Pet-friendly holiday rentals in Downtown Sarasota

4.9 out of 5 average rating, 159 reviews

A cozy bedroom features a queen-sized bed with white linens and a decorative pillow. Soft light from two bedside lamps enhances the warm wooden accents. The room includes two windows with wooden blinds, allowing for natural light, and a piece of artwork is prominently displayed on the wall.

Flat in Burns Square

Adorable Historic & Charming Walkable Safe Area

Our historic building was built in the 1950's as the main gateway into Sarasota from the south. Nestled between high-end residential Laurel Park, Palm Avenue and Hudson Bayou. Centrally located between Siesta & Lido Beaches. Next to the Bayfront Marina, Whole Foods, Selby Gardens, Opera, Library, Performance & Movie Theaters, restaurants, shopping, nightlife, boat/water activity/rentals, parks, spas, public transport, 10 minutes to airport. Walking area and free trolleys, moped & scooter rental.

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.

A light-filled entryway features a wall of glass shelving with decorative items. Double glass doors provide access to the outdoor space, which is partially visible through the glass. A small mat lies on the floor near the entrance.

4.91 out of 5 average rating, 213 reviews

Sunshine Suite, Minutes to Beach,Tropical Paradise

The Sunshine Suite.Lots of natural light in this totally updated modern 3 bed/1 bath home.It is a completely separate dwelling w separate entry from the other dwelling on the property sharing no common walls. Smart thermostat & door lock. Keyless entry.Brand new AC, gas oven, quartz counter w/ custom marble backsplash, modern & comfortable furniture, private outdoor area, gas BBQ grill, off street parking.Great location! Minutes to Siesta Key beach, shopping/UTC, interstate, hospital & downtown

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, 156 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 .

4.92 out of 5 average rating, 283 reviews

The exterior of the cottage features a welcoming entrance with a bold red door, flanked by lush tropical plants and a pathway lined with pebbles. Natural light enhances the clean, white facade set against the vibrant greenery.

Bungalow in Sarasota

Downtown Bungalow - Beaches, Dining, Attractions

Welcome to The Shady Place! This charming, family-friendly bungalow is a quiet, private oasis in the heart of downtown. Here, you’ll be close to all area beaches including world-famous Siesta Key-rated by Trip Advisor as the #1 beach in the US, SRQ airport, golf courses, Legacy Trail, UTC mall, Mote Aquarium, Bayfront Marina, The Bay park, St. Armands Circle, Robarts Arena, Ed Smith Stadium-spring training home of the Baltimore Orioles, & Downtown Sarasota’s restaurants, activities & nightlife.

Guest suite in Indian Beach-Sapphire Shores

A bright living space is showcased with wooden paneling and a ceiling fan. A cozy bed is adorned with a yellow blanket, while a colorful area rug adds warmth. A seating area with a couch and a workspace are visible, alongside a flat-screen TV and kitchenette.

4.98 out of 5 average rating, 266 reviews

The Sapphire Suite

Beautifully elegant suite with a relaxing touch. A pleasant mix of Hispanic and Modern decor in a newly renovated living area complete with all necessities such as wifi, an outdoor patio and your own free parking. The suite is located MINUTES away from all of Sarasota's famous hotspots! It is down the street from Jungle Gardens. A 10minute walk to The Ringling Museum. 10minute drive to Downtown, 15 minute drive to both Siesta Key and St. Armand's Circle. It could not be located more ideally!

Guest house in Gillespie Park

An outdoor patio area is shown, featuring a round table with four red metal chairs. Potted plants flank the table, and string lights hang overhead, creating an inviting space. French doors lead into the interior, framed by lush greenery.

4.84 out of 5 average rating, 339 reviews

Sarasota Getaway Guest House

Fully private & not shared with others Seasonal rates commence Nov 1 2023 - April 30, 2024 Longer Term Lower Rate Rentals commence May 1, 2024 - Nov 24 (Long Term rental rates available - please contact) Enjoy the luxuries of staying in the Gillispie Park area Dog Park, Tennis, Pickleball...... Walking distance to downtown where guests can find wonderful dining, entertainment, Saturday morning Farmers Market and much more Close to beaches and Arts and Entertainment and St. Armands Circle

4.88 out of 5 average rating, 295 reviews

A single-story home is surrounded by greenery and palm trees, showcasing a light green exterior. A narrow pathway leads to the entrance, flanked by decorative planters. The white fence adds charm and defines the front yard, with large windows allowing natural light into the interiors.

Villa in Laurel Park

Duplex - just mins to Siesta Beach - Pet Friendly

This is a 2/1 in Sarasota's Historic Laurel Park that offers a great downtown and beach experience! Walk/bike to historic downtown with shops, restaurants, bars, boutiques, parks, and music/theater. Minutes from the best beaches in the U.S. Enjoy the lanai & fenced backyard for privacy . Grill & enjoy your favorite beverage while watching your favorite show on the lanai ! Enjoy taking your pet for a walk & check out the historic homes in the area! Short term rental number VR24-00222

Guest suite in Siesta Key

4.91 out of 5 average rating, 189 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, 112 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!

Superhost

A cozy bedroom features a black metal bed frame with a light gray bedspread. A white pillow and a yellow decorative pillow are arranged on the bed. Natural light enters through a nearby window, and a piece of wall art depicting cattle is displayed above the bed.

Flat in Sarasota

4.85 out of 5 average rating, 157 reviews

Cute & Clean 2 Bedroom, 1 Bath Apartment

Welcome to our charming and cozy Airbnb retreat! Nestled in a vibrant neighborhood, our beautifully designed space offers comfort and convenience for your stay. Enjoy the stylish decor, ample natural light, and modern amenities that will make you feel right at home. Our location is perfect for exploring the best that the area has to offer. With numerous cafes, restaurants, and shops just a short walk away, you'll have plenty of options for entertainment and dining.

A private backyard features a heated saltwater pool surrounded by a spacious patio area. Sun loungers are arranged along the edge of the pool, while trees and shrubbery provide a sense of seclusion. Soft clouds drift in the blue sky above.

4.95 out of 5 average rating, 120 reviews

Coastal Getaway *With Bikes & NEW Saltwater Pool*

Just outside of Downtown near the Legacy Trail, this home is located in a quiet neighborhood only 15 minutes from the Siesta Key Beach. The home stands out with its bright and airy design, brand new saltwater pool in the private backyard, and its breezy living room. The large master bathroom rain shower is perfect to wash off the leftover sand from the beach. You can also spend your evenings grilling out back or playing corn hole in the patio area.

Popular amenities for Downtown Sarasota pet-friendly home rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Pet-friendly house rentals

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, 102 reviews

2 BR House 1.6 miles from Siesta Key Beach

The modern kitchen features a large island with a marble countertop, topped with an arrangement of fresh fruits and drinks. A light fixture adds a soft glow above the island, while a cozy seating area with a dark sofa and brick wall can be seen in the background.

4.86 out of 5 average rating, 111 reviews

Sarasota Getaway “Have some fun under the sun.”

The exterior of the villa is displayed, featuring a welcoming blue-green door and two large windows framed in white. A small potted plant accents the entrance, while a pathway leads to the door, surrounded by well-maintained grass and greenery.

4.87 out of 5 average rating, 117 reviews

Charming Villa 14 mins away from Siesta Key Beach

A private pool is surrounded by a spacious patio with paver stones, offering an inviting area for relaxation. Several lounge chairs and a small table with decorative seating are positioned near the water. Lush greenery borders the yard, enhancing the secluded feel.

4.77 out of 5 average rating, 113 reviews

Pool house by the bay

An inviting living space showcases a comfortable seating arrangement, including two black lounge chairs and a stylish dining area. Natural light floods through large windows, illuminating a decorative shelf filled with coastal decor. A circular rug adds a touch of warmth to the wood flooring.

4.96 out of 5 average rating, 130 reviews

5 Star! Walk/Bike DTN ~ 5 mi to Lido Beach Pets Ok

The spacious living area features a comfortable couch adorned with patterned pillows, a wooden coffee table, and colorful rugs. Natural light floods in through large windows, and an open layout connects to the dining area and kitchen, which is visible in the background.

4.98 out of 5 average rating, 124 reviews

Sunshine House, close to Downtown

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

4.95 out of 5 average rating, 100 reviews

A single-story home is showcased with a light exterior and grey roof. Blue shutters adorn the windows, while lush greenery and colorful landscaping enhance the front yard. A screened wraparound porch offers additional outdoor space. The property is bordered by a paved walkway.

Home in Arlington Park

Sarasota 2B/2B Near Siesta Key/Arlington Park/SMH

Pet-friendly home rentals with a pool

4.95 out of 5 average rating, 37 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.

Apartment in Siesta Key

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

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, 81 reviews

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

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

4.89 out of 5 average rating, 242 reviews

A welcoming living space is visible through an opening, featuring a comfortable blue chair and a wall-mounted TV. Natural light filters through a window, illuminating the white walls and partially covering a cozy bed with blue and white bedding in the adjacent area.

Guest house in Sarasota

Supercute Beach Themed Retreat Free Parking Wi-FI

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, 229 reviews

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

Home in Downtown Sarasota

4.94 out of 5 average rating, 47 reviews

Serenity Springs | Private Heated Pool + Waterfall

Apartment in Indian Beach-Sapphire Shores

The living space features a modern open floor plan with a comfortable blue sofa and a dining area with a stylish light fixture above. A large window provides natural light, and various decorative elements, including plants and wall art, enhance the ambiance.

4.94 out of 5 average rating, 32 reviews

Condo Downtown Sarasota. Sunsets, GYM, POOL/SPA

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.

4.84 out of 5 average rating, 291 reviews

Private Siesta Beach House Oasis with Heated Pool.

Private, pet-friendly home rentals

Home in Downtown Sarasota

The dining area features a wooden table set with placemats and a decorative tray, complemented by light-colored chairs. A small bouquet of flowers adds a touch of nature. The kitchen is visible in the background, showcasing cabinets and a stainless-steel dishwasher against a neutral wall.

4.9 out of 5 average rating, 42 reviews

Fully Equipped Beach Home Near Beaches/Downtown

4.89 out of 5 average rating, 65 reviews

A cozy studio space features a queen bed with crisp linens, a retro-style green fridge, and open shelving. Large glass doors lead to an outdoor area surrounded by greenery. Natural light illuminates the wooden flooring and thoughtfully curated decor, creating a welcoming atmosphere.

Guest house in Sarasota

Cocoanut Cottage • Pup-Friendly & Near Downtown

Home in Downtown Sarasota

4.96 out of 5 average rating, 50 reviews

Beach Escape near Downtown | Heated pool, LUX yard

4.95 out of 5 average rating, 59 reviews

A modern studio space features a grey sectional couch accompanied by a tan throw blanket. A small dining table is positioned near the kitchenette, which is equipped with a stove and refrigerator. Natural light enters through window blinds, illuminating the neutral walls and wood flooring.

Guest house in Sarasota

Sarasota Bayside Hideaway

4.91 out of 5 average rating, 44 reviews

A well-lit living area features a light-colored sofa and a neutral armchair, complemented by a round wooden coffee table. A vibrant blue area rug anchors the space. Large windows offer natural light, while decorative elements include wall art and plants for a refreshing touch.

Bungalow in Sarasota

3bdr Bay st bungalow near beach downtown siestakey

An open living area features a comfortable seating arrangement, including a sofa and armchairs. A medium-sized table is situated in front of the sofa, with a flat-screen television mounted on the wall. An adjacent kitchen, highlighted by a large island with two bar stools, is visible.

4.96 out of 5 average rating, 55 reviews

Sarasota Coastal Cottage

Superhost

The exterior of the duplex is showcased with a welcoming pathway lined by lush landscaping. A large tree provides shade, while the combination of modern wood accents and light-colored siding reflects the property's charming design. Natural light filters through the nearby foliage.

Cottage in Gillespie Park

4.88 out of 5 average rating, 16 reviews

Walkable to Downtown and Parks Brand New Furniture