Pet-friendly vacation rentals in Longboat Key

4.96 out of 5 average rating, 102 reviews

Condo in Holmes Beach

Steps to the beach! Condo with pool 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, Keurig , balconies off of each bedroom, 1-car garage, washer/dryer, heated shared pool, and access to all the beach necessities (toys, umbrellas, chairs, tent, bicycles, SUP, 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!

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, 199 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.

4.98 out of 5 average rating, 161 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

4.86 out of 5 average rating, 137 reviews

Home in Longboat Key

Summer House longboat key

Luxurious waterfront home with bay and and canal view, new custom kitchen with a view to the pool and your own private tiki bar, dock that can accommodate up to 21 ft boat , whole house just received a complete inside and out make over. Tropical coconut palms, outside patio and grill. Fish on the dock and watch dolphins and manatee. Truly a tropical paradise just 7 minute Walk to your own private beach. minutes from St Armand’s circle. feel free to reach out with any questions or requests

Townhouse in Longboat Key

A spacious bedroom features a large bed with white linens and decorative pillows. A comfortable green bench is positioned at the foot of the bed. Natural light fills the room through multiple windows adorned with bamboo shades, while a television and dresser complete the space.

4.84 out of 5 average rating, 44 reviews

Cedars Tennis -Gorgeous 2 bed, 3 level Townhouse

Kick back and relax in this calm, stylish space. In Cedars East, across from beach AND on the bay. Sleeps 6 - california king master & double bed upstairs. All new carpets upstairs and full laundry in the unit too! Lovely enclosed balcony overlooking trees and boardwalk. Couple of trek bikes available - 10 min walk/ 3 min cycle to beach. Large shared swimming pool, tiki bar, fitness center, tennis on site. Jetty, boardwalk & walk paths. Excellent location, pets allowed. RRR-00819. 2023

4.98 out of 5 average rating, 247 reviews

Two wooden Adirondack chairs are positioned on a deck overlooking a serene lake. A floating dock extends into the water, featuring two red lounge cushions. The clear blue sky enhances the tranquil atmosphere, with greenery visible along the shoreline.

Cottage in Tampa

Bay Lake Cottage

You’ll have the Entire 500sq ft Cottage & private entry, deck/dock, all to yourself. Located on a 37-acre private ski lake. Key-pad entry, private parking. 1 king bed, 1 bath, queen sofa bed, washer/dryer, WiFi, smart TV’s, blackout curtains,shampoo,conditioner,hairdryer,WiFi. Fully stocked kitchen, smokeless grill, wine fridge upon request, k-cup/drip coffee machine. The lake has bass, we provide fishing poles/tackle box. Rentable Kayaks & Canoe. Dogs okay, sorry no cats, pet fee $50.

A private heated pool features a waterfall, surrounded by lush tropical landscaping and palm trees. Seating options include teal lounge chairs and white sunbeds, while the pool deck is complemented by a well-maintained lawn area. Colorful plants enhance the tranquil outdoor space.

4.97 out of 5 average rating, 102 reviews

Salty Harbor AMI pool retreat near the Beach

Charming Salty 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: -Ask us if your dates don't fit our calendar! -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

Apartment in Bradenton Beach

4.91 out of 5 average rating, 137 reviews

Newly Remodeled Beachfront Studio - On the sand!

ONE SHELL COVE on Anna Maria Island has been totally remodeled after Hurricanes Helene and Milton. Wonderful studio floor plan with amazing kitchen. Beautiful view of the waves and the beach right outside your window. Grab your towel, take a few steps and you're on the beach. The sand comes right up to your door in this ground floor unit. Amazing Location Walk to some restaurants Free Trolley goes up and down the Island Rent Kayaks and Paddleboards and enjoy the Beach

4.93 out of 5 average rating, 151 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.

A private lagoon-style pool is surrounded by lush tropical landscaping. A small rock waterfall flows into the gently curved pool, which is complemented by comfortable seating. Sunlight filters through the foliage, creating a serene outdoor retreat.

4.97 out of 5 average rating, 146 reviews

Twin Palms: Big House Steps to Beach w/Lush Pool

Twin Palms is home to NY Times best-selling food writer and chef and her tech husband. Infant/kid/pet-friendly just 5 min. walk to the beach. Private lagoon-style *heated* saltwater/low chlorine pool amid lush landscaping with gorgeous rock waterfall. New appliances, HVAC, 60-inch Sony HDTV, Italian leather reclining sofas, BBQ, beach gear, three king bedrooms, all linens provided. Classic Florida one-level home - no stairs. Managed directly by owners, so no crazy fees.

4.97 out of 5 average rating, 191 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.

4.9 out of 5 average rating, 399 reviews

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.

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.

Popular amenities for Longboat Key pet-friendly home rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Pet-friendly house rentals

4.94 out of 5 average rating, 33 reviews

Ocean72 | Heated Pool & Spa | 2BR Near Beach

A bright living area is highlighted by a large window with views of lush greenery. A light wood floor complements the modern furnishings, which include a blue couch with yellow cushions, a wood coffee table, and a round dining table for four.

4.83 out of 5 average rating, 30 reviews

+ Anna Maria Seaside Escape +

4.91 out of 5 average rating, 34 reviews

A bright living area features a spacious white sofa centered beneath a large woven light fixture. Tropical plants are situated near large windows that allow natural light to fill the space. A neutral rug complements the light-colored furniture and decor.

Home in Arlington Park

Coastal Retreat near Siesta Key Beach and Downtown

4.84 out of 5 average rating, 293 reviews

A secluded backyard features a heated pool surrounded by lush greenery and flowering plants. Tropical palm trees and colorful potted plants enhance the tranquil atmosphere, while the tiled pool edge adds a touch of contemporary design.

Home in Sarasota

Private Siesta Beach House Oasis with Heated Pool.

4.91 out of 5 average rating, 122 reviews

A charming yellow home is set against a backdrop of palm trees, with a brick paved driveway leading to a two-car garage. Lush greenery surrounds the property, providing a sense of privacy and tranquility.

Home in Siesta Key

Siesta Key, FL - Casa Berano

5 out of 5 average rating, 4 reviews

Island Vibe 7

5 out of 5 average rating, 10 reviews

A modern living area features large windows allowing natural light to brighten the space. A comfortable couch and a wooden coffee table create a welcoming seating arrangement. A wall-mounted television is positioned above a streamlined cabinet, providing a clean and uncluttered aesthetic.

Home in Sunset Beach

Gorgeous New Beach Home w/ Stunning Water Views

5 out of 5 average rating, 19 reviews

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.

Home in Cove

“Topside” luxury home in Cortez Village

Pet-friendly home rentals with a pool

Condo in Indian Beach-Sapphire Shores

A balcony is showcased with a sunset view over the canal and bay. Two wooden bistro tables are set, featuring turquoise cups and a small floral centerpiece. The railing provides an unobstructed view of the waterfront and surrounding landscape.

5 out of 5 average rating, 4 reviews

Resort Pool/Spa, Fitness Center, Waterfront Views!

5 out of 5 average rating, 14 reviews

Home in Bradenton

Family Pool Getaway Near Beaches & IMG Academy

An outdoor dining area is set with a glass table and six blue chairs, shaded by a blue umbrella. In the background, a swimming pool with surrounding tropical plants invites relaxation, while a spa is visible nearby, offering a serene ambiance.

4.81 out of 5 average rating, 90 reviews

Private pool, only two blocks .3 miles from beach!

5 out of 5 average rating, 7 reviews

Pool, Bikes & BBQ Included! 2min to Beach!

4.93 out of 5 average rating, 45 reviews

A wooden walkway leads from a palm tree-lined entrance to a sandy beach. The ocean is visible in the background, showcasing rolling waves under a clear blue sky. Gentle sunlight illuminates the natural landscape, highlighting the serene environment.

Condo in Bradenton Beach

Sandcastle Dreams

4.9 out of 5 average rating, 40 reviews

Home in Bradenton Beach

AMI Dock of the Bay - "On the Water" 1st Floor

4.97 out of 5 average rating, 69 reviews

A private pool is bordered by a spacious stone deck, complemented by lounge chairs and a small table. A vibrant yellow umbrella provides shade, while palm trees and blue skies enhance the outdoor setting.

Home in Bradenton

Stylish Pool Home • Near IMG & Beaches • Top Rated

4.88 out of 5 average rating, 178 reviews

A charming cottage is set against a vibrant blue exterior, featuring a thatched umbrella over a small outdoor seating area with four chairs. Lush green shrubs and sandy pathways enhance the inviting entrance, while palm trees are visible in the background under clear blue skies.

Bungalow in Anna Maria

Bay Breeze Cottages #2

Private, pet-friendly home rentals

4.92 out of 5 average rating, 74 reviews

The image captures a shared pool area surrounded by lush greenery and palm trees. Lounge chairs with blue umbrellas are positioned around the pool, which is enclosed with a white fence. A pathway leads through well-maintained landscaping, enhancing the inviting outdoor space.

Condo in Saint Armands

Steps from Lido Beach & St. Armands Circle

4.96 out of 5 average rating, 47 reviews

A clear, inviting pool is surrounded by a landscaped area with tropical plants and palm trees. The bright orange exterior of the building contrasts with the lush greenery. Chaise lounge chairs are positioned nearby for relaxation.

Condo in Siesta Key

Siesta Key Village, Pool, Beach Access 4-min Walk

Vacation home in Sarasota

An open kitchen and living area feature modern cabinetry and stainless steel appliances. A large kitchen island provides seating, while a cozy living space is equipped with a sectional sofa and an armchair. Natural light flows through the sliding glass doors, showcasing the outdoor scenery.

4.92 out of 5 average rating, 49 reviews

Waterside Retreat: Modern 2BR, Mins to Beach & Apt

4.98 out of 5 average rating, 60 reviews

A spacious living area features a modern sectional sofa with plush cushions in neutral tones. A circular coffee table rests on a soft area rug. A vibrant grass wall adds a touch of greenery, while a dining table with chairs is visible in the background.

Condo in Holmes Beach

Luxury 2BR Oceanfront Condo + Rooftop Patio

4.94 out of 5 average rating, 35 reviews

A screened-in lanai accommodates a private pool, with sunlight reflecting off the clear blue water. Surrounding greenery provides a sense of tranquility. A sitting area is visible, alongside a dining table ready for gatherings, enhancing the outdoor relaxation space.

Home in Venice

RELAX:) Vacation pool home (Shamrock Park&Beaches)

Bungalow in Bradenton Beach

A bright living area features light walls and soft furnishings. A cozy sofa faces a modern television displaying a beach scene. A circular mirror adds depth, while a wooden table and chair provide a comfortable workspace. Natural light fills the space through sheer curtains.

4.96 out of 5 average rating, 24 reviews

Barefoot Boho- Breezy Bungalow on the Beach!

4.88 out of 5 average rating, 92 reviews

The open-plan kitchen and dining area features stainless steel appliances, including a refrigerator and a washer-dryer unit. Light-colored cabinetry and decorative tile accents complement the space, which is illuminated by natural light streaming through the windows. A modern dining table is surrounded by transparent chairs.

Guesthouse in Bradenton

Brand new 1 bedroom, 1 bath Guest House! Sleeps 3

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.