rentals in Cortez

An inviting entrance displays turquoise walls accented by a vibrant orange door. Two orange chairs are positioned at a small round table, enhancing the outdoor seating area. Decorative elements, including shells and a colorful wall sculpture, create a welcoming atmosphere.

4.98 out of 5 average rating, 109 reviews

Cortez Lighthouse Cottage / Entire Cottage

Entire Lighthouse Cottage 2 Bedroom 2 Bath, Full Kitchen with LOTS OF EXTRAS. Very Tropical , Spacious & Relaxing . Historical Cortez Fishing Village 1 1/2 miles away. 2 Miles From Gulf Of Mexico, Beautiful Beaches, 🏖🏝Shopping, Restaurants, Golf, Fishing, Boating, Jet Ski, Fishing Charters, Dolphin Sight Seeing Tours & Much More. Come Join The Fun In The Sun (WE DO REQUIRE A $75.00 PET FEE . LIMIT 2 PETS ) HUGE FIELD FOR KIDS & PETS TO RUN & PLAY.

4.85 out of 5 average rating, 134 reviews

Cottage in Cortez

Ty's Canal Cottage

"Welcome to Ty's Cottage in Historic Cortez Fishing Village, which is one of Florida's last working fishing villages. Located within walking distance to well known Starfish, Swordfish, Tide Tables Restaurants and Tyler's Homemade ice cream. A short 1.3 mile walk to Anna Maria Island with gorgeous beaches. Short driving distance to beautiful golf courses such as IMG Academy Golf and Manatee County Golf Course. Local fishing charters for outstanding fishing. Outdoor sitting area on canal."

A charming exterior view of the bungalow is presented, featuring a wooden walkway leading to a brightly colored entrance. Lush palm trees surround the property, and a privacy fence encloses the spacious yard, creating a tranquil atmosphere.

4.74 out of 5 average rating, 109 reviews

The "Love shack" Bungalow

The "Love Shack" Bungalow is the Perfect Place for a Couples Getaway! It's also great for someone who is looking for a Nice Peaceful Relaxation Spot. Approx 1.5 Miles to the Beach. It's Very Secluded with a Privacy Fence Surrounding it. Beautifully Updated Inside with Granite Counters & Blue Colorful Epoxy Floors. Super-Fast Wi-Fi & 50" Smart TV with Free Movies & Apps. There's a Large Screened in Lanai with a Table, A Gas BBQ Grill, Washer & Dryer & a Big Fenced in Yard. We are Pet Friendly!

Superhost

A spacious living area features a large sectional sofa in a neutral tone and decorative throw pillows. Natural light filters through the window, illuminating a coffee table adorned with a small potted plant. A piece of artwork adds color to the wall.

4.83 out of 5 average rating, 137 reviews

The Shell House-Near Beach-Enclosed Private Pool

This beautifully decorated Cortez home is just minutes to Anna Maria Island and the gulf beaches. Not feeling the sand today, no problem! Relax out back at the large private pool or take a nap on the large comfortable outdoor sectional in front of the pool TV. We are located close to the Cortez Fishing Village, beach shops, several restaurants, live music, boat & jet ski rental shops! We pride ourselves on the guest experience, so let us help you fall in love with the place we call home!

A sparkling blue pool is surrounded by a stone deck and lush greenery. Lounge chairs are positioned beside the pool, with a covered patio in the background. The water canal and boats are visible beyond the backyard, under clear blue skies.

5 out of 5 average rating, 48 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.

4.98 out of 5 average rating, 105 reviews

Home in Sarasota

Family Friendly w/Free Heated Pool Near Beach

Welcome to Vistalodgings Villa Del Sol where families have fun ☀ 3 bedrooms: 1 king, 1 queen, 1 full, 1 twin bed and 2 full bathrooms ☀ Fully equipped kitchen: Keurig dual coffee maker, waffle maker, air fryer, electric kettle, blender, mixer, pots and pans ☀ Dining area for 8 ☀ Fast speed internet Wi-Fi ☀ Heated pool free of charge ☀ EV charger ☀ Shuffleboard, Pac-man arcade ☀ 5 Smart TVs with Disney Plus ☀ Bikes, beach chairs, umbrellas, cooler, beach toys ☀ Iron

4.98 out of 5 average rating, 108 reviews

Cottage in Bradenton

Cortez ~ Grouper Cottage. BRING YOUR BOAT!

This waterfront home with a private dock and boat slip is the perfect place to get away. Grouper Cottage is an ideal cozy place to unwind and enjoy sunsets and dolphins. You will fall in love with this refurbished historic cottage—set in a private, tranquil setting, with picturesque palm trees and mangroves surrounding the property's shoreline. Cortez dockside cottages is nestled on an acre with a compromise of old Florida with the historical background a laid back Island vibe.

An outdoor pool area is enclosed with a screened lanai, featuring a clear blue pool with a sun shelf. Comfortable seating is provided nearby, along with a barbecue grill. Lush palm trees and a canal view are visible in the background.

5 out of 5 average rating, 54 reviews

3BR/3BA + Waterfront! Hot tub + Pool + Beaches!

🌊🌴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-(1 paddle board available for use) Private Dock: Conveniently dock your boat right at the house (27 ft max) Pool & Hot Tub: Relax and rejuvenate.

4.97 out of 5 average rating, 143 reviews

The bedroom features a spacious bed with decorative pillows and a light blue throw. An accent bench sits at the foot of the bed, while a round mirror reflects soft lighting from a chandelier. A patterned wallpaper adds a coastal touch, enhancing the serene ambiance.

Apartment in Bradenton

KING Bed + Anna Maria Island Beaches + Beach Gear!

⚓️🦩Welcome to the Coastal Flamingo! Your nautical getaway that combines style, fun, and the serene beauty of the Gulf Coast. This cozy, vibrant themed condo is the perfect destination for your next Beach vacation. Walking distance to Palma Sola Beach Causeway, where you can enjoy sun-bathing, horseback riding, jet skiing, and fishing! 5 mins or less from the Gulf of Mexico and powdery white sand beaches of Anna Maria Island! Kick back and relax in this coastal escape!

5 out of 5 average rating, 17 reviews

An aerial view captures a modern three-level home featuring multiple balconies and a sparkling heated pool on the lower level. The surrounding landscape includes lush greenery, with the bay visible in the background, creating a serene ambiance during dusk.

Home in Cortez

Bayview Pointe! Luxury home! Near Anna Maria isle!

Welcome to Bayview Pointe, your home away from home, a brand new gorgeous three-level vacation home in an exciting new eco-friendly community that connects luxury with sustainable living. - Less than a Mile to World Class Beaches of Anna Maria Island - Gorgeous Bay View - Private Heated Pool - Elevator for easy access to different home levels - Tesla Charging Station - Close to Restaurants and Activities - Boat Launch Facility with Bay access

5 out of 5 average rating, 9 reviews

Rustic Coastal Escape| Pool | Fire Pit

Welcome to Rustic Coastal Escape, a charming 3-bedroom, 2-bath retreat inspired by relaxed beach living and vintage coastal style nestled in historic Cortez village. Thoughtfully decorated with rustic touches and coastal décor throughout, this home offers a warm, inviting atmosphere perfect for families, couples, and friends looking to unwind near Florida’s Gulf Coast. The beach is just a 2 minute drive or just a 15 to 20 minute walk away.

A cozy living area features a gray futon with checked throw pillows. A rustic coffee table sits in front, complementing the light wood flooring. Natural light filters through multiple windows, framed with light curtains, highlighting the simple decor.

4.86 out of 5 average rating, 35 reviews

BlueMoon by the Bay

Come stay and enjoy this newly renovated one bedroom one bath stylish beach base camp only 1.2 miles from beautiful Anna Maria Island and only steps away from your own beach by the bay. It offers a queen sized bed, a queen futon, washer and dryer, 2 separate parking spots, screened in lanai, grill, beach chairs. Bring your fishing poles. Located at Parrot Cove Marina. Only 10 minute drive to IMG Academy! Cortez Fishing Village

Popular amenities for Cortez family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.96 out of 5 average rating, 200 reviews

A spacious bedroom features a large bed with striped bedding, complemented by two nightstands with lamps. Sliding glass doors open to a private backyard with a plunge pool. Natural light floods the room, highlighting the warm wooden ceiling and inviting decor.

Home in Holmes Beach

Sea AMI

A spacious outdoor living area is shown, featuring a seating arrangement with floral-patterned cushions and a wooden coffee table. A dining table, set for six, is positioned nearby. The screened lanai offers views of the pool, surrounded by greenery and clear blue skies.

5 out of 5 average rating, 102 reviews

NEW Saltwater Pool + Spa | Mins to AMI Beaches/IMG

The outdoor area features a spacious swimming pool surrounded by lush tropical plants and shaded by a screen enclosure. A hot tub is positioned beside the pool, and the bright blue water reflects the clear sky above.

4.91 out of 5 average rating, 114 reviews

Exquisite modern home with pool - 10 min to beach

Superhost

A view of the beach is presented, with turquoise waters stretching into the distance. Several parked cars are visible in the foreground, alongside a lush green landscape. Umbrellas and beach chairs can be seen near the shoreline, indicating a vibrant beach atmosphere.

Home in Holmes Beach

4.86 out of 5 average rating, 100 reviews

B100 step to the sugar sand gulf front view & pool

4.98 out of 5 average rating, 132 reviews

A bright living room features a large, light-colored couch adorned with patterned cushions. A swing chair hangs in the corner, and a coffee table sits in front of the couch. Soft lighting and large windows enhance the cozy atmosphere.

Home in Sarasota

Cozy Boho Bungalow Pool/Spa QR Code Walkthrough

A private pool area is surrounded by palm trees and shaded by umbrellas. The inviting water reflects blue skies, while a colorful float adds a playful touch. Comfortable seating is arranged around the pool, creating a relaxed outdoor atmosphere.

4.87 out of 5 average rating, 170 reviews

Spring is in the air - HTD Pool*Hot Tub*Game RM

4.98 out of 5 average rating, 207 reviews

A spacious living and dining area features a table set for four with light-colored chairs. A comfortable sofa is arranged against the wall, and large sliding glass doors allow natural light to flood the space, providing views of the nearby lake and greenery.

Apartment in Bradenton

Shorewalk full condo AnnaMaria Beaches IMG

4.9 out of 5 average rating, 107 reviews

Bungalow in Palmetto

Island Home 5 min to Park, 25 min to Beach, Pool

Family- and pet-friendly home rentals

4.94 out of 5 average rating, 17 reviews

A private pool is enclosed by a safety fence and framed by lush tropical landscaping. Colorful pool floats rest on the surface of the clear water, while a wooden deck leads to the pool area, creating an inviting outdoor space for relaxation.

Home in Palmetto

Designer 2BR Retreat w/ Private *Heated* Pool!

5 out of 5 average rating, 12 reviews

Stunning Water Views, Boat Dock & Heated Pool/Spa

A well-maintained front yard features lush green grass and a large agave plant. The house, showcasing a contemporary design, is flanked by palm trees. A driveway leads to a two-car garage, with additional landscaped areas adding to the outdoor appeal.

4.99 out of 5 average rating, 88 reviews

Dockside Dreams w/ Pool and Spa

A bright and spacious retreat features a heated pool within a screened enclosure, allowing for outdoor enjoyment. The living area showcases modern decor with ample natural light. The kitchen offers sleek cabinets and countertops, while a cozy sleeping area presents a well-dressed spacious bed for comfort.

4.93 out of 5 average rating, 61 reviews

Pets Are Welcome/ Heated Pool/ Close to AMI

The living area features a sectional sofa and armchairs in calming tones, complemented by a wooden dining table with high chairs. A built-in television unit is accented by decorative shelves. Natural light filters through large windows, and a ceiling fan adds to the comfort.

4.93 out of 5 average rating, 73 reviews

NEW! Casa Corallo ● At Anna Maria Island Beaches

4.88 out of 5 average rating, 59 reviews

A light-filled living area is furnished with a curved sectional sofa adorned with colorful cushions. A round coffee table rests on a floral-patterned rug, surrounded by decorative plants and coastal-themed artwork. Large sliding doors lead to an outdoor space, framed by sheer curtains.

Apartment in Bradenton

J&J Island Time

5 out of 5 average rating, 30 reviews

Townhouse in Bradenton

Family Vacay+3 miles to AMI & IMG+Beach Paradise!

4.97 out of 5 average rating, 199 reviews

A clear blue pool is surrounded by palm trees and a well-maintained patio area. Lounge chairs are arranged nearby, and a dining set is visible in the background, enhancing the outdoor space. The sun-filled setting creates a vibrant atmosphere.

Flat in Holmes Beach

Crows Nest at Spinnakers Vacation Cottages

Family-friendly home rentals with a pool

5 out of 5 average rating, 13 reviews

A Piece of Paradise to kick back and relax!

Superhost

A green outdoor putting area is featured on a well-maintained artificial turf surface, complete with two holes and flags indicating the target. In the background, a screened enclosure is visible, with a portion of the backyard showcasing landscaping under a clear blue sky.

4.74 out of 5 average rating, 407 reviews

Vacation home heated pool Turf yard putting green

5 out of 5 average rating, 23 reviews

Villa in Bradenton

Lilo & Stitch Ohana Villa|Heated Pool Near AMI

A tranquil outdoor space features a heated pool surrounded by stone pavers. Comfortable lounge chairs are positioned nearby, and a modern fire pit offers seating. The restored stone house stands in the background, framed by palm trees under a clear blue sky.

4.97 out of 5 average rating, 34 reviews

100 yr Old Stone Home + Pool + 9 miles to beaches

A screened-in pool area is shown, featuring a clear blue pool with sunlight reflecting off its surface. Lush greenery surrounds the space, including palm trees and other tropical plants visible through the screens.

5 out of 5 average rating, 25 reviews

Luxury Coastal Getaway, minutes from AMI!

4.91 out of 5 average rating, 68 reviews

Home in Holmes Beach

Family Condo with Heated Pool Spa and Mini-Golf

An illuminated pool radiates a tranquil blue hue under a night sky, surrounded by lounge chairs and palm trees. A cabana offers shaded seating in the background, while vibrant outdoor décor enhances the relaxing ambiance of the outdoor space.

5 out of 5 average rating, 9 reviews

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