Houses for Rent in Siesta Key, FL

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270 Island Cir, Sarasota, FL, 34242

ABOUT THIS HOME
Siesta Key house for rent
Beautiful Annual fully furnished 4 bed/3 bath house with a bonus den available in Siesta Key , FL for $11,000 a month. This incredible home, at just a tad under 3300 square feet, has a three-way spli

1/50

$11,000/mo

4 beds3 baths3,277 sq ft

270 Island Cir, Sarasota, FL 34242

Available 10/01 • Laundry in unit • Dishwasher

4820 Featherbed Ln, Sarasota, FL, 34242

ABOUT THIS HOME
Siesta Key house for rent
Welcome to Bin Paradise! Enjoy your own little slice of paradise, just one mile from the breathtaking Siesta Key Beach! Avoid those pesky mosquitos while you relax in the screened-in lanai with your v

1/48

$10,000/mo

4 beds2 baths2,119 sq ft

4820 Featherbed Ln, Sarasota, FL 34242

Dogs welcome • Parking • A/C

614 Treasure Boat Way, Sarasota, FL, 34242

ABOUT THIS HOME
Siesta Key house for rent
AVAILABLE MAY and August 2024And MAY AND AUGUST 2025Beautiful house on Siesta Key with private pool (not heated) and generous space. 15 min walk to the beach!This charming 3-bedroom, 2-bathroom priva

1/22

$6,554/mo

3 beds2 baths1,821 sq ft

614 Treasure Boat Way, Sarasota, FL 34242

Laundry in unit • Parking • A/C

5310 Hidden Harbor Rd, Sarasota, FL, 34242

NEW 29 HRS AGO

ABOUT THIS HOME
Siesta Key house for rent
Luxury island living at its best on Siesta Key! This home is available now for annual lease. In the Hidden Harbor Community, the canopy covered paver roads lead you to this beautiful three bedroom, tw

1/32

$7,500/mo

3 beds2 baths— sq ft

5310 Hidden Harbor Rd, Sarasota, FL 34242

Pets welcome • Car-dependent • Swimming Pool

216 Tenacity Ln, Sarasota, FL, 34242

ABOUT THIS HOME
Siesta Key house for rent
There is nothing like this on Siesta Key available for rental on short term basis. This is truly a beach house, immaculate and beautiful! While there are many gulf front condos, and single family home

1/28

$34,995/mo

3 beds4 baths2,454 sq ft

216 Tenacity Ln, Sarasota, FL 34242

Dogs welcome • Parking • A/C

114 Avenida Veneccia, Sarasota, FL, 34242

ABOUT THIS HOME
Siesta Key house for rent
SEASONAL: Siesta Key Village Cottage...Tropical Oasis awaits you! Just 2 minute stroll to Siesta beach or to Siesta Village! Beautiful 2 bedroom, 2 bath cottage that sleeps 6/8 with serene fenced yard

1/29

$4,900/mo

2 beds1.5 baths957 sq ft

114 Avenida Veneccia, Sarasota, FL 34242

Pets welcome • Laundry in unit • Parking

5024 Commonwealth Dr, Sarasota, FL, 34242

ABOUT THIS HOME
Siesta Key house for rent
Open from December 15th to January 15th 2022. Rented from January 15th to March 31, 2023. Available all of April~ Extraordinary Key West style single family pool home is a 3 Bedroom 3.5 Bath positione

1/38

$10,710/mo

3 beds3.5 baths2,468 sq ft

5024 Commonwealth Dr, Sarasota, FL 34242

Parking • A/C • Dishwasher

339 Avenida de Paradisio, Sarasota, FL, 34242

ABOUT THIS HOME
Siesta Key house for rent
scape to luxury in our serene Sarasota home! ????Relax in your private oasis with a sparkling pool, hot tub, and expansive backyard. Enjoy the open-concept living area and three cozy bedrooms designed

1/17

$15,000/mo

3 beds2 baths1,716 sq ft

339 Avenida de Paradisio, Sarasota, FL 34242

Pets welcome • Parking • A/C

338 Avenida de Paradisio, Sarasota, FL, 34242

ABOUT THIS HOME
Siesta Key house for rent
An Ascendia Property! This spacious, fully-updated 3 bedroom/bathroom pool house is big enough for you, your friends, and your family...and it is ON A CANAL- you might be able to see dolphins and mana

1/45

$6,500/mo

3 beds3 baths1,735 sq ft

338 Avenida de Paradisio, Sarasota, FL 34242

Pets welcome • Laundry in unit • Parking

726 Birdsong Ln, Sarasota, FL, 34242

ABOUT THIS HOME
Siesta Key house for rent
WOW! Enjoy a little slice of heaven on the World Famous Siesta Key! This beautifully renovated turnkey 3 bedroom 2 bath, heated pool home, is just a short distance to the #1 rated beaches and the quai

1/54

$5,000/mo

3 beds2 baths1,822 sq ft

726 Birdsong Ln, Sarasota, FL 34242

Dogs welcome • Parking • A/C

5242 Winding Way, Sarasota, FL, 34242

ABOUT THIS HOME
Siesta Key house for rent
Adorable home for rent on Siesta Key. Less than one mile walk to the beach! Open floorplan with tasteful modern furnishings and huge back porch with no rear neighbors all on a quiet little circle neig

1/15

$3,000/mo

2 beds2 baths1,102 sq ft

5242 Winding Way, Sarasota, FL 34242

Dogs welcome • Parking • A/C

612 Canal Rd, Sarasota, FL, 34242

ABOUT THIS HOME
Siesta Key house for rent
ANNUAL RENTAL! Again, an annual rental (12 months) on Siesta Key - FURNISHED - Fantastic Location!!!! Immaculate & Adorable, Beachy ! This 2 bedroom 1 bath Beach Cottage- Walk to beach and the Village

1/6

$2,495/mo

2 beds1 bath1,129 sq ft

612 Canal Rd, Sarasota, FL 34242

Parking • A/C • Car-dependent

5238 Winding Way, Sarasota, FL, 34242

ABOUT THIS HOME
Siesta Key house for rent
AVAILABLE FOR 2025 SEASON!! Enjoy this beautiful 3-bedroom and 3-bathroom remodeled home on Siesta key, named the #1 Beach in the country! Brand new pool set to be completed fall 2023. We are LESS TH

1/65

$16,000/mo

3 beds3 baths1,620 sq ft

5238 Winding Way, Sarasota, FL 34242

Parking • A/C • Dishwasher

5151 Oakmont Pl, Sarasota, FL, 34242

ABOUT THIS HOME
Siesta Key house for rent
Annual Rental. Spacious 3 bedroom, 2 bath home on Siesta Key available for an annual rental. This unfurnished home is approx. 1.5 miles from one of the best beaches in the country - Siesta Key Beach!

1/21

$3,999/mo

3 beds2 baths1,953 sq ft

5151 Oakmont Pl, Sarasota, FL 34242

Pets welcome • Laundry in unit • Parking

5129 Sandy Cove Ave, Sarasota, FL, 34242

ABOUT THIS HOME
Siesta Key house for rent
An Ascendia Property! **Listing reflects off season rate. Monthly rental rates as follows: (JANUARY - APRIL - peak season: $18,000/month), (MAY - DEC - off season: $15,000/month). Available beginning

1/65

$15,000/mo

3 beds3 baths2,823 sq ft

5129 Sandy Cove Ave, Sarasota, FL 34242

Parking • A/C • Dishwasher

1250 N Portofino Dr Unit 203MARLIN, Siesta Key, FL, 34242

ABOUT THIS HOME
Siesta Key house for rent
AVAILABLE SEPTEMBER THROUGH DECEMBER, 2024. Off season rental $3500 p/m. BOOKED JANUARY THROUGH APRIL, 2025. This 2nd floor, completely renovated 2 bedroom, 2 full bath condo in Siesta Harbor with pri

1/21

$3,500/mo

2 beds2 baths929 sq ft

1250 N Portofino Dr Unit 203MARLIN, Siesta Key, FL 34242

Swimming Pool • Fitness Center

5024 Higel Ave, Sarasota, FL, 34242

ABOUT THIS HOME
Siesta Key house for rent
An Ascendia Property! Spectacular is an understatement when describing this updated Siesta Key CANAL FRONT POOL HOME. Once you step inside you'll notice an open-airy floor plan, beautifully decorated

1/59

$10,500/mo

3 beds3 baths1,999 sq ft

5024 Higel Ave, Sarasota, FL 34242

Parking • A/C • Car-dependent

417 Island Cir, Sarasota, FL, 34242

ABOUT THIS HOME
Siesta Key house for rent
Welcome to Caribbean Dream! Discover the epitome of island-style luxury as you step into this stunning retreat, nestled just moments away from the pristine shores of Siesta Key Beach. Renowned for its

1/59

$15,000/mo

4 beds3.5 baths2,972 sq ft

417 Island Cir, Sarasota, FL 34242

Pets welcome • Parking • A/C

130 Island Cir, Sarasota, FL, 34242

ABOUT THIS HOME
Siesta Key house for rent
Open April 2025 and 2024 off-season months August through October. Located on Palm Island on Siesta Key, this whimsical 3 bedroom, 3 bath bungalow will amaze and delight your senses! The attention to

1/35

$10,500/mo

3 beds3 baths2,206 sq ft

130 Island Cir, Sarasota, FL 34242

Pets welcome • Parking • A/C

432 Avenida De Mayo Unit A, Siesta Key, FL, 34242

ABOUT THIS HOME
Siesta Key house for rent
Available after 4/13/25 Whether you are looking for an ADVENTURE-PACKED GETAWAY or a TRANQUIL DESTINATION...look no further! This home offers and amazing and unique location! Just down the street from

1/32

$3,000/mo

2 beds1 bath772 sq ft

432 Avenida De Mayo Unit A, Siesta Key, FL 34242

Dogs welcome • Laundry in unit • Parking

211 Island Cir, Sarasota, FL, 34242

ABOUT THIS HOME
Siesta Key house for rent
AVAILABLE 2025 SEASON... 90 DAY MIN.AVAILABLE APR.-DEC. 2024...30 DAY MIN.Fabulous pool home located in one of Siesta Keys most sought after areas. Interior is nicely furnished. Take a late night swim

1/35

$14,000/mo

3 beds2 baths1,200 sq ft

211 Island Cir, Sarasota, FL 34242

Pets welcome • Parking • A/C

5226 Calle de Costa Rica, Sarasota, FL, 34242

ABOUT THIS HOME
Siesta Key house for rent
SIESTA KEY, Adorable 2/2 SFH with a private saltwater pool for the wonderful beach getaway. This house is located near by the award winning Siesta Key Beach(5 minutes away) and Siesta Village((two min

1/73

$6,000/mo

2 beds2 baths1,100 sq ft

5226 Calle de Costa Rica, Sarasota, FL 34242

Dogs welcome • Laundry in unit • Parking

5216 Calle de Costa Rica, Sarasota, FL, 34242

ABOUT THIS HOME
Siesta Key house for rent
An Ascendia Group Property! **Listing reflects off season rate. Monthly rental rates as follows: (JANUARY - APRIL - peak season: $8,600/month), (MAY - DEC - off season: $4,500/month). Available beginn

1/35

$4,500/mo

3 beds2 baths1,290 sq ft

5216 Calle de Costa Rica, Sarasota, FL 34242

Parking • A/C • Dishwasher

432 Avenida De Mayo Unit B, Siesta Key, FL, 34242

ABOUT THIS HOME
Siesta Key house for rent
**Pets welcome with a $250 refundable pet fee and $300 Non-refundable Pet Deposit. Must notify us prior to booking*** This FULLY REMODELED 1-BR, 1-BA COTTAGE accommodates up to THREE guests. It is IDE

1/19

$2,250/mo

1 bed1 bath460 sq ft

432 Avenida De Mayo Unit B, Siesta Key, FL 34242

Pets welcome • Parking • Somewhat walkable

657 Calle de Peru, Sarasota, FL, 34242

ABOUT THIS HOME
Siesta Key house for rent
An Ascendia Property! **Listing reflects peak season rate. Monthly rental rates as follows: (JANUARY - APRIL - peak season: $8,500/month), (MAY - DEC - off season: $5,500/month). The rental rate in th

1/32

$8,500/mo

3 beds2 baths1,139 sq ft

657 Calle de Peru, Sarasota, FL 34242

Pets welcome • Parking • A/C

5519 Azure Way, Sarasota, FL, 34242

ABOUT THIS HOME
Siesta Key house for rent
Sprawling 4 bed. plus Waterfront/Pool/Spa home is only 4 min. to World famous Siesta Key Beach!!!Tucked away on the little "island "of Azure Way you are afforded privacy with water views . Perfect for

1/26

$12,000/mo

4 beds3 baths2,460 sq ft

5519 Azure Way, Sarasota, FL 34242

Parking • A/C • Car-dependent

5516 Avenida del Mare, Sarasota, FL, 34242

ABOUT THIS HOME
Siesta Key house for rent
An Ascendia Group Property! **Listing reflects mid-season rate. Monthly rental rates as follows: (JANUARY - APRIL - peak season: $15,000/month), (MAY - JUNE - mid-season: $10,000/month), (JULY - SEPTE

1/60

$10,000/mo

3 beds2 baths2,259 sq ft

5516 Avenida del Mare, Sarasota, FL 34242

Pets welcome • Parking • A/C

5740 Midnight Pass Rd Unit 303F, Siesta Key, FL, 34242

ABOUT THIS HOME
Siesta Key house for rent
Yes!!! Available August 1 2024 through October 31 2024 - Enjoy Full Gulf of Mexico Views for the entire month in Paradise of Siesta Key Enjoypanoramic views of the #1 beach in the USA, Siesta Key! Th

1/51

$10,500/mo

2 beds2 baths1,337 sq ft

5740 Midnight Pass Rd Unit 303F, Siesta Key, FL 34242

Parking • A/C • Car-dependent

5557 Shadow Lawn Dr, Sarasota, FL, 34242

ABOUT THIS HOME
Siesta Key house for rent
Want to be able to walk three blocks to Siesta Key beach? Vacation here and you can! This private 3 bedroom 2 1/2 bathroom pool home is warm and inviting and lushly landscaped. There is large screen

1/40

$9,000/mo

3 beds2.5 baths2,189 sq ft

5557 Shadow Lawn Dr, Sarasota, FL 34242

Pets welcome • Parking • A/C

5577 Contento Dr, Sarasota, FL, 34242

ABOUT THIS HOME
Siesta Key house for rent
An Ascendia Property! **Listing reflects off season rate. Monthly rental rates as follows: (JANUARY - APRIL - peak season: $12,000/month), (MAY - DEC - off season: $5,000/month). The rental rate in th

1/41

$5,000/mo

2 beds2 baths1,424 sq ft

5577 Contento Dr, Sarasota, FL 34242

Pets welcome • Parking • A/C

5719 Riegels Point Rd, Sarasota, FL, 34242

ABOUT THIS HOME
Siesta Key house for rent
Amazing opportunity, to find a rental like this hidden gem! Live your best life with the island lifestyle and enjoy the best of both worlds with the beach and boating. DEEP SAILBOAT WATER BOATING or t

1/72

$18,000/mo

5 beds4.5 baths3,714 sq ft

5719 Riegels Point Rd, Sarasota, FL 34242

Pets welcome • Parking • A/C

5572 Cape Aqua Dr, Sarasota, FL, 34242

ABOUT THIS HOME
Siesta Key house for rent
Looking for an annual rental on Siesta Key. This is the one!!! Two block walk to the beach.. quick walk to the village. Very clean and well maintained Siesta Key pool home. The home is fenced in and p

1/1

$5,000/mo

4 beds3 baths1,860 sq ft

5572 Cape Aqua Dr, Sarasota, FL 34242

Pets welcome • A/C • Car-dependent

5640 Cape Leyte Dr, Sarasota, FL, 34242

ABOUT THIS HOME
Siesta Key house for rent
An Ascendia Property! **Listing reflects off season rate. Monthly rental rates as follows: (JANUARY - APRIL - peak season: $11,500/month), (MAY - DEC - off season: $8,000/month). Available beginning N

1/58

$8,000/mo

3 beds2 baths2,002 sq ft

5640 Cape Leyte Dr, Sarasota, FL 34242

Pets welcome • A/C • Dishwasher

144 Garden Ln, Sarasota, FL, 34242

ABOUT THIS HOME
Siesta Key house for rent
Beautiful single family home One block to Shell Beach!! This quaint ranch with lucious vegitation on a quiet street is fenced in for extra privacy. 3 bedrooms and 2.5 baths, outdoor shower, bright liv

1/19

$5,000/mo

4 beds2.5 baths1,702 sq ft

144 Garden Ln, Sarasota, FL 34242

A/C • Car-dependent • Minimal transit

301 Avenida Madera Unit B, Siesta Key, FL, 34242

ABOUT THIS HOME
Siesta Key house for rent
Current Availability: 4/6/2025 This is THE location! Just steps to the Village cafe and the Hub Bar and Grille, and a shortwalk to the beach. Our 2 bedroom 2 bath beautifully updated property offers a

1/18

$12,600/mo

2 beds2 baths1,144 sq ft

301 Avenida Madera Unit B, Siesta Key, FL 34242

Pets welcome • Parking • A/C

95 Sandy Hook Rd, Sarasota, FL, 34242

ABOUT THIS HOME
Siesta Key house for rent
6 Month Minimum... Private Beach! Private Beach! Private Beach! SANDY HOOK's "BEACH-COMER COTTAGE" Available NOW!!!!!!! IN SANDY HOOK, DIRECTLY ON THE GULF AT BIG PASS. ENJOY YOUR OWN private Beach!!!

1/14

$30,000/mo

3 beds3 baths3,395 sq ft

95 Sandy Hook Rd, Sarasota, FL 34242

Parking • A/C • Car-dependent

1257 S Portofino Dr Unit 36, Sarasota, FL, 34242

ABOUT THIS HOME
Siesta Key house for rent
OPEN JANUARY, FEBRUARY 2025 DUE TO A CANCELLATION. Available August 1, 2024 - February 28, 2025. Siesta Harbor is surrounded by the Intracoastal Waterway with Harbor and Bay views from every unit. Thi

1/72

$4,400/mo

1 bed2 baths780 sq ft

1257 S Portofino Dr Unit 36, Sarasota, FL 34242

Parking • A/C • Dishwasher

1257 S Portofino Dr Unit 38ALBA, Sarasota, FL, 34242

ABOUT THIS HOME
Siesta Key house for rent
DECEMBER SPECIAL *** $3,900! Welcome to Siesta Harbor! Siesta Key Turnkey furnished ground floor 2/2 condo. Remodeled with beautiful kitchen, new stainless steel appliances, granite countertops, remod

1/96

$3,900/mo

2 beds2 baths929 sq ft

1257 S Portofino Dr Unit 38ALBA, Sarasota, FL 34242

Parking • A/C • Dishwasher

5740 Midnight Pass Rd Unit 207F, Siesta Key, FL, 34242

ABOUT THIS HOME
Siesta Key house for rent
Available Now... Gulf and Bay Club Annual Rental Opportunity... Enjoy basking in theglow of gorgeous sunsets on Siesta Key in this 2-bedroom/2-bath condominium located in the well-known Gulf & Bay Cl

1/36

$3,600/mo

2 beds2 baths1,340 sq ft

5740 Midnight Pass Rd Unit 207F, Siesta Key, FL 34242

Parking • A/C • Patio/Balcony

22 Sandy Cove Rd, Sarasota, FL, 34242

ABOUT THIS HOME
Siesta Key house for rent
An Ascendia Property! **Listing reflects peak season rate. Available for the month of January 2025, for a 30-night minimum stay and March 2025 for a 30-night minimum stay or longer. If you rent for lo

1/60

$6,700/mo

1 bed1 bath532 sq ft

22 Sandy Cove Rd, Sarasota, FL 34242

Dogs welcome • Parking • A/C

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Based on information submitted to the MLS GRID as of Mon Sep 09 2024. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.

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