Top 10 Vacation Rentals With Private Pool In Siesta Key, Florida - Updated 2022

Carla
Carla 
Updated

Siesta Key in west Florida is recognized as one of the best beaches in the US. And we’re not just talking about the amenities. At the Great International Sand Challenge, Siesta Key was rated as having the “world’s finest, whitest sand”, beating the Bahamas and Grand Cayman! Dazzling white and powdery fine sand, the 99 percent pure quartz sand of Siesta Key does not contain any coral or shell fragments. Affectionately known as “Sarasota’s Favorite Island,” Siesta Key is an 8-mile (12.8-kilometer) long, crescent-shaped barrier connected to the mainland by two bridges. From water-inspired attractions to boating and fishing excursions to sunbathing, there is so much to do in Siesta Key. Why not go on a well-deserved trip to Siesta Key and book a stay at a vacation rental with a pool for privacy? In this article, we have gathered our top Siesta Key vacation rentals with a private pool. Read on to learn more.

1. Stylish home with tiki hut and hot tub (from USD 3162)

This chic yet cozy canary yellow home with a fantastic backyard is like being in a resort. This rental is conveniently located on Sunset Pointe in the heart of Siesta Key Village and less than a one-minute walk from the beach. The home has five bedrooms and four bathrooms: there are three master suites on the ground floor and a fourth bedroom and loft on the second. Step out onto the patio and generous backyard with tropical landscaping. There’s more than enough comfortable seating for you and your guests. The backyard also features a private tiki hut and a heated pool and hot tub. The interiors of the house are spacious, with each bedroom inspired by Siesta Key’s beauty.

The Pool House - THE BEST BACK YARD ON SIESTA KEY. SLEEPS 16. Nearly Beachfront
Siesta Key, Florida, United States
22 reviews  Wifi Available
Entire home 7 Beds 16 Guests 5 Bedrooms 4 Bathrooms

Accommodates: 16

Top guest reviews
Amenities & Room:
the pool and backyard ambience are amazing
private pool and jacuzzi was awesome
there is tons of room and a gorgeous back yard with pool and hot tub
Cleanliness:
the home was super clean updated and had everything we needed
the decor the cleanliness the backyard the amazing service we received from dana and her team
Host:
bedrooms are very quiet and the home is quite kid friendly
Location:
the location is amazing
location is great house is beautiful
absolutely love the house and the location
house was beautiful and in a great location
property is well maintained and in as absolutely perfect location
Read more reviews

2. Luxurious hideaway with heated pool (from USD 376)

This luxurious Siesta Key plantation home features a solar power-heated and covered pool. The 2,900-square-foot (269-square-meter) vacation rental has three bedrooms and two bathrooms, perfect for a group of six. The villa is absolutely private, as it is nestled in a residential cul de sac. The pool deck is covered by a lanai, allowing you and your companions to enjoy the warm sun throughout the day. The property is surrounded by key lime, coconut, and banana trees, giving you even more quiet and seclusion. At the heart of the home is an open-plan great room with a formal dining area adorned with rustic yet vibrantly colored décor. The nearby kitchen is well-appointed with steel appliances.

Luxurious Key West plantation home SOLAR HEATED POOL FREE FIBRE WIFI, BIKES
80 reviews  Wifi Available
House 6 Guests 3 Bedrooms 2 Bathrooms

Accommodates: 6
Minimum Nights: 7
Refund Policy : 100% refund if you cancel at least 14 days before check-in.

Top guest reviews
Amenities & Room:
Everything was like clockwork and pretty much anything you need for the house
Little bit of trouble getting in on arrival
Had all the comforts of home
It was nice to be able to cook if we wanted - kitchen very well equiped and grill by the pool
Had a wonderful time Enjoyed the pool (a bit cold for my 2 year old)
Cleanliness:
Very clean and the bed was extremely comfortable
Cleanliness is a top priority for me and it was super clean
Host:
The owner is so nice and helpful
John answered all my questions quickly & kindly I totally recommend this property
Though the weather was perfect all week the pool was a bit chilly for us to swim
The host was extremely helpful prior during and after our stay Could not have asked for more Thoroughly recommend this property and can't wait to return
the owner has thought of all the little things that help make a stay comfortable and most important to me
Location:
Five nice bikes are provided Several nice restaurants in the village and if you are Gluten Free like me
Perfect place to stay A short easy bike ride to the Siesta beach and village
Charming house in great location on Siesta Key short distance from the village Beautiful home that met all our needs
It's literally 2 minutes from the Siesta Key beach by car or couple of minutes more by bicycle ( kindly provided)
The house i very well equipped and in perfect shape
Read more reviews

3. Private retreat with lagoon views (from USD 344)

Not only does this home have a private pool lanai, but it also provides picture-perfect views of Heron Lagoon. This lagoon house has two bedrooms and two bathrooms, ideal for a party of six. Situated in a large wooded estate, this vacation rental features a private dock on the scenic Heron Lagoon. The newly furnished and decorated home is perfect for swimming, fishing, and kayaking. Tucked away in this private waterfront retreat is a large screened patio just steps away from the master bedroom. The living space and master bedroom overlook the lagoon, with sweeping views of the seawater through sliding glass doors that bring in the outdoors. If you are looking for peace, tranquility, and easy access to Siesta Key, then this is your vacation rental.

Waterfront hideaway on Siesta Key in Sarasota, Florida
145 reviews  Wifi Available
House 6 Guests 2 Bedrooms 2 Bathrooms

Accommodates: 6
Minimum Nights: 3
Refund Policy : 100% refund if you cancel at least 14 days before check-in.

Top guest reviews
Amenities & Room:
view of lagoon from pool area and house is amazing
Cleanliness:
the house itself was spotless and nicely decorated
Host:
hosts were attentive and so nice
tammy was wonderfully helpful and thoughtful
Location:
this property fit the bill while being close to everything
what a beautiful gem very private and lovely place in a great quiet location
such a sweet place to spend our anniversary
it’s six h a great place we loved going bike riding every morning down siesta key
Read more reviews

4. Elegant oasis with lakefront views (from USD 405)

Perfect for up to eight guests, this villa, which is surrounded by a lake and lush tropical gardens, has three bedrooms and two baths. The vacation home sits on a quiet cul de sac bordered on two sides by Lake Nancy, a nature lover’s delight. Swim in the heated pool, sit on the lanai or terrace, or take a 15-minute walk to Siesta Key’s beaches and shops. Large glass doors lead out to the poolside and lanai overlooking the lakefront. Enjoy delicious meals with your loved ones in the formal dining area. There is plenty of attractive seating throughout this luxurious home, lending the place to quiet reading or engaging conversation. Each color-themed room is lavishly furnished and decorated.

Siesta Key Lakefront Oasis, 3 Bd Home, Heated Pool
33 reviews Superhost  Wifi Available
Entire home 5 Beds 8 Guests 3 Bedrooms 2 Bathrooms

Accommodates: 8

Top guest reviews
Amenities & Room:
it was great fun to ride bicycles to dinner shops & the beach the pool each evening was wonderful
the pool is a good size and has a cool water feature
Cleanliness:
very clean and nicely appointed
everything was extremely well thought out clean easy to use and the house was very stylish
beatifully furnished sparkly clean and in a great location
a good spring clean is in order including washing of the pillows/coverlets
Host:
owner very responsive to questions
the house location and the host were all absolutely amazing
judith is an attentive hostess and every day spent here was appreciated
Location:
safe location great beaches impeccable house excellent support from judith
the location is very nice as it is in a quiet area and walkable to town
it is a nice quiet spot yet very close to the village and beaches
this place is not just nice it's paradise
Read more reviews

5. Beach bungalow with canal views (from USD 521)

If you’re looking for a brand-new vacation rental listing, consider this one-of-a-kind beach bungalow. It is centrally located near Siesta Beach, shops, and restaurants. It also features a private heated pool and a boat dock. This cozy beach cottage has an enclosed front porch that offers views of the famous Siesta Key canal. Watch the village trolley and people pass by. The backyard, on the other hand, has dining and entertainment areas. Truly original, this seafoam and teal-toned gem is a fourth-generation home that maintains its Florida beach house charm. There are two bedrooms and one bath, as well as an outdoor shower, perfect for a group of six visitors.

One-of-a-kind*Beach, Village, Dock & Private Pool!
Siesta Key, Florida, United States
76 reviews Superhost  Wifi Available
Entire home 4 Beds 6 Guests 2 Bedrooms 1 Bathrooms

Accommodates: 6

Top guest reviews
Amenities & Room:
the pool was perfect along with along the appliance
we grilled on gas grill and had friends for dinner eating at outside table with lights at night
marko and kellie’s place is gorgeous cozy warm has everything you will need
this is our 2nd visit to rad's cozy cottage and we absolutely love staying here
the space is absolutely gorgeous and so comfortable
Cleanliness:
very clean and welcoming
great house very clean and spacious
the house was spotlessly clean very well organized and comfortable
the house itself is beautiful and extremely clean/organized
the house was super clean and decorated so nicely
Host:
the owners are attentive & kind
the hosts provided wonderful and accurate recommendations in their binder
the host was really kind always available and lovely
the hosts were very helpful and the welcome basket was a thoughtful touch
marko was an awesome host he was always available with any questions or concerns
Location:
location is perfect
the location is super convenient
great location to beach and downtown
in a perfect location walking distance to so much
amazing house in an amazing location
Read more reviews

6. Waterfront sanctuary with hot tub (from USD 386)

Located five minutes away from Siesta Beach, this waterfront property overlooks Grand Canal. Enjoy your Siesta Key sanctuary, which boasts 2,746 square feet (255 square meters) of tastefully decorated living, dining, and leisure space. Ideal for swimming, boating, or fishing, the vacation rental sleeps six guests, and it has three bedrooms and two baths. Guests are greeted by an expansive living room with a large sunroom. To the property’s right are a private heated pool and a spacious patio with plenty of sitting areas.

***Walk to Beach! 5 min-Canalfront~PrivatePOOL/HotTub
75 reviews  Wifi Available
House 6 Guests 3 Bedrooms 2 Bathrooms

Accommodates: 6
Minimum Nights: 7
Refund Policy : 100% refund if you cancel at least 60 days before check-in.

Top guest reviews
Amenities & Room:
the kitchen was well-equipped and the grill was great
ceiling fan in master bedroom did not work making it very warm to sleep
had a well stocked kitchen and nice grill which we also used
mimi will make you sign “ side “ agreements that include energy consumption and pool addendums
Cleanliness:
it should not be the renters responsibility to clean a jacuzzi
the house is spacious and very clean with lots of amenities
clean with all the amenities
Host:
mimi (owner) was friendly honest and very informative
the owner mimi gonzalez was great to deal with
mimi is a tremendous host very responsive to any needs you may have
mimi was very engaging and extremely helpful right from the time we booked and throughout our stay
Location:
perfect location and plenty to do
perfect location loved the bikes pool was amazing
the hammock was everyone's first choice the proximity to the beach restaurants and park was ideal
if there is anything you would need mimi is close enough and very responsive
thanks for providing such a nice place for us to stay while at siesta key
Read more reviews

7. Secluded beach house with hot tub (from USD 464)

Searching for a secluded beach rental with a private pool and hot tub that can also be enjoyed at night? Then look no further. This comfortable vacation home is 1.4 miles (2.25 kilometers) from the beach. Situated in a quiet residential neighborhood, Siesta Peace Retreat has two bedrooms and two bathrooms. Lounge by the pool or take a dip in the warm hot tub. Laze on a hammock in the backyard or practice yoga in the colorful relaxation zone. Enjoy your meals in the modern kitchen indoors or outdoors. Watch TV in the soothing living room or hip lanai.

Siesta Peace Retreat NOW a Private home rental
Siesta Key, Florida, United States
74 reviews  Wifi Available
Entire home 2 Beds 4 Guests 2 Bedrooms 2 Bathrooms

Accommodates: 4

Top guest reviews
Amenities & Room:
loved being indoors and we loved spending hours in the patio and pool
it’s a very nice house with lots of space nice bathrooms & soft comfortable beds
the open-air pool is a rare find and allows for good star gazing in the evenings
nicest back yard and pool i’ve ever been in
our room and bathroom was private and comfortable
Cleanliness:
the house in siesta key was not only very clean it was amazing too
it’s a nice well-furnished clean home
the place is beautifully decorated and well kept sparkling clean
overall a great stay if you don’t have high cleanliness standards
host her home is very clean the pool is amazing and her suggestion board was very thoughtful
Host:
tracy was an amazing host
the hosts are very responsive and helpful
tracy was the most accommodating and welcoming host anyone could ask for
tracy is a wonderful host full of recommendations and tips about exploring the area
what a super host she knows everything on the key
Location:
it’s location is perfect
this place is beautiful and within walking distance from town
adorable space in a great location
super helpful thoughtful and her place is in the perfect location
this place is totally a peace retreat the neighborhood is quite
Read more reviews

8. Private waterfront home with hot tub (from USD 397)

This waterfront home is private - it’s fenced in, and the lot across the overlooking canal is bare. It is a short eight-minute stroll from the beach. This summer home has a very roomy and fully equipped kitchen that’s great for entertaining. Enjoy your morning coffee in the sunroom, go kayaking in the canal, or take a dip in your own waterfall pool or spa hot tub. As darkness falls, barbecue some summer favorites by the outdoor grill or cozy up by the fire pit.

Private Home-Walk 2 Village/Beach-Heated Pool/Spa❤️
Siesta Key, Florida, United States
28 reviews Superhost  Wifi Available
Entire home 3 Beds 6 Guests 2 Bedrooms 2 Bathrooms

Accommodates: 6

Top guest reviews
Amenities & Room:
sleeping arrangements were very comfortable
randy and halie provide all the amenities to make your stay comfortable and relaxing
we also enjoyed the beautiful pool and hot tub
Cleanliness:
this home was very clean and exactly what we expected
the home was very clean and quiet
super clean stylish decor great location beds were very comfortable and the spa was great
the place was everything we had wanted: clean convenient to everything thoughtful touches bright and spacious
nice clean home in a great location
Host:
randy the host was excellent communicating with us
randy was a great host
host was very helpful and responsive to any/all questions
owner very responsive and nice
the hosts were so great to work with and crazy fast at responding
Location:
great property location was perfect: walk to village; walk to beach
amazing location everything was great
a beautiful house in a great location
its got a fantastic location relative to the village and it's a short walk to the beach
the location is perfect in the siesta key village with everything you need right at your fingertips
Read more reviews

9. Charming getaway with heated waterfall pool (from USD 750)

Experience designer beach living at this gorgeous cottage featuring a heated saltwater waterfall pool. Perfect for a group of seven, this 1,800-square-foot (167-square-meter) home has three bedrooms and three bathrooms. Sea Palm Cottage, as the vacation rental property is called, was recently remodeled so that guests feel like they are in an island paradise. Everything, including the beach, retail outlets, and dining spots, is conveniently located from this charming getaway. Take a dip in the private tropical pool. Lounge in the living area that is brightly decorated with the hues of the ocean. Enjoy breakfast by the kitchen, have a hearty lunch in the outdoor kitchen, or savor dinner in the more formal dining space.

CLEANED to new standards: 4bedroom/3bath HOUSE ACROSS FROM BEACH/Private Pool
Sarasota , FL, US
cottage 7 Guests 3 Bedrooms 3 Bathrooms

10. Charming home with backyard pool (from USD 240)

Looking for a smaller vacation rental that is big on modern amenities and conveniences? This 1940s home, located not far from Siesta Beach, was recently upgraded to include a private pool and barbecue grill. The pristine white summer cottage has 1,000 square feet (93 square meters) of cozy living space. Great for a group of five, the home has two bedrooms and one bath. The quaint but up-to-date kitchen also has a bar with views of the pool outside.

Siesta Beach Vacation Rental
Siesta Key, FL, US
House 5 Guests 2 Bedrooms 1 Bathroom
Top guest reviews
Amenities & Room:
just as advertised nice patio pool
the pool was the perfect touch for us
it's only a block from the beach we also loved the pool it was perfect
Cleanliness:
this property was very clean and well maintained
the house was comfortable and clean and we would stay again in a heartbeat
the house had everything we needed and was very clean
cottage and pool were very clean and owner was very friendly and easy to work with
very clean great location and excellent amenities
Host:
the owner was so sweet
the owners were very welcoming and responded very quickly
gary and his mom janice were very responsive nice and house was as explained
the pool was nice to have and gary was very helpful one day after it had rained
Location:
great location loved the pool
the house had everything great location
great place a few minutes walk from the public beach
this property is awesome close to the beach and village the house was so nice and clean
the location of this cottage is wonderful if you want to be across the street from the beach
Read more reviews

A must-visit island paradise

Siesta Key is a must-visit island paradise. You can plan your trip around this destination without getting bored. Aside from spending the day on the gulf waters or relaxing in your vacation rental, ride the free trolley that goes around the island. Explore Siesta Key’s shores, whether it’s at Siesta Beach, Crescent Beach, or Turtle Beach. Shop at the farmers market, play a round of golf, watch an evening performance, check out the shops, try out the restaurants, and more.

Disclosure: Trip101 selects the listings in our articles independently. Some of the listings in this article contain affiliate links.

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Carla is a freelance travel writer who enjoys planning itineraries, visiting art museums, and reading ebooks. Before jumping into freelancing at the height of the COVID-19 pandemic, she was a...Read more

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