Cheap Vacation Rentals in Siesta Key

(19 rentals)
booking message booking message
Siesta Key Studio
Studio | 1 BA | Sleeps 2 | Quick View
Sleeps 2, 0 Bedrooms, 1 Bathroom
5 reviews

Distance to beach: 0.3 miles to Siesta Key Beach access 10

$142

avg/night

$142
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Rentals by owner

About this property

*Calendar month rentals only*******SPECIAL - March and April 2024 - $200 per night plus utilities - 14 night minimum****May - November (seven-month lease) - $1750 per month plus utilities May - November (three-month lease) - $2500 per month plus utilities December - $3900 per month plus utilities January, ...

View all property information

Property Type

Siesta Key Studio

Featured review

"Perfect peaceful pet friendly bungalow"

I recently had the pleasure of staying for three months in this cozy bungalow on Palm Island in the heart of Siesta Key. Nestled amidst lush vegetation and just a short walk from the beach and Siesta Key ...

See all reviews

Show less

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

$151

avg/night

$151
avg per night
View Details

Key Amenities

  • Pet friendly

About this property

Quaint 1 bedroom bungalow with Murphy Bed that folds into the wall during the day providing additional living space. Living room w/leather furniture, french doors opening to a private brick patio. 2 TV's with DVD players. Kitchen offers a mini convection oven w/built in rottiserie for up to full ...

View all property information

Property Type

Siesta Key Condo

Show less

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

$151

avg/night

$151
avg per night
View Details

Key Amenities

  • Pool

About this property

Beautiful ground floor unit with screened porch at White Sands located just a few blocks from Siesta Key public beach. Unit sleeps 4, 2 Cable TV's , wireless internet ( Siesta 4 Rent is not responsible for tech support), community coin laundry right outside the door, covered parking, community pool ...

View all property information

Property Type

Siesta Key Condo

Show less

Siesta Key Studio
Studio | 1 BA | Sleeps 4 | Quick View
Sleeps 4, 0 Bedrooms, 1 Bathroom
3 reviews

$153

avg/night

$153
avg per night
View Details

Key Amenities

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

About this property

We are proud of our Siesta Key Condo at Ebb Tide. This Florida Beach Rental is in the heart of Crescent Beach. Once you park your car there is no need to use a car for the rest of your stay. A short 1 1/2 block walk and your toes are enjoying the lush, white (quartz) sands of the crescent beach.The ...

View all property information

Property Type

Siesta Key Studio

Featured review

"A little piece of Paradise."

The condo was absolutely amazing, and very affordable. Perfect for a couple, so close to the bay and the beach. The condo had everything needed for our stay. Will definitely book again. I love going to ...

See all reviews

Show less

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

$156

avg/night

$156
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Pet friendly
  • Pool

About this property

Newly renovated 1/1 condo with everything you need to relax or work from home! Bedroom offers a king size bed, large closet, dresser, two nightstands with storage, desk equipped with keyboard, mouse, printer and laptop stand, and large TV with WiFi connection to watch all your favorite apps. There’s ...

View all property information

Property Type

Siesta Key Condo

Featured review

"We enjoyed your wonderful condo!"

We really enjoyed your beautiful condo and we’re so comfortable there and had a great time. We loved the beach-themed decorating so much And the king sized bed was so cold for table that we want to buy ...

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

$159

avg/night

$159
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 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

$161

avg/night

$161
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 Condo
1 BR | 1 BA | Sleeps 4 | Quick View
Sleeps 4, 1 Bedroom, 1 Bathroom
7 reviews

$163

avg/night

$163
avg per night
View Details

Key Amenities

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

About this property

Our little piece of paradise is a one bedroom condominium ideal for couples or young families. We are located at 73 Avenida Messina in unit #7 on the ground floor of the Gulf Holiday Apartments. We are 300 ft. from the Gulf of Mexico and about a five minute walk from the village - known for its shops, ...

View all property information

Property Type

Siesta Key Condo

Featured review

"Condo #6"

We enjoyed staying in Condo #6 for two nights before Hurricane Helene arrived. We evacuated and weren’t able to return. We hope to stay here again in the future. We have stayed in these condos for ...

See all reviews

Show less

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

$173

avg/night

$173
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

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

$178

avg/night

$178
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen

About this property

VILLAGE WEST - Deluxe Ground Floor Vacation Condo in Siesta Key Village with Heated PoolLocated right in the Heart of Siesta Village, Sarasota FL - Short Walk to Crescent BeachVILLAGE WEST: This Siesta Key one bedroom ground floor condo vacation rental is located right in the heart of Siesta Village ...

View all property information

Property Type

Siesta Key Condo

Featured review

"Great location!"

The location of this rental was perfect. We were able to walk into the village to shop and eat within a few minutes. Drive time to local attractions was minimal.

See all reviews

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

$178

avg/night

$178
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
1 BR | 1 BA | Sleeps 2 | Quick View
Sleeps 2, 1 Bedroom, 1 Bathroom
3 reviews

$182

avg/night

$182
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Pool

About this property

The Siesta Key vacation condo rental is a one bedroom / one bathroom individually owned condominium at the Gulf and Bay Club Bayside and is furnished with the basic household items necessary for normal living. This unique Old Key West style condo is fully equipped with an emphasis on vacation living. ...

View all property information

Property Type

Siesta Key Condo

Featured review

"March Getaway!"

Siesta Key was very beautiful and a great place to visit. The accommodations were very nice, clean and comfortable. We hope to visit this area again next year.

See all reviews

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

$189

avg/night

$189
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 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

$195

avg/night

$195
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 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

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 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

$195

avg/night

$195
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
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

$199

avg/night

$199
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
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 Condo
2 BR | 1.5 BA | Sleeps 4 | Quick View
Sleeps 4, 2 Bedrooms, 1.5 Bathrooms
2 reviews

Distance to beach: 850 feet to Crescent Beach

$199

avg/night

$199
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 #532 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

"Great stay in siesta keys"

This 2 bedroom ground floor condo was comfortable, clean, stylish and centrally located. It was fully stocked eith cleaning and cooking supplies as well as hairdryer and iron. We had a great time and ...

See all reviews

Show less

Map
Expand map Close map
Siesta Key Vacation Rentals