Pet-friendly holiday rentals in Siesta Key

4.97 out of 5 average rating, 235 reviews

A compact sleeping area is furnished with a wooden bed frame and a colorful assortment of throw pillows. A modern air conditioning unit is mounted above, while a bedside table holds a lamp. Light streams in through the window adorned with wooden blinds.

Flat in Bayou Oaks

Modern Private Apartment 1 Block from Sarasota Bay

One block from Sarasota Bay - completely remodeled and fully furnished guest apartment with a Miami deco feel. The unit is a little over 300 sf with full kitchen, one bathroom w/ shower, comfy queen bed, several stools/ chairs, flat screen tv, wifi, off-street parking, six USB ports for easy charging and sitting area outdoors on front porch. Five minutes to downtown or SRQ airport, 15 minutes to Lido Beach, and 25 minutes to Siesta Beach with easy access to University Parkway or Fruitville Rd.

Flat in Indian Beach-Sapphire Shores

A spacious living area is featured with a large flat-screen television mounted on the wall. Two comfortable chairs are placed adjacent to a round ottoman, decorated with a variety of plants and a small basket. Natural light filters in through large windows, offering a view of the surrounding landscape.

4.97 out of 5 average rating, 159 reviews

Early Chkin, Elevator-4th fl 2mins-DT, 7mins-Airpt

Beach ready Apt!! Echo/white noise machine Beside Ringling College! 2 minutes from downtown Sarasota 7 mins - Airport Corner Apt Steps to the elevator 2 bicycles & 2 escooters Escape the ordinary and immerse yourself in an extraordinary stay at our unique Airbnb that's on a main road . 60+ amenities from a secure room safe to a luxurious, indulgent bed. Essential amenities such as grocery stores/pharmacies/ & CVS. less than a mile away. Send me a message if you have any questions .

Superhost

A swing chair hangs from the ceiling in a cozy living space, complemented by a dark sectional sofa and a round coffee table. A decorative rug adds warmth to the wooden floor, while a wall-mounted television and a piece of artwork provide visual interest.

4.81 out of 5 average rating, 168 reviews

1 House 1400sq. ft. 12 min from Siesta Key!

12 min. from Siesta Key Beach!! Perfect cozy vacation home in quiet, friendly neighborhood. Central to lots of shopping/restaurants. 1-king, 1-queen, bunk beds w/ 1-full & 1-twin. Dog & cat friendly w/ large private fenced yard, & 1-men's & 1-women's bike. Air hockey table w/ board games & pool toys. Fully loaded kitchen & W/D. Spacious living w/ large sectional, swing chair, & all bedrooms come w/ TVs & free Netflix & Hulu. Looking forward to hosting you! Message me anytime w/ questions.

4.9 out of 5 average rating, 178 reviews

Guest suite in Sarasota

Sweet, pet friendly Siesta Suite

Sweet spot with the best of both Sarasota and Siesta Key - your private oasis for relaxing and rejuvenating. Whether you choose to chill or find adventure it is all within reach! Siesta Key beaches, Village with shops, restaurants, and bars; Sarasota culture, arts, and entertainment; quaint Gulf Gate shops and eateries ...the possibilities truly are endless. Regardless of how you choose to spend your time here, you will be sure to create lasting memories to share and leave wanting more.

4.97 out of 5 average rating, 101 reviews

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.

Home in Holmes Beach

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

An open living area is presented, featuring a blue couch and a wooden coffee table. A dining table with four chairs sits nearby, complemented by a kitchen with white cabinetry and modern appliances. A Christmas tree adds a seasonal touch, while windows allow natural light.

4.96 out of 5 average rating, 104 reviews

2 BR House 1.6 miles from Siesta Key Beach

Discover the charm of Sarasota in our newly remodeled 2BR/1BA vacation home. Just 1.6 miles from beautiful Siesta Key Beach! Enjoy your morning coffee on a brick patio surrounded by flowers and sunshine. Our comfy beds, blackout curtains, and quiet neighborhood ensure a sweet deep sleep. FIOS wifi and three smart TVs; a fully-equipped kitchen; and a sparkling new bathroom with two sinks, huge mirror, and marble shower offer all the comforts and convenience of home. We welcome you!

Superhost

A modern living area features a comfortable sectional sofa, accented by textured cushions. A flat-screen TV is mounted on the wall above a wood panel, while large sliding doors invite natural light and provide access to the patio. Indoor plants add a touch of greenery.

Apartment in Siesta Key

4.84 out of 5 average rating, 128 reviews

Siesta Key Condo: Beach, Pool & Village Fun!

Escape to paradise in our newly renovated 2-bedroom condo, perfectly situated a block from Siesta Key Village. Enjoy the convenience of walking to bars and restaurants, plus two parking spots if you prefer to drive. Relax by the community heated pool or take an 8-minute stroll to the award-winning beach. Explore the area using the free trolley, or venture to downtown Sarasota. This dog-friendly condo offers Wi-Fi, a smart TV, in-unit laundry, and essential home and beach gear.

4.86 out of 5 average rating, 115 reviews

Trendy & Relaxing: Close to Beach ~ Pool ~ Hot Tub

Discover your perfect Siesta Key getaway in this vibrant 3BR, pet freindly duplex in the peaceful South Village. Just steps from the Gulf Coast beaches, this private retreat blends colorful décor, modern comfort, and playful outdoor fun. Lounge by the private 𝐡𝐞𝐚𝐭𝐞𝐝 𝐩𝐨𝐨𝐥, soak in the 𝐡𝐨𝐭 𝐭𝐮𝐛, or enjoy the backyard murals perfect for families, groups, and beach lovers. Book now for an unforgettable stay! <b>☀ Private Pool ☀ BBQ Grill ☀ Easy Beach Access</b>

Guest suite in Siesta Key

4.9 out of 5 average rating, 193 reviews

Cozy Studio - quick walk to #1 Siesta Key Beach!

Recently renovated and updated! Adorable studio just steps from Siesta Key Village, and a quick walk to the beach. Spend your day exploring the key, swimming in the ocean, and experiencing the local restaurants and shops. Enjoy coffee in the mornings on the patio, and use the available bikes to catch a beautiful sunset each night. **Please note: - No excessive noise or Parties/Events will be allowed** - No Smoking inside the unit** - Quiet hours from 10 PM to 7 AM**

A bright pink flamingo float adorns the clear, inviting waters of the heated pool. Two white umbrellas provide shade for the striped lounge chairs nearby. Flower pots add a touch of greenery to the poolside area, which is enclosed by a white privacy fence.

4.94 out of 5 average rating, 114 reviews

Oasis by Siesta Key Beach and Downtown SRQ w/pool

Enjoy Sarasota in one of the most desirable neighborhoods by Siesta Key! Truly an elite location, take Siesta Dr down to the well-documented #1 beach in the US in around 10 mins. Flourishing Downtown Sarasota is just 5 mins away. The house features a brand new heated pool, fenced in back yard with pavers, open concept living, beautiful kitchen with everything you need, upgraded bathrooms and plenty of space for a big family. We look forward to hosting you and yours!

4.77 out of 5 average rating, 160 reviews

An outdoor lounge area features soft pink seating, including a sofa and armchair, against a backdrop of warm wood paneling. A standing lamp provides ambient lighting, and large windows offer a view of the surroundings. A patterned area rug adds texture to the space.

Guest suite in Sarasota

Private Suite • 10-Min Walk to Siesta Beach, Shops

🌴 Welcome to Your Cozy Siesta Key Getaway Relax in this private, well-appointed pied-à-terre located in a quiet, walkable neighborhood, just a 10-minute (0.5 mile) walk to Siesta Beach Access #12. . Perfect for couples or solo travelers looking for a comfortable, convenient home base near it all. The kitchenette is ideal for light cooking/reheating, and includes: Microwave, Refrigerator, Keurig Coffee maker, Teapot Small stove/oven, Basic dishware and utensils

4.97 out of 5 average rating, 116 reviews

The studio features a modern kitchen with white cabinetry and a large countertop. A flat-screen TV is mounted on the wall, and natural light enters through sliding glass doors that lead to the private garden. A compact dining table and a plush blue ottoman add functionality.

Apartment in Sarasota

Modern Studio · 5 min from Siesta Beach

Stylish ground-floor studio designed for couples or solo travelers, just a 5-minute drive from world-famous Siesta Key Beach. A great choice if you’re looking for a calm, well-located space with thoughtful comfort. Pet-friendly stay – $10 one-time pet fee per booking, unlimited pets. An ideal base for beach days, local dining, or a relaxed Florida getaway. About 1 mile from the property, guests may also enjoy access to a beautiful community pool that is heated.

Popular amenities for Siesta Key pet-friendly home rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Pet-friendly house rentals

A modern living area features a light-colored sofa accompanied by a wooden coffee table. The room is enhanced by a large wall art piece depicting a beach scene. An open layout is evident, with a view of a kitchen area and bar seating in the background.

4.91 out of 5 average rating, 133 reviews

15Min to Siesta, Central, Beach Supplies

A screened-in pool area features a crystal-clear heated pool with lounge chairs positioned nearby. An umbrella provides shade over a seating area, surrounded by lush greenery and fencing that enhances privacy.

4.95 out of 5 average rating, 230 reviews

Cozy 2BD/2BA with Heated Pool Near Siesta Key

A screened-in heated pool area is featured, reflecting clear blue skies and fluffy clouds. Comfortable outdoor seating is positioned beside the pool, complementing the serene atmosphere. The pool area is framed by a spacious deck, enhancing the overall inviting design.

4.84 out of 5 average rating, 105 reviews

Perfect Getaway 3bd/2bth Private Heated Pool

5 out of 5 average rating, 29 reviews

A private entrance features a white fence and gate with the number 1825 displayed prominently. The pathway is paved with bricks and flanked by lush greenery and colorful flowers, leading to the home's inviting entrance.

Home in Gillespie Park

The Gecko Bungalow - DT Sarasota

4.91 out of 5 average rating, 120 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

4.97 out of 5 average rating, 117 reviews

Home in Arlington Park

The Wisteria Oasis W/swings, heated pool & hot tub

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.

4.95 out of 5 average rating, 223 reviews

Modern, Bright Downtown SRQ A-Frame West of Trail

A charming blue house is presented with a gabled roof and dormer windows. Lush greenery and colorful flowers surround the entrance, which features a white door and inviting walkway. The bright sky with scattered clouds complements the vibrant exterior and landscaped yard.

5 out of 5 average rating, 26 reviews

Casa Playa Sleeps 6

Pet-friendly home rentals with a pool

4.92 out of 5 average rating, 48 reviews

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.

Holiday home in Sarasota

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

5 out of 5 average rating, 18 reviews

Cottage in Siesta Key

House with pool 1 block to village, 3blks to beach

A relaxing outdoor space features a sparkling swimming pool surrounded by lounge chairs with red and white stripes. Tall palm trees stand nearby, adding a tropical touch, while serene water views and lush greenery are visible in the background.

4.91 out of 5 average rating, 78 reviews

Oceanfront Home with Heated Pool in Fishers Haven

A modern one-story home is framed by lush landscaping and mature trees. The façade features a sleek, dark exterior with large windows and a symmetrical entrance. A paved driveway leads up to the two-car garage, enhancing the welcoming curb appeal.

4.96 out of 5 average rating, 68 reviews

Stunning New 3 bed 3 bath pool home by Siesta Key!

4.88 out of 5 average rating, 32 reviews

Bungalow in Holmes Beach

250 steps from Beach Access! Heated pool and spa

4.82 out of 5 average rating, 22 reviews

Apartment in Sarasota

100 ft to Beach – 1BR Siesta Key Escape

Apartment in Holmes Beach

4.96 out of 5 average rating, 101 reviews

Steps to the beach! Condo with pool at The Terrace

4.9 out of 5 average rating, 396 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

Private, pet-friendly home rentals

A serene outdoor space is highlighted by a heated saltwater pool and a six-person spa. Comfortable lounge chairs line the pool area, and an outdoor grill is situated nearby. The setting is complemented by a vibrant sunset, enhancing the tranquil atmosphere.

5 out of 5 average rating, 84 reviews

Luxury 3/3 with Heated Pool, Spa, & Putting Green!

4.73 out of 5 average rating, 55 reviews

A vibrant sunset casts golden reflections on the calm water, with shades of orange and pink filling the sky. The horizon features a sun dipping into the sea, creating a serene atmosphere. The shoreline is visible, adding depth to the tranquil coastal scene.

Tiny home in Siesta Key

Siesta Key Beach 100 feet from Romantic Unit!

A serene outdoor space features a sparkling pool surrounded by vibrant tropical plants and potted flowers. Comfortable blue lounge chairs are positioned next to the pool, providing a relaxing area for enjoyment. Bright red umbrellas offer shade for added comfort.

4.98 out of 5 average rating, 66 reviews

Serene 3BR family retreat | Firepit & POOL

5 out of 5 average rating, 6 reviews

Home in Siesta Key

Sea Escape - Located in Siesta Key Village!

5 out of 5 average rating, 12 reviews

Flat in Siesta Key

New listing - Heated Pool, Walk to Beach!

5 out of 5 average rating, 73 reviews

A serene beach scene captures the sun setting on the horizon, casting warm hues across the sky and reflecting on the gentle waves. The shoreline appears tranquil, inviting relaxation as the day's light slowly fades.

Guest suite in Sarasota

Ocean Breeze Retreat 6min to Siesta BEACH!

4.94 out of 5 average rating, 17 reviews

Apartment in Sarasota

Sunny Lanai w/ Pool Views • Minutes to Siesta Key

The exterior of a charming blue house is captured, framed by two palm trees. A small porch with steps leads to the entryway, while white landscaping stones accentuate the yard. Two white lounge chairs are positioned invitingly in front of the house.