Pet Friendly Vacation Rentals in Sarasota, FL

Come enjoy the relaxed vibe of Siesta Key! The beautiful white sand beaches that make Siesta Key the #1 beach in the US are not even a five-minute stroll away. Siesta Key Village and the famous 3 miles of the softest 99.. This two story, 4 bedroom 3 1/2 bathroom home features a huge heated pool with spa and an incredible outdoor living space for relaxing to the soothing sounds of the pools water features or livening things up and entertaining your family and guests. The property is private and secluded from neighbors and surroundings by a wall. As you enter through the front door on the main l.......

4.9 Star Review

4 Bedrooms - 3 Baths - Sleeps 8
Sarasota Vacation Rental

Pet Friendly - Pets Allowed

Your Ultimate Beach Escape on Lido Key, Florida — Steps from the Sand & St. Armands Circle NEWLY RENOVATED!!! Ready for the ultimate Lido Beach getaway? This charming unit offers the perfect launchpad for your Florida adventures, delivering incredible access to all the Lido Key magic! Step inside to a comfortable haven designed for relaxed beach living. You'll find a king-size bed in the primary bedroom for peaceful nights, and a queen-size bed in the second bedroom, providing ample space for your group. The living room features a smart TV and a cozy seating area with a sleeper sofa, whil.......

3.0 Star Review

2 Bedrooms - 1 Baths - Sleeps 6
Sarasota Vacation Rental

Pet Friendly - Pets Allowed

Let's be ’s better at the beach! Come play in the sand with a drink in your hand on Lido Key Beach, FL! NEWLY RENOVATED!!! Ready to swap your shoes for flip-flops? Discover Mermaid For A Day, a vibrant studio unit on Lido Key, offering the ultimate beachside escape! This is where comfort meets unparalleled convenience, putting you right in the heart of Lido's magic. Inside, you'll find everything you need for a carefree vacation: a cozy king-size bed for restful nights, a refreshing walk-in shower, and a full kitchen ready for your beach-day snacks or morning coffee. The living area is de.......

5.0 Star Review

Studio 1 Baths - Sleeps 4
Sarasota Vacation Rental

Pet Friendly - Pets Allowed

Downtown Sarasota Private Vacation Home - Minutes to Lido Key Beach, St. Armands Circle, and all that Downtown Sarasota, FL has to offer! Our 3-bedroom, 3 Bathroom private vacation home offers a fantastic property perfect for your relaxing South Florida Gulf Coast Vacation. - 3 Bedrooms / 3 Bathrooms - 5 miles to popular Gulf Coast Beaches - Fully Equipped Kitchen - Dining for 4 at the dining table - Spacious Patio and Backyard with outdoor seating area - Parking for three cars in the driveway - Beach Equipment for guest use (Beach Towels, 4 Chairs, and a Cooler) - Baby and Child Items Availab.......

5.0 Star Review

3 Bedrooms - 3 Baths - Sleeps 6
Sarasota Vacation Rental

Pet Friendly - Pets Allowed

Presents: Bahama Breeze! This beautiful coastal home is nestled in the heart of Sarasota, just 15 minutes away from both Lido Key Beach and Siesta Key Beach! With a backyard oasis, this cozy home is a haven to return to after a day at the #1 beach in the US, Siesta Key Beach! - Private Heated Pool - heated at NO extra cost from Nov 21 - April 1st - Pet Friendly - Outdoor TV - Located Next to the Gorgeous Legacy Trail! - Grill - Adult Bikes - Outdoor Dining + Sitting Area - Private Backyard - Beach Supplies Wake up with your morning cup of coffee enjoyed from the beautiful screened-in porch ove.......

5.0 Star Review

3 Bedrooms - 2 Baths - Sleeps 8
Sarasota Vacation Rental

Pet Friendly - Pets Allowed

Presents: Sea Esta! Experience this stunning, newly-renovated home in the heart of Sarasota, located just 10 minutes away from Siesta Key Beach! From the gorgeous interior, to the INCREDIBLE outdoor oasis with a heated saltwater pool and putting green, this home has everything that you and your loved ones need for your next dream vacation, including: • Heated Saltwater Pool - heated at NO extra cost from Nov 21 - April 1st • Turf in Back Yard w/ a Putting Green • Bikes for free • Sun Deck in Pool w/ Lounge Chairs • Pool + Beach Supplies • Resort-Like Back Yard w/ .......

5.0 Star Review

3 Bedrooms - 2 Baths - Sleeps 6
Sarasota Vacation Rental

Pet Friendly - Pets Allowed

Presents: Sapphire Shores! Welcome to this breathtaking 3-story sanctuary, nestled in the heart of Sarasota, Florida! Just 15 minutes away from the beaches and downtown, this luxurious property offers a true haven of opulence and relaxation! This destination has an extensive amenity list, including: - Private 40' Lap Pool w/ Sun Decks - Ocean Views From The Home - Fireplace - A Game Room - 2 Bars - Kayaks + Bikes - Jura x8 Espresso Machine - Private Balconies off of Each Room w/ French Doors! Experience this incredible home, where the attention to detail can be felt throughout the entire home!.......

4.9 Star Review

5 Bedrooms - 5 Baths - Sleeps 10
Sarasota Vacation Rental

Pet Friendly - Pets Allowed

Presents: Sea Pointe! Step into your newly furnished coastal haven in beautiful Sarasota, Florida. Nestled in the heart of a tropical paradise, just 15 minutes away from the beach, this exquisite property promises an enchanting getaway for those in search of ultimate relaxation and rejuvenation. Your extensive amenity list includes: - Private Heated Pool - heated at NO extra cost from Nov 21 - April 1st - Indoor Hanging Swing - 55" Outdoor TV - Outdoor Lounge Furniture - Pet Friendly!!! - Patio + Grill Experience the Sunshine State from the comforts of this beautiful coastal home! When you fir.......

4.9 Star Review

3 Bedrooms - 2 Baths - Sleeps 8
Sarasota Vacation Rental

Pet Friendly - Pets Allowed

Presents: Royal Palms Oasis! This incredible pet-friendly stay in Sunny Sarasota is your dream vacation in paradise! Located in the heart of Pinecraft, just 15 minutes away from Siesta Key Beach. The home is fully loaded with family friendly amenities: - Private Heated Pool - heated at NO extra cost from Nov 21 - April 1st - Pickleball Court (not regulation size) - Putt Putt Course - Shuffleboard Court - Basketball Court - 2 Living Rooms! - Pet-Friendly w/ Private Backyard ​​​​​​​- Pool + Beach Supplies When you first enter the home, you are greeted with not .......

4.9 Star Review

3 Bedrooms - 2 Baths - Sleeps 8
Sarasota Vacation Rental

Pet Friendly - Pets Allowed

Steps to everything pet-friendly downtown Sarasota has to offer! Walk or bike to restaurants, shops, marina, Bayfront, Whole Foods, Coffee Shops, Opera or Symphony 7 minutes to Lido Key Beach and St. Armands Circle 6 minutes to Ed Smith Stadium Oriole's Baseball, Ringling College, Opera, Symphony 5 minutes to the 54 acre Bay Park & Marina Jacks 2 minutes to Main Street Restaurants, Shops, Spirits and Live Music 2 minutes to Starbucks and Coffee Houses 2 minutes to Publix and Whole Foods 15 minutes to Siesta Key Step across the street to the 10 acre Park with 2 Dog Parks, Playground, Tennis, Pi.......

4.9 Star Review

3 Bedrooms - 3 Baths - Sleeps 10
Sarasota Vacation Rental

Pet Friendly - Pets Allowed

Key Differentiators & Amenities ∆ Central downtown Sarasota—walk to shops, restaurants, arts venues, and marina ∆ 1 spacious bedroom, 1 updated bathroom (perfect for couples, solo travelers, or business guests) ∆ Pet-friendly: beds, bowls, blankets, waste bags, and secure fenced dog run provided ∆ Free reserved on-site parking—rare downtown convenience ∆ High-Speed WiFI throughout unit ∆ WorkSpace Desk for Remote Work to be accomplished ∆ 2 Smart TVs with streaming services ∆ Fully equipped kitchen with modern appliances and generous storage â.......

4.9 Star Review

1 Bedrooms - 1 Baths - Sleeps 3
Sarasota Vacation Rental

Pet Friendly - Pets Allowed

Key Differentiators & Amenities ∆ Central downtown Sarasota—walk to shops, restaurants, arts venues, and marina ∆ 1 spacious bedroom, 1 updated bathroom (perfect for couples, solo travelers, or business guests) ∆ Pet-friendly: beds, bowls, blankets, waste bags, and secure fenced dog run provided ∆ Free reserved on-site parking—rare downtown convenience ∆ High-Speed WiFI throughout unit ∆ WorkSpace Desk for Remote Work to be accomplished ∆ 2 Smart TVs with streaming services ∆ Fully equipped kitchen with modern appliances and generous storage â.......

5.0 Star Review

1 Bedrooms - 1 Baths - Sleeps 2
Sarasota Vacation Rental

Pet Friendly - Pets Allowed

Steps to everything pet-friendly downtown Sarasota has to offer! Walk or bike to restaurants, shops, marina, Bayfront, Whole Foods, Coffee Shops, Opera or Symphony 7 minutes to Lido Key Beach and St. Armands Circle 6 minutes to Ed Smith Stadium Oriole's Baseball, Ringling College, Opera, Symphony 5 minutes to the 54 acre Bay Park & Marina Jacks 2 minutes to Main Street Restaurants, Shops, Spirits and Live Music 2 minutes to Starbucks and Coffee Houses 2 minutes to Publix and Whole Foods 15 minutes to Siesta Key Step across the street to the 10 acre Park with 2 Dog Parks, Playground, Tennis, Pi.......

4.9 Star Review

3 Bedrooms - 3 Baths - Sleeps 8
Sarasota Vacation Rental

Pet Friendly - Pets Allowed

Step into your own private oasis near Siesta Key in Sarasota! - Luxurious 4-bedroom retreat for up to 10 guests - Elegant interiors with a gourmet kitchen - Spacious patio and refreshing pool - Minutes from Siesta Key's beaches, dining & attractions - Perfect blend of relaxation & convenience Book your stay today and make memories to last a lifetime in sunny Sarasota! Indulge in resort-style living near Siesta Key in Sarasota! This luxurious 4-bedroom retreat is designed to accommodate up to 10 guests, making it the perfect getaway for families or groups. With a refreshing pool and elegant int.......

5.0 Star Review

4 Bedrooms - 2 Baths - Sleeps 10
Sarasota Vacation Rental

Pet Friendly - Pets Allowed

. Welcome to Casa Tranquilo! Book this beautifully renovated 3-bedroom, 2-bath modern home in an upscale Sarasota neighborhood, just 11 minutes from Siesta Key Beach. Ideally located near Siesta Key Village, Trader Joe’s, bike rentals, and local favorites like Rico’s Pizza & Pasta, it’s the perfect spot for both relaxation and convenience. LOCATION HIGHLIGHTS: - Upscale Sarasota neighborhood - Just 11 minutes to Siesta Key Beach - 3.5 miles to Siesta Key Village for dining, shopping & nightlife - Close to Trader Joe’s, bike rentals, and casual dining like Rico’s Pizza .......

5.0 Star Review

3 Bedrooms - 2 Baths - Sleeps 8
Sarasota Vacation Rental

Pet Friendly - Pets Allowed

. Welcome to Island Reef - Bayside With Private Beach! This beautiful 2-bedroom, 2-king suite unit in Island Reef on Siesta Key’s south end offers a private beach experience just across the street. Enjoy luxurious resort amenities including two heated pools, tennis/pickleball courts, docks, and a fishing pier, all with stunning Gulf and bay views. Watch incredible daily sunrises and sunsets for the ultimate relaxing getaway. Great monthly rental that allows you to bring your dog along! LOCATION HIGHLIGHTS: - South end of Siesta Key with private beach access just across the street - Stunni.......

5.0 Star Review

2 Bedrooms - 2 Baths - Sleeps 4
Sarasota Vacation Rental

Pet Friendly - Pets Allowed

. Welcome to Lulu’s Crescent Cottage #2~ Book this charming duplex on Siesta Key just a 5-minute walk from Crescent Beach. This updated retreat offers everything you need for a fabulous stay, plus a shared heated dipping pool. Whether you prefer relaxing on the soft white sands or filling your days with beach runs, jet skis, or fishing, your perfect getaway is waiting! LOCATION HIGHLIGHTS: - Located on Siesta Key, just a 5-minute walk to Crescent Beach Access #13 - Walkable to local favorites like Toasted Mango Café (8 minutes) and Big Water Fish Market (shorter walk) - Quick trolley r.......

5.0 Star Review

2 Bedrooms - 2 Baths - Sleeps 6
Sarasota Vacation Rental

Pet Friendly - Pets Allowed

. Welcome Lulu's Crescent Cottage #1! Your perfect Siesta Key getaway awaits at LuLu’s Crescent, a charming standalone newly renovated duplex cottage just a 5-minute walk to Crescent Beach. This updated retreat features everything you need plus a shared heated dipping pool with the neighboring cottage. Relax under an umbrella, stroll the beach, or enjoy water adventures—paradise is waiting! LOCATION HIGHLIGHTS: - Located on Siesta Key, just a 5-minute walk to Crescent Beach Access #13 - Walkable to local favorites like Toasted Mango Café (8 minutes) and Big Water Fish Market (shor.......

5.0 Star Review

2 Bedrooms - 2 Baths - Sleeps 6
Sarasota Vacation Rental

Pet Friendly - Pets Allowed

. Welcome to Starfish Contemporary Home! Fully renovated home on the south end of Sarasota with a private saltwater pool, perfect for family relaxation! Just 2.8 miles from Siesta Key’s Crescent Beach, enjoy sun-soaked days on the soft quartz sands or unwind by the pool. For adventure seekers, charter a deep-sea fishing trip, rent jet skis, or explore countless nearby activities. LOCATION HIGHLIGHTS: - South end of Sarasota near Siesta Key’s Crescent Beach - 2.8 miles to Crescent Beach soft quartz sands - Close to Gulf Gate neighborhood restaurants, cafes, and local favorites - Minut.......

4.9 Star Review

3 Bedrooms - 2 Baths - Sleeps 8
Sarasota Vacation Rental

Pet Friendly - Pets Allowed

Spring comes alive at this creekside retreat, where gentle breezes and the songs of local birds fill your mornings. Spend your days paddling along the winding creek, explore nearby sandy beaches, or cast a line for fishing. Discover local culture at nearby museums & art galleries; return to unwind in the heated pool, enjoy friendly competition in the game room, or curl up for a cozy movie night in the spacious living room. Nature, adventure, and relaxation unite for the perfect spring getaway. Waterfront Family Retreat with Heated Pool Nestled between Anna Maria Island & Siesta Key Welcome to .......

4.9 Star Review

4 Bedrooms - 2 Baths - Sleeps 10
Sarasota Vacation Rental

Pet Friendly - Pets Allowed

Immerse Yourself in Luxury at this Waterfront Oasis: Picture yourself stepping into a spacious 5-bedroom haven (4,617 sq ft!) with a private entrance, offering unforgettable experiences for the whole family. This luxurious beach home boasts spectacular views from four private balconies, a rooftop deck with 360-degree panoramas, and a two-level pool and spa with a covered deck, bar, and outdoor TV - perfect for entertaining under the Florida sun. Unwind and rejuvenate in one of the two master bedrooms, each offering a private sanctuary. The home even features an elevator and an oversized garage.......

5.0 Star Review

5 Bedrooms - 4 Baths - Sleeps 10
Sarasota Vacation Rental

Pet Friendly - Pets Allowed

Bring the whole family as this home features 3 bedrooms and 2 1/2 baths. This very spacious home is almost 2,600 square feet with plenty of room to relax. Huge open living area. You will love the fenced backyard featuring multiple seating areas and a pool to relax in. Portable putting green and safe ax throwing. Lot's of space. It is steps away from the world famous St. Armand's circle featuring fabulous restaurants, coffee shops, beauty salon and a variety of other shopping. 6 minute walk to the beach, 5 min drive to Mote Aquarium, 7 min drive to beautiful Selby Gardens. There is always plent.......

5.0 Star Review

3 Bedrooms - 2 Baths - Sleeps 8
Sarasota Vacation Rental

Pet Friendly - Pets Allowed

A Jewel on St. Armands Circle! The location makes this spacious 3BR+Casita/3BA with a private pool in a botanical setting a perfect month long vacation spot. This residence has it all for those who want to be right by the circle, Lido Beach, and downtown Main Street- the heart of the city. This residence is brimming with updates and remarkable touches to add texture and style. The soaring ceilings create abundant space, complemented by transom windows, a wall of sliders, crown molding, striking wood accents, and recessed lighting. The open plan seamlessly connects the great room to the dining .......

0.0 Star Review

4 Bedrooms - 3 Baths - Sleeps 8
Sarasota Vacation Rental

Pet Friendly - Pets Allowed

This 1-bedroom home is in a prime location & has EVERYTHING you need for an amazing vacation in Sarasota, FL! • Shared Outdoor Patio • Fire Pit • Hammock • Dedicated Workspace • Fully Stocked Kitchen • Drip & Keurig Coffee Maker • Plush Bed • High Speed WIFI • Family Friendly - High Chair & Pack ’n Play • Dog Friendly • Street Parking - 1 car Welcome to Pineapple 1 – Your Sarasota Escape! This charming 1-bedroom, 1-bathroom apartment offers a cozy retreat perfect for up to 2 guests. Whether you’re in town for a beach getaway.......

5.0 Star Review

1 Bedrooms - 1 Baths - Sleeps 2
Sarasota Vacation Rental

Pet Friendly - Pets Allowed

This 1-bedroom home is in a prime location & has EVERYTHING you need for an amazing vacation in Sarasota, FL! • Shared Outdoor Patio • Fire Pit • Hammock • Dedicated Workspace • Fully Stocked Kitchen • Drip & Keurig Coffee Maker • Plush Bed • High Speed WIFI • Family Friendly - High Chair & Pack ’n Play • Dog Friendly • Street Parking - 1 car Welcome to Pineapple #2 – Your Sarasota Escape! This charming 1-bedroom, 1-bathroom apartment offers a cozy retreat perfect for up to 2 guests. Whether you’re in town for a beach getawa.......

4.7 Star Review

1 Bedrooms - 1 Baths - Sleeps 2
Sarasota Vacation Rental

Pet Friendly - Pets Allowed

This 1-bedroom home is in a prime location & has EVERYTHING you need for an amazing vacation in Sarasota, FL! • Shared Outdoor Patio • Fire Pit • Hammock • Fully Stocked Kitchen • Drip & Keurig Coffee Maker • Plush Bed • High Speed WIFI • Family Friendly - High Chair & Pack ’n Play • Dog Friendly • Street Parking - 1 car Welcome to Pineapple #3 – Your Sarasota Escape! This charming 1-bedroom, 1-bathroom apartment offers a cozy retreat perfect for up to 4 guests. Whether you’re in town for a beach getaway, a romantic escape, or ju.......

4.5 Star Review

1 Bedrooms - 1 Baths - Sleeps 4
Sarasota Vacation Rental

Pet Friendly - Pets Allowed

This 3-bedroom home is in a prime location & has EVERYTHING you need for an amazing vacation in Sarasota, FL! • Private Pool • Outdoor Patio • Private Balcony • Board & Card Games • Fully Stocked Kitchen • Drip & Keurig Coffee Maker • Plush Beds • High Speed WIFI • Family Friendly - High Chair & Pack ’n Play • Washer & Dryer • Dog Friendly • Ample Parking Welcome to your Sarasota getaway! This beautifully appointed home offers the perfect blend of comfort, style, and convenience for families and groups alike. With 3 spacious bedr.......

4.6 Star Review

3 Bedrooms - 2 Baths - Sleeps 6
Sarasota Vacation Rental

Pet Friendly - Pets Allowed

Gather your favorite people and escape to this unforgettable 9BR 7BA retreat designed for group getaways, bachelorette weekends, weddings, and once-in-a-lifetime celebrations.

✔ 2 Houses – 9BRs – Sleeps 26
✔ 2 Living Areas
✔ 2 Kitchens
✔ Backyard (Hot Tub, BBQ, Fire Pit...)
✔ Games
✔ High-Speed Wi-Fi
✔ Smart TVs
✔ Free Parking
✔ Pets & Events OK (with approval)

With space for up to 26 guests across two stylish homes, this property offers the perfect mix of comfort, privacy, and .......

5.0 Star Review

9 Bedrooms - 4 Baths - Sleeps 16
Sarasota Vacation Rental

Pet Friendly - Pets Allowed

Gather your favorite people and escape to this unforgettable 4BR 3BA retreat designed for group getaways, bachelorette weekends, weddings, and once-in-a-lifetime celebrations.

✔ House – 4BRs – Sleeps 14
✔ 2 Living Areas
✔ Massive Kitchen
✔ Backyard (BBQ, Fire Pit, Shower,...)
✔ Games
✔ High-Speed Wi-Fi
✔ Smart TVs
✔ Free Parking (4 cars)
✔ Pets & Events OK (with approval)

With space for up to 14 guests across two floors this property offers the perfect mix of comfort, privacy, a.......

4.9 Star Review

4 Bedrooms - 2 Baths - Sleeps 16
Sarasota Vacation Rental

Pet Friendly - Pets Allowed

We’re a local family sharing our Sarasota home, just a short walk to downtown and minutes to Lido Beach. With a heated saltwater pool, hot tub, kid gear, and stocked kitchen, it’s ready for families, friends, and beach-loving groups to settle in and relax.

The space
⭑Master Bedroom:⭑
✔ King bed, ensuite bathroom, ensuite bathroom, private balcony
✔ Plush linens, extra pillows, room-darkening shades, dresser, freestanding closet

⭑Second Bedroom:⭑
✔ Queen bed, premium bedding, dresser,, extra blankets. .......

4.8 Star Review

5 Bedrooms - 3 Baths - Sleeps 12
Sarasota Vacation Rental

Pet Friendly - Pets Allowed

This walkable downtown Sarasota home is ideal for families and friend groups. It’s spacious, pet-friendly, and stocked with thoughtful touches, plus just minutes from Lido Beach. We love welcoming guests with a treat, local tips, and space to relax together.

The space
⭑Master Bedroom:⭑
✔ King bed, ensuite bathroom, ensuite bathroom, private balcony
✔ Plush linens, extra pillows, room-darkening shades, dresser, freestanding closet

⭑Second Bedroom:⭑
✔ Queen bed, premium bedding, dresser,, extra blankets. Thi.......

4.7 Star Review

5 Bedrooms - 3 Baths - Sleeps 13
Sarasota Vacation Rental

Pet Friendly - Pets Allowed

Traveling with a group of family and friends? Book this stunning 10BR 8BA getaway that can accommodate up to 25 guests for a bachelorette party, wedding, or a large gathering. Settle in two houses before stepping outside to luxuriate in the upscale pool, hot tub, or explore the thrilling attractions of the Gulf Coast.

✔ 2 Houses with 10 Bedrooms
✔ 2 Living Areas
✔ 2 Full Kitchens
✔ Swimming Pool & Hot Tub
✔ BBQ Grills
✔ Fire Pits
✔ Games
✔ High-Speed Wi-Fi
✔ Smart TVs
✔ Parking

.......

5.0 Star Review

1 Bedrooms - 7 Baths - Sleeps 16
Sarasota Vacation Rental

Pet Friendly - Pets Allowed

This is a charming and luminous condo of 958 sq. ft. fully furnished with great taste. It will be perfect to enjoy your stay in Sarasota with an amazing water view! It features 1 bedroom, 1 den (a bedroom without a window), 1.5 bathroom, kitchen, and cozy living room with large sliding doors to the terrace. On the third floor of the brand new luxury residence (with an elevator). ★Living Area: Next you will find the very luminous living room. Large sliding windows let the light in and you can enjoy the beautiful view on the water and the bay to your left with the beautiful sunset! It featu.......

5.0 Star Review

2 Bedrooms - 1 Baths - Sleeps 4
Sarasota Vacation Rental

Pet Friendly - Pets Allowed

the property manager was built for the discerning traveler who’s seeking a truly unforgettable experience! Each home is thoughtfully designed down to the last detail, with you–our guest–in mind. Our team delivers service that’s every bit as impressive as our luxury vacation homes, with a consistent, personalized touch from start to finish. No hidden fees, just transparent pricing and advertising. The result? Unmatched value for travelers who expect more from their getaway. This Siesta Key luxury vacation rental is ideal for any family or group despite age ranges, and it has.......

5.0 Star Review

5 Bedrooms - 5 Baths - Sleeps 14
Sarasota Vacation Rental

Pet Friendly - Pets Allowed

the property manager was built for the discerning traveler who’s seeking a truly unforgettable experience! Each home is thoughtfully designed down to the last detail, with you–our guest–in mind. Our team delivers service that’s every bit as impressive as our luxury vacation homes, with a consistent, personalized touch from start to finish. No hidden fees, just transparent pricing and advertising. The result? Unmatched value for travelers who expect more from their getaway. There are so many outdoor living spaces to enjoy here! The resort style, saltwater heated pool and spa.......

5.0 Star Review

6 Bedrooms - 6 Baths - Sleeps 16
Sarasota Vacation Rental

Pet Friendly - Pets Allowed

the property manager was built for the discerning traveler who’s seeking a truly unforgettable experience! Each home is thoughtfully designed down to the last detail, with you–our guest–in mind. Our team delivers service that’s every bit as impressive as our luxury vacation homes, with a consistent, personalized touch from start to finish. No hidden fees, just transparent pricing and advertising. The result? Unmatched value for travelers who expect more from their getaway. You're going to love this pool area! With an oversized resort style, saltwater heated pool and spa, su.......

5.0 Star Review

6 Bedrooms - 7 Baths - Sleeps 16
Sarasota Vacation Rental

Pet Friendly - Pets Allowed

the property manager was built for the discerning traveler who’s seeking a truly unforgettable experience! Each home is thoughtfully designed down to the last detail, with you–our guest–in mind. Our team delivers service that’s every bit as impressive as our luxury vacation homes, with a consistent, personalized touch from start to finish. No hidden fees, just transparent pricing and advertising. The result? Unmatched value for travelers who expect more from their getaway. This incredible 2-home estate combines the best of both luxury residences – Salty Oak and Siesta .......

0.0 Star Review

1 Bedrooms - 14 Baths - Sleeps 37
Sarasota Vacation Rental

Pet Friendly - Pets Allowed

the property manager was built for the discerning traveler who’s seeking a truly unforgettable experience! Each home is thoughtfully designed down to the last detail, with you–our guest–in mind. Our team delivers service that’s every bit as impressive as our luxury vacation homes, with a consistent, personalized touch from start to finish. No hidden fees, just transparent pricing and advertising. The result? Unmatched value for travelers who expect more from their getaway. This extraordinary dual-home coastal retreat combines two neighboring residences—Crescent Beach H.......

0.0 Star Review

1 Bedrooms - 11 Baths - Sleeps 28
Sarasota Vacation Rental

Pet Friendly - Pets Allowed

the property manager was built for the discerning traveler who’s seeking a truly unforgettable experience! Each home is thoughtfully designed down to the last detail, with you–our guest–in mind. Our team delivers service that’s every bit as impressive as our luxury vacation homes, with a consistent, personalized touch from start to finish. No hidden fees, just transparent pricing and advertising. The result? Unmatched value for travelers who expect more from their getaway. Welcome to the Sabal Estate—an extraordinary dual-home property located just one block from Siest.......

0.0 Star Review

1 Bedrooms - 17 Baths - Sleeps 41
Sarasota Vacation Rental

Pet Friendly - Pets Allowed

the property manager was built for the discerning traveler who’s seeking a truly unforgettable experience! Each home is thoughtfully designed down to the last detail, with you–our guest–in mind. Our team delivers service that’s every bit as impressive as our luxury vacation homes, with a consistent, personalized touch from start to finish. No hidden fees, just transparent pricing and advertising. The result? Unmatched value for travelers who expect more from their getaway. Welcome to your dream escape on Lido Key. This extraordinary dual-home estate combines two stunning re.......

0.0 Star Review

1 Bedrooms - 14 Baths - Sleeps 32
Sarasota Vacation Rental

Pet Friendly - Pets Allowed

the property manager was built for the discerning traveler who’s seeking a truly unforgettable experience! Each home is thoughtfully designed down to the last detail, with you–our guest–in mind. Our team delivers service that’s every bit as impressive as our luxury vacation homes, with a consistent, personalized touch from start to finish. No hidden fees, just transparent pricing and advertising. The result? Unmatched value for travelers who expect more from their getaway. The outdoor living areas and entertainment spaces are incredible! Let's start with the multi-sport cou.......

5.0 Star Review

7 Bedrooms - 8 Baths - Sleeps 19
Sarasota Vacation Rental

Pet Friendly - Pets Allowed

the property manager was built for the discerning traveler who’s seeking a truly unforgettable experience! Each home is thoughtfully designed down to the last detail, with you–our guest–in mind. Our team delivers service that’s every bit as impressive as our luxury vacation homes, with a consistent, personalized touch from start to finish. No hidden fees, just transparent pricing and advertising. The result? Unmatched value for travelers who expect more from their getaway. This home was built with your vacation in mind! The pool area is a tropical paradise, with a resort st.......

5.0 Star Review

5 Bedrooms - 6 Baths - Sleeps 16
Sarasota Vacation Rental

Pet Friendly - Pets Allowed

the property manager was built for the discerning traveler who’s seeking a truly unforgettable experience! Each home is thoughtfully designed down to the last detail, with you–our guest–in mind. Our team delivers service that’s every bit as impressive as our luxury vacation homes, with a consistent, personalized touch from start to finish. No hidden fees, just transparent pricing and advertising. The result? Unmatched value for travelers who expect more from their getaway. This home was built with your vacation in mind, starting with the exterior entertainment spaces via th.......

5.0 Star Review

5 Bedrooms - 6 Baths - Sleeps 16
Sarasota Vacation Rental

Pet Friendly - Pets Allowed

the property manager was built for the discerning traveler who’s seeking a truly unforgettable experience! Each home is thoughtfully designed down to the last detail, with you–our guest–in mind. Our team delivers service that’s every bit as impressive as our luxury vacation homes, with a consistent, personalized touch from start to finish. No hidden fees, just transparent pricing and advertising. The result? Unmatched value for travelers who expect more from their getaway. The fenced in back yard and the amenities tied to it are simply world class, featuring amenities like:.......

5.0 Star Review

6 Bedrooms - 7 Baths - Sleeps 18
Sarasota Vacation Rental

Pet Friendly - Pets Allowed

the property manager was built for the discerning traveler who’s seeking a truly unforgettable experience! Each home is thoughtfully designed down to the last detail, with you–our guest–in mind. Our team delivers service that’s every bit as impressive as our luxury vacation homes, with a consistent, personalized touch from start to finish. No hidden fees, just transparent pricing and advertising. The result? Unmatched value for travelers who expect more from their getaway. With just over 4,000 square feet of interior living, 7 bedrooms + 7 full baths and 1 half bath, tons o.......

5.0 Star Review

7 Bedrooms - 7 Baths - Sleeps 18
Sarasota Vacation Rental

Pet Friendly - Pets Allowed

the property manager was built for the discerning traveler who’s seeking a truly unforgettable experience! Each home is thoughtfully designed down to the last detail, with you–our guest–in mind. Our team delivers service that’s every bit as impressive as our luxury vacation homes, with a consistent, personalized touch from start to finish. No hidden fees, just transparent pricing and advertising. The result? Unmatched value for travelers who expect more from their getaway. The Siesta Estate was a dream that has become a reality! There is nothing like it anywhere! Located on.......

5.0 Star Review

1 Bedrooms - 14 Baths - Sleeps 36
Sarasota Vacation Rental

Pet Friendly - Pets Allowed

the property manager was built for the discerning traveler who’s seeking a truly unforgettable experience! Each home is thoughtfully designed down to the last detail, with you–our guest–in mind. Our team delivers service that’s every bit as impressive as our luxury vacation homes, with a consistent, personalized touch from start to finish. No hidden fees, just transparent pricing and advertising. The result? Unmatched value for travelers who expect more from their getaway. This one has the wow factor for sure! It’s perfect for your large family or group travel event! W.......

0.0 Star Review

8 Bedrooms - 9 Baths - Sleeps 22
Sarasota Vacation Rental

Pet Friendly - Pets Allowed

the property manager was built for the discerning traveler who’s seeking a truly unforgettable experience! Each home is thoughtfully designed down to the last detail, with you–our guest–in mind. Our team delivers service that’s every bit as impressive as our luxury vacation homes, with a consistent, personalized touch from start to finish. No hidden fees, just transparent pricing and advertising. The result? Unmatched value for travelers who expect more from their getaway. This home is perfect for any vacation, any family or group regardless of age ranges, and it has proven.......

5.0 Star Review

5 Bedrooms - 6 Baths - Sleeps 14
Sarasota Vacation Rental

Pet Friendly - Pets Allowed

the property manager was built for the discerning traveler who’s seeking a truly unforgettable experience! Each home is thoughtfully designed down to the last detail, with you–our guest–in mind. Our team delivers service that’s every bit as impressive as our luxury vacation homes, with a consistent, personalized touch from start to finish. No hidden fees, just transparent pricing and advertising. The result? Unmatched value for travelers who expect more from their getaway. This home was built with your vacation in mind, and when paired with our unmatched service and ameniti.......

5.0 Star Review

6 Bedrooms - 6 Baths - Sleeps 16
Sarasota Vacation Rental

Pet Friendly - Pets Allowed

the property manager was built for the discerning traveler who’s seeking a truly unforgettable experience! Each home is thoughtfully designed down to the last detail, with you–our guest–in mind. Our team delivers service that’s every bit as impressive as our luxury vacation homes, with a consistent, personalized touch from start to finish. No hidden fees, just transparent pricing and advertising. The result? Unmatched value for travelers who expect more from their getaway. This house is special! You must see this 60 foot long waterslide to believe it - it's a water park in .......

5.0 Star Review

6 Bedrooms - 6 Baths - Sleeps 18
Sarasota Vacation Rental

Pet Friendly - Pets Allowed

the property manager was built for the discerning traveler who’s seeking a truly unforgettable experience! Each home is thoughtfully designed down to the last detail, with you–our guest–in mind. Our team delivers service that’s every bit as impressive as our luxury vacation homes, with a consistent, personalized touch from start to finish. No hidden fees, just transparent pricing and advertising. The result? Unmatched value for travelers who expect more from their getaway. Looking for your Lost Shaker of Salt? Well, you've found it in this luxury rental home on Siesta Key t.......

5.0 Star Review

7 Bedrooms - 8 Baths - Sleeps 19
Sarasota Vacation Rental

Pet Friendly - Pets Allowed

the property manager was built for the discerning traveler who’s seeking a truly unforgettable experience! Each home is thoughtfully designed down to the last detail, with you–our guest–in mind. Our team delivers service that’s every bit as impressive as our luxury vacation homes, with a consistent, personalized touch from start to finish. No hidden fees, just transparent pricing and advertising. The result? Unmatched value for travelers who expect more from their getaway. From the location and unmatched service to the provided amenities starting with the exterior entertain.......

0.0 Star Review

5 Bedrooms - 6 Baths - Sleeps 16
Sarasota Vacation Rental

Pet Friendly - Pets Allowed

the property manager was built for the discerning traveler who’s seeking a truly unforgettable experience! Each home is thoughtfully designed down to the last detail, with you–our guest–in mind. Our team delivers service that’s every bit as impressive as our luxury vacation homes, with a consistent, personalized touch from start to finish. No hidden fees, just transparent pricing and advertising. The result? Unmatched value for travelers who expect more from their getaway. This is a show stopping luxury vacation home! With 4,000 square feet of interior living space, 6 bedro.......

5.0 Star Review

6 Bedrooms - 7 Baths - Sleeps 18
Sarasota Vacation Rental

Pet Friendly - Pets Allowed

This top floor condo of 896 sq. ft. is fully furnished with a charming decoration and high end furniture. It will be perfect to enjoy your stay in Sarasota with a water view! It features 1 bedroom, 1.5 bathroom, kitchen, and lovely living room with large sliding doors to the vast terrace. On the 5th floor of the brand new luxury residence (with an elevator). ★Living Area: Next you will find the very luminous living room and kitchen in tones of white and blue. Large sliding windows let the light in and you can enjoy the beautiful view on the water and the bay to your left with the beautifu.......

5.0 Star Review

1 Bedrooms - 1 Baths - Sleeps 4
Sarasota Vacation Rental

Pet Friendly - Pets Allowed

This unique combination of three homes offers a total of 3 bedrooms, is in a prime location, and has EVERYTHING you need for an amazing vacation in Sarasota, FL! • Shared Outdoor Patio • Fire Pit • Hammock • Dedicated Workspace • Fully Stocked Kitchen • Drip & Keurig Coffee Maker • Plush Beds • High Speed WIFI • Family Friendly-High Chair & Pack ’n Play • Dog Friendly • Street Parking Welcome to Pineapple Paradise #1–3, a unique Sarasota retreat comprising three private homes combined into one stay, perfectly designed for groups .......

0.0 Star Review

3 Bedrooms - 3 Baths - Sleeps 8
Sarasota Vacation Rental

Pet Friendly - Pets Allowed

** NEW LISTING** Escape to this relaxing Siesta Key vacation home with a private heated pool, just minutes from the world-famous quartz sand of Siesta Key Beach and the restaurants, bars, and shops of Siesta Village. Perfect for families, couples, or small groups, this comfortable 2-bedroom, 2-bath Sarasota retreat sleeps up to 6 guests and offers the ideal mix of beach access, privacy, and convenience. Spend your days exploring the Gulf Coast, then return home to relax in your private backyard pool, fenced dog-friendly yard, and outdoor grilling area. Whether you're here for beach days, boati.......

0.0 Star Review

2 Bedrooms - 2 Baths - Sleeps 6
Sarasota Vacation Rental

Pet Friendly - Pets Allowed

Coastal comfort awaits at this 3-bed, 2-bath waterfront retreat in Siesta Key for 6 guests. Enjoy your private paradise with a pristine swimming pool and a private dock on a tranquil waterway. Just moments from the world-famous Siesta Key Beach and the vibrant Siesta Key Village, this home is your perfect island escape. Welcome to your perfect Siesta Key escape. This inviting 3-bedroom, 2-bath home comfortably accommodates up to 6 guests and offers the ideal blend of comfort, convenience, and coastal charm. After a day at the beach, unwind in your private pool and relaxing hot tub, creating th.......

0.0 Star Review

3 Bedrooms - 2 Baths - Sleeps 6
Sarasota Vacation Rental

Pet Friendly - Pets Allowed

Minutes to Siesta Key Beach, this Sarasota home is made for effortless group getaways. Start your mornings by the private screened pool, unwind on the cabana daybed, and gather in bright open living spaces designed for connection. Enjoy a fully equipped kitchen, 3 full bathrooms, and a separate studio offering extra space and privacy. Centrally located with quick access to St. Armands Circle, The Ringling, and Mote Marine Laboratory & Aquarium—perfect for dining, culture, and family fun 🌴 📌 NOTE: A digital rental agreement MUST be signed prior to arrival, and you will need t.......

0.0 Star Review

4 Bedrooms - 3 Baths - Sleeps 10
Sarasota Vacation Rental

Pet Friendly - Pets Allowed

Escape to this beach inspired bungalow with a fully equipped kitchen and a fenced yard to relax in the sunny outdoors. Only 10 minutes to Siesta Key Beach! Enjoy the Sarasota beaches, museums, parks and downtown Sarasota, all just minutes away. Centrally located to grocery stores and restaurants. From coastal decor to comfortable beds, every part of your experience was thoughtfully curated by the owners to allow you to sit back, so feel free to put your feet up and relax at Barefoot Bungalow,

The space
Upon entering the home you will find an open concept area including t.......

5.0 Star Review

2 Bedrooms - 2 Baths - Sleeps 6
Sarasota Vacation Rental

Pet Friendly - Pets Allowed