5 Bedroom or Larger Vacation Rentals in Sarasota, FL

Experience luxury in this stunning 6BR coastal retreat. - Private pool and spa with deeded beach access - Gourmet kitchen with granite countertops and stainless steel appliances - Spacious game/workout room and movie theater - Smart home features including intercom and alarm system - Lush tropical landscaping with outdoor gathering spaces - Exceptional Siesta Key Oasis with 6 Bedrooms, Deeded Beach Access, and Luxury Amenities! - Just 800 feet from Bayfront Marina Discover the epitome of Siesta Key luxury in this stunning 6BR coastal retreat, complete with a private pool, spa, and deeded beach.......

5.0 Star Review

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

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

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

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

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