Siesta Key Vacation Rentals with Boat Dock

(48 rentals)
booking message booking message
Siesta Key Condo | On the beach
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 Bedrooms, 2 Bathrooms
44 reviews

$342

avg/night

$342
avg per night
View Details

Key Amenities

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

About this property

A millionaire's retreat! This completely remodeled first floor unit with view of the Gulf of Mexico and amazing sunsets awaits you on Siesta Key. Walk out the lanai door directly to the beach where children can play within view or walk over the boardwalk to the blue-green waters of the Gulf within ...

View all property information

Property Type

Siesta Key Condo

Featured review

"You WILL NOT be disappointed with this condo!!!"

I have nothing but rave reviews of this rental - the location, the condo itself and the owners. We had an amazing time and they had anything and everything that you could want in the condo. We will definitely ...

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
47 reviews

$342

avg/night

$342
avg per night
View Details

Key Amenities

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

About this property

This magnificent unit has been completely remodeled and is on the ground floor with beautiful water views and spectacular sunsets. Walk out the rear lanai door directly onto the beach where children can play within view or walk over the boardwalk to the blue-green waters of the Gulf of Mexico within 100 ...

View all property information

Property Type

Siesta Key Condo

Featured review

"Little piece of heaven"

I can't say enough about this property absolutely heaven out your front door is a beautiful Bay with manatees playing in it pretty much every day we were able to be there!! out the back door you're about ...

See all reviews

Show less

Siesta Key Villa | On the beach
2 BR | 2 BA | Sleeps 7 | Quick View
Sleeps 7, 2 Bedrooms, 2 Bathrooms

Distance to beach: 0.0 miles to Siesta Key

$287

avg/night

$287
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Pool

About this property

Escape to your private oasis on Siesta Key! This spacious villa offers the best of both worlds: direct access to the #1-rated Siesta Key Beach through your own private beach area, and stunning views of the Intracoastal Waterway where you can watch boats go by or launch your own kayak. Unwind in comfort ...

View all property information

Property Type

Siesta Key Villa

Show less

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

Distance to beach: 0.1 miles to Crescent Beach on Siesta Key

$192

avg/night

$192
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Pool
  • Rentals by owner

About this property

This 2nd floor, completely renovated 2 bedroom, 2 full bath condo in Siesta Harbor with private beach access and overlooking its own private harbor is the perfect getaway to the #1 beach on Siesta Key in Sarasota, Florida. This unit is located near the community pool and hot tub along with guest grilling ...

View all property information

Property Type

Siesta Key Condo

Featured review

"Siesta Sand Dollar"

We had an amazing stay at Maria's place at Siesta Harbor. Everything had just been updated and was very modern and beautiful. We would highly recommend her unit and we are looking forward to going back ...

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
78 reviews

Distance to beach: 0.0 feet to We are directly on the beach and direct oceanfront

$326

avg/night

$326
avg per night
View Details

Key Amenities

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

About this property

Our condo is directly on the beach and is direct oceanfront (Gulf-front). Unfortunately, there are properties on this site that falsely claim to be beachfront / oceanfront. We encourage travelers to ask property owners to verify those claims. When we travel over 1,000 miles to enjoy a beach vacation ...

View all property information

Property Type

Siesta Key Condo

Featured review

"PERFECT BEACH CONDO"

This condo was amazing! The hosts were very polite and responsive. The condo was clean and well-equipped with everything we needed, including a beach wagon, chairs, sand toys, umbrellas, a boogie board, ...

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
11 reviews

$390

avg/night

$390
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Kitchen
  • Oceanfront
  • Pool
  • Rentals by owner

About this property

My ground floor rental is directly on the beach on the Gulf of Mexico, with incredible views and sunsets! The lanai has a back door directly out to the Beach. The front of my unit faces the Lagoon where we have a FREE DOCK for your boat or other water craft. (So you have water views in both directions)! ...

View all property information

Property Type

Siesta Key Condo

Featured review

"Amazing"

This unit offers an amazing view of the ocean and sunsets. Perfect get away spot, great location, clean and has everything you need to enjoy your stay. We will be back in 2014!

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 Condo | On the beach
1 BR | 1 BA | Sleeps 4 | Quick View
Sleeps 4, 1 Bedroom, 1 Bathroom
43 reviews

$298

avg/night

$298
avg per night
View Details

Key Amenities

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

About this property

This magnificent unit is on the third floor with spectacular unobstructed views of the Gulf! This unit has been completely renovated with beautiful natural stone tile throughout, updated kitchen and bathroom and brand new furniture, coastal pictures, decorative accessories, bedding, new paint throughout. ...

View all property information

Property Type

Siesta Key Condo

Featured review

"Just Perfect"

Location was amazing - views spectacular, nothing separating us from the beautiful gulf. Condo - was missing nothing and needed nothing additional. Clean. Stocked. Convenient. Comfortable. Owners - ...

See all reviews

Show less

Siesta Key Condo
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 Bedrooms, 2 Bathrooms
4 reviews
owner special
Owner special: We have opening for Thanksgiving! We are also have openings for 1/4 thru 2/1 2025! Book now!

Distance to beach: 0.1 miles to Crescent Beach Siesta Key

$257

avg/night

$257
avg per night
Owner special:
We have opening for Thanksgiving! We are also have openings for 1/4 thru 2/1 2025! Book now!

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

About this property

Welcome to The Anchorage Yacht and Tennis Club across from the beautiful sands of Crescent Beach on Siesta Key. Sitting directly on the intercoastal waterway where you can park your boat, jet ski, kayak, and paddleboard. This complex has an Olympic size pool, three lighted tennis courts, pickleball nets. ...

View all property information

Property Type

Siesta Key Condo

Featured review

"Unit 403"

The place is absolutely beautiful. Great views and amenities! Close to walking distance to most things. Would definitely stay here again!

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
7 reviews

$377

avg/night

$377
avg per night
View Details

Key Amenities

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

About this property

This colorful custom2rd floor unit has a commanding view of the Gulf of mexico. This special unit has been decorated by a pro, and shows it! unit, perfect for people who can take excellent care of things and appreciate the fine nature of this unit. From the modern kitchen, you will enjoy Siesta ...

View all property information

Property Type

Siesta Key Condo

Featured review

"perfect spot"

Fisherman's cove is the ultimate spot for a peaceful getaway. Your host Carrie is a wonderful, warm and thoughtful person. You won't find anyone better. Her condo Is perfectly located on the corner of the ...

See all reviews

Show less

Siesta Key Condo
2 BR | 1.5 BA | Sleeps 4 | Quick View
Sleeps 4, 2 Bedrooms, 1.5 Bathrooms
2 reviews

Distance to beach: 950 feet to Crescent Beach

$194

avg/night

$194
avg per night
View Details

Key Amenities

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

About this property

Direct-with-Owner Rental Discounts: Midnight Cove #714 offers "All-In Price" 10% to 25% Discounted Rental Rates from $946 to $2,488 /Wk Depending on the Season ($150 departure cleaning extra - $400.00 refundable security deposit required) & SAVINGS from $163 to $621 /Wk from the listed ...

View all property information

Property Type

Siesta Key Condo

Featured review

"Siesta Key Midnight Cove 714, Convienient, 1st Floor Condo, Great Complex"

Midnight Cove has all the amenities for a great getaway on Siesta Key. The complex has great beach access, beach chairs with attendant on the beach, nice pool ,fitness center and two BBQ grill areas. The ...

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

$236

avg/night

$236
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
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 Bedrooms, 2 Bathrooms
5 reviews

$272

avg/night

$272
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Pool
  • Rentals by owner

About this property

Beautiful 2 Bedroom, 2 Full bath condo. Close to everything, right on Crescent Beach, voted #1 beach twice in the last 5 years. King in the master, 2 full size beds in the second.

View all property information

Property Type

Siesta Key Condo

Featured review

"Jamaica Royal"

We loved our stay here. Right on the beach and great pool close to our condo. Clean and spacious. Maybe could use a few updates but we were mainly here at night for sleeping so it worked well for us.

See all reviews

Show less

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

$339

avg/night

$339
avg per night
View Details

Key Amenities

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

About this property

Enjoy our 2br 2 bathroom ground floor condo. 30’ to the pool, tennis courts, Weber gas grills, and picnic table . Or cross the street to private deeded beach access on the #1 beach in the US. Enjoy bayside fishing on the fishing deck. 1280 square feet of living space. Roku tv’s and ...

View all property information

Property Type

Siesta Key Condo

Featured review

"Cold escape"

We always enjoy our stay at Gulf and Bay Bayside!!! Condos are perfect! We always meet new people who have become friends and can’t wait to see them again next year!!!

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
8 reviews

$347

avg/night

$347
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Kitchen
  • Oceanfront
  • Pool
  • Rentals by owner

About this property

Our Condo is on beautiful Turtle Beach at the southern and most private end of Siesta Key directly on the Gulf of Mexico. When we say directly, we mean directly and not merely a Gulf “View” or a long car ride or a long walk to the Gulf. We call it “Paradise” and you could not ...

View all property information

Property Type

Siesta Key Condo

Featured review

"Excellent Condo A306"

We stayed at A306 the third week of April 2023. Our stay was well beyond expectation and this location & Unit is the best overall rental we’ve experienced in 25+ years of Florida vacationing. 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
13 reviews

$345

avg/night

$345
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
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 Bedrooms, 2 Bathrooms
8 reviews

Distance to beach: 0.2 miles to Siesta Key

$277

avg/night

$277
avg per night
View Details

Key Amenities

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

About this property

NEWLY REMODELED - LUXURY WATERVIEW CONDO FOR COUPLES or Families GETAWAY - POOLS, GYM, TENNIS - Walk to beach, town, shopping, top restaurants, live music, and entertainment. Walk out of the front door of this fantastic condo, grab your beach gear and take a short walk and you'll hit the beach ...

View all property information

Property Type

Siesta Key Condo

Featured review

"Great place!"

This was our first time back to Siesta Key in 20 years and we loved this condo! The location is right between the two villages, so super easy to grab a trolly to dine or shop. The beach is a pretty short ...

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

Distance to beach: 100 yards to Turtle Beach

$305

avg/night

$305
avg per night
View Details

Key Amenities

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

About this property

Enjoy your home away from home in beautiful Siesta Key! This great 2-bedroom, 2-bath has everything you need for a wonderful, relaxing vacation. This prime location makes it convenient to get to the beach. Just walk a single flight of stairs (or elevator) and you're on the beach where you can enjoy ...

View all property information

Property Type

Siesta Key Condo

Show less

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

$277

avg/night

$277
avg per night
View Details

Key Amenities

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

About this property

This first floor colorful unit sleeps 6 and you will love the sandy beach just outside the lanai door with comfortable patio chairs. Walk past the dune to enjoy more beach and the Gulf of Mexico. A lovely spot to watch sunsets. The unit is upgraded and comfortable for couples traveling together or with ...

View all property information

Property Type

Siesta Key Condo

Show less

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

$429

avg/night

$429
avg per night
View Details

Key Amenities

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

About this property

Very private - empty lot across the canal and fenced in. Walk to the islands best restaurants, bars, shops and ice cream parlors. The beach is a short stroll (8 min), use free golf cart taxi or ride provided bikes with tow behind cart! Siesta is well known for its #1 beach in the USA!

View all property information

Property Type

Siesta Key House

Show less

Siesta Key Townhome
2 BR | 2.5 BA | Sleeps 6 | Quick View
Sleeps 6, 2 Bedrooms, 2.5 Bathrooms
3 reviews

$248

avg/night

$248
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

About this property

This spacious, beautifully decorated and updated 2 BR/2.5 bath townhome overlooks the canal and boat basins and is located directly across the street from the gorgeous Siesta Beach. The kitchen and all baths have been renovated and the newly furnished living room features a sofa bed and 55” smart ...

View all property information

Property Type

Siesta Key Townhome

Featured review

"Had a great vacation."

The townhouse was in a perfect location overlooking an inlet and very close to the beach. Unit well maintained, beautifully furnished. Would stay again!

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
2 reviews
owner special
Owner special: Damage free beachfront building. Beach views are wonderful. What can we do for you? 10/31/24

Distance to beach: 0.0 miles to Siesta Key beach also know as "Crescent Beach"

$355

avg/night

$355
avg per night
Owner special:
Damage free beachfront building. Beach views are wonderful. What can we do for you? 10/31/24

View Details

Key Amenities

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

About this property

Best beachfront view on Siesta Key from remodeled two bedroom and two bathroom beachfront condo. Stay for the unbelievably beautiful beachfront balcony views. Enjoy the modern open floor plan with beach views from most rooms. Beautifully furnished apartment you will be proud of. Upgraded, secure WiFi. Spectacular ...

View all property information

Property Type

Siesta Key Condo

Featured review

"Any last minute availability for February"

Hello I was looking to see if you had any last minute availability for February ? Sorry to contact through the review I could not find an email address to send a request. Thank you for your time best Joann

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

Distance to beach: 0.0 miles to Siesta Key beach also known as "Crescent Beach"

$368

avg/night

$368
avg per night
View Details

Key Amenities

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

About this property

Unit 404's furnishings were updated in November 2022. The million dollar five star view you want and can now enjoy. Fully equipped modern, clean kitchen with a big beach view, stainless steel appliances, ice maker, dish washer, granite counters and back splashes and custom cabinets. Two types ...

View all property information

Property Type

Siesta Key Condo

Featured review

"A wonderful stay at Siesta Key"

We had a wonderful time at Charley and Nancy's condo. His condo is beautiful and very well maintained. They have recently purchased all new living room furniture, it was very pretty as well as comfortable. ...

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

$359

avg/night

$359
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Kitchen
  • Oceanfront
  • Pool
  • Rentals by owner

About this property

Fisherman's Cove Condominiums have the best Location on Siesta Key! It is surrounded by water with the Gulf of Mexico on the west side and a private lagoon that leads to the inter-coastal waterway (ICW) on the east side. Swim, surf, boat, kayak, paddle board, fish, gather sea shells and shark’s ...

View all property information

Property Type

Siesta Key Condo

Show less

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

Distance to beach: 20 feet to Turtle Beach, Siesta Key

$320

avg/night

$320
avg per night
View Details

Key Amenities

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

About this property

Beautiful beach inspired decor...Fresh, airy and calm...perfect relaxing unit with all the comforts of home and more to enjoy a fun filled time at the beach!!!!!

View all property information

Property Type

Siesta Key Condo

Show less

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

$230

avg/night

$230
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Pool
  • Rentals by owner

About this property

Roomy 2 bedroom, 2 full bath condo in prime Siesta Key location. Comfortably furnished living room, dining area, all linens and fully equipped kitchen included, ceiling fans in all rooms, Flat screen tv in living room with DVD player and a flat screen in the master bedroom. Master bedroom has queen-size ...

View all property information

Property Type

Siesta Key Condo

Featured review

"Comfortable unit"

The property was nice and comfortable. The children enjoyed the pool that was close to the unit. Owner promptly responds if we had questions.

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

Distance to beach: 30 yards to Turtle Beach

$305

avg/night

$305
avg per night
View Details

Key Amenities

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

About this property

Bright and inviting, this popular unit has floor to ceiling sliding glass doors from the lanai, offering breathtaking third floor views. Beautiful white porcelain tile leads to new bamboo laminate flooring, which is just one of the many recent upgrades. The open kitchen has comfortable counter seating ...

View all property information

Property Type

Siesta Key Condo

Featured review

"Holmes Beach Rental"

We loved our visit and loved the condo. The views were amazing . The only compliant would be the living room furniture was not comfortable. And the kitchen could use more kitchen items. But we dealt with ...

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

$305

avg/night

$305
avg per night
View Details

Key Amenities

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

About this property

This cozy beach house awaits your visit! Magnificent view of the Gulf of Mexico and evening sunset from lanai.... Peaceful Intercoastal inlet views and sunrise from front door... This little nest has been newly "stem to stern" furnished and equipped for your comfort. Coastal Living as its ...

View all property information

Property Type

Siesta Key Condo

Featured review

"Perfect sunsets, great lanai and best location"

Nice quiet location on Turtle Beach. Best sunset views, right on the beach and all the amenities one needs for a perfect beach holiday. Added bonus of docks for boats/kayaks, heated pool and gated entry. ...

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

$305

avg/night

$305
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Pool

About this property

This colorful and well cared for unit has a new owner! The view from your lanai will include sunset and will be magnificent! No other property on Siesta Key is built this close to the Gulf of Mexico where you can hear the waves from your lanai and master bedroom windows. The furnishings are very comfortable ...

View all property information

Property Type

Siesta Key Condo

Show less

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

Distance to beach: 800 feet to Siesta Key Beach

$177

avg/night

$177
avg per night
View Details

Key Amenities

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

About this property

Brand New Condo, completely renovated. 2 Bedroom, 2 Bath large condo with granite kitchen and baths. Tile deck flooring. Full water views from our 6th floor location. See all the way to end of Anna Marie on clear day. Ringling bridge, downtown Sarasota, Lido and Bird Key views. King bed in master ...

View all property information

Property Type

Siesta Key Condo

Show less

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

$304

avg/night

$304
avg per night
View Details

Key Amenities

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

About this property

Gorgeous unit and beautifully furnished with an incredible 2nd floor view of the Gulf of Mexico. Sleeps six comfortably with a king master and a full size bed along with a twin in the guest room, plus a queen sleeper sofa. Two DVD players with movie collection; a CD player and CD collection; & beach ...

View all property information

Property Type

Siesta Key Condo

Featured review

"Amazingly Fantastic."

The beach, Turtle Beach, not so great, but good to soak up the sun and be close by. Amenities were very good, staff exceptional, condo was awesome. Everything needed was there. Very clean, neat,

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

Distance to beach: 30 feet to Turtle Beach

$305

avg/night

$305
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Kitchen
  • Oceanfront

About this property

Within just a few feet of the beach, our condominium home features a well equipped kitchen with granite counter tops, luxury vinyl flooring, a leather sectional couch, recliner chairs, teak furnishings, ceiling fans in all rooms, a 55 inch smart TV in the living room and a flat screen TV in each bedroom ...

View all property information

Property Type

Siesta Key Condo

Featured review

"Oldie but Goodie"

We’ve traveled many places in our lives ( especially all over Florida) and this is one of our favorites. From the moment we requested more info on Bill and JoAnn’s condo until today at check out the ...

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

$921

avg/night

$921
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 Condo
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 Bedrooms, 2 Bathrooms
1 review

$275

avg/night

$275
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Rentals by owner

About this property

Home away from home.... I enjoy my coffee and cocktails at waterfront lanai and when I travel, I would love someone to enjoy it as well. I live in this condo, therefore, this unit has everything you may need and more. Boating, fishing, paddle boarding, kayaking, biking to Siesta Key Beach or free trolley ...

View all property information

Property Type

Siesta Key Condo

Featured review

"Spectacular"

We’ve been vacationing in Sarasota/Turtle Beach for over 10 years. This condo is our ABSOLUTE FAVORITE! Very nicely decorated & accommodating. We love that it is located on the bay. It is GREAT for fishing ...

See all reviews

Show less

Siesta Key Villa
2 BR | 2 BA | Sleeps 5 | Quick View
Sleeps 5, 2 Bedrooms, 2 Bathrooms
16 reviews

Distance to beach: 400 yards to Crescent Beach

$261

avg/night

$261
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

About this property

The Sand Dollar is a private villa located at the quiet, well run and exceedingly clean "beach to bay" community of Horizons West. A maximum of 50% of Horizons West properties are rented so the community has a more residential feel than many others on the island. The villa has been recently ...

View all property information

Property Type

Siesta Key Villa

Featured review

"Perfect Stay!"

This E-8 villa is in the perfect location for a family visit. It’s just steps from the bay and a short walk to the pools and beach. The villa itself is very clean and spacious. It’s located in a residential ...

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

Distance to beach: 200 yards to Siesta Key Crescent Beach

$239

avg/night

$239
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

About this property

DISCOUNT SPECIAL - 15% OFF THE PUBLISHED RATE FROM JULY 1 - July 14 We invite you to stay in our spacious 2 bed 2 bath condo, 'Siesta Chillin', across from the beautiful crystal sands of Crescent Beach on Siesta Key. Siesta Chillin has been recently updated and has all the conveniences of ...

View all property information

Property Type

Siesta Key Condo

Featured review

"Siesta Central - The Anchorage!!"

We stayed at the Anchorage in unit 305. It faces the city and the inner coastal lagoon. We were treated to a dolphin show one evening when they entered the lagoon searching for food!! This location ...

See all reviews

Show less

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

Distance to beach: 0.5 miles to Siesta Key Main Beach

$159

avg/night

$159
avg per night
View Details

Key Amenities

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

About this property

Sweet and spacious one bedroom condo in a Siesta Key Luxury Resort Building - Harbor Towers Yacht & Racquet Club. Great view of the historic waterfall in front of building, Palm Trees and Blue Skies and Great Sun Sets. 2 Pools (1 for kids), Fitness Room, , 3 lighted Tennis courts, boat marina, gazebo, ...

View all property information

Property Type

Siesta Key Condo

Featured review

"Absolutely gorgeous property"

Absolutely gorgeous property. The grounds and the property were kept beautifully. All of the amenities that were promised, were there. Being so close to the beach was a plus. There was no need to rent a ...

See all reviews

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

$409

avg/night

$409
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool

About this property

Very nice 4 Bedroom home on a canal just about 5 blocks to Siesta Village. offering: 1 car garage, Duet washer/ dryer, Private pool, decorated with a Island flare. Tile throughout and nice granite and stainless kitchen. Beautiful setting pool and patio overlooking Canal with boat dock. (Boat lift unavailable). ...

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

$183

avg/night

$183
avg per night
View Details

Key Amenities

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

About this property

Two bedroom, two bath condo available for minimum monthly rental. Beautiful, quiet location, beach front property and pool available.

View all property information

Property Type

Siesta Key Condo

Show less

Siesta Key Condo
1 BR | 1 BA | Sleeps 2 | Quick View
Sleeps 2, 1 Bedroom, 1 Bathroom
9 reviews

$245

avg/night

$245
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Rentals by owner

About this property

You have access to a deeded walkway from your condo to the beach while living directly on the intercoastal waterway with a great view. The intercoastal waterway, with its parade of all types of boats and dolphins swimming by, is visible from practically every room. This 2nd floor, 1 Bedroom/1 Bath ...

View all property information

Property Type

Siesta Key Condo

Featured review

"Wonderful!"

This condo is perfect. Comfortable lanai with an excellent view of the intercoastal. Well appointed home (Best one we have ever stayed in). Everything in the condo was organzied and easy to find. Walk ...

See all reviews

Show less

Siesta Key Condo
2 BR | 1.5 BA | Sleeps 5 | Quick View
Sleeps 5, 2 Bedrooms, 1.5 Bathrooms

Distance to beach: 250 feet to Siesta Key

$202

avg/night

$202
avg per night
View Details

Key Amenities

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

About this property

On Siesta Key - Quick walk to Siesta Key's world famous beach. Beautiful and private, this updated condo with granite kitchen and tile floors overlooks the bay inlet and boat basin. Across street from world famous beach. Fully amenitied condo in amentied condo complex. Large community pool, tennis ...

View all property information

Property Type

Siesta Key Condo

Show less

Siesta Key Apartment
2 BR | 1.5 BA | Sleeps 4 | Quick View
Sleeps 4, 2 Bedrooms, 1.5 Bathrooms
6 reviews

$185

avg/night

$185
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Pool
  • Rentals by owner

About this property

Vacation rental close to the # 1 beach in the USA - Siesta Key on the Gulf of Mexico (Sarasota) Siesta Key, awarded for its pristine, powdery white beaches and its azur blue waters is the perfect escape from everyday life. *** It seems like a miracle that Midnight Cove II again was extremely ...

View all property information

Property Type

Siesta Key Apartment

Featured review

"Perfect"

We spent 18 days at the unit. The Unit is beautiful and clean. We enjoyed the location and hope to return next year.

See all reviews

Show less

Siesta Key Cottage
1 BR | 1 BA | Sleeps 2 | Quick View
Sleeps 2, 1 Bedroom, 1 Bathroom
4 reviews

Distance to beach: 0.5 miles to Siesta Key Beach

$156

avg/night

$156
avg per night
View Details

Key Amenities

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

About this property

*Calendar month rentals only* May - November (seven-month lease) - $2000 per month plus utilities May - October (three-month lease) - $2900 per month plus utilities December - $4900 per month plus utilities January, February, and March - $5900 per month plus utilities April - $4900 per month plus ...

View all property information

Property Type

Siesta Key Cottage

Featured review

"Excellent pet-friendly bungalow"

This studio was perfect for our 4 week stay in Siesta Key! The neighborhood is beautiful and quiet-and everyone we met was so friendly-to us and to our dog! Every day we walked into the Village-where ...

See all reviews

Show less

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

Distance to beach: 0.5 miles to Siesta Beach access 7

$232

avg/night

$232
avg per night
View Details

Key Amenities

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

About this property

*Calendar month rentals only* May-October (six-month lease) - $3500 per month plus utilities November & December - $6900 per month plus utilities January, February, & March - $8900 per month plus utilities April - $7900 per month plus utilities 50% deposit upon booking, balance 90 prior ...

View all property information

Property Type

Siesta Key Bungalow

Featured review

"My stay at the Canal Place in Siesta Bungalows"

I am thoroughly enjoying my stay at Siesta Bungalows!!! My place is clean, quiet, and in a fabulous location!! I am about a 5 minute walk to the village and only a 7 min walk from the breathtaking Siesta ...

See all reviews

Show less

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

$172

avg/night

$172
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