Siesta Key Vacation Rentals with Private Pool

(61 rentals)
booking message booking message

3 BR | 2 BA | Sleeps 6 | Quick View

1

Distance to beach: 20 yards to Crescent Beach, Siesta Key

$440

avg/night

View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pool
  • Private pool

About this property

Unit 608 is a large 3 bedroom, 2 bath high-rise unit in Horizons West, Siesta Key, Florida. The unit has recently undergone a complete makeover by a Chicago designer. The interior was fully demolished and rebuilt. No detail or expense was spared in completing the perfect beach condo: large panoramic ocean ...

View all property information

Property Type

Siesta Key Condo

"Stunning Condo"

My family stayed in this stunning condo and absolutely loved it. Beautiful views, fabulous modern furniture, high tech TVs and sound system, awesome high end kitchen and baths.

See all reviews

Show less

2 BR | 1.5 BA | Sleeps 4 | Quick View

28
owner special
Owner special: December dates available! Enjoy all the Christmas decorations on our beautiful island!

Distance to beach: 200 yards to Crescent Siesta Key Beach

$266

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pool
  • Private pool
  • Rentals by owner

About this property

Located in beautiful Siesta Key, Fl (consistently ranked #1 beach in the US!!) in Midnight Cove 1, this bayside condo spoils its occupant with all the amenities and luxuries needed for a relaxing, tropical vacation. Nestled amid lush landscaping in this gated community, our unit is newly remodeled and ...

View all property information

Property Type

Siesta Key Condo

"Great location, clean property"

My husband and I stayed here with our two toddlers and a baby. This was the perfect location. We were able to walk to the beach and the pools with ease. The condo had everything you possibly needed. We ...

See all reviews

Show less

2 BR | 2 BA | Sleeps 6 | Quick View

1

$394

avg/night

View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Private pool
  • Rentals by owner

About this property

RENOVATED 2020!!! From the lanai and your private patio, you are directly on the beach where it is easy to keep an eye on the children playing, or walk down to the Gulf of Mexico for a swim. Located on Turtle Beach, Siesta Key's quiet south end - this lovely Gulf front first floor unit with large ...

View all property information

Property Type

Siesta Key Condo

"Beautiful Condo!"

This Condo is well appointed and is in the perfect spot right on the beach of the Gulf! We we're ableto walk out to the beach from our back door and see the canal out the front. We cooked in the kitchen ...

See all reviews

Show less

Key Amenities

  • Air conditioning
  • Beachfront
  • Kitchen
  • Oceanfront
  • Pool
  • Private pool

About this property

There is no way you can get closer to the water than this! Sitting outside and having your morning coffee listening to the waves is so relaxing. Having a glass of wine and watching the sun set is the perfect way to end the day. This amazing unit has it all! The Primary bedroom has a king bed and its ...

View all property information

Property Type

Siesta Key Condo

"Life on the Beach"

The location was what I wanted which was to be near the gulf so I could easily swim and enjoy the serenity of the gulf at my fingertips. The accommodations met my needs with plenty of kitchen supplies ...

See all reviews

Show less

Key Amenities

  • Air conditioning
  • Beachfront
  • Kitchen
  • Oceanfront
  • Private pool
  • Rentals by owner

About this property

THE BEACH IS CALLING AND I MUST GO!! *We invite you to come stay with us in the Crescent Arms South Tower--Condo 601S--directly on the #1 famous Crescent Beach with a FULL view of the Gulf on a private 32 foot lanai.*Decorated in a "beachy motif" with granite counter tips in the kitchen ...

View all property information

Property Type

Siesta Key Condo

"Beauty at the Beach"

I highly recommend condo 601 South/ Beauty at the Beach! Elaine was very accommodating and her condo was the most coziest, beautiful, and relaxing place that I have stayed in a very long time. It had everything ...

See all reviews

Show less

1 BR | 1 BA | Sleeps 4 | Quick View

6

Distance to beach: 100 yards to Crescent Beach

$280

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Private pool
  • Rentals by owner

About this property

Simply relaxing one bedroom condo with a king bed facing the pool area and just a few steps to the private entrance to" Siesta Key #1 beach" white quartz sand beach . Additionally a Lazyboy queen memory foam sofa sleeper for separate sleeping area if needed Unit includes a full kitchen for ...

View all property information

Property Type

Siesta Key Condo

"Sea Crest #26"

Great people. Great weather. Great beach access, loved the sunsets. TV had no directions on how to navigate. Loved being close to Captain Curt’s restaurant. Loved the Old Florida charm.

See all reviews

Show less

2 BR | 2 BA | Sleeps 5 | Quick View

5

Distance to beach: 100 feet to Crescent Beach

$400

avg/night

View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Kitchen
  • Oceanfront
  • Pool
  • Private pool

About this property

Relax and listen to the waves while sitting on your private lani. You're on the top floor (6th) of the Siesta Breakers Condominium, a private, gated facility with direct access to Crescent Beach, the #1 Top Rated beach in the USA.This luxury 2 bedroom 2 bath apartment, has been kept up to date ...

View all property information

Property Type

Siesta Key Condo

"Perfect"

Siesta Breakers is the perfect place to get away. This condo was wonderful and had everything we needed! You couldn’t ask for more beauty, comfort, and relaxation! This is the perfect place.

See all reviews

Show less

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Private pool

About this property

Welcome to Bay Isle Bliss, a luxurious 3 bedroom, 2 bathroom vacation home that offers a serene retreat from the hustle and bustle of everyday life. Located just 0.3 miles from Shell Beach and 1.7 miles from Siesta Key Village, this exquisite property provides the perfect vacation getaway for families, ...

View all property information

Property Type

Siesta Key House

"Perfect pet-friendly property"

Great location close to the beach and Sarasota downtown. The property is completely fenced, and located in a very quiet neighborhood. My kids enjoyed the pool and the hot tub...We will visit again.

See all reviews

Show less

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Private pool

About this property

Welcome to Floritas Key, a vibrant yet coastal bungalow located on the northern end of Siesta Key. This delightful retreat offers an unforgettable experience, with its stunning private heated pool and prime location that puts you just moments away from the best attractions and natural beauty this area ...

View all property information

Property Type

Siesta Key House

"Fabulous Place"

Excellent Location close to the Crescent Beach and Restaurants. I would stay there again the next time I visit Siesta Key.

See all reviews

Show less

3 BR | 2 BA | Sleeps 8 | Quick View

4.8 rating on other travel sites

$606

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Private pool

About this property

Escape to Baydream Bungalow, a charming 3 bedroom villa nestled on the northern end of Siesta Key. This quaint home offers a peaceful island retreat, ensuring a memorable stay for you and your loved ones.Situated a short distance of only 0.6 miles, Shell Beach welcomes you to indulge in the serenity ...

View all property information

Property Type

Siesta Key House

Show less

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Private pool

About this property

Welcome to Casa Leone, a luxurious home nestled on the northern end of Siesta Key. This exquisite property offers an array of amenities and comforts to ensure a memorable and relaxing stay.As you ascend up the stairs to the main level of the home, you will be greeted by a spacious and elegantly decorated ...

View all property information

Property Type

Siesta Key House

"Casa Tegula Review..."

We LOVED Casa Tegula!!! The house was very clean and stocked with everything we needed. Location was wonderful, only a short walk to the ocean and shops. Sara at The Cottages on the Key was AMAZING and ...

See all reviews

Show less

1 BR | 1 BA | Sleeps 3 | Quick View

Distance to beach: 20 yards to Crescent Beach, Siesta Key

$319

avg/night

View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pool
  • Private pool

About this property

Unit 113 is one of the largest, 1 bedroom hi-rise units in Horizons West, Siesta Key, Florida and has recently undergone a full renovation by a Chicago designer. The interior was fully demolished and rebuilt. No detail or expense was spared in completing the perfect beach condo: large panoramic ocean ...

View all property information

Property Type

Siesta Key Condo

Show less

Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pool
  • Private pool
  • Rentals by owner

About this property

If you are looking for a terrific vacation spot tastefully decorated, clean, and comfortable, you just found it. You can be as lazy as the sun and free as the Gulf breeze. We are not underselling ourselves when we say we have the 'Best Location' on 'Crescent Beach.' Experience the ...

View all property information

Property Type

Siesta Key Condo

"Owner"

This condo Crescent Arms 501 North is a Direct Front 180 Degree View of the Beach & Gulf of Mexico Some of the Reviews are not our Condo Joan

See all reviews

Show less

3 BR | 2 BA | Sleeps 10 | Quick View

Distance to beach: 0.7 miles to Siesta Key Beach

$450

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool
  • Rentals by owner

About this property

Hard to find home near #1 Siesta Key Beach and Village with all the amenities. The space Welcome to island life!Luxurious 3 bed/2 bath with spectacular water view and walking distance to the village restaurants, shopping, and #1 beach in America!Enjoy your heated pool, hot tub, fire pit, and ...

View all property information

Property Type

Siesta Key House

Show less

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Private pool

About this property

Welcome to Crescent Cottage, a charming villa nestled on the southern end of Siesta Key. With its luxurious backyard oasis and perfect location, this delightful retreat is the perfect accommodation for your next island getaway.As you step inside Crescent Cottage, you will find 4 bedrooms and 3 full ...

View all property information

Property Type

Siesta Key House

"Vacation 2020"

I visited siesta key and loved my stay. Stayed in the village Evey thing was In walking distance.beach was walking distance

See all reviews

Show less

3 BR | 3 BA | Sleeps 10 | Quick View

4.7 rating on other travel sites

$231

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Private pool

About this property

Escape to Casita Morning Star, a magnificent retreat that offers nothing but luxury and relaxation. This coastal villa can be rented separately or as a whole as The Solaster, providing you with the flexibility to choose the perfect accommodation for your vacation. With its prime location just a short ...

View all property information

Property Type

Siesta Key House

Show less

4 BR | 3 BA | Sleeps 12 | Quick View

2

Distance to beach: 1 miles to Siesta Key Beach

$348

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Private pool

About this property

Welcome to Casa Stolida, your luxurious tropical oasis on the Southern end of Siesta Key. This stunning beach house offers an unparalleled experience for large groups seeking both privacy and space. With 4 bedrooms and 3 full baths, it is the perfect choice for family reunions, group getaways, or special ...

View all property information

Property Type

Siesta Key House

"Bliss"

Home was fantastic! Maintenance was speedy on my TV problem and fixed it while I was out at the beach. I stayed with three couples. Beds were comfortable for all. Unit had everything we needed. Steps from ...

See all reviews

Show less

4 BR | 3 BA | Sleeps 12 | Quick View

2

Distance to beach: 5 miles to Siesta Key Beach

$503

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Private pool

About this property

Welcome to Casa Mahalo, a stunning vacation home that promises to exceed all your expectations. Nestled in the heart of Siesta Key Village, this extraordinary retreat offers an abundance of luxurious amenities and unparalleled convenience for an unforgettable getaway.Located just a two-minute walk ...

View all property information

Property Type

Siesta Key House

"Very comfortable and Clean"

Lily Casita is truly a Cozy Sarasota Home . We were greeted to the home with lights on and music playing the home was very clean and equipped with anything you may need. This was our first time in the ...

See all reviews

Show less

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Private pool

About this property

Welcome to Island Escape, a breathtaking haven located within the heart of Siesta Key! This gorgeous 4-bedroom, 2.5-bathroom home has just undergone a stunning renovation, ensuring that every moment of your stay is filled with comfort and luxury.Step inside and be greeted by a beautifully designed ...

View all property information

Property Type

Siesta Key House

"Great Vacation Home"

Very nice house with many amenities. Short walk to the beach. Great place for a family vacation!Carla

See all reviews

Show less

4 BR | 3 BA | Sleeps 8 | Quick View

5.0 rating on other travel sites

$357

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

Welcome to Siesta Soul, a captivating retreat located just steps from the vibrant Siesta Key Village. This enchanting vacation home offers an ideal location and a backyard oasis, providing the perfect blend of convenience and relaxation for your Siesta Key getaway.Siesta Soul features four bedrooms ...

View all property information

Property Type

Siesta Key House

Show less

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Private pool

About this property

Welcome to Villa Castile, a luxurious retreat located just outside the vibrant Siesta Key Village. This stunning vacation home offers the perfect blend of sophistication and comfort, providing an unforgettable experience for your stay. Whether you're seeking relaxation by the private heated pool, ...

View all property information

Property Type

Siesta Key House

"Excellent Property"

Super close to Siesta Village’s shops and restaurants, plus an easy walk to the beach. Very comfortable home, well equipped with everything you need for a great stay.

See all reviews

Show less

4 BR | 3 BA | Sleeps 12 | Quick View

4.9 rating on other travel sites

$348

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Private pool

About this property

Welcome to Casa Tegula, your luxurious tropical oasis on the Southern end of Siesta Key. This stunning beach house offers an unparalleled experience for large groups seeking both privacy and space. With 4 bedrooms and 3 full baths, it is the perfect choice for family reunions, group getaways, or special ...

View all property information

Property Type

Siesta Key House

Show less

3 BR | 3.5 BA | Sleeps 8 | Quick View

5.0 rating on other travel sites

$238

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

Welcome to Serenity Cottage, a tranquil cottage located on the southern end of Siesta Key. This remarkable vacation home offers a serene escape where you can unwind, relax, and create cherished memories in a beautiful coastal setting.Step inside and discover a recently renovated kitchen that will ...

View all property information

Property Type

Siesta Key House

Show less

3 BR | 3 BA | Sleeps 10 | Quick View

5.0 rating on other travel sites

$346

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

Welcome to Latitude Adjustment, your ultimate waterfront retreat on the beautiful island of Siesta Key! Prepare to be enchanted by the beauty of this captivating home, combining stunning canal and an unbeatable location, ensuring an unforgettable stay for every guest.Upon arrival, you'll be greeted ...

View all property information

Property Type

Siesta Key House

Show less

3 BR | 2 BA | Sleeps 8 | Quick View

5.0 rating on other travel sites

$1208

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

Escape to Bali Hai House, a stunning waterfront home located on the tropical island of Siesta Key. This exceptional property offers a truly blissful retreat with an array of exciting amenities and convenient proximity to Siesta Key Village and Siesta Key Public Beach Access.Situated less than 1 mile ...

View all property information

Property Type

Siesta Key House

Show less

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Private pool

About this property

Welcome to Casa Ohana, a stunning vacation home that promises to exceed all your expectations. Nestled in the heart of Siesta Key Village, this extraordinary retreat offers an abundance of luxurious amenities and unparalleled convenience for an unforgettable getaway.Located just a two-minute walk ...

View all property information

Property Type

Siesta Key House

"Great place!"

Nice pool! Beautiful area and nice area. We will Be visiting soon and bringing the family. Smooth time.

See all reviews

Show less

Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pool
  • Private pool
  • Rentals by owner

About this property

This 5th floor two bedroom, two bath condo is totally and completely renovated. Be one of the first guests to stay in this beautifully renovated condo. New tile throughout. There are two bedroom suites with private baths. Each bedroom has new slider doors that open to screened in lanai with beautiful ...

View all property information

Property Type

Siesta Key Condo

"Relaxing getaway"

We had a really nice week in this condo just steps to the beach. The powdery white sand never gets hot.The condo has all of the essentials and more. Very comfortable. And there’s a nice pool if want to ...

See all reviews

Show less

3 BR | 3 BA | Sleeps 6 | Quick View

3

$314

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Private pool
  • Rentals by owner

About this property

Great house on Siesta key with pool and kanal. You can do fishing on the backside or have a jetski, boat there. Sometime you can see seacows on the kanal. 3 bedroom with 3 bath and a nice heated pool tp play in. Nice and quiet place it is, and so close to the Village and beach. Enjoy the place.

View all property information

Property Type

Siesta Key House

"Perfect Location"

Located close to the village and within walking distance of the beach. Plenty of room for families and amenities which included bikes for all ages. The pool is heated and such a great perk!

See all reviews

Show less

2 BR | 2 BA | Sleeps 6 | Quick View

10
owner special
Owner special: Due to a cancellation, our 2 BR condo in Siesta Key is available March 2 - 16th; min 2 wks rental.

Distance to beach: 0.3 miles to Crescent Beach on Siesta Key

$194

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

Siesta Key Condo - Siesta Key ParadiseLooking for a vacation rental in Siesta Key? Look no further... we have a two bedroom first floor condo located on the spacious, gorgeous landscaped grounds of Midnight Cove ii.Enjoy great views from our lanai watching boats, yachts, and wildlife on the Intracoastal ...

View all property information

Property Type

Siesta Key Condo

"Siesta key condo"

Absolutely loved our stay at Siesta Key. The condo is clean, well equipped with everything you need, easy access to food and the beach. Would definitely stay here again

See all reviews

Show less

2 BR | 2 BA | Sleeps 6 | Quick View

3

Distance to beach: 0.4 miles to Siesta Key Beach

$505

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool
  • Rentals by owner

About this property

Location, location, location!! New pool and spa just completed! Waterfall edge from spa to pool and deck jets. New landscaping with additional seating areas near pool and canal. Also, lots of green space to enjoy too!Canal home in heart of the Siesta Key Village, no need for a car! Steps away ...

View all property information

Property Type

Siesta Key House

"Excellent"

The house was extremely clean and nothing was missing. Loved my stay from beginning to end. Melissa checked in a few times to make sure I was happy. I would stay at this home again. It has raised my bar ...

See all reviews

Show less

3 BR | 2 BA | Sleeps 6 | Quick View

Distance to beach: 400 feet to Siesta Beach

$779

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Pet friendly
  • Private pool

About this property

Prime location being only two minutes walk to Siesta Beach entrance from this attractive three bedroom, two bath florida ranch! You live around the ground level pool with ;arge patio doors from the two living areas and kitchen. The home has been freshened with a very nice decor and new furnishing. The ...

View all property information

Property Type

Siesta Key House

Show less

5 BR | 4 BA | Sleeps 13 | Quick View

11

Distance to beach: 400 feet to Siesta Beach

$901

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Private pool

About this property

Excellent location at only 120 Yards To The Cool White Quartz Sand Of Siesta Beach! ?This Home Has Water Frontage on a Navigable Canal to the Bay And Then The Gulf of Mexico , Pool, Hot Tub And BBQ Area Within A Screen Enclosure. There Is A Nice Sized Sunning Patio As Well With Views Down The Waterway. ...

View all property information

Property Type

Siesta Key House

"Wonderful home and stay on Siesta Key"

The home was perfect, even nicer than the pictures made it look. Very clean, great layout and integration of the home into the outside pool area. Bathrooms seem recently remodeled and are very clean and ...

See all reviews

Show less

1 BR | 1 BA | Sleeps 2 | Quick View

1

Distance to beach: 0.0 miles to Siesta Key Main Beach

$199

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Private pool
  • Rentals by owner

About this property

PENTHOUSE WATER VIEWS! Sweet Penthouse Condo on Siesta Key with Spectacular Water Views everywhere. Truly, my photos do not do these views justice....This is resort living on beautiful Siesta Key! Located in a resort setting at Harbor Towers Yacht & Racquet Club, there are 2 heated pools, 3 lighted ...

View all property information

Property Type

Siesta Key Condo

"Great Visit! We will be back!"

Everything thing about this experience was great. Location, apartment, pool, walk to beach and the host’s responsiveness was exactly what we needed. Will definitely book with Sue again.

See all reviews

Show less

3 BR | 3 BA | Sleeps 6 | Quick View

6

Distance to beach: 200 feet to Siesta Key Public Beach

$338

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool
  • Rentals by owner

About this property

Single family home with private heated caged pool. Large open floor plan in living area to kitchen and enclosed pool and deck. 3 bedrooms, 2 of which are master suites with ensuite full baths, flat screen TV's, king beds, and sliding glass doors to either caged pool deck or open air sundeck. 3rd ...

View all property information

Property Type

Siesta Key House

"UNBELIEVABLE"

This house was beyond expectation! The outdoor living area/kitchen was like nothing we have ever rented. The pool was absolutely perfect. The interior of the home was wonderful! The only negative things ...

See all reviews

Show less

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Private pool
  • Rentals by owner

About this property

The lifestyleLive the Siesta Key lifestyle: • Short walk to the beautiful white sand beaches • Linger in the vibrant cafes and shops of The Village • Kayak along the key’s Grand Canal • Spend afternoons relaxing in the pool • Enjoy Siesta’s famous sunsets ...

View all property information

Property Type

Siesta Key Cottage

Show less

1 BR | 1 BA | Sleeps 3 | Quick View

10

Distance to beach: 0.5 miles to Siesta Key Main Beach

$181

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Pool
  • Private pool
  • Rentals by owner

About this property

Sweet Siesta Key Condo, Spacious and Quiet One Bedroom (with 2 Queen beds in bedroom), walking distance to Siesta Key Main Beach, and a nice 0.9 mile sidewalk walk, or bike or free trolley, to Siesta Key Village. You really don't even need a car on this vacation. There is a free Siesta Key Trolley ...

View all property information

Property Type

Siesta Key Condo

"Great place to stay"

Perfect location, situated right in the middle of the village and the south bridge. Restaurants and entertainment either way. It's a 2 min walk to the beach. The condo had everything I needed to make my ...

See all reviews

Show less

3 BR | 2 BA | Sleeps 8 | Quick View

$434

avg/night

View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool

About this property

CHARMING 3 BEDROOM PRIVATE HOME LOCATED IN THE QUIET SUB-DIVISION OF SIESTA ISLES. RELAX ON VACATION WITH ALL THE AMENITIES OF HOME. PRIVATE POOL, 2 CAR GARAGE, WASHER / DRYER, CHARCOAL GRILL, AND MUCH MORE. HOME OFFERS 2 LIVING ROOMS, ( ONE WITH LEATHER FURNITURE AND 53" T.V.), 6 T.V.'S, 2 ...

View all property information

Property Type

Siesta Key House

Show less

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

Beautiful house on Siesta Key with private pool and generous space. 15 min walk to the beach! This charming 3-bedroom, 2-bathroom private home is located in discreet residential neighborhood, on the beautiful Siesta Key island. It offers a large fenced outdoor area, with a private pool, plenty of parking ...

View all property information

Property Type

Siesta Key House

Show less

3 BR | 2 BA | Sleeps 7 | Quick View

$543

avg/night

View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool

About this property

ENJOY THIS 3 BEDROOM, 2 BATH PRIVATE HOME LOCATED ON A CANAL IN BEAUTIFUL SIESTA KEY VILLAGE. OPEN FLOOR PLAN WITH LOTS OF SPACE, TILE FLOORS, A PRIVATE POOL ON A CANAL. DESIGNER KITCHEN WITH SOLID WOOD CABINETS, GRANITE COUNTERTOPS AND VIKING APPLIANCES. LAUNDRY ROOM WITH FULL SIZE WASHER / DRYER AND ...

View all property information

Property Type

Siesta Key House

Show less

3 BR | 2 BA | Sleeps 8 | Quick View

1

$430

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Private pool
  • Rentals by owner

About this property

Comfortable private home with salt water heated pool. Bike ride or walk to the beach and to the village shops restaurants and bars.

View all property information

Property Type

Siesta Key House

"Definitely more than 5 stars for this property"

I’ve rented several Siesta Key properties, but this is definitely my favorite. The home is located very close to the public beach down a quiet cul de sac. The neighbors were all friendly and the area ...

See all reviews

Show less

4 BR | 3 BA | Sleeps 8 | Quick View

$583

avg/night

View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool

About this property

ENJOY THIS 4 BEDROOM, 3 BATH PRIVATE HOME LOCATED ON A CANAL IN BEAUTIFUL SIESTA ISLES. OPEN FLOOR PLAN WITH LOTS OF SPACE, HARD WOOD FLOORS, A CAGED PRIVATE POOL WITH STUNNING VIEWS FROM EVERY ANGLE. LAUNDRY ROOM WITH FULL SIZE WASHER / DRYER AND WIRELESS INTERNET ACCESS, (SIESTA 4 RENT IS NOT RESPONSIBLE ...

View all property information

Property Type

Siesta Key House

Show less

3 BR | 2 BA | Sleeps 8 | Quick View

$554

avg/night

View Details

Key Amenities

  • Air conditioning
  • Private pool

About this property

TRULY THE BEST OF BOTH WORLDS- BEAUTIFUL CANAL HOME JUST TWO BLOCKS TO WORLD-FAMOUS SIESTA KEY BEACH. COME RELAX IN THIS BEAUTIFUL 3 BEDROOM / 2 BATH HOME LOCATED IN THE QUIET NEIGHBORHOOD OF SIESTA ISLES WITH A GORGEOUS POOL. (NOTE POOL CAGE SHOWN IN SOME PHOTOS IS NO LONGER THERE.) THIS FABULOUS REMODELED ...

View all property information

Property Type

Siesta Key House

Show less

3 BR | 2.5 BA | Sleeps 8 | Quick View

$604

avg/night

View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool

About this property

WATCH PARROTS FLY OVERHEAD FROM THIS 3 BEDROOM , 2 .5 BATH, HOME WITH POOL, FANTASTIC UNIQUE LOCATION NESTLED JUST A SHORT DISTANCE TO BOTH SIESTA KEY’S ‘VILLAGE’ AND TO THE BEACH! QUIET NEIGHBORHOOD. LARGE DECK SURROUNDS ALMOST ½ OF THE HOUSE: PARKING FOR 2 CARS IN DRIVEWAY. ...

View all property information

Property Type

Siesta Key Condo

Show less

$826

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Private pool
  • Rentals by owner

About this property

Create memories with friends and family at this unique, and spacious property only 10 minutes from Siesta Key Beach.. It is perfect for large groups or reunions as this house includes 3 separate living spaces and has a total of 13 beds. Right behind the main house, not only will you find a fun area to ...

View all property information

Property Type

Siesta Key Estate

Show less

4 BR | 2.5 BA | Sleeps 10 | Quick View

$623

avg/night

View Details

Key Amenities

  • Air conditioning
  • Private pool

About this property

Welcome to paradise! Your oasis awaits you. 4 bedrooms, 2.5 bath luxury townhome with a private pool is just 1 block from Siesta Village and only 2 blocks from the beach! Five star amenities include; Fully stocked gourmet kitchen with granite counter tops, top of the line stainless steel appliances, laundry ...

View all property information

Property Type

Siesta Key Condo

Show less

3 BR | 3 BA | Sleeps 6 | Quick View

$565

avg/night

View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool

About this property

BEAUTIFUL, PRIVATE 3 BEDROOM / 3 BATH HOME LOCATED IN THE QUIET RESIDENTIAL NEIGHBORHOOD OF SIESTA ISLES. JUST 5 BLOCKS FROM THE WORLD FAMOUS SIESTA KEY BEACH WITH EASY ACCESS. HOME IS FULLY RENOVATED AND NEWLY FURNISHED FOR YOUR ENJOYMENT WITH AN OPEN FLOOR PLAN WITH LOTS TO OFFER. FULLY EQUIPPED KITCHEN ...

View all property information

Property Type

Siesta Key House

Show less

3 BR | 3 BA | Sleeps 10 | Quick View

$503

avg/night

View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool

About this property

COME RELAX IN THIS BEAUTIFUL 3 BEDROOM / 3 BATH UPDATED POOL HOME LOCATED IN A BEAUTIFUL SIESTA KEY NEIGHBORHOOD. HOME OFFERS NEW FURNISHINGS, GRANITE COUNTERTOPS, STAINLESS STEEL APPLIANCES, HIGH-SPEED INTERNET WITH BOOSTER, (SIESTA 4 RENT IS NOT RESPONSIBLE FOR TECH SUPPORT). ENJOY THE LARGE PRIVATE ...

View all property information

Property Type

Siesta Key House

Show less

3 BR | 3.5 BA | Sleeps 8 | Quick View

$503

avg/night

View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool

About this property

ENJOY THIS 3 BEDROOM, 3 1/2 BATH UNIQUE PRIVATE HOME LOCATED ON TWO CANALS JUST EAST OF SIESTA VILLAGE. THE HOME WAS BUILT IN THE TRUE SARASOTA SCHOOL OF ARCHITECTURE DESIGN TO TAKE ADVANTAGE OF AIR FLOW AND LIGHT BUT ORIENTED SO THAT YOU NEVER HAVE DIRECT SUNLIGHT AT ANY TIME OF THE DAY. OPEN FLOOR PLAN ...

View all property information

Property Type

Siesta Key House

Show less

3 BR | 2 BA | Sleeps 6 | Quick View

Distance to beach: 1 miles to Turtle Beach

$385

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Pet friendly
  • Private pool
  • Rentals by owner

About this property

New Listing Siesta Key, Florida !!100% 5 Star reviews on AirBnB and VRBO, save fees by booking direct here 14-30 day minimum. Discounts for multiple monthly stays.Hibiscus Hideaway A Private Tropical Retreat located in one of the nicest neighborhoods on Siesta Key.Enjoy peacefulness ...

View all property information

Property Type

Siesta Key House

Show less

2 BR | 2 BA | Sleeps 6 | Quick View

$488

avg/night

View Details

Key Amenities

  • Air conditioning
  • Oceanfront
  • Private pool

About this property

BREATHTAKING GULF FRONT, 2 BEDROOM / 2 BATH UNIT IN THE BEAUTFUL CRYSTAL SANDS COMPLEX. GRANITE COUTERTOPS, TILE FLOORS IN KITCHEN, BATHS and LIVING ROOM, AND WOOD FLOORING IN BEDROOMS. LEATHER FURNITURE, 3 FLAT SCREEN T.V.'S, WASHER / DRYER AND SCREENED LANAI OFF ALL ROOMS WITH DIRECT ACCESS. HIGH ...

View all property information

Property Type

Siesta Key Condo

Show less

Map
Expand map Close map
Siesta Key Vacation Rentals