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Vacation Rentals in Siesta Key
Find the perfect Cheap Vacation Rentals, Vacation Rental Deals and Luxury Villas in Florida, Colorado, California, Hawaii, South Carolina, Outerbanks and more! Get Last Minute Deals on Beach Houses, Ski cabins, Family Vacation Rentals and Pet Friendly Vacation Rentals now at How2Vacation.com!
Featured Vacation Rental Companies
Sunnyside Properties - Siesta Key Vacation Rental Accommodations
A unique collection of family owned and operated premier rental units. From Gulf front units at Turtle Beach, to a townhouse across from the powder white sand of Siesta Key Public Beach, to some terrific properties in the heart of Siesta Village. One-bedroom units for a romantic getaway or 14-bedrooms for a family vacation. Whatever you need...we can help! Click on the link below to go to our website for additional information about our properties and services. Phone Number: 888-786-6979 (or 940-455-7361)
Siesta 4 Rent Vacation Rentals
Siesta 4 Rent offers: Studios to 5 Bedroom homes here on Beautiful Siesta Key Beach. According to Doctor Beach, Siesta Key was voted the #1 Best Beach in Florida. We have served Siesta Key since 1997, and being a family run business offer excellent service to our guests. Look at our website for all the property pictures, rates and availability. You may also book online at www.siesta4rent.comPhone Number: 941-349-5500
Vacation Rentals in Siesta Key
Siesta Dunes - Siesta Key 105
- 2 Bedrooms, 2 Bathrooms, Sleeps 6
- Comfortable ground floor condo, has new kitchen, glassed in porch and patio
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- $950
weekly
Palm Aire - Sarasota
- 2 Bedrooms, 2 Bathrooms, Sleeps 4
- Beautiful town home available for seasonal rental. Nearby golf in this popular location close to Bradenton and Sarasota both. Minutes…
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- $3000
monthly
Sea Village - Siesta Key G1
- 2 Bedrooms, 2 Bathrooms, Sleeps 4
- Beautiful unit in desirable Sea Village. Outstanding views of Big Pass and Gulf. Unit is upgraded inside with new dishwasher…
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- Contact Owner
Sea Plume Way - Siesta key
- 4 Bedrooms, 3 Bathrooms, Sleeps 8
- Gorgeous home on the intercoastal. 4th sleeping area separate from house, and includes living area. Perfect home for vacationer with…
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- $7500
monthly
Turtle Bay - Siesta Key 104A
- 2 Bedrooms, 2 Bathrooms, Sleeps 4
- One of the nicest units you will see! Lovely complex with docks, pool, tennis and beach right across the street.…
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- Contact Owner
Bay Tree - Siesta key 202C
- 2 Bedrooms, 2 Bathrooms, Sleeps 6
- Gorgeous view of the Sarasota Bay. Private gulf access across the street and private cabana to store your beach chairs.…
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- $800
weekly
Siesta Breakers - Siesta Key 604
- 2 Bedrooms, 2 Bathrooms, Sleeps 4
- Spend your vacation directly on the beach. Great sunsets. Shopping and restaurants nearby.
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- Contact Owner
Bay Tree - Siesta key 105B
- 1 Bedroom, 1 Bathroom, Sleeps 4
- This one bedroom has great view of bay and is lovely. Equipped with all you need for a great vacation.…
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- $2600
monthly
Island Reef - Siesta Key 506C
- 2 Bedrooms, 2 Bathrooms, Sleeps 6
- Nicely decorated unit with gulf view. Guest BR has 2 Queen beds.
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- $5000
monthly
Siesta Dunes - Siesta Key 106
- 2 Bedrooms, 2 Bathrooms, Sleeps 4
- This condo community is situated on 13 acres of gulf front property. This beautiful condo has hardwood floors, lovely furnishings…
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- Contact Owner
The Inlets - Siesta Key #36
- 2 Bedrooms, 2 Bathrooms, Sleeps 4
- This condo overlooks beautiful Turtle Lagoon on south Siesta Key. Price subject to change, drastic discounted rates for off season.
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- $3200
monthly
The Inlets - Siesta Key/The Inlets #33
- 2 Bedrooms, 2 Bathrooms, Sleeps 4
- This condo has beautiful view of Turtle lagoon on south end of Siesta Key.
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- Contact Owner
Siesta Breakers - Siesta Key 208
- 2 Bedrooms, 2 Bathrooms, Sleeps 7
- Great views from the living room and balcony of the pool and beach.
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- Contact Owner
Siesta Breakers - Siesta Key Penthouse 517
- 3 Bedrooms, 3 Bathrooms, Sleeps 7
- Gorgeous views from this direct gulf front 2 story condo. Lots and lots of living space!
- from
- Contact Owner
Harbor Towers - Sarasota
- 1 Bedroom, 1 Bathroom, Sleeps 4
- Tasteful and comfortable, this one bedroom condo has everything you want on vacation. Short walk to the beach, beautiful tennis…
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- Contact Owner
Midnight Cove - Sarasota
- 2 Bedrooms, 2 Bathrooms, Sleeps 6
- Watch the boats go by in this spacious condo located right on the bay. Beach access is directly across street.…
- from
- Contact Owner
"Island" 368 Canal Rd.
- 1 Bedroom, 1 Bathroom, Sleeps 2
- 1 Bedroom, King Bed, Queen sleep sofa, ("The Island" is our Honeymoon suite, has a fireplace and open deck) Deluxe…
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- Contact Owner
"The Magnolia House" 317 Canal Rd.
- 2 Bedrooms, 2 Bathrooms, Sleeps 0
- 2 Bedroom, 2 Bath, with king beds and sleeper sofas, fully equipped kitchen and laundry room. Walking distance to Siesta…
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- Contact Owner
321 Canal Rd.
- 2 Bedrooms, 2 Bathrooms, Sleeps 4
- Downstairs 2 Bedroom / 2 Bath, Washer & dryer. 2 TV's covered parking 1 King Bed / 2 Twin's Sleeps…
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- Contact Owner
"Key Largo" 603 Beach Rd.
- 1 Bedroom, 1 Bathroom, Sleeps 2
- 1 Bedroom, 2nd floor, king bed, queen sleeper sofa. Across the street from beach. Walking distance to Siesta Key Village.…
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- Contact Owner
"The Sandpiper" 5830 Midnight Pass Rd.
- 1 Bedroom, 0 Bathroom, Sleeps 1
- 1 Bedroom King Bed, Double Sleeper Sofa, Patio. Pools (3), Shuffle Board, Beach Access, WIFI, 2 TVs
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- Contact Owner
"Peaceful Waters" 6151 Midnight Pass Rd.
- 1 Bedroom, 1 Bathroom, Sleeps 4
- 1 Bedroom - 1 Bath, upstairs, king bed, queen and twin sleeper sofas. Opens to a screen lanai with canal…
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- Contact Owner
"Hibiscus" 368 Canal Rd.
- 1 Bedroom, 0 Bathroom, Sleeps 2
- 1 Bedroom, King Bed, queen sleeper, ground level. Pet Friendly, WIFI. No pool
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- $435
weekly
"Menorca" 378 Canal Rd
- 1 Bedroom, 1 Bathroom, Sleeps 1
- Studio/Efficiency, Queen Bed, Next to pool. Pool Access, WIFI
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- $435
weekly
Bay Tree - Siesta Key 305 A
- 2 Bedrooms, 2 Bathrooms, Sleeps 6
- Awesome, panoramic gulf view from this well appointed 2/2 condo. Lovely complex with pool, and rental includes use of private…
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- Contact Owner
Tortuga - Siesta Key 106C
- 2 Bedrooms, 2 Bathrooms, Sleeps 4
- Newly updated unit in gulf side condominium. Heated indoor/outdoor pool. Docks available across the street.
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- $3800
monthly
Kensingtron Park - Sarasota
- 2 Bedrooms, 2 Bathrooms, Sleeps 4
- This is a beautiful home, totally redone. Large tile, granite, stainless in kit. and bath. Large fenced yard. Crown molding,…
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- Contact Owner
Sea Club II - Siesta Key 8A
- 2 Bedrooms, 2 Bathrooms, Sleeps 4
- Beautiful heated pool with a view of the ICW. Access to beach across street.
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- Contact Owner
Island Reef - Siesta Key 106 A
- 2 Bedrooms, 2 Bathrooms, Sleeps 6
- Large first floor condo right on beach with office
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- $5000
monthly
Harbor Towne - Siesta Key 1273
- 2 Bedrooms, 2 Bathrooms, Sleeps 4
- Ground floor condo at the nautical ambiance at Harbour Towne. This unit has a direct view of boast basin and…
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- $2500
monthly
Trinity Village Condos - SARASOTA 224
- 2 Bedrooms, 2 Bathrooms, Sleeps 4
- Darling condo that can be rented seasonal or annually
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- Contact Owner
Arbor Greens - Stoneybrook 2314
- 2 Bedrooms, 2 Bathrooms, Sleeps 4
- LOVELY ARBOR GREENS CONVINCING MODEL, UPDATED WITHIN THE PAST 2 YEARS. NON-GOLF SECTION, BUT COUNTRY CLUB MEMBERSHIP AVAILABLE. 2/2 PLUS…
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- Contact Owner
Stoneybrook - Sarasota 2105
- 2 Bedrooms, 2 Bathrooms, Sleeps 6
- VERY NICE UNIT WITH GREAT VIEW OF #2 TEE AND FAIRWAY. STONEY BROOK AMENITIES INCLUDE: STATE OF THE ART CLUBHOUSE,…
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- $189900
monthly
The Meadows - Sarasota
- 3 Bedrooms, 2 Bathrooms, Sleeps 6
- Beautiful villa overlooks the golf course. Many amenities at this spacious and tastefully furnished property. 3 month minimum rental, and…
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- $3600
monthly
Midnight Pass Rd - Siesta Key
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- 2 Bedrooms, 2 Bathrooms, Sleeps 6
- This duplex has 2 stories for each side. Shared washer and dryer with other side. Pool amenities at neighboring resort.…
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- Contact Owner
Midnight Pass Rd - Siesta Key
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- 2 Bedrooms, 2 Bathrooms, Sleeps 5
- Each side of this duplex is 2 stories. Walk to shopping, beach, and restaurants. Shared washer and dryer with other…
- from
- Contact Owner
Island Reef - Siesta Key 305A
- 2 Bedrooms, 2 Bathrooms, Sleeps 6
- Great view of Turtle Beach from this beautiful condo and community. Rates may change, please e-mail for current monthly rate.
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- $5100
monthly
Villa Maria - Sarasota A
- 2 Bedrooms, 2 Bathrooms, Sleeps 6
- Lovely and cozy 2 bedroom condo 1/3 mile from Siesta Beach. Season rates are $950 a week. Cleaning fee may…
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- Contact Owner
Bay Tree - Sarasota 207 A
- 2 Bedrooms, 2 Bathrooms, Sleeps 6
- Gorgeous remodeled gulf front condo! Upgraded and large kitchen. Each bedroom has a queen bed and there is a pull…
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- $4200
monthly
Calle de la Siesta - Siesta Key
- 2 Bedrooms, 2 Bathrooms, Sleeps 4
- Unique 2br, 2b, 2 story home.......walk to beach and very popular Siesta Key Village.
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- $2200
monthly
"Hummingbird Unit A"
- 2 Bedrooms, 2 Bathrooms, Sleeps 4
- 2 Bd/2 Bath, 2 King beds, Queen sleeper sofa, 1 screened porch
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- $787
weekly
"Crescent" 5259 Calle Menorca
- 1 Bedroom, 0 Bathroom, Sleeps 0
- 1 Bedroom, King Bed, Queen sleep sofa, Free Standing Cottage, screened porch. Pet Friendly, WIFI, No Pool
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- $583
weekly
Siesta Beach Tree House
- 4 Bedrooms, 3 Bathrooms, Sleeps 10
- This fabulous 'Siesta Beach Treehouse' is located just one block from the beach. No need to drive or park. It…
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- $1800
weekend
Custom Waterfront Estate
- 4 Bedrooms, 3 Bathrooms, Sleeps 12
- Description: Susan and I built and designed this spacious, modern custom estate home to retire in. Life has led us…
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- $1800
weekend
Bay Tree - Siesta Key
- 2 Bedrooms, 2 Bathrooms, Sleeps 6
- Well appointed 4th floor unit with direct gulf view of Turtle Beach! Lovely established community and on the quiet end…
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- Contact Owner
Stoneybrook - Stoneybrook Clubside 3201 3201
- 2 Bedrooms, 2 Bathrooms, Sleeps 4
- Beautiful 2/2 with gorgeous view of #3 tees and most of fairway #3. Lake views also. Golf membership includes fitness,…
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- Contact Owner
Bay Tree - Siesta Key 201A
- 2 Bedrooms, 2 Bathrooms, Sleeps 4
- Immaculate 2nd floor condo with view of pool, and gulf behind. Unit comes with private cabana for storing beach accessories.…
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- Contact Owner
Crescent Arms - Siesta Key Villa 14
- 2 Bedrooms, 2 Bathrooms, Sleeps 6
- Spacious villa close to pool and beach. This unit comes with garage, and can readily accomodate space for a large…
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- Contact Owner
Siesta Shores - Siesta Key 4
- 1 Bedroom, 1 Bathroom, Sleeps 2
- Darling one bedroom cottage and directly across the street from easy beach access. Just a few blocks from Siesta Key…
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- Contact Owner
