Family-Friendly rentals near Cortez Beach

Adirondack chairs in soft blue are positioned on the sandy beach, offering scenic views of the ocean and coastline. The sun reflects off the water, enhancing the tranquil atmosphere, while a distant figure strolls along the shore. Lush greenery borders the sandy area.

4.94 out of 5 average rating, 157 reviews

Beach Escape & Pool, steps to Beach & restaurants

One block from beautiful beach & waterfront dining. Newly renovated Villa in quaint quiet condo building close to everything on Anna Maria Island. Pickleball across the street. Pool literally out your back door. Perfect for a small family or a romantic getaway. *Min. renter age 25. Two minute walk to beach, trendy Bridge Street shops, marina, restaurants, bars, boat tours, mini golf and more. Brand new beds, furniture & appliances. Kitchen has everything you need. Beach supplies in hall closet.

A private heated pool is surrounded by tropical landscaping and palm trees, creating a serene outdoor space. Two lounge chairs are positioned beside the pool, and a small table is visible on the lawn. Bright sunlight casts a warm glow over the vibrant plants.

4.95 out of 5 average rating, 114 reviews

Breezy Harbor AMI pool retreat near the Beach

Charming Breezy Harbor sits in a quaint, exclusive corner of AMI and boasts a private heated pool and ample parking for 2 vehicles and even a boat: -We typically have shorter stays available, just ask! -If you don't have a single 50Lb pet, please discuss it with us -One of the twin boutique MyAnnaMariaStay homes, look us up! You'll love the luxury mid-century feel, lush yard, and a 6-min walk to the beach, Publix or the trolley stop. AMI was voted a top 50 vacation spot in the world in 2024

Bungalow in Bradenton Beach

A tranquil outdoor space features a wooden dining table surrounded by eight chairs set on a tiled patio. A small, curved swimming pool is framed by lush tropical plants, and umbrellas provide shaded areas. The vibrant greenery creates a serene atmosphere.

4.91 out of 5 average rating, 110 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!

4.99 out of 5 average rating, 165 reviews

Condo in Longboat Key

Silver Sands By the Sea: Open Christmas!

This charming seaside condo is directly on the pristine white sands and serene blue waters of the Gulf of Mexico in exclusive Longboat Key, Florida! Located on the second floor, overlooking the heated pool and ocean, this dreamy one-bedroom condo is optimal for sunset viewing from a private, screened lanai. Take a 30-second walk to the pool and onward to the secluded beach with loungers and sun umbrellas. Enjoy a relaxing vacation at our peaceful condo at Silver Sands Gulf Beach Resort!

4.98 out of 5 average rating, 150 reviews

A spacious living area features a light-colored sofa against a vibrant tropical leaf mural. A sleek white entertainment unit holds a flat-screen TV, complemented by a decorative lamp and a colorful area rug underfoot. Natural light filters through window blinds.

Condo in Bradenton

KING Bed + AMI Beaches + Beach Gear!

🎙️🦩Welcome to the Retro Flamingo! Your tropical 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 retro “Old Florida” themed condo!

A private pool area is surrounded by lush greenery and palm trees. The curved pool features clear blue water, complemented by lounge chairs and a shaded seating area. A second-story balcony offers scenic views, while a barbecue grill is positioned nearby for outdoor dining.

5 out of 5 average rating, 36 reviews

Sunset View Pet Friendly w/Pool Beach Home

Perfect Location! Our 3 bed/2 bath home just across the street from the beach & walking to shops & restaurants. Includes 1 king, 1 queen, & 2 twins beds. 2 living rooms each have a sleeper sofa & TV. Upstairs has additional eating area & access to balcony. Both bathrooms are equipped w/showers, hair dryer, & essentials. Full kitchen w/ breakfast bar. Enjoy a sunset from the 2nd floor balcony. Private pool, covered patio w/large eating area, WiFi, AC, washer/dryer, dishwashe

5 out of 5 average rating, 5 reviews

NEW! Beach Views!-Gulf Front!~Heated Pool!

Relax with the whole family at this peaceful place to stay. Welcome to Seagrape Cottage, a gorgeous and newly renovated vacation getaway with a brand-new private pool. This four-bedroom and four-bathroom home is conveniently located right across the street from the stunning white sands of Cortez Beach and is near Bridge Street, which offers a great place to fish, shop, and try new restaurants. Enjoy island life on your tropical getaway by booking Seagrape Cottage!

4.93 out of 5 average rating, 281 reviews

Guest suite in Bradenton

Kayak w/ Dolphins - Private Entrance Studio

Paddle with dolphins in Palma Sola Bay from this private-entrance, 2-room studio with living room, bedroom w/ queen, bathroom, food prep area (no kitchen sink). Two TVs, WIFI. Dock access in back yard includes use of kayaks/canoe or docking your boat. Quiet on dead-end street. Owner lives in back of house facing canal (see photo). Your space is private with a tropical street entrance & access to the back yard. Non-shedding dog considered with prior approval.

Guesthouse in Bradenton Beach

A vibrant yellow cottage is depicted with a landscaped area featuring palm trees and a gravel yard. Colorful adirondack chairs in pastel shades of pink and blue offer seating options, creating a casual outdoor space. Nearby cottages are visible, enhancing the beachfront setting.

4.99 out of 5 average rating, 197 reviews

Bradenton Beach Sunsets 1, Anna Maria Island, FL

Fully furnished water view beach cottage located on beautiful Anna Maria Island directly across the street from white sand beach and Gulf of Mexico. 1 Bedroom 1 bath unit that sleeps 4 with the queen pull out couch. Beach chairs/umbrellas/Boogie boards/laundry room, etc. provided. Three blocks from historic Bridge Street with lively restaurants and bars. Free island trolley and across the bridge from Cortez fishing village. Free off-street parking.

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, 116 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!

Cottage in Bradenton Beach

4.88 out of 5 average rating, 293 reviews

One Block to Beach - Ohana Hale Beachside 2 BR

COMPLETELY REMODELED February 2025! Aloha and welcome to our Island Home Ohana Hale AMI! Our home is designed for the ultimate beach vacation experience, featuring 2 cozy bedrooms and 1.5 baths. The open kitchen and living area create a spacious, inviting atmosphere, perfect for relaxation and fun. Be sure to check out our amazing 3rd-floor shared deck—it's the perfect place to watch stunning sunsets over the Gulf of Mexico.

4.93 out of 5 average rating, 146 reviews

A cozy sleeping area is highlighted by a framed beach scene above a bed adorned with green and white patterned pillows. A white tray holds two glasses and a small potted plant, positioned on a white quilt. Light wood paneling accents the walls.

Tiny home in Bradenton

Cozy, relaxing studio 17 minutes from the beach.

This is a (small) space in my home (162 square feet), renovated, cozy and beautiful, Fully equipped so you can enjoy a pleasant and comfortable stay. Totally private and independent. Located in a very quiet and safe neighborhood, just 17 minutes from Anna Maria and other beautiful beaches, nature reserves and other attractions. ready for 1 or 2 people.( We have another beautiful stay for 2 people on the same property).

Popular amenities for family-friendly rentals near Cortez Beach

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

Guesthouse in St. Petersburg

A private backyard features a heated pool surrounded by lush tropical plants and trees. The pool has a gentle curve and is accompanied by stone steps leading into the water. A small seating area is partially visible in the background, set amongst vibrant greenery.

4.98 out of 5 average rating, 227 reviews

Central Cozy Cottage w/ Heated Pool & Hot Tub!

4.97 out of 5 average rating, 118 reviews

A spacious living room features a large grey sectional sofa with teal accent pillows, a wooden coffee table, and a light blue area rug. Large glass doors provide access to an outdoor area, while a vibrant seascape painting adorns the wall.

Apartment in Bradenton

Sweet Retreat at Shorewalk!

4.97 out of 5 average rating, 155 reviews

SLeePs 18-JaCuZZi-2kingSuites-Pickleball-2babyCrib

4.98 out of 5 average rating, 194 reviews

A fire table is positioned near large glass windows that frame a stunning sunset over the water. The reflection of the vibrant sunset is visible in the water, while the outdoor landscape is softly illuminated by the fading light.

Condo in Bradenton

Luxury 3/3 Margaritaville Resort

4.94 out of 5 average rating, 119 reviews

The Peachy Beach House, steps to the gulf

A spacious living area features a blue sofa and striped armchair, complemented by a wooden coffee table. Large windows allow natural light to illuminate the room, showcasing views of the turquoise Gulf. Light-colored cabinetry and decorative shelving enhance the inviting atmosphere.

4.99 out of 5 average rating, 156 reviews

★Right on the beach ★ Relax and Enjoy ♥ Sunsets!

A comfortable living area features a sectional sofa and a coffee table on a patterned rug. A large flat-screen television is mounted on a wood-accented wall. Natural light filters through sheer curtains, and a decorative plant adds a touch of greenery to the space.

4.98 out of 5 average rating, 119 reviews

Beach House with jacuzzi near AnnaMariaIsland

4.9 out of 5 average rating, 189 reviews

Black Friday Deals NOW -Sunshine, Fun & Holidays

Family- and pet-friendly home rentals

An aerial view showcases a spacious, heated swimming pool adjacent to a vibrant outdoor recreation area featuring a pickleball court and nearby children's playground equipment. The lush green lawn is neatly bordered by privacy fencing, enhancing the inviting atmosphere for recreation and relaxation.

5 out of 5 average rating, 53 reviews

Pickleball, Axe Throwing, Mini-Golf, Bowling, IMG

A resort-style pool is illuminated at night, showcasing vibrant blue and purple hues. A round, heated spa is visible to the side, surrounded by lush tropical vegetation. Several lounge chairs are positioned near the pool, and a large umbrella provides shade.

4.85 out of 5 average rating, 54 reviews

AMI Cortez Beach Retreat "Views" Resort-style Pool

4.96 out of 5 average rating, 101 reviews

Condo in Holmes Beach

Steps to the beach! Updated Condo at The Terrace

4.95 out of 5 average rating, 218 reviews

A distinctive triangular structure features large glass windows, showcasing vibrant lighting from within. The exterior is surrounded by landscaped greenery and decorative white stones, enhancing the inviting appearance. Palm trees and a tidy paved driveway contribute to the overall charm and unique architectural design.

Home in Sarasota

Modern, Bright Downtown SRQ A-Frame West of Trail

4.98 out of 5 average rating, 97 reviews

An open-concept living area features exposed wooden beams and light hardwood flooring. A dining area with a table and chairs is positioned near a fully equipped kitchen. Glass double doors lead to a cozy sleeping space with a bed and large windows, allowing natural light to fill the room.

Cottage in Bradenton

Cortez ~ Grouper Cottage. BRING YOUR BOAT!

Apartment in Holmes Beach

A serene outdoor area features a clear blue swimming pool, flanked by palm trees. Comfortable lounge chairs are positioned alongside the pool, and a shaded dining table is visible in the background. The white exterior of the building reflects a bright, inviting atmosphere.

4.96 out of 5 average rating, 186 reviews

Cabin 2 at Spinnakers Vacation Cottages

A screened enclosure surrounds a private swimming pool, providing a sunny outdoor space. Comfortable seating is visible alongside a dining area with a table and chairs. Lush greenery and palm trees can be seen in the background, enhancing the tropical atmosphere.

5 out of 5 average rating, 16 reviews

“Topside” luxury home in Cortez Village

A heated saltwater pool is surrounded by lush tropical vegetation, creating a serene atmosphere. Poolside seating is offered by several lounge chairs, alongside a shaded area with an umbrella. Sunlight reflects off the water's surface, enhancing the tranquil setting.

4.97 out of 5 average rating, 183 reviews

STEPs to BEACH! /Heated Salt Pool/Sunsets/5 STAR!

Family-friendly home rentals with a pool

A serene outdoor pool is framed by tropical landscaping, featuring lounge chairs and a dining area. Sunlight reflects on the clear water, enhancing the inviting atmosphere, while a covered seating space offers shade for relaxation.

5 out of 5 average rating, 7 reviews

Family Tides B – Pool, Rooftop & Gulf/Bay View

An inviting pool area is surrounded by lush tropical plants, featuring a curved pool and a spacious wooden deck. Seating includes colorful lounge chairs and a shaded dining area with a grill. An orange umbrella offers additional shade, enhancing the outdoor relaxation space.

4.67 out of 5 average rating, 3 reviews

Angie's Place! 2br/2ba, heated pool and a view of

An outdoor lounge area is showcased under a wooden ceiling, featuring a heated pool and elegant patio furnishings. A television is mounted on the wall, and a dining set is positioned nearby, with a barbecue grill just outside the lounging space, surrounded by tropical landscaping.

5 out of 5 average rating, 52 reviews

Book Family Tides 7 Nts get 3 FREE~Pool~Beach view

Townhouse in Holmes Beach

An aerial view captures the coastal neighborhood, showcasing a collection of charming homes with grey rooftops. The vibrant blue ocean and sandy beach are visible in the background, while lush palm trees surround the area, contributing to the serene island atmosphere.

4.99 out of 5 average rating, 151 reviews

Heated Pool & Spacious Lanai! Steps from Beach!

A panoramic view of the Gulf of Mexico is visible from the private balcony, featuring a sleek railing and two outdoor chairs. The serene sky meets the ocean horizon, while beach vegetation frames the picturesque shoreline.

4.9 out of 5 average rating, 31 reviews

Sandcastle Splash - Beachfront Condo

An aerial view showcases a private pool surrounded by lush tropical landscaping. The pool features a unique shape with gentle curves, and a sun lounger is placed nearby. The composition highlights the vibrant greens of palm trees framing the pool area.

4.97 out of 5 average rating, 33 reviews

Location! Beach Access/Trolley/ Restaurants!

A cozy outdoor seating area features two blue chairs positioned near a glass-top table with a glowing fire feature. The background showcases serene water views, surrounded by palm trees and residential homes, under a colorful sunset sky.

5 out of 5 average rating, 41 reviews

Heated Pool, Elevator, Dock, Waterfront, Fire Pit

5 out of 5 average rating, 13 reviews

Casa Bonita

Family-friendly home rentals with Wifi

The exterior of a modern two-story house is illuminated by soft evening light. A spacious deck is adorned with wooden chairs, and palm trees frame the entrance, enhancing the tropical ambiance. The house showcases a sleek design with large windows and a welcoming entrance.

4.99 out of 5 average rating, 89 reviews

Gulf Beach Front! Walk to Restaurants + Pier!

A vibrant outdoor space is showcased with a table and chairs under a large umbrella, surrounded by lush greenery. The game room features a pool table and retro arcade games, while cozy seating areas inside invite relaxation. A glimpse of the heated pool is visible in the courtyard.

4.93 out of 5 average rating, 43 reviews

Super Clean, Heated Pool & Hot Tub, 6mi to beach

An inviting outdoor lanai is shown, featuring comfortable seating with colorful cushions. A wooden coffee table holds glassware, while a heated pool glistens in the background, surrounded by lush greenery. The screened area offers a seamless connection to the tranquil outdoor environment.

5 out of 5 average rating, 94 reviews

Heated Pool-Game Room-EV-Near AMI Beaches/IMG!

An outdoor area features a heated pool surrounded by lounge chairs, a pickleball court, and a putting green, all enhanced by tropical landscaping. The interior reveals a comfortable game room with arcade games and modern amenities, providing a relaxing atmosphere for all guests.

5 out of 5 average rating, 25 reviews

Fall Special! - Family Fun - 9 min to Beach

The image captures a serene waterfront scene with several boats docked along a calm canal. Lush greenery and tropical plants frame the area, while a lawn leads to a small pathway. A grill is positioned nearby, complementing the outdoor setting.

4.97 out of 5 average rating, 30 reviews

Close to Anna Maria, Coquina Beach, Cortez, IMG

A serene water view is presented, with green waters reflecting palm trees and surrounding foliage. A row of condominium units is visible, featuring balconies and seating areas, lined by a rocky edge that enhances the tranquil ambiance.

Island Oasis Retreat

4.98 out of 5 average rating, 90 reviews

A spacious bed is centered in the room, dressed in a striped quilt. Two bedside lamps provide soft lighting, while framed artwork and a decorative sign enhance the calming atmosphere. A cozy seating area is positioned nearby, complementing the restful environment.

Guest suite in Bradenton

Sand Dollar Oasis - private entrance, private bath