Pet-friendly holiday rentals in Lido Key

A welcoming entryway showcases a simple wooden console table with small potted plants. Above, a serene painting depicting a boat complements the neutral wall. The view to the right reveals a sun room filled with natural light, providing a connection to the private backyard.

4.95 out of 5 average rating, 180 reviews

Newly Renovated Ranch Minutes From Beach/Downtown

Newly renovated cozy home with all new furnishings and appliances. 2 bedrooms 1 bathroom with an eat in kitchen, sun room, and comfy living room. Stream shows or work virtually with our high speed WIFI. Grab the provided beach chairs, umbrella, and cooler to enjoy Lido Key or Siesta Key Beaches, both within a short drive. Wind down & grab drinks/dinner in downtown Sarasota or relax in the backyard. Several golf courses nearby or catch Orioles spring training at Ed Smith stadium 1.5 miles away.

Superhost

The cottage features a welcoming exterior with a screened-in lanai, framed by decorative beams and charming window boxes. Lush greenery surrounds the property, and a large tree adds to the tranquil setting. A pathway leads to the front door, enhancing the inviting atmosphere.

Cottage in Sarasota

4.8 out of 5 average rating, 280 reviews

Cozy Cottage by the Bay

Charming and historic decorator cottage near Downtown Sarasota. Located in the highly desirable, quiet, and safe neighborhood of Indian Beach - Sapphire Shores. Just a short drive to some of the nations top rated beaches like Siesta Key Beach. One of the best features of the home is the enclosed lanai at the front of the house. Perfect for enjoying Florida's coveted indoor/outdoor living. It has a private fenced in backyard, with a fire pit. Off street parking for 2 cars in the driveway.

4.74 out of 5 average rating, 125 reviews

A welcoming living area displays a neutral color palette, featuring a comfortable gray sofa and a light wood coffee table. A large television is mounted on a wall adorned with ocean-themed art. Soft natural light filters in, creating a serene atmosphere.

Home in Nokomis

Cozy Beach Cottage

Welcome to your peaceful retreat just 3.3 miles from Casey Key Beach and 5 miles from the Myakka River. Enjoy your private dock on Shackett Creek just a block away, or explore The Legacy Trail less than a mile from your door. Downtown Venice is only 3.5 miles away with great dining and shopping . Spend your days hunting for fossilized shark teeth, kayaking, biking, or relaxing at home by the outdoor fire pit. Whether you’re here to unwind or explore, Nokomis is a nature lover’s paradise!

5 out of 5 average rating, 37 reviews

Clean/Bright Happy home Centrally located. Pets OK

Bright & Comfy Downtown Home 1 Mi to Main St, Near Trolley to Lido Beach in quiet, centrally located downtown neighborhood just minutes from all Sarasota’s top attractions! This updated home features new furnishings, a spacious fenced backyard, and a screened lanai—perfect for families & pets. Amenities: WiFi, You Tube TV , Washer/Dryer, Beach gear, BBQ, Boat parking, Pet-friendly. Walk to grocery store. 2 mi to waterfront dining & boat trips Near Legacy Bike Trail & Payne Park

Superhost

The backyard features a heated pool with a jacuzzi tub, surrounded by a spacious patio area. A putting green and a shaded area with palm trees are present, along with a canal view in the background. Colorful kayaks lean against the side, adding a pop of color.

Home in Siesta Key

4.85 out of 5 average rating, 13 reviews

Waterfront KEY home w/ Pool, HotTub, mins to beach

Minutes from the beach, marina, & village center- your tropical paradise awaits you at this bright 5 bedroom 3 bathroom vacation rental house. Boasting a heated private pool with jacuzzi tub. There’s even a putting green on site to polish your golf skills. Families can decide between enjoying the private pool, nearby beach, charter boats, eco tours, or shopping and dining. Enjoy friendly competition via arcade Pac Man or Golden Tee Golf games located right in the lower level!

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, 118 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

5 out of 5 average rating, 4 reviews

Beautiful Historic Ringling house!

Welcome to the John Ringling House, a three-bedroom and two-bathroom one-of-a-kind masterpiece on the National Historic Registry and is a 1924 Historic John Ringling Estate. Located in the prestigious John Ringling Estates neighborhood, this home is a quick stroll to St. Armands Circle, known for premier shopping and luxury dining, and is near the award-winning Gulf of Mexico Beaches. Immerse yourself in the island's rich history while enjoying a luxury vacation!

4.95 out of 5 average rating, 22 reviews

Home in Siesta Key

Luxury Canal-Front Home + Heated Pool Near Beach

This is a thoughtfully renovated canal-front residence near Siesta Beach. A private pool and screened patio offer a refined and tranquil retreat with direct canal views. Bright interiors and carefully curated details create an atmosphere of timeless, understated luxury. Just an 8-minute walk from the world-famous beach, yet surrounded by complete peace and privacy. This home is designed for guests who appreciate discreet luxury and elevated comfort.

4.92 out of 5 average rating, 75 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 Sarasota

Steps from Lido Beach & St. Armands Circle

Come getaway and enjoy yourself along with your loved ones or just for a private relaxing break from it all. This One Bedroom/One Bath apartment w/ Lanai(Screened Balcony), and shared Pool/Jacuzzi is located steps from the beautiful Lido Beach, boutique shopping, spa's and incredible dining on St. Armands Circle. If your looking to have everything you need from world famous beaches to historical sites and great food around the corner come and stay!

4.92 out of 5 average rating, 49 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

Located on historic Whitaker Bayou, a small inlet off Sarasota Bay, this is a prime water front and spacious unit designed in the Modern Style. Property is located just a few minutes from Main Street, many Bayfront parks, World class beaches, arts centers and Sarasota-Bradenton International Airport. Interior furnishings curated from top designer brands (DWR, Bludot, Casper).

A vibrant pool is surrounded by a fenced yard, featuring greenery and decorative plants. Two lounge chairs are positioned near the pool, providing a space for relaxation. Sunlight filters through the leaves above, creating playful shadows on the water's surface.

4.93 out of 5 average rating, 71 reviews

Beautiful Florida Bungalow

Beautiful peaceful paradise in the heart of Sarasota. There are two bedrooms, two full baths and a bonus room. Enjoy the outdoors in the fully fenced yard with a beautiful pool. Only two blocks away from the Bay. Close to Ringling College of Art and Design, the Ringling Museum, Theater and only minutes to downtown. A wonderful place to relax and enjoy what the area has to offer.