House in Siesta Key, FL
6 guests · 3 bedrooms · 3 baths
Reasons to book
Guests love it hereGuests give this property a top rating
Great for petsBring all your friends and family, even the furry ones
High-end valueWell priced for this area
About this house rental
Welcome to your dream getaway on Siesta Key! This beautifully appointed, fully renoavted 3-bedroom, 3-bathroom waterfront home offers the perfect blend of comfort, luxury, and island living. Nestled on a quiet canal just minutes from the world-renowned Siesta Beach, this private retreat is ideal for families, couples, or boating enthusiasts. Pet Friendly - all pets must be approved by management. Pet Fee $250.
Key Features:
3 Spacious Bedrooms – Comfortably accommodates families, couples, or small groups
Pet Friendly - All pets must be approved by management. Pet Fee $250.
Private Heated Pool – Soak up the sun or take a refreshing dip any time of year
Canal Access with Private Boat Dock – Bring your boat or rent one locally to explore Sarasota Bay and the Gulf
Just Minutes from Siesta Key Beach – Walk, bike, or drive to one of America’s top-rated beaches with powdery white sand
Fully Stocked with Beach Gear – Includes chairs, umbrellas, towels, and coolers for hassle-free beach days
Gourmet Kitchen – Equipped with everything you need to prepare meals at home
Unbeatable Siesta Key Location – Close to Siesta Village shops, restaurants, and the vibrant nightlife of downtown Sarasota
Modern Comforts Throughout – High-speed Wi-Fi, smart TVs, laundry, and stylish furnishings for a relaxing stay
Spacious Outdoor Entertaining Area – Perfect for grilling, dining al fresco, or lounging by the pool with tropical views
Welcome to Siesta Key, a sun-drenched barrier island on Florida’s Gulf Coast, known for its laid-back charm, vibrant beach village, and the world-famous Siesta Beach, consistently ranked among the best in the U.S. thanks to its soft, powdery white quartz sand.
Whether you're seeking a relaxing retreat or an adventure-filled escape, Siesta Key offers something for everyone. Spend your days swimming in crystal-clear turquoise waters, paddleboarding along gentle bays, or exploring the lush mangrove tunnels by kayak. In the evening, stroll through the lively Siesta Key Village, where you'll find open-air dining, boutique shopping, and live music under the stars.
With easy access to downtown Sarasota, top-notch golf courses, art galleries, and nature preserves, Siesta Key is the perfect blend of tropical tranquility and cultural sophistication.
This island paradise is a beloved destination for families, couples, and snowbirds alike—and once you visit, you’ll understand why guests return year after year.
If you still have any questions concerning our homes, rates, availability calendar, amenities, policies, or otherwise, please contact our team and we will be happy to assist you.
Gulf Coast Holiday Homes offer a wide range of services including:
- An any day arrival policy and length of stay requirements starting at just 7-nights.
- We have a professional property manager and maintenance systems meaning you’ll experience the service you deserve.
- Professional housekeeping pre-stay and during stay if requested.
- 'Guide Books' allowing you to be able to add experiences to your itinerary and see some of our recommendations.
- 'Preferred Vendors' menaing you can trust the company you use for rentals.
All properties listed with Gulf Coast Holiday Homes benefit from an interactive 'Guide Book' which will be sent ahead of arrival and will include the house manual, check in instructions, preferred vendors and unique information about the home.
Step inside to discover an open-concept living area filled with natural light, coastal-inspired décor, and all the modern amenities you need. The fully equipped kitchen features quartez countertops, stainless steel appliances, and a breakfast bar, perfect for morning coffee or evening cocktails.
Each of the three spacious bedrooms offers a serene escape with plush bedding and en-suite or nearby bathrooms. The master suite includes direct access to the pool deck and a spa-like bathroom with walk-in shower.
Outdoors, your own private heated pool awaits, surrounded by tropical landscaping and a sun-soaked patio complete with lounge chairs and a BBQ grill. Just steps away, the private boat dock gives you direct access to the waterway, bring your boat or rent one nearby and explore Sarasota Bay or head out to the Gulf.
Beach chairs, towels, and bikes for your convenience
Whether you're relaxing by the pool, launching off for a day on the water, or strolling the charming shops and restaurants of Siesta Village, this exceptional home is your gateway to the ultimate Florida vacation.
Property can be accessed via electronic door code, sent to allow guests on day of arrival.
Directions: Take I-75 South to Exit 205 for FL-72 W toward Sarasota. Continue on FL-72 W, which becomes Stickney Point Rd. Turn right onto Midnight Pass Rd, heading south. Turn left onto Avenida De Paradisio; the destination will be on your left just before the cul-de-sac.
Parking is available on site for a maximum of 3 cars in the driveway. Parking is available on the street. The garage is not available to guests.
This property must be rented for a minimum of 30 nights. If the travel dates you are looking for don’t appear to be available, please contact our reservations team directly and we will see if we can accommodate your request at your property of choice, or another comparable home in our portfolio.
Prior to your stay, we require you to complete a pre-arrival form and sign & agree to our rental conditions.
Accidental Damage Insurance: Accidental Damage Insurance is included within all guest stays at Gulfcoast Holiday Homes. On this property, for stays greater than 29 nights, an additional $90 will be due as the current rates are for 29 nights or less. For additional blocks of 30 nights past 59 nights you, will be charged $71.
Guests must cancel at least 60 days before check-in to receive a full refund for all nights, minus a 10% processing fee.
Guests must cancel at least 30 days before check-in to receive a 50% refund for all nights.
If a guest cancels less than 30 days before check-in, you’ll be charged 100% for all nights.
We strongly recommend that you purchase your own travel insurance for your protection.
Key Features:
3 Spacious Bedrooms – Comfortably accommodates families, couples, or small groups
Pet Friendly - All pets must be approved by management. Pet Fee $250.
Private Heated Pool – Soak up the sun or take a refreshing dip any time of year
Canal Access with Private Boat Dock – Bring your boat or rent one locally to explore Sarasota Bay and the Gulf
Just Minutes from Siesta Key Beach – Walk, bike, or drive to one of America’s top-rated beaches with powdery white sand
Fully Stocked with Beach Gear – Includes chairs, umbrellas, towels, and coolers for hassle-free beach days
Gourmet Kitchen – Equipped with everything you need to prepare meals at home
Unbeatable Siesta Key Location – Close to Siesta Village shops, restaurants, and the vibrant nightlife of downtown Sarasota
Modern Comforts Throughout – High-speed Wi-Fi, smart TVs, laundry, and stylish furnishings for a relaxing stay
Spacious Outdoor Entertaining Area – Perfect for grilling, dining al fresco, or lounging by the pool with tropical views
Welcome to Siesta Key, a sun-drenched barrier island on Florida’s Gulf Coast, known for its laid-back charm, vibrant beach village, and the world-famous Siesta Beach, consistently ranked among the best in the U.S. thanks to its soft, powdery white quartz sand.
Whether you're seeking a relaxing retreat or an adventure-filled escape, Siesta Key offers something for everyone. Spend your days swimming in crystal-clear turquoise waters, paddleboarding along gentle bays, or exploring the lush mangrove tunnels by kayak. In the evening, stroll through the lively Siesta Key Village, where you'll find open-air dining, boutique shopping, and live music under the stars.
With easy access to downtown Sarasota, top-notch golf courses, art galleries, and nature preserves, Siesta Key is the perfect blend of tropical tranquility and cultural sophistication.
This island paradise is a beloved destination for families, couples, and snowbirds alike—and once you visit, you’ll understand why guests return year after year.
If you still have any questions concerning our homes, rates, availability calendar, amenities, policies, or otherwise, please contact our team and we will be happy to assist you.
Gulf Coast Holiday Homes offer a wide range of services including:
- An any day arrival policy and length of stay requirements starting at just 7-nights.
- We have a professional property manager and maintenance systems meaning you’ll experience the service you deserve.
- Professional housekeeping pre-stay and during stay if requested.
- 'Guide Books' allowing you to be able to add experiences to your itinerary and see some of our recommendations.
- 'Preferred Vendors' menaing you can trust the company you use for rentals.
All properties listed with Gulf Coast Holiday Homes benefit from an interactive 'Guide Book' which will be sent ahead of arrival and will include the house manual, check in instructions, preferred vendors and unique information about the home.
Step inside to discover an open-concept living area filled with natural light, coastal-inspired décor, and all the modern amenities you need. The fully equipped kitchen features quartez countertops, stainless steel appliances, and a breakfast bar, perfect for morning coffee or evening cocktails.
Each of the three spacious bedrooms offers a serene escape with plush bedding and en-suite or nearby bathrooms. The master suite includes direct access to the pool deck and a spa-like bathroom with walk-in shower.
Outdoors, your own private heated pool awaits, surrounded by tropical landscaping and a sun-soaked patio complete with lounge chairs and a BBQ grill. Just steps away, the private boat dock gives you direct access to the waterway, bring your boat or rent one nearby and explore Sarasota Bay or head out to the Gulf.
Beach chairs, towels, and bikes for your convenience
Whether you're relaxing by the pool, launching off for a day on the water, or strolling the charming shops and restaurants of Siesta Village, this exceptional home is your gateway to the ultimate Florida vacation.
Property can be accessed via electronic door code, sent to allow guests on day of arrival.
Directions: Take I-75 South to Exit 205 for FL-72 W toward Sarasota. Continue on FL-72 W, which becomes Stickney Point Rd. Turn right onto Midnight Pass Rd, heading south. Turn left onto Avenida De Paradisio; the destination will be on your left just before the cul-de-sac.
Parking is available on site for a maximum of 3 cars in the driveway. Parking is available on the street. The garage is not available to guests.
This property must be rented for a minimum of 30 nights. If the travel dates you are looking for don’t appear to be available, please contact our reservations team directly and we will see if we can accommodate your request at your property of choice, or another comparable home in our portfolio.
Prior to your stay, we require you to complete a pre-arrival form and sign & agree to our rental conditions.
Accidental Damage Insurance: Accidental Damage Insurance is included within all guest stays at Gulfcoast Holiday Homes. On this property, for stays greater than 29 nights, an additional $90 will be due as the current rates are for 29 nights or less. For additional blocks of 30 nights past 59 nights you, will be charged $71.
Guests must cancel at least 60 days before check-in to receive a full refund for all nights, minus a 10% processing fee.
Guests must cancel at least 30 days before check-in to receive a 50% refund for all nights.
If a guest cancels less than 30 days before check-in, you’ll be charged 100% for all nights.
We strongly recommend that you purchase your own travel insurance for your protection.
Amenities at Sunnyside Up Cottage - Walk to Siesta Beach, Waterfront Home by The Bay & Key Collection
Non-smoking
Pets allowed
Family friendly
Map of Siesta Key, FL
Ratings and reviews
Summary of reviewsThe house is very clean, well-equipped, with a great location for easy access to the beach and village. Perfect for families with ample space and amenities.
10 / 10Outstanding·Aug 2025
We loved this house and location! It was so clean when we arrived and we even had a little goodie basket to welcome us. So nice! We can’t wait to spent many more vacations in this home.
8 / 10Excellent·Jun 2025
This was our 5th stay at Sunnyside Up. The updates after the hurricane are beautiful. We enjoy the pool but were surprised by all the weeds this year around the pool. There was a new lock on the front door that worked every other use. However overall our stay was great. We typically reserve the next year while staying but due to the increased price we are considering other options.
10 / 10Outstanding·Apr 2025
the house was spotless upon arrival! the neighborhood was so quiet and peaceful. the owner was great at responding to questions that I had. Id defiantly stay again!
6 / 10Average·Sep 2022
We recently stayed with two couples and a 1 yr old. The house has a sunken living room that made us all trip several times. Baby included. There’s no markings around the sunken floor to make you aware.
The pool/patio area is very run down. The patio furniture is terrible. The box is filled with moldy/musty toys & such. There’s two gravity chairs but they were so old and seats completely ripped we couldn’t sit on them. There’s also only one lounger -that was plastic & uncomfortable - and the patio table & 4 chairs had the powder coating peeling off every time we sat in them & onto us. For us we wanted to be outside the most - the outdoor area just lacked everything. It was not comfortable at all. The pics made it look so much better. There’s also no pool alarms on the sliding doors and no child/baby gate by pool so our daughter couldn’t be out with us. (She’s walking now). We didn’t trust it. We thought this was a vacation home rule that needed to be followed everywhere.
Location was close to the village. We walked most nights to dinner & for coffee in the mornings.
The house could def use some upgrades. We felt the pics are from years prior. For the price, location, etc it just was lacking to us. Plus lacking some important safety features.
$$$$
Top rated by guests
9.6Outstanding
(65 Ratings)
The house is very clean, well-equipped, with a great location for easy access to the beach and village. Perfect for families with ample space and amenities.
From real guest reviews summarized by AIDon't miss out! Price and availability may change
