Pet-friendly home rentals near Anna Maria Island

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, 54 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!

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.

4.96 out of 5 average rating, 198 reviews

Be an AMI

This stylish and light home offers single-level private accommodations. The recently updated interior and private backyard oasis with plunge pool offers the perfect space for a truly relaxing and enjoyable vacation. Inside, the stylish and comfy space has room for everyone to spread out and relax while enjoying the two flat screen TVs. No expense was spared in designing and furnishing this home. The sleeper sofa pulls out to a memory foam queen bed, meaning the cottage can comfortably sleep 4.

4.96 out of 5 average rating, 101 reviews

Condo in Holmes Beach

Steps to the beach! Updated Condo at The Terrace

Just 200 steps from the white sands of Holmes Beach, this beautifully updated 2BR/2BA condo has everything to offer! Our unit features high-speed internet, coffee maker, blender, balconies off of each bedroom, 1-car garage, washer/dryer, heated shared pool, and access to all the beach necessities (toys, umbrellas, chairs, tent, cart). This unit sleeps 6 (1-King, 1-Queen, & Full size sofa bed). LOCATION, LOCATION! You'll be just steps from restaurants, cafés, shops, and the free island trolley!

4.99 out of 5 average rating, 150 reviews

A private outdoor space features lush greenery framing a stone pathway leading to a wooden seating area. The area is adorned with tropical plants, creating a serene ambiance. A small bar-height table with stools is visible in the background.

Bungalow in Oldsmar

salt living at its best

- Resort Style Water front - Stand alone - Hot tub - Sunrise / sunset views on dock - free Kayaks - Internet / YouTube cable - 65” smart TV - Spacious Bedroom with king size bed, walk in closet and flat TV - Washer and Dryer in unit - Designated work space -Pet friendly - Fenced private patio - Free 2 cars / Boat Parking. - Central location ( beaches, restaurants, Tampa, St Pete’s, safety Harbor, Dunedin - 11 minutes from Ruth Eckerd event Hall - Pristine clean - Coffee station - Dining area

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, 113 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

4.99 out of 5 average rating, 77 reviews

A serene backyard pool area is framed by lush palm trees, creating a tropical oasis. A semi-circular seating area under a Tiki umbrella provides a shaded spot next to the pool. Adjacent seating and a grill enhance this inviting outdoor space.

Cottage in Holmes Beach

Poolside Oasis on Anna Maria Island!

Remodeled cottage with a lush tropical backyard, which boasts a Private Heated pool with Waterfall and Swim-up Tiki Table, turf putting green ,Weber Grill, patio bar with 55” Outdoor Smart TV! Calypso is outfitted with a cozy Coastal decor, you feel that vacation vibe as soon as you walk in the door. The kitchen offers quartz countertops with Stainless Steel appliances. Both bedrooms have King size beds, living room has a queen sleep sofa. All furniture was brand new in December of 2024

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, 88 reviews

NEW saltwater pool/spa! Amazing outdoor space!

Spend your days playing in the pool and soaking up the sun at this coastal escape! The huge screened lanai includes a pristine saltwater pool with a spillover spa and sun ledge, and large covered outdoor living and dining space. The updated 3 bedroom, 2 bath interior is bright and spacious, with a lot of natural light and nearly every room flows out to the pool. Located in a quiet neighborhood with quick access to Anna Maria Island beaches, IMG, walking trails, parks, shopping & restaurants!

4.78 out of 5 average rating, 267 reviews

Tropical Oasis - Private Pool - Close Beaches

Enjoy a tropical Paradise with private pool. Beautiful palms and an over-sized private pool. This beautiful pool home is only a short drive to Anna Maria Island. Floridas most beautiful white beaches on the Gulf Coast. Pool heating available. Huge master bedroom with attached full bath and access to the pool area. Free high speed WIFI. Smart TV in living room queen room. 2 parking spaces. Convenient to beach bars, golf, shopping. 25 Min. Sarasota and 45 Min. Tampa Airport.

4.93 out of 5 average rating, 150 reviews

The outdoor area features a heated pool with a rock waterfall, surrounded by lounge chairs. A thatched Tiki hut provides shaded seating, set within tropical landscaping. The villa's light blue exterior and white furnishings enhance the inviting atmosphere of the space.

Condo in Holmes Beach

Blanco at Sunset Villas on Anna Maria Island

Back Open Jan '25! Located just 200 steps from the beach you’ll have your feet in the sand in no time. A comfortable living area + fully equipped kitchen. Furnished with island décor and local art. Everything you need including a heated pool, large patio with a Tiki hut, tropical gardens, plus a private outdoor area with a shower for your comfort. Walk to everything – grocery, pharmacy, ice cream, breakfast, pizza, donuts, and the beach which is less than 2 minutes away.

4.97 out of 5 average rating, 180 reviews

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.

Home in Bradenton Beach

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

Less than a 2 min WALK to the white sand beaches of the Gulf, this 4 BR home comfortably sleeps 8. Large bedrooms & a spacious floor plan (the kitchen, dining and living rooms flow together), the house is perfect for families. The bedrooms are split 2+2 & paired with bathrooms on opposite ends of the house (a pocket door adds privacy). Private heated saltwater pool sits amidst the tropical yard. Hop on the free trolley and explore Florida's gorgeous Anna Maria Island.

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, 392 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.

Bungalow in Indian Shores

An aerial view showcases a cluster of charming two-story homes nestled near the beach. The golden hues of the sunset reflect off the water, while the sandy shore and gentle waves create a serene coastal atmosphere.

5 out of 5 average rating, 222 reviews

Quiet Beachfront Bungalow on Florida’s Gulf Coast

Welcome to The Sunset Beach Bungalow! This top-floor luxury water-front home located in Indian Shores, FL has been completely remodeled. Our serene getaway is situated on the Gulfs Coast. The large deck looks out over the water, providing a calming sanctuary to which you can retreat any time of day or night. Our home is over 1000 sq. ft and is newly furnished with plenty of room to relax during your stay. Our beach is private so there aren’t large crowds!

Popular amenities for pet-friendly home rentals near Anna Maria Island

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Pet-friendly house rentals

An aerial view of the outdoor space reveals a heated saltwater pool shaped like a lagoon, surrounded by lounge chairs and umbrellas. A full-size pickleball court takes center stage, complemented by a nearby mini-golf putting green and a trampoline, all set within lush landscaping.

4.9 out of 5 average rating, 20 reviews

New! Luxurious Retreat w/ Resort Amenities by AMI!

The outdoor area showcases a heated saltwater pool enclosed by a screen, with vibrant citrus-themed murals on the walls. Soft lighting from string lights illuminates the space, enhancing the inviting atmosphere during twilight. A spacious sun deck offers seating and relaxation areas.

4.99 out of 5 average rating, 112 reviews

Saltwater heated pool w/ massage chair + hot tub

Superhost

A lagoon-style heated pool is nestled among tropical landscaping, featuring a winding shape and sun shelf for lounging. A covered cabana with outdoor seating is visible to the left, while lush palm trees and greenery frame the serene outdoor space.

4.6 out of 5 average rating, 10 reviews

Coconut Lagoon – Pet Friendly AMI Stay w/ Pool

A bright dining area features a round glass table surrounded by four white upholstered chairs. A blue circular rug lies beneath the table, and large glass doors provide views of the nearby canal, enhancing the natural light in the space.

5 out of 5 average rating, 5 reviews

Manatee Retreat B

Superhost

An inviting outdoor space features a spacious pool surrounded by a screened lanai. Comfortable seating areas are visible, with vibrant cushions and a backdrop of large glass doors leading into the house. Soft evening light creates a warm atmosphere, enhancing the tranquil setting.

4.85 out of 5 average rating, 48 reviews

Fall Specials! - Close to AMI, IMG, Beaches

4.87 out of 5 average rating, 15 reviews

Home in Cortez

Cortez Chateau! Private boat dock and short stays!

Superhost

An aerial view of a saltwater pool, featuring a unique V-shape design surrounded by elegant stone tiles. Two lounge chairs in vibrant blue and red are positioned nearby, offering a relaxing spot under the sun, complemented by lush tropical greenery.

4.76 out of 5 average rating, 37 reviews

Enjoy AMI sunsets | Chic home w/ Saltwater pool!

5 out of 5 average rating, 5 reviews

3 Blks to Beach + Sun Soak Game Room + Cabana Bar!

Pet-friendly home rentals with a pool

4.97 out of 5 average rating, 30 reviews

Ocean72, 2bed 2bath with pool

5 out of 5 average rating, 15 reviews

A private heated pool is surrounded by a spacious stone patio, featuring comfortable lounge chairs. Lush greenery provides a tropical backdrop, while a charming cottage with turquoise siding is visible nearby. Soft sunlight reflects on the tranquil water, enhancing the peaceful ambiance of this outdoor area.

Home in Siesta Key

Toes In The Sand | Private Pool, Walk to Beach!

A landscaped pathway lined with tropical greenery leads to a charming cottage in soft green hues. Palm trees sway gently in the breeze, complementing the vibrant foliage that encircles the entrance. Bright blue skies create a cheerful atmosphere above the home.

5 out of 5 average rating, 48 reviews

Key Lime Cottage by Beach Boutique Rentals

5 out of 5 average rating, 6 reviews

New! Boat Dock + Dolphins + Beaches + Hot tub!

5 out of 5 average rating, 6 reviews

An inviting living area features a spacious sectional sofa adorned with vibrant pillows and a cozy fireplace. Large glass doors provide natural light and views of the outdoor pool area, while a unique coffee table complements the mid-century modern design.

Home in Siesta Key

Mid-Century Modern, Pool, Mins to Siesta Key Beach

5 out of 5 average rating, 9 reviews

An aerial view showcases a bayfront home surrounded by lush greenery and mature trees. A private dock extends into the water, while the infinity pool and surrounding lounge areas are visible in the backyard, contributing to the serene waterfront setting.

Home in St. Petersburg

Mid Mod Waterfront Home with Pool + Hot Tub

4.96 out of 5 average rating, 26 reviews

King Bed/Pool/Game Room/Fire Pit/Hammock/Near AMI

An outdoor space features a newly constructed pickleball court, complemented by a heated pool and a raised deck. Surrounding tropical foliage provides a natural backdrop, while a vibrant sunset casts a warm glow over the setting.

4.99 out of 5 average rating, 82 reviews

Cottage w/ Pickleball Outdoor Oasis 2 mi to Beach

Private, pet-friendly home rentals

4.98 out of 5 average rating, 97 reviews

The living area features a seating arrangement with two blue sofas and a light coffee table. A ceiling fan is present, along with a beige recliner. Large glass doors open to a lanai, allowing natural light to fill the room, complemented by coastal-themed art on the walls.

Condo in Holmes Beach

A Coastal Retreat Steps From the Sea

4.92 out of 5 average rating, 66 reviews

Apartment in Bradenton

Riverfront 2BR • Near Anna Maria Island

A heated pool is surrounded by tropical plants and lounge chairs, providing a serene setting. Soft lighting creates a relaxing atmosphere as evening approaches. A pergola stands nearby, enhancing the outdoor space.

5 out of 5 average rating, 24 reviews

The Toasty Coconut in Anna Maria

A private backyard swimming pool is surrounded by tropical landscaping and six lounge chairs positioned for sunbathing. The pool features clear blue water, with a paved patio area and a white fence providing privacy. Palm trees and decorative plants enhance the inviting outdoor setting.

4.95 out of 5 average rating, 55 reviews

Gone Coastal - private heated pool near AMI/beach

4.98 out of 5 average rating, 47 reviews

Renovated Chic Home Near Beaches, IMG & Downtown

The duplex features a light blue exterior with a welcoming porch adorned with yellow and blue chairs. Lush palm trees and vibrant landscaping enhance the outdoor space, while a clear blue sky adds brightness to the scene. Graveled parking is visible in front of the unit.

4.94 out of 5 average rating, 96 reviews

Do you love the beach?

Townhouse in Holmes Beach

The spacious living area features a comfortable sectional sofa adorned with decorative pillows, a textured area rug, and a stylish coffee table. Natural light flows through large glass doors, connecting the indoor space to the outdoors. Open access to the kitchen and dining area enhances an inviting atmosphere.

5 out of 5 average rating, 76 reviews

Steps from the beach, private pool in Holmes Beach

A spacious outdoor area is presented, featuring a shaded seating area with cushions. A sparkling jacuzzi glistens under string lights, creating a lively ambiance. An artificial grass section offers space for games, while lounge chairs and a fire pit enhance comfort for relaxation. Pets are welcomed.

4.97 out of 5 average rating, 39 reviews

Vibrant/modern home/back yard oasis, near beaches

Pet-friendly home rentals with a hot tub

A light-filled living area features a comfortable sofa and a wooden coffee table, set on a striped rug. A flat-screen television is positioned on the side, and botanical-themed artwork decorates the walls, contributing to a serene and inviting environment.

4.92 out of 5 average rating, 315 reviews

Home near Anna Maria Beach w/ Hot Tub + Fire Pit

4.92 out of 5 average rating, 13 reviews

A wooden pier extends into calm waters, flanked by lush greenery. Soft lights illuminate the walkway, which leads toward a vibrant sunset sky painted in shades of pink and purple. The tranquil setting invites leisurely strolls and scenic views of the bay.

Home in Palmetto

SeaScape

A comfortable living area is furnished with a gray sofa and decorative pillows. A large beanbag sits on the textured rug, while a medium-sized TV is positioned on a light-colored console. Natural light fills the space through sliding glass doors, adorned with sheer curtains.

4.96 out of 5 average rating, 113 reviews

Waterfront View Mins To AMI Beaches

A private outdoor space features a cushioned hot tub under a gazebo. Two lounge chairs with turquoise cushions are placed nearby on a wooden deck, surrounded by lush greenery. A textured outdoor rug adds warmth to the area, enhancing the overall relaxation vibe.

4.9 out of 5 average rating, 124 reviews

Tropical Cottage w SPA near Anna Maria Island IMG

A single-story house is framed by lush greenery and plants, with a well-kept lawn in the foreground. A driveway leads to a garage door, while a covered porch is visible with outdoor seating for relaxation.

5 out of 5 average rating, 7 reviews

Cottage by the Sea

4.9 out of 5 average rating, 113 reviews

A view of a heated saltwater pool is framed by two lounge chairs, positioned on a grassy area. Red umbrellas provide shade for seating areas, and a spacious patio can be seen in the background, featuring modern outdoor furniture and a neutral-colored house.

Home in Clearwater

Beach or Golf Getaway • Heated Pool/Spa • Pets OK

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, 158 reviews

Black Friday Deals NOW - Holidays at the Villa

An outdoor space is featured, showcasing a hot tub and a dining area with a table set for guests. Light fixtures hang from the wooden ceiling, and greenery is present, adding a natural touch. A relaxed atmosphere is created by the open layout.