Siesta Key Vacation Rentals with Private Pool

(59 rentals)
booking message booking message
Siesta Key Apartment | On the beach
9 BR | 9 BA | Sleeps 25 | Quick View
Sleeps 25, 9 Bedrooms, 9 Bathrooms
3 reviews

$315

avg/night

$315
avg per night
View Details

Key Amenities

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

About this property

Our seven apartment beach house is located 100 yards from the beach at Access #7 and one-block from the tropical Village of Siesta Key. Heated pool and spa along with our poolside surfboard bar and barbecue give our guests many choices to very their daily routine. Our 1st and 2nd floor above ground level ...

View all property information

Property Type

Siesta Key Apartment

Featured review

"Best place in the keys"

This place is one of a kind. It has everything you need. Our family rents out the entire place every couple years. The location is amazing...right by the village and beach. The rooms are clean and bug free!!! ...

See all reviews

Show less

Siesta Key Condo
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 Bedrooms, 2 Bathrooms
13 reviews

Distance to beach: 0.0 miles to Siesta Key Public Beach

$362

avg/night

$362
avg per night
View Details

Key Amenities

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

About this property

This 2-bedroom, 2 bath Siesta Key condo can sleep 6 comfortably with a pull-out queen sofa bed and total square feet of 1,773! The beautifully decorated updated condo, with newly tiled bathrooms offers a comfortable, home-away-from-home feel. Sit on your private 20 ft deck and enjoy the view of a lake ...

View all property information

Property Type

Siesta Key Condo

Featured review

"Siesta Key get away"

We loved the beautiful condo. It was our first trip to Siesta Key and we enjoyed it thoroughly. The condo was well kept, fully furnished for the most part and the Mgmt team was there to help us when we ...

See all reviews

Show less

Siesta Key Condo | On the beach
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 Bedrooms, 2 Bathrooms
9 reviews

$307

avg/night

$307
avg per night
View Details

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

Featured review

"Beware of Horrible Communication"

My husband and I intended to stay here in early February. On several occasions we reached out to customer service regarding damage from the hurricane. A letter was sent that only said “some amenities ...

See all reviews

Show less

Siesta Key Condo | On the beach
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 Bedrooms, 2 Bathrooms
1 review

$374

avg/night

$374
avg per 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

Featured review

"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

Siesta Key Condo
2 BR | 1.5 BA | Sleeps 4 | Quick View
Sleeps 4, 2 Bedrooms, 1.5 Bathrooms
31 reviews
owner special
Owner special: February dates available, we had no damage from the hurricane!

Distance to beach: 200 yards to Crescent Siesta Key Beach

$242

avg/night

$242
avg per night
Owner special:
February dates available, we had no damage from the hurricane!

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

Featured review

"Great place!"

Great place to stay! Has everything you need for a great beach stay. The condo was clean, decorated nicely, and offered beach supplies. It was only a short walk to the beach as well. The host was great ...

See all reviews

Show less

Siesta Key Condo | On the beach
1 BR | 1 BA | Sleeps 3 | Quick View
Sleeps 3, 1 Bedroom, 1 Bathroom

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

$292

avg/night

$292
avg per 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

Siesta Key Apartment
3 BR | 2.5 BA | Sleeps 7 | Quick View
Sleeps 7, 3 Bedrooms, 2.5 Bathrooms

$387

avg/night

$387
avg per night
View Details

Key Amenities

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

About this property

This charming Siesta Key vacation rental home offers a beautiful kitchen, dining area, living room, and outdoor patio. The property includes access to a heated pool shared between the two units in the house. Located in the heart of Siesta Key Village, it's just a 3-minute walk to the #1 beach in ...

View all property information

Property Type

Siesta Key Apartment

Show less

Siesta Key House
Studio | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 0 Bedrooms, 2 Bathrooms

$500

avg/night

$500
avg per night
View Details

Key Amenities

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

About this property

Comfortable and peaceful home with private saltwater pool and hot tub, 1.4 miles from the beach; 1 mile to the village. I have beach gear. Plenty of chairs, an umbrella, towels and coolers. Beautiful private back yard with grill and smoker in quiet neighborhood. Very comfortable and peaceful retreat. ...

View all property information

Property Type

Siesta Key House

Show less

Siesta Key Condo | On the beach
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 Bedrooms, 2 Bathrooms
13 reviews

$351

avg/night

$351
avg per night
View Details

Key Amenities

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

About this property

This outstanding condo, A203, is on the second floor, accessible using the elevator or outside stairwell and is completely renovated with modern tile flooring throughout, updated kitchen and baths, and new furniture! The kitchen has granite counter tops with tiled back splash, and modern appliances including ...

View all property information

Property Type

Siesta Key Condo

Featured review

"Wish we could have stayed longer!"

We stayed on Turtle Bay and had a wonderful view of the Gulf from our second floor balcony. The condo was clean and the decor was fun to look at. They had so many extras available: laundry detergent, ...

See all reviews

Show less

Siesta Key Condo | On the beach
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 Bedrooms, 2 Bathrooms
6 reviews

$403

avg/night

$403
avg per night
View Details

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

Featured review

"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

Siesta Key Condo | On the beach
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 Bedrooms, 2 Bathrooms
5 reviews

$349

avg/night

$349
avg per night
View Details

Key Amenities

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

About this property

This vacation rental condo is directly on the beach and is direct oceanfront (Gulf-front). Unfortunately, there are properties that falsely claim to be beachfront / oceanfront. We encourage travelers to ask property owners to verify those claims. We are excited to announce that B108 has recently been ...

View all property information

Property Type

Siesta Key Condo

Featured review

"Outstanding"

This is our third year in a row staying at Fishermans Cove. Our first year we were in a second floor condo these last two years we had ground floor and wouldn’t have it any other way. Everything is spotless, ...

See all reviews

Show less

Siesta Key House
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 Bedrooms, 2 Bathrooms
3 reviews

Distance to beach: 0.4 miles to Siesta Key Beach

$550

avg/night

$550
avg per 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

Featured review

"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

Siesta Key House
3 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 3 Bedrooms, 2 Bathrooms
2 reviews

$295

avg/night

$295
avg per night
View Details

Key Amenities

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

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

Featured review

"great location to the Village and beach"

A wonderful location on Siesta Key--we loved being able to walk to the Village and easily walk to the beach. The house has an open feeling with a large living/eating/kitchen area. I cooked a good bit ...

See all reviews

Show less

Siesta Key Condo | On the beach
2 BR | 2 BA | Sleeps 5 | Quick View
Sleeps 5, 2 Bedrooms, 2 Bathrooms
5 reviews

Distance to beach: 100 feet to Crescent Beach

$372

avg/night

$372
avg per 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

Featured review

"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

Siesta Key Condo | On the beach
3 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 3 Bedrooms, 2 Bathrooms
2 reviews

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

$407

avg/night

$407
avg per 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

Featured review

"Wonderful place to stay!"

Recently, we stayed at a Fisherman’s Cove for Spring Break. What a wonderful place to stay! Close to the ocean/beach and the condo had everything we needed!

See all reviews

Show less

Siesta Key House
3 BR | 2.5 BA | Sleeps 8 | Quick View
Sleeps 8, 3 Bedrooms, 2.5 Bathrooms

$422

avg/night

$422
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

Welcome to Hemingway House, a charming retreat located on the northern end of Siesta Key. This delightful home offers a perfect blend of comfort and convenience, ensuring an unforgettable vacation experience. Just a short 5-minute walk will lead you to the serene shores of Shell Beach, where you can soak ...

View all property information

Property Type

Siesta Key House

Show less

Siesta Key House
3 BR | 2 BA | Sleeps 8 | Quick View
Sleeps 8, 3 Bedrooms, 2 Bathrooms
5.0 rating on other travel sites

$355

avg/night

$355
avg per 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

Siesta Key House
3 BR | 3 BA | Sleeps 10 | Quick View
Sleeps 10, 3 Bedrooms, 3 Bathrooms
1 review

$249

avg/night

$249
avg per night
View Details

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 rental duplex offers the perfect blend of sophistication and comfort, providing an unforgettable experience for your stay. Whether you're seeking relaxation by the private heated ...

View all property information

Property Type

Siesta Key House

Featured review

"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

Siesta Key House
4 BR | 3 BA | Sleeps 12 | Quick View
Sleeps 12, 4 Bedrooms, 3 Bathrooms
4 reviews

$390

avg/night

$390
avg per night
View Details

Key Amenities

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

About this property

Welcome to Casa Ohana, a stunning vacation rental duplex 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 ...

View all property information

Property Type

Siesta Key House

Featured review

"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

Siesta Key House
3 BR | 3 BA | Sleeps 10 | Quick View
Sleeps 10, 3 Bedrooms, 3 Bathrooms
4.7 rating on other travel sites

$265

avg/night

$265
avg per night
View Details

Key Amenities

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

About this property

Escape to Casita Morning Star, a magnificent vacation rental duplex 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 ...

View all property information

Property Type

Siesta Key House

Show less

Siesta Key House
3 BR | 2 BA | Sleeps 8 | Quick View
Sleeps 8, 3 Bedrooms, 2 Bathrooms
2 reviews

$289

avg/night

$289
avg per night
View Details

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

Featured review

"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

Siesta Key House
4 BR | 3 BA | Sleeps 12 | Quick View
Sleeps 12, 4 Bedrooms, 3 Bathrooms
2 reviews

Distance to beach: 5 miles to Siesta Key Beach

$392

avg/night

$392
avg per night
View Details

Key Amenities

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

About this property

Welcome to Casa Mahalo, a stunning vacation rental duplex 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 ...

View all property information

Property Type

Siesta Key House

Featured review

"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

Siesta Key House
4 BR | 3 BA | Sleeps 12 | Quick View
Sleeps 12, 4 Bedrooms, 3 Bathrooms
2 reviews

Distance to beach: 1 miles to Siesta Key Beach

$338

avg/night

$338
avg per 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 vacation rental duplex 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 ...

View all property information

Property Type

Siesta Key House

Featured review

"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

Siesta Key House
4 BR | 3 BA | Sleeps 12 | Quick View
Sleeps 12, 4 Bedrooms, 3 Bathrooms
4.9 rating on other travel sites

$338

avg/night

$338
avg per 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 vacation rental duplex 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, ...

View all property information

Property Type

Siesta Key House

Show less

Siesta Key House
4 BR | 3 BA | Sleeps 10 | Quick View
Sleeps 10, 4 Bedrooms, 3 Bathrooms
2 reviews

$394

avg/night

$394
avg per night
View Details

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

Featured review

"Perfect for families!"

Beautiful home with perfect layout for families. Any issues we had were resolved in a timely manner: very clean.

See all reviews

Show less

Siesta Key House
4 BR | 2.5 BA | Sleeps 12 | Quick View
Sleeps 12, 4 Bedrooms, 2.5 Bathrooms
2 reviews

$412

avg/night

$412
avg per night
View Details

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

Featured review

"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

Siesta Key Condo | On the beach
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 Bedrooms, 2 Bathrooms
6 reviews

$337

avg/night

$337
avg per night
View Details

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

Featured review

"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

Siesta Key Condo
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 Bedrooms, 2 Bathrooms
10 reviews
owner special
Owner special: Mar 15 - 22, 2025 AND Mar 29 - Apr 5, 2025 just opened up in our 2 bedroom condo in Siesta Key.

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

$197

avg/night

$197
avg per night
Owner special:
Mar 15 - 22, 2025 AND Mar 29 - Apr 5, 2025 just opened up in our 2 bedroom condo in Siesta Key.

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

Siesta Key Condo - Siesta Key Paradise Looking 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

Featured review

"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

Siesta Key House
3 BR | 3 BA | Sleeps 6 | Quick View
Sleeps 6, 3 Bedrooms, 3 Bathrooms
3 reviews

$314

avg/night

$314
avg per 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

Featured review

"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

Siesta Key Condo
1 BR | 1 BA | Sleeps 4 | Quick View
Sleeps 4, 1 Bedroom, 1 Bathroom
6 reviews

Distance to beach: 100 yards to Crescent Beach

$261

avg/night

$261
avg per 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

Featured review

"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

Siesta Key Condo | On the beach
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 Bedrooms, 2 Bathrooms
2 reviews

$302

avg/night

$302
avg per night
View Details

Key Amenities

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

About this property

MONTHLY RENTAL. Introducing our BEAUTIFUL NEW LISTING! Nestled within this premier condominium complex, our home offers direct access to the highly acclaimed Siesta Key Beach without the need to cross any streets. Our home away from home is perfect for those seeking a winter retreat or anyone seeking ...

View all property information

Property Type

Siesta Key Condo

Featured review

"CASARINA on Siesta Key Beach-#1 Beach, Place to Visit, Hosts"

To start off with Chris and Jeannie are the best hosts to deal with. Easy going, prompt if anything is needed! They share their lovely home with us vacation lovers visiting literally the #1 Beach-Siesta ...

See all reviews

Show less

Siesta Key House
3 BR | 3 BA | Sleeps 6 | Quick View
Sleeps 6, 3 Bedrooms, 3 Bathrooms
7 reviews

Distance to beach: 200 feet to Siesta Key Public Beach

$330

avg/night

$330
avg per 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

Featured review

"Siesta Beach"

Absolutely the best location! House was clean and has everything you need. Especially liked pulling wagon with all the beach items the short distance to the beach. Owners very helpful and quickly replaced ...

See all reviews

Show less

Siesta Key House
3 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 3 Bedrooms, 2 Bathrooms
2 reviews

Distance to beach: 400 feet to Siesta Beach

$684

avg/night

$684
avg per 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 large patio doors openings from the two living areas and kitchen/dinning area. The home has been freshened with a very nice decor ...

View all property information

Property Type

Siesta Key House

Featured review

"Perfect Beach Getaway at Siesta Key"

Out stay at this beach vacation home was nothing short of spectacular! From the moment we arrived, we were captivated by the stunning views of the ocean. The home is just steps away from the pristine, powdery ...

See all reviews

Show less

Siesta Key House
5 BR | 4 BA | Sleeps 13 | Quick View
Sleeps 13, 5 Bedrooms, 4 Bathrooms
13 reviews

Distance to beach: 400 feet to Siesta Beach

$927

avg/night

$927
avg per 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

Featured review

"Amazing home!"

We had an amazing time with our family at this home in SK! David (property manager) was incredibly responsive to our questions and even stopped by to introduce himself when we arrived! The space was ...

See all reviews

Show less

Siesta Key House
3 BR | 3.5 BA | Sleeps 8 | Quick View
Sleeps 8, 3 Bedrooms, 3.5 Bathrooms

$424

avg/night

$424
avg per 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

Siesta Key House
3 BR | 2 BA | Sleeps 8 | Quick View
Sleeps 8, 3 Bedrooms, 2 Bathrooms

$397

avg/night

$397
avg per 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

Siesta Key House
3 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 3 Bedrooms, 2 Bathrooms

Distance to beach: 1 miles to Turtle Beach

$385

avg/night

$385
avg per 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 through owner on this site. Discounts for multiple monthly stays. Available June, August, September and October and December 15, 2024 - January 18, 2025 Not available January 18 - May 16, 2025 Hibiscus ...

View all property information

Property Type

Siesta Key House

Show less

Siesta Key Condo
1 BR | 1 BA | Sleeps 3 | Quick View
Sleeps 3, 1 Bedroom, 1 Bathroom
10 reviews

Distance to beach: 0.5 miles to Siesta Key Main Beach

$239

avg/night

$239
avg per 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. Please note that RATES ALREADY INCLUDE 13% TAXES. Condo is walking distance to Siesta Key Main Beach, and a nice 0.9 mile sidewalk walk (or bike or free trolley) to Siesta Key Village. Six new Pickleball courts and 2 Tennis Courts ...

View all property information

Property Type

Siesta Key Condo

Featured review

"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

Siesta Key House
4 BR | 2.5 BA | Sleeps 9 | Quick View
Sleeps 9, 4 Bedrooms, 2.5 Bathrooms

$500

avg/night

$500
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool

About this property

Tucked away amid the tropical tranquility of Siesta Keys Grand Canal, this remodeled home delivers on design, location and lifestyle. Featuring four bedrooms, two-and-one-half baths and a one-car garage and washer and dryer. Beautiful hardwood floors, solid wood cabinetry and sleek granite countertops. ...

View all property information

Property Type

Siesta Key House

Show less

Siesta Key House
4 BR | 2 BA | Sleeps 8 | Quick View
Sleeps 8, 4 Bedrooms, 2 Bathrooms

$459

avg/night

$459
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool

About this property

A piece of Paradise..... Come relax in this beautiful 4 Bedroom, 2 full bath pool home offering large livingroom and family room, caged heated pool and spa, (spa is non-functional and is maintained at pool temperature.) 1 car garage ( owner keeps one car in garage), washer/dryer. Home located just 1 mile ...

View all property information

Property Type

Siesta Key House

Show less

Siesta Key Condo
1 BR | 1 BA | Sleeps 4 | Quick View
Sleeps 4, 1 Bedroom, 1 Bathroom

Distance to beach: 300 feet to Siesta Key Beach

$238

avg/night

$238
avg per night
View Details

Key Amenities

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

About this property

Welcome to Unit 104 at Crescent Royale! Only a hop, skip and jump (well, technically 100 steps away) from the pristine Siesta Key Beach where you should be prepared to get swept off your feet by the jaw-dropping, sunset views from your very own screened lanai. This cozy 1 bedroom, 1 bath unit boast ...

View all property information

Property Type

Siesta Key Condo

Show less

Siesta Key House
4 BR | 3 BA | Sleeps 8 | Quick View
Sleeps 8, 4 Bedrooms, 3 Bathrooms

$486

avg/night

$486
avg per 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

Siesta Key House
3 BR | 2 BA | Sleeps 8 | Quick View
Sleeps 8, 3 Bedrooms, 2 Bathrooms
1 review

$464

avg/night

$464
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool

About this property

WELCOME TO PARADISE! COME RELAX IN THIS BEAUTIFUL 3 BEDROOM / 2 BATH GRAND CANAL HOME LOCATED IN THE QUIET NEIGHBORHOOD OF SIESTA ISLES., WALKING DISTANCE TO THE BEACH. THIS FABULOUS REMODELED HOME FEATURES A CUSTOM GOURMET KITCHEN AND OPEN FLOOR PLAN PERFECT FOR ENTERTAINING. HIGH-SPEED INTERNET AVAILABLE, ...

View all property information

Property Type

Siesta Key House

Featured review

"522 Canal Rd"

Great vacation rental home with tile floors throughout making it a perfect beach home. The house has four bedrooms three of which have their own private, full bathroom. Siesta-4-Rent Management was great ...

See all reviews

Show less

Siesta Key House
3 BR | 3 BA | Sleeps 10 | Quick View
Sleeps 10, 3 Bedrooms, 3 Bathrooms

$422

avg/night

$422
avg per 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

Siesta Key Condo
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 Bedrooms, 2 Bathrooms

$422

avg/night

$422
avg per 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

Siesta Key House
3 BR | 2 BA | Sleeps 8 | Quick View
Sleeps 8, 3 Bedrooms, 2 Bathrooms
1 review

$400

avg/night

$400
avg per night
View Details

Key Amenities

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

About this property

Comfortable private 3bedroom 2 bath home, open concept floor plan. The hone has a salt water heated pool. You can bike ride or walk to the main siesta key beach pavilion. There you can play pickleball or enjoy the service at the snack bar or continue out to the white quartz sand and clear waters of the ...

View all property information

Property Type

Siesta Key House

Featured review

"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

Siesta Key Condo
Studio | 1 BA | Sleeps 2 | Quick View
Sleeps 2, 0 Bedrooms, 1 Bathroom
1 review

Distance to beach: 0.0 miles to Siesta Key Main Beach

$199

avg/night

$199
avg per night
View Details

Key Amenities

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

About this property

PENTHOUSE WATER VIEWS! RESORT LIVING ON SIESTA KEY at Harbor Towers Yacht & Racquet Club, gives you the best of both worlds - Beach and Resort! PENTHOUSE CONDO WITH WATER VIEWS: Spacious 1 bedroom Condo with 2 Queen beds - one queen bed in spacious Bedroom, and second Queen Bed is a brand new ...

View all property information

Property Type

Siesta Key Condo

Featured review

"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

Siesta Key House
3 BR | 2 BA | Sleeps 10 | Quick View
Sleeps 10, 3 Bedrooms, 2 Bathrooms

Distance to beach: 0.7 miles to Siesta Key Beach

$499

avg/night

$499
avg per 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

Siesta Key Condo
5 BR | 3.5 BA | Sleeps 14 | Quick View
Sleeps 14, 5 Bedrooms, 3.5 Bathrooms

$643

avg/night

$643
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool

About this property

*** SPECIAL OFFER -- 20% OFF FOR AUGUST, SEPT. and OCT. 2024 RENTALS.***This 3600 sq ft., 5 Bedroom 3.5 Bath, Townhome Offers, Private heated pool, ** Please be aware that the pool is refreshing, but has limited space for larger parties. many balconies overlooking the pool. Beautiful custom kitchen, with ...

View all property information

Property Type

Siesta Key Condo

Show less

Siesta Key Condo
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 Bedrooms, 2 Bathrooms
3 reviews

$174

avg/night

$174
avg per night
View Details

Key Amenities

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

About this property

This two bedroom(master King bed), second bedroom double bed/ single bed (with pull out trundle) full kitchen, dining, living room and lanai open into living space. Out back you sit on the bay and across the street is number 1 beach in the U.S. Pool heated year round 80 degrees, grill areas and laundry ...

View all property information

Property Type

Siesta Key Condo

Featured review

"Very nice host and home. Home needs work."

The owner could not have been nicer. The home is beautiful but does need attention to details like, no ice from icemaker, hot water takes forever to get to kitchen and master bath. Carpet in bedroom needed ...

See all reviews

Show less

Map
Expand map Close map
Siesta Key Vacation Rentals