Pet-friendly holiday rentals in Siesta Key

4.97 out of 5 average rating, 232 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.

4.91 out of 5 average rating, 173 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.

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, 101 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!

4.96 out of 5 average rating, 141 reviews

A sparkling pool is surrounded by a spacious patio, featuring lounge chairs and a vibrant red umbrella. Lush tropical landscaping creates a serene retreat, providing an inviting space for relaxation and leisure under a clear blue sky dotted with fluffy white clouds.

Home in Arlington Park

Mid-Century Oasis with Pool in Arlington Park 1

A perfect blend of Sarasota’s architectural heritage and contemporary elegance right in the heart of Arlington Park. This bright, newly renovated 2 bed/2 bath & pull out sofa in a mid-century gem offers a serene escape, providing a refreshing interplay of historical charm and modern luxury. Enjoy the separate sunroom/office for those working from home, or use as an extra sleeping space with comfy pull out sofa. Take a break with a quick dip in the sparkling pool. VR24-00160

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, 152 reviews

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

Beach ready Apt!! 2 minutes from downtown Sarasota 7 mins - Airport Cornerr apartment Steps to the elevator 2 bicycles & 2 escooters Escape the ordinary and immerse yourself in an extraordinary stay at our unique Airbnb on a main road . Beside ARTS & DESIGN COLLEGE!! 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 .

Guest suite in Siesta Key

4.91 out of 5 average rating, 188 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, 110 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!

The exterior of the duplex presents a welcoming entrance with a covered front porch and seating. Lush greenery and small potted plants enhance the home's facade. The driveway is visible, leading to the well-maintained lawn and fenced backyard area.

4.94 out of 5 average rating, 105 reviews

1 Bed 1 bath 7 mins to the beach

This charming 1 bedroom 1 bath space has a calming coastal vibe with dedicated driveway parking, front porch, and fenced backyard. This unit is newly renovated and furnished, and is part of a duplex with a large shared backyard. It is within walking/biking distance or a short drive to grocery stores and restaurants, and 7 mins to Siesta Key - FL's #1 beach! Longboat Key, St. Armands, Turtle Beach, and Downtown are all a short drive away!

4.93 out of 5 average rating, 106 reviews

An inviting outdoor space features a heated saltwater pool surrounded by paver stones. Lounge chairs are positioned along the poolside, with lush greenery and tropical plants enhancing the landscape. A pergola provides shaded seating, creating a comfortable area for relaxation and entertainment.

Home in Arlington Park

Sea Esta | Private Saltwater POOL + Putting Green!

BNB Breeze Presents: Sea Esta! Experience this stunning home in the heart of Sarasota, located just 10 minutes away from Siesta Key Beach! From the gorgeous interior, to the INCREDIBLE outdoor oasis, this home has it all! • Heated Saltwater Pool - heated at NO extra cost from Nov 21 - April 1st • E-Bikes (For Rent) • Resort-Like Back Yard w/ a Pergola, Turf + Putting Green • Pool + Beach Supplies • Fun Outdoor Swinging Dining Table

A living area is depicted with a neutral color palette and light hardwood flooring. A blue sofa and a wooden coffee table sit in front of a television on a console. A dining area with a table and chairs is visible in the background, alongside large sliding doors leading to an outdoor space.

4.96 out of 5 average rating, 117 reviews

Siesta Beach home w/ private access, walk to town!

Welcome to your own private getaway directly on Siesta Beach! Meticulous, updated unit with amazing location to the village and access to tow You will literally, walk out your door, down the steps, and directly onto the beautiful, fine, powdery white sand of Siesta Key Beach. Private Paradise directly on the white powdery sand of Siesta Key! 2 bedroom 3 bathroom beachfront home with Gulf views that sleeps 8.

4.89 out of 5 average rating, 160 reviews

A cozy living area features a blue sectional sofa accompanied by decorative pillows and a side table with a lamp. A wall clock adds a modern touch, while large sliding glass doors offer views of the outdoor space. A dark blue accent chair complements the scene.

Apartment in Sarasota

6 min to Siesta Beach | Heated Pool | Lake View

🌴 Stylish Retreat Near Siesta Key & Heated Pool! Welcome to your perfect Sarasota getaway! This 720 sq. ft. pet-friendly home offers a , heated pool access, and a prime location just 6 minutes from Siesta Key Beach. Whether you're here for a beach vacation, a family trip, or a remote work retreat, this home has everything you need for a comfortable and stress-free stay.

4.87 out of 5 average rating, 419 reviews

A spacious room features a king size bed with coordinating pillows and light bedding. A chic chandelier hangs from the ceiling, illuminating the space. Natural light enters through the window, while a comfortable seating area with decorative pillows and a coffee table complete the inviting environment.

Guest house in Sarasota

The Cottage, very close to Siesta Beach!

The cottage was built in 1926 and is in a Historic Neighborhood. Our location is a 10 min car ride to the #1 Rated Siesta Key Beach and a short stroll to popular eateries and shopping areas. The cottage is cozy and has all the essentials of home. Private entrance, backyard, kitchenette with a full fridge. Ideal for 2 people but can accommodate more. Dogs welcome

Popular amenities for Siesta Key pet-friendly home rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Pet-friendly house rentals

Superhost

5 out of 5 average rating, 4 reviews

Casa Del Mar - Luxury Home w/ Private Heated Pool!

An open kitchen showcases a spacious countertop with three black bar stools positioned at the natural wood bar. Modern stainless steel appliances and cabinetry are visible in the background, complemented by bright lighting and a view of lush greenery through the nearby sliding doors.

4.93 out of 5 average rating, 40 reviews

Beach Bungalow (Hot Tub + Hammock!) by Siesta Key

Superhost

A charming exterior view features a single-story home surrounded by tropical landscaping. Lush palm trees and other foliage create a serene atmosphere. The gravel driveway leads to the entrance, which is framed by a clean, modern facade and bordered by decorative stone and plants.

4.5 out of 5 average rating, 12 reviews

Walk to Beach & Siesta Village

5 out of 5 average rating, 10 reviews

Pool house with outdoor shower, 10 minutes from SK

4.86 out of 5 average rating, 106 reviews

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

A well-appointed backyard features a heated saltwater pool surrounded by elegant stone decking. Lush green artificial grass lines the pool area, enhancing the design. Comfortable lounge chairs are positioned nearby, offering a relaxing space for enjoyment under the shade of sleek umbrellas.

4.94 out of 5 average rating, 88 reviews

Private Heated Saltwater Pool & Spa 1 mi to Beach

A serene pool area is surrounded by lush greenery and wooden fencing. Aquamarine water reflects sunlight, while a few poolside lounge chairs in turquoise invite relaxation. Potted plants add a touch of color, and a floating pool accessory rests on the surface.

4.94 out of 5 average rating, 115 reviews

5Stars Tiki, Heated Pool, Close to Beaches and ALL

A comfortable living area features a woven sofa adorned with blue patterned cushions. A sleek coffee table is positioned in front, with decor items neatly arranged on shelves behind it. Natural light enters through the window, complemented by indoor plants that add a touch of greenery.

4.92 out of 5 average rating, 26 reviews

Sweet Siesta Cottage

Pet-friendly home rentals with a pool

4.99 out of 5 average rating, 79 reviews

A private balcony is showcased with two white lounge chairs and a small table. Lush palm trees provide greenery, while a heated pool can be seen beyond the railing. Sunlight filters through the trees, creating a serene outdoor space.

Flat in Sarasota

Beechwood Suites B

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, 64 reviews

Serene 3BR family retreat | Firepit & POOL

5 out of 5 average rating, 16 reviews

Cottage in Siesta Key

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

A spacious screened-in pool area features a bright blue pool alongside lounge chairs. Strings of lights illuminate the space as the sunset casts a warm glow. Lush greenery surrounds the area, providing a tranquil setting for relaxation and entertainment.

5 out of 5 average rating, 17 reviews

Salt Water Heated Pool|Arcade Games|Game Room

5 out of 5 average rating, 22 reviews

Luxury Sport Vacation Pool House-Downtown Sarasota

The spacious backyard features a heated pool illuminated with purple lighting, surrounded by lounge chairs and umbrellas. A dining table for eight sits nearby, with a cozy fire pit area providing evening ambiance. Pool floats are present, enhancing recreational options.

4.97 out of 5 average rating, 34 reviews

Luxe Oasis Mins to Beach & Downtown w/Heated Pool

A private heated pool is surrounded by comfortable lounge chairs and a dining table. An umbrella provides shade, while tropical plants enhance the serene outdoor space. A gas grill is positioned nearby, inviting guests to enjoy outdoor cooking.

5 out of 5 average rating, 8 reviews

Villa Castile | Short Walk To SK Beach & Village!

An expansive outdoor area surrounds a sparkling pool, framed by lush grass and swaying palms. Comfortable loungers are positioned beside the pool on newly laid pavers. A serene backdrop features the home's exterior with large windows, under a clear blue sky accented by fluffy white clouds.

5 out of 5 average rating, 16 reviews

Tropical Oasis | Fully Remodeled | Private Pool

Private, pet-friendly home rentals

4.95 out of 5 average rating, 41 reviews

An inviting entrance opens to a well-lit living space featuring a red sectional sofa and a dining area with white chairs around a round table. Light wooden flooring extends throughout, and a large mirror reflects the bright atmosphere.

Flat in Sarasota

Modern Bungalow Patio & Grill 10 min to Siesta Key

5 out of 5 average rating, 5 reviews

The front view of the bungalow features a welcoming entrance framed by tall palm trees. The light blue exterior contrasts with the lush greenery surrounding the property. A driveway leads to the entrance, inviting visitors to explore the charming cottage just steps away from the beach.

Cottage in Sarasota

Charming 2BD Bungalow Close to Crescent Beach!

Superhost

A spacious living area features a mix of comfortable seating, including a purple sofa and a black armchair. Large glass doors provide a view of the outdoor space and the surrounding landscape. A dining area is visible with a table set for four, accented by floral decor.

Apartment in Siesta Key

4.88 out of 5 average rating, 52 reviews

Dreamview • 1BR - Siesta Key Beach Sunset View

An aerial view of a single-story home with a blue exterior and a metal roof highlights a private pool surrounded by a spacious patio. Lush landscaping and palm trees create a tropical atmosphere, while a shaded seating area under the umbrella invites relaxation.

5 out of 5 average rating, 42 reviews

Waterfront Retreat | Heated Pool & Boat Dock

5 out of 5 average rating, 22 reviews

Flat in Siesta Key

Gertrude Siesta | 8-steps Beach Path, 4-min Dining

4.92 out of 5 average rating, 89 reviews

A covered seating area is furnished with comfortable wicker chairs and lounge chairs featuring green cushions. Lush plants and palm trees enhance the outdoor space, while a view of the shared garden can be seen in the background. A book and a sun hat rest on a side table.

Flat in Sarasota

Perfect location- minutes to Siesta or DT w/pool

An open living space features warm wooden floors and large windows that provide ample natural light. A circular dining table is surrounded by six wire chairs. A modern chandelier hangs above the table, while a comfortable chair is positioned nearby, creating an inviting gathering area.

5 out of 5 average rating, 30 reviews

Sanctuary by the Sea