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Siesta Key long stay rentals
Stay a week, a month or longer in a comfortable place all your own
Featured long stay living spaces - Siesta Key
Properties highly-rated for stays of 28 nights or longer, with space to feel right at home
Showing deals for:2 Feb - 2 Mar
Image gallery for Cozy Siesta Key Escape – Walk to Turtle Beach, Bayfront Patio, Boat Dock, Street View & Beach Gear!
9.29.2 out of 10, Wonderful, (10 reviews)
Wonderful
(10 reviews)
Cozy Siesta Key Escape – Walk to Turtle Beach, Bayfront Patio, Boat Dock, Street View & Beach Gear!
Siesta Key, FL
6% off
Price is AU$13,969
AU$13,969
for 28 nights, 1 apartment
AU$499 per night
includes taxes & fees
Image gallery for Tiny House Yellow Lifeguard Stand- pet friendly
9.69.6 out of 10, Exceptional, (44 reviews)
Exceptional
(44 reviews)
Tiny House Yellow Lifeguard Stand- pet friendly
Sarasota, FL
12% off
Price is AU$12,861
AU$12,861
for 28 nights, 1 apartment
AU$459 per night
includes taxes & fees
Image gallery for Cozy Newly Remodeled Studio Apt-5 miles from the Famous Siesta Key Beach!!!🏝
9.69.6 out of 10, Exceptional, (12 reviews)
Exceptional
(12 reviews)
Cozy Newly Remodeled Studio Apt-5 miles from the Famous Siesta Key Beach!!!🏝
Sarasota, FL
10% off
Price is AU$13,104
AU$13,104
for 28 nights, 1 apartment
AU$468 per night
includes taxes & fees
Image gallery for Tiny Coral Oasis- beachy tiny house for your getaway
9.09.0 out of 10, Wonderful, (20 reviews)
Wonderful
(20 reviews)
Tiny Coral Oasis- beachy tiny house for your getaway
Sarasota, FL
13% off
Price is AU$13,179
AU$13,179
for 28 nights, 1 apartment
AU$471 per night
includes taxes & fees
Image gallery for Waterfront sunrise views on beautiful Siesta Key minutes from beach and downtown
1010 out of 10, Exceptional, (8 reviews)
Exceptional
(8 reviews)
Waterfront sunrise views on beautiful Siesta Key minutes from beach and downtown
Siesta Key, FL
8% off
Price is AU$15,451
AU$15,451
for 28 nights, 1 apartment
AU$552 per night
includes taxes & fees
Image gallery for Siesta Zen – 2BR Steps to Siesta Key Beach & Village
9.69.6 out of 10, Exceptional, (67 reviews)
Exceptional
(67 reviews)
Siesta Zen – 2BR Steps to Siesta Key Beach & Village
Siesta Key, FL
12% off
Price is AU$30,427
AU$30,427
for 28 nights, 1 home
AU$1,087 per night
includes taxes & fees
Image gallery for Siesta Key Heated pool Home. Walk to Beach/Village. Check our monthly rate!
1010 out of 10, Exceptional, (1 review)
Exceptional
(1 review)
Siesta Key Heated pool Home. Walk to Beach/Village. Check our monthly rate!
Siesta Key, FL
26% off
Price is AU$35,962
AU$35,962
for 28 nights, 1 home
AU$1,284 per night
includes taxes & fees
Image gallery for Cypress Inn - Modern home close to Siesta Key
1010 out of 10, Exceptional, (1 review)
Exceptional
(1 review)
Cypress Inn - Modern home close to Siesta Key
Sarasota, FL
13% off
Price is AU$18,386
AU$18,386
for 28 nights, 1 home
AU$657 per night
includes taxes & fees
Image gallery for Siesta Key Retreat Sarasota Florida
1010 out of 10, Exceptional, (41 reviews)
Exceptional
(41 reviews)
Siesta Key Retreat Sarasota Florida
Siesta Key, FL
13% off
Price is AU$64,575
AU$64,575
for 28 nights, 1 home
AU$2,306 per night
includes taxes & fees
Image gallery for Siesta Key 1brm Condo - Easy Beach Access
7.07.0 out of 10, Good, (7 reviews)
Good
(7 reviews)
Siesta Key 1brm Condo - Easy Beach Access
Siesta Key, FL
8% off
Price is AU$15,233
AU$15,233
for 28 nights, 1 apartment
AU$544 per night
includes taxes & fees
Image gallery for 3 Bedroom 2 1/2 bath House on the Grand Canal, the heart of Siesta Key, w/pool
9.89.8 out of 10, Exceptional, (83 reviews)
Exceptional
(83 reviews)
3 Bedroom 2 1/2 bath House on the Grand Canal, the heart of Siesta Key, w/pool
Siesta Key, FL
9% off
Price is AU$36,756
AU$36,756
for 28 nights, 1 home
AU$1,313 per night
includes taxes & fees
Image gallery for Tiny House Siesta- perfect tiny house for two!
7.07.0 out of 10, Good, (2 reviews)
Good
(2 reviews)
Tiny House Siesta- perfect tiny house for two!
Sarasota, FL
12% off
Price is AU$12,452
AU$12,452
for 28 nights, 1 apartment
AU$445 per night
includes taxes & fees
Image gallery for VACATION COUNTRY HOUSE ON EQUINE RANCH
1010 out of 10, Exceptional, (33 reviews)
Exceptional
(33 reviews)
VACATION COUNTRY HOUSE ON EQUINE RANCH
Sarasota, FL
17% off
Price is AU$14,308
AU$14,308
for 28 nights, 1 home
AU$511 per night
includes taxes & fees
Image gallery for Pet friendly modern home, 2.7miles to Siesta Key!
9.89.8 out of 10, Exceptional, (9 reviews)
Exceptional
(9 reviews)
Pet friendly modern home, 2.7miles to Siesta Key!
Sarasota, FL
15% off
Price is AU$17,102
AU$17,102
for 28 nights, 1 home
AU$611 per night
includes taxes & fees
Image gallery for Vibrant Modern Escape, Walk to Dining, Near Beach
1010 out of 10, Exceptional, (3 reviews)
Exceptional
(3 reviews)
Vibrant Modern Escape, Walk to Dining, Near Beach
Sarasota, FL
21% off
Price is AU$10,439
AU$10,439
for 28 nights, 1 apartment
AU$373 per night
includes taxes & fees
Image gallery for Pup-approved Winter Escape - Sunshine, Comfort, Beaches & Fun await!
1010 out of 10, Exceptional, (1 review)
Exceptional
(1 review)
Pup-approved Winter Escape - Sunshine, Comfort, Beaches & Fun await!
Sarasota, FL
13% off
Price is AU$23,718
AU$23,718
for 28 nights, 1 home
AU$847 per night
includes taxes & fees
Image gallery for In the heart of Siesta Key Village | Walk to Beach | Dog Friendly | Fully renovated & remodeled
9.29.2 out of 10, Wonderful, (19 reviews)
Wonderful
(19 reviews)
In the heart of Siesta Key Village | Walk to Beach | Dog Friendly | Fully renovated & remodeled
Siesta Key, FL
5% off
Price is AU$27,061
AU$27,061
for 28 nights, 1 apartment
AU$966 per night
includes taxes & fees
Image gallery for Casa Mar #9-Studio Siesta Key
7.07.0 out of 10, Good, (2 reviews)
Good
(2 reviews)
Casa Mar #9-Studio Siesta Key
Siesta Key, FL
12% off
Price is AU$14,428
AU$14,428
for 28 nights, 1 apartment
AU$515 per night
includes taxes & fees
Image gallery for Heated Pool | Popular Beach Club Complex Siesta Key | Short Walk to Private Beach | Ready to Book!
9.89.8 out of 10, Exceptional, (29 reviews)
Exceptional
(29 reviews)
Heated Pool | Popular Beach Club Complex Siesta Key | Short Walk to Private Beach | Ready to Book!
Siesta Key, FL
5% off
Price is AU$33,779
AU$33,779
for 28 nights, 1 apartment
AU$1,206 per night
includes taxes & fees
Image gallery for Sarasota FL Modern Historic 1 bedroom 1 bath 10 min to Siesta Beach and Downtown
9.49.4 out of 10, Exceptional, (9 reviews)
Exceptional
(9 reviews)
Sarasota FL Modern Historic 1 bedroom 1 bath 10 min to Siesta Beach and Downtown
Sarasota, FL
8% off
Price is AU$6,930
AU$6,930
for 28 nights, 1 home
AU$248 per night
includes taxes & fees
Image gallery for Private Beach, Gulf View from Balcony, Heated Pools, $185 Free Activities Daily, Outdoor Workout
1010 out of 10, Exceptional, (77 reviews)
Exceptional
(77 reviews)
Private Beach, Gulf View from Balcony, Heated Pools, $185 Free Activities Daily, Outdoor Workout
Siesta Key, FL
5% off
Price is AU$33,988
AU$33,988
for 28 nights, 1 apartment
AU$1,214 per night
includes taxes & fees
Image gallery for BEAUTIFUL 2/2 VILLAS, KING BED, High speed Wi-Fi, Heated Pool and Jacuzzi!
9.69.6 out of 10, Exceptional, (50 reviews)
Exceptional
(50 reviews)
BEAUTIFUL 2/2 VILLAS, KING BED, High speed Wi-Fi, Heated Pool and Jacuzzi!
Sarasota, FL
8% off
Price is AU$23,302
AU$23,302
for 28 nights, 1 villa
AU$832 per night
includes taxes & fees
Image gallery for Stylish Coastal 3BR • Pool • Near Downtown & Sand
1010 out of 10, Exceptional, (5 reviews)
Exceptional
(5 reviews)
Stylish Coastal 3BR • Pool • Near Downtown & Sand
Sarasota, FL
13% off
Price is AU$30,107
AU$30,107
for 28 nights, 1 home
AU$1,075 per night
includes taxes & fees
Image gallery for Jungle Nook | Waterfront + Grill!
1010 out of 10, Exceptional, (4 reviews)
Exceptional
(4 reviews)
Jungle Nook | Waterfront + Grill!
Sarasota, FL
16% off
Price is AU$21,823
AU$21,823
for 28 nights, 1 home
AU$779 per night
includes taxes & fees
Peace of mindOur Book with Confidence Guarantee gives you 24/7 support
More quality timeFrom booking to staying, the whole process is simple and enjoyable
All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
More for lessMore space, more privacy, more amenities — more value