$17,000 Per Month
- 5 Beds
- 5 Baths
- 3,126 Sq Ft
- House for Rent
5624 Cape Leyte Dr, Sarasota, FL 34242
5624 Cape Leyte Dr, Sarasota, FL 34242$17,000 Per Month
5624 Cape Leyte Dr, Sarasota, FL 34242
5624 Cape Leyte Dr, Sarasota, FL 34242$4,018
Total Monthly Price
5855 Midnight Pass Rd Unit SI ID1578366P, Siesta Key, FL 34242
The advertised rate of $4,018/month is the lowest available price, based on a 30 day(s) stay with a move-in date of August 23, 2026.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can be
$9,500 Per Month
6415 Midnight Pass Rd Unit 602, Sarasota, FL 34242
6415 Midnight Pass Rd Unit 602, Sarasota, FL 34242$11,685
Total Monthly Price
1179 Lake House Cir Unit SI ID1578383P, Siesta Key, FL 34242
The advertised rate of $11,685/month is the lowest available price, based on a 30 day(s) stay with a move-in date of August 24, 2026.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can be
$22,000 Per Month
3939 Higel Ave, Sarasota, FL 34242
3939 Higel Ave, Sarasota, FL 34242$9,240
Total Monthly Price
338 Avenida de Paradisio Unit SI FL1-ID1590869P, Siesta Key, FL 34242
The advertised rate of $9,240/month is the lowest available price, based on a 30 day(s) stay with a move-in date of August 24, 2026.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can be
$15,000 Per Month
1308 Old Stickney Point Rd Unit WP3, Sarasota, FL 34242
1308 Old Stickney Point Rd Unit WP3, Sarasota, FL 34242$5,846
Total Monthly Price
1400 Cove II Place Unit SI FL2-ID1578373P, Sarasota, FL 34242
The advertised rate of $5,846/month is the lowest available price, based on a 30 day(s) stay with a move-in date of August 24, 2026.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can be
$1,971
Total Monthly Price
6040 E Peppertree Way Unit SI FL2-ID1591458P, Siesta Key, FL 34242
The advertised rate of $1,972/month is the lowest available price, based on a 30 day(s) stay with a move-in date of August 23, 2026.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can be
$2,639
Total Monthly Price
60 Avenida Veneccia Unit SI ID1591521P, Siesta Key, FL 34242
The advertised rate of $2,639/month is the lowest available price, based on a 1 month(s) stay with a move-in date of September 15, 2026.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can
$26,975
Total Monthly Price
339 Avenida de Paradisio Unit SI ID1578371P, Siesta Key, FL 34242
The advertised rate of $26,976/month is the lowest available price, based on a 1 month(s) stay with a move-in date of April 3, 2027.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can be
$5,368
Total Monthly Price
5760 Midnight Pass Rd Unit SI ID1545688P, Siesta Key, FL 34242
The advertised rate of $5,369/month is the lowest available price, based on a 1 month(s) stay with a move-in date of November 1, 2026.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can
$2,479
Total Monthly Price
60 Avenida Veneccia Unit SI FL2-ID1591442P, Siesta Key, FL 34242
The advertised rate of $2,480/month is the lowest available price, based on a 1 month(s) stay with a move-in date of September 7, 2026.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can
$7,890
Total Monthly Price
6327 Midnight Cove Rd Unit SI ID1578382P, Siesta Key, FL 34242
The advertised rate of $7,891/month is the lowest available price, based on a 30 day(s) stay with a move-in date of August 24, 2026.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can be
$5,304
Total Monthly Price
60 Avenida Veneccia Unit SI ID1591490P, Siesta Key, FL 34242
The advertised rate of $5,305/month is the lowest available price, based on a 30 day(s) stay with a move-in date of January 2, 2027.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can be
$5,564
Total Monthly Price
6265 Midnight Pass Rd Unit SI FL2-ID1545741P, Siesta Key, FL 34242
The advertised rate of $5,564/month is the lowest available price, based on a 30 day(s) stay with a move-in date of July 18, 2027.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can be
$6,789
Total Monthly Price
5885 Midnight Pass Rd Unit SI FL2-ID1546103P, Siesta Key, FL 34242
The advertised rate of $6,789/month is the lowest available price, based on a 1 month(s) stay with a move-in date of September 30, 2026.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can
$7,706
Total Monthly Price
349 Avenida Madera Unit SI ID1578360P, Siesta Key, FL 34242
The advertised rate of $7,706/month is the lowest available price, based on a 30 day(s) stay with a move-in date of August 23, 2026.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can be
$3,996
Total Monthly Price
1500 Midnight Cove II Place Unit SI ID1591484P, Siesta Key, FL 34242
The advertised rate of $3,996/month is the lowest available price, based on a 30 day(s) stay with a move-in date of August 24, 2026.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can be
$8,272
Total Monthly Price
60 Avenida Veneccia Unit SI FL2-ID1591445P, Siesta Key, FL 34242
The advertised rate of $8,273/month is the lowest available price, based on a 1 month(s) and 2 day(s) stay with a move-in date of February 1, 2027.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed
$5,773
Total Monthly Price
1037 W Peppertree Dr Unit SI FL3-ID1546456P, Sarasota, FL 34242
The advertised rate of $5,774/month is the lowest available price, based on a 30 day(s) stay with a move-in date of August 24, 2026.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can be
$7,548
Total Monthly Price
324 Avenida Madera Unit SI ID1578359P, Siesta Key, FL 34242
The advertised rate of $7,549/month is the lowest available price, based on a 1 month(s) stay with a move-in date of September 7, 2026.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can
$2,500
Total Monthly Price
3985 Roberts Point Rd Unit Siesta Key Apartment, Siesta Key, FL 34242
Fully furnished, intercoastal waterfront detached garage apartment on one of the most desirable streets on far north end of Siesta Key. Could be set up as 1 or 2 bedroom. Month to month lease available, discount for longer commitments. All standard services and utilities included in rent price. Price includes one bay of a two car garage for covered parking. Unlimited pool and dock use 7a-9p
$4,000 Per Month
1250 N Portofino Dr Unit 301, Sarasota, FL 34242
Gorgeous updated 2 BR, 2 Bath condo on a Canal Available Now Through December 31st or April 1, 2027 and beyond! Sailboat water, fishing pier, private beach access directly across the street. Beautifully furnished vacation home with water view from main bedroom, Livingroom and lanai. End unit so more light and larger kitchen space. Everything you will need for your beach vacation. Amenities
Rosie DiPasquale JUDITH GUZZI & ASSOCIATES LLC
$13,770
Total Monthly Price
5165 Sandy Cove Ave Unit SI ID1578384P, Siesta Key, FL 34242
The advertised rate of $13,770/month is the lowest available price, based on a 1 month(s) stay with a move-in date of September 13, 2026.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it
$9,500 Per Month
1055 W Peppertree Dr Unit 603AA, Sarasota, FL 34242
Just steps from Crescent Beach, this unit has 2 bedrooms and 2 full bathrooms. Complete with a full kitchen supplied with the necessary items you need for cooking (pots/pans, dishes, utensils) and a 12-cup standard coffee maker and has a Keurig.The formal dining area has seating for 6. This flows into the living area that has comfortable couch seating, a fan, access to the lanai and a 55"
Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE
$9,304
Total Monthly Price
5780 Midnight Pass Rd Unit SI ID1591412P, Siesta Key, FL 34242
The advertised rate of $9,305/month is the lowest available price, based on a 1 month(s) stay with a move-in date of November 19, 2026.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can
$7,400 Per Month
1338 Siesta Bayside Dr Unit 1338C, Sarasota, FL 34242
Indulge in the ultimate coastal lifestyle with this charming 2-bedroom, 2-bathroom first-level condo in the heart of Gulf & Bay Club Bayside on Siesta Key, Florida. As you enter, the coastal vibes welcome you into a thoughtfully designed space adorned with beach-inspired decor and sunlit interiors. Step through the sliding glass doors onto your private screened-in lanai, where the gentle
Andy Moore GULF COAST REALTY & MANAGEMENT
$11,637
Total Monthly Price
5613 Cape Leyte Dr Unit SI ID1591441P, Siesta Key, FL 34242
The advertised rate of $11,637/month is the lowest available price, based on a 30 day(s) stay with a move-in date of August 25, 2026.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can be
$7,500 Per Month
5830 Midnight Pass Rd Unit 54, Sarasota, FL 34242
Discover your own slice of paradise at Jamaica Royale! This beautifully updated and tastefully decorated 1-bedroom, 1-bathroom condo is just steps from the refreshing waters of heated Pool #1 and a short stroll to the world-famous, powdery whit e sands of Siesta Key Beach. Enjoy the convenience of your assigned covered parking space located right outside your door.Inside, the condo is
Robert Bevington SHOWTIME REALTY
$5,213
Total Monthly Price
4879 Commonwealth Dr Unit SI ID1591481P, Siesta Key, FL 34242
The advertised rate of $5,214/month is the lowest available price, based on a 30 day(s) stay with a move-in date of August 24, 2026.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can be
$5,970 Per Month
6020 Midnight Pass Rd Unit 12, Sarasota, FL 34242
This beautifully updated Villa 12 at Aloha Kai is ready to give the perfect beach getaway. Just steps from the villa, you can stroll along the beach with your morning coffee and return in time for a breathtaking sunset. The screened porch provides a lovely spot to enjoy the balmy afternoon breezes in comfort. Located on Siesta Key, a popular barrier island on Florida’s West Coast, Aloha Kai is a
Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE
$11,340
Total Monthly Price
3951 Roberts Point Rd Unit SI ID1591435P, Siesta Key, FL 34242
The advertised rate of $11,340/month is the lowest available price, based on a 30 day(s) stay with a move-in date of August 23, 2026.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can be
$8,500 Per Month
5216 Calle de Costa Rica, Sarasota, FL 34242
Listing reflects peak season rate. Available months: July 2026, August 2026, October 2026, November 2026 December 2026, January 2027, March 2027 and April 2027. Imagine a place where the warm sunshine beckons you to relax, unwind, and truly escape the everyday. Welcome to House of the Sun, a delightful 3-bedroom, 2-bathroom island bungalow meticulously designed for your ultimate Siesta Key
Beth Dilley ASCENDIA REAL ESTATE
$2,395 Per Month
5649 Midnight Pass Rd Unit 803, Siesta Key, FL 34242
SIESTA KEY LIVING!! This unfurnished 2 bed/2 bath residence has a remodeled kitchen with faux granite countertops, a new microwave, dishwasher, fans throughout, tile floors throughout, and a screened porch. Enjoy the beautifully manicured 7 acres with live oaks, palm trees, tropical flowers, and flowering shrubs. A courtyard path leads to boat docks in a sheltered marina that connects to the
$4,500 Per Month
5253 Avenida Del Mare, Sarasota, FL 34242
Listing price reflects off season rate, in season rates will be higher. Escape to paradise at this beautiful vacation retreat located on the coveted north end of Siesta Key. Nestled in a quiet residential neighborhood, this spacious and elegantly appointed home offers the perfect blend of privacy, comfort, and convenience—just minutes from world-famous Siesta Key Beach and Siesta Key Village.
Beth Dilley ASCENDIA REAL ESTATE
$2,200 Per Month
212 Pass Key Rd, Siesta Key, FL 34242
Oceanview unit in Siesta Key
$9,500 Per Month
1389 Siesta Bayside Dr Unit 1389F, Sarasota, FL 34242
Indulge in opulent coastal living with this luxurious 3-bedroom, 2-bathroom second-floor, two-level condo in the prestigious Gulf & Bay Club Bayside on Siesta Key, Florida. This impeccably designed residence offers a unique and spacious layout, with the primary bedroom occupying its own private floor for the utmost in privacy and elegance.As you enter, the living room, dining room, and
Andy Moore GULF COAST REALTY & MANAGEMENT
Call for Price
797 Beach Rd Unit 305, Sarasota, FL 34242
Welcome to Your Slice of Paradise – Crescent Royale 3053D Tour URL: AVAILABILITY, PRICING and BOOKING HERE: Note: 7 day minimum required booking.Fully remodeled and infused with a modern coastal flair, this deluxe one-bedroom, one-bath condo is the ultimate Siesta Key escape. With over 820 square feet of bright, open living space, you’ll find all the bells and
$7,050 Per Month
1055 W Peppertree Dr Unit 703AA, Sarasota, FL 34242
This luxurious condo is in a Gulf-side High-rise and is located on the 7th floor. This condo has 2 bedrooms and 2 full bathrooms.A fully equipped kitchen awaits you with cabinet lighting, a ceiling fan and a breakfast bar for 3. It is supplied with the necessary items you need for cooking (pots/pans, dishes, utensils) and a 12-cup standard coffee maker and a Keurig.The formal dining room
Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE
Showing Results 1 - 40, Page 1 of 7
Siesta Key, located on a barrier island off the coast of Sarasota, Florida, is renowned for its pristine Siesta Beach, which boasts white quartz sand and was ranked the No. 2 beach in the United States by TripAdvisor in 2023. The island spans 8 miles, with most homes and activities concentrated on the north end, particularly around the downtown area and the quaint village district. This area features a variety of unique shops, restaurants, and nightclubs, enhancing the island's vibrant local flavor. Residents enjoy great walkability and a convenient trolley service that traverses the island. Housing options on Siesta Key include modern styles, Spanish Mediterraneans, ranch-style homes, cozy cottages, coastal-style homes, and several condominium complexes with amenities like pools and tennis courts. Dining highlights include the Toasted Mango Café, Miguel’s, and Captain Curt’s Crab & Oyster Bar, located roughly 3 miles south along the Midnight Pass corridor. The island also offers attractions such as Crescent Beach and Turtle Beach, with facilities for tennis, volleyball, and fishing. Education is served by the highly rated Out-of-Door Academy on the island and top-rated Sarasota County Schools, including Southside Elementary, Brookside Middle, and Riverview High. Siesta Key is accessible via the Siesta Key North Bridge and the Stickney Point Bascule Bridge, with the Sarasota Bradenton International Airport just 10 miles away.
There are currently 251 homes available for rent in Siesta Key, FL. The median rent is $5,500 per month, with condos at $5,500.
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Number of Homes for Rent
251
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Median Rent
$5,500
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Median Condo Rent
$5,500
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