Vacation Rentals By Owner In Siesta Key, FL

Villa

Jamaica Royale #11- Everything NEW, 3 Heated Pools, Right on the Beach!

Siesta Key, Florida, United States

Bed

Bath

Sleeps

Exceptional(10)

$199.59

Welcome to Bay Oaks, your Siesta Key Condominium complex featuring spacious condos for you and your family to vacation right in the heart of the action and entertainment Siesta Key Florida has to offer. This community offers complimentary covered parking with your rental for one car, community swimming pool, and other amenities to make your stay a wonderful experience!brbrThis unit is a 2 Bedroom, 1 Bathroom condo located on the ground floor of building D. Ground floor access makes it easy to get to both for those young and old, with no stairs or elevator to have to use to access. The condo is tastefully updated with everything you need to make your stay spectacular, including small kitchen with oven, stovetop, dishwasher, microwave, and basic kitchen utensils needed for those dinners at home. The living room has plenty of seating for the occupancy of the home, along with a dining room table for comfort. Attached to the living room is a fully covered patio, completely screened in, allowing you to enjoy the weather of Sunny Florida without being bothered by pesky mosquitoes while trying to relax. brbrThe 2 bedrooms feature both a Queen size bed in the master room, along with a bunk style Full mattress with a twin on top. The perfect arrangement for a family with several children. The bottom bed is definitely large enough for a couple as well, if you have two parties traveling together. Throughout the home is all the amenities you could ask for, including beach chairs, beach cooler, TV's, internet, cable, and more!brbrReserve your next vacation at Bay Oaks today!

Vacation Home Away From Home at Bay Oaks D41

Siesta Key, Florida, United States

Bed

Bath

Sleeps

Very Good(1)

$326.26

The Anchorage Resort on Siesta Key - Includes Resort Amenities and Private Beach Access!brbrOur 2 bedroom, 2 bathroom, private vacation condo is a great option for anyone wanting a home base to enjoy the best of all that Siesta Key has to offer.brbr* Anchorage Resort Condo on Siesta Key br* 2 Bedrooms / 2 Bathroomsbr* Eighth Floor Condo with Balcony overlooking North-Western Siesta Keybr* Fully equipped Kitchen with Seating for 4 at the Dining Tablebr* Beach Supplies include - 4 Beach Chairs, Beach Towels, Beach Umbrella, Cooler & Beach Cartbr* Community Pool- Largest pool on the Key!br* Gated Community and Parking includedbr* Siesta Key Trolley- Free pickup in front of the Resort entrancebr* Private Beach access to Crescent Beach across the street!br* 25-year minimum age to rent restrictionbrbrBEDROOMS (Eighth Floor Condo)brBedroom 1: One King Bed (Ensuite Bathroom) / Balcony Access / 32 TVbrBedroom 2: One Queen Bed, One Twin Bed / Balcony Access / 32 TVbrbrThe Anchorage Resort Amenity Access Included with Rental:br* Olympic-size poolbr* 3 Lighted Tennis/Pickleball Courtsbr* Shuffleboardbr* Community BBQ areabr* Individual Picnic areas along the Canal/Intracoastal Waterwaybr* Exercise Roombr* Bike & Kayak Racks (subject to availability)br* Boat Dock/Seawallbr* Coin-Operated Washer/Dryer on Each Floorbr* Private Beach access to Crescent Beach across the streetbrbrPool Information:br- Community Poolbr- HeatedbrbrResort Parking Rules:brThe resort allows a maximum of 2 cars.brVehicles must be registered with the front office during office hoursbrbrHOA Rules:brThe lead guest must be age 25 or older. ID is checked upon registration at the resort.brNo pets are allowedbrJanuary 1 - April 16 Rentals are 7-night minimums beginning and ending on Saturdays only.brbrDistances from Resort to Shopping & Attractions:br* Daiquiri Deck South Siesta Key- 5-minute walk across the streetbr* Crescent Beach Private Beach Access- 7-minute walk across the streetbr* Toasted Mango Cafe - 9-minute walkbr* Siesta Key Watersports - .6 milebr* Siesta Key Village- 2.7 (trolley stop)br* Publix at Sarasota Pavilion- 1.4 milesbr* Marie Selby Botanical Gardens - 6 milesbr* Sarasota Bradenton Airport (SRQ) - 11 milesbr brWhy Choose this Rental br- Professionally managed to serve all your needsbr- Management company has over 26 years of experience hosting well over 200,000 familiesbr- Go straight to your rental with online email check-inbr- 24/7 on-call maintenancebr- Free On-Site Parkingbr- Smoke-free and pet-free for your comfortbr- Towels and linens are providedbr- Complimentary WiFibr brOur Starter Welcome packet supplies:br- 2 rolls of toilet paper per bathroombr- 1 hotel-size bar of soap per bathroombr- 1 hotel-size shampoo/conditioner per full bathroombr- 1 roll of paper towelsbr- 2 packets of dishwasher detergentbr- Size 13-gallon Trash bagsbrAny supplies beyond this are up to the guest to replenish, we do not restock these items. brNo salt/pepper or cleaning supplies are stocked due to safety issues. brThis is an industry-standard practice.br brFOR GUESTS WHO BOOK 30 NIGHTS OR LONGER STAYS: (This does not apply if you are staying less than 30 nights.)brWe will collect a $1,500 deposit.brBalance is due 60 days prior to arrivalbrIf canceled 90 days or more before arrival, we keep $250.00. $1,250.00 will be refunded.brIf canceled between 61 and 89 days prior to arrival, we keep the $1,500.00 deposit.brNo cancellation or modification 60 days or less prior to arrival.

Anchorage Resort 8th Floor Condo in Siesta Key with Resort Amenities and Private Beach Access!

Siesta Key, Florida, United States

Bed

Bath

Sleeps

Exceptional(10)

$249.92

Escape to a tranquil oasis on Siesta Key! This charming studio unit boasts a queen-sized Murphy bed, perfect for a romantic getaway or relaxing retreat. Enjoy breathtaking pool views from the comfort of your own space, and step outside to find yourself mere steps away from the soft white sands and crystal-clear waters of the Gulf of Mexico. This ideal location combines the best of both worlds: serene relaxation and easy access to all that Siesta Key has to offer.

Casa Mar - Unit 27 Studio Pool View

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$318.88

Coastal comfort with relaxing pool views at Casa Mar Unit 12A on Siesta Key. This inviting 1-bedroom, 1-bath condo offers a bright and easy layout just steps from the island’s world-famous white sand beaches, making it an ideal retreat for couples or small families looking to unwind.brbrInside, the living area provides comfortable seating along with a sofa bed for additional guests. The kitchen is fully equipped for preparing meals at home, and the adjacent Florida room creates a sunny space perfect for morning coffee or quiet afternoons. The bedroom offers a peaceful setting for restful nights, while the bathroom includes all essential comforts for a convenient stay.brbrGuests of Casa Mar enjoy access to two community swimming pools, private beach access with complimentary beach chairs, picnic and BBQ areas, and recreational courts including tennis and pickleball. Covered parking is included for added convenience.brbrLocated in the heart of Siesta Key, the property is close to local dining, shopping, and entertainment while still offering a quiet and relaxing atmosphere. Casa Mar Unit 12A is a comfortable and well-situated option for enjoying everything the Gulf Coast has to offer.

Casa Mar - Unit 12A 1 Bedroom 1 Bath Pool View

Siesta Key, Florida, United States

Bed

Bath

Sleeps

Exceptional(1)

$326.36

The bright beachy unit is the perfect vacation getaway for those seeking a relaxing and rejuvenating beach experience. This beautifully decorated condo is located just steps away from the pristine white sands and crystal-clear waters of Siesta Key Beach.brInside, you will find a stylishly furnished living space that exudes a coastal charm. The condo features an open-concept layout, allowing for a seamless flow between the living, dining, and kitchen areas. Large windows fill the space with natural light and offer breathtaking views of the surrounding tropical landscape.brThe condo is equipped with all the amenities you need for a comfortable stay. The kitchen is fully stocked with appliances and cookware, making it easy to prepare delicious meals. brThe condo complex also has a pool and lounge area, perfect for cooling off and socializing with other guests.brIn addition to its prime beachfront location, the condo is conveniently located near popular attractions, restaurants, and shops. Whether you want to spend your days lounging on the beach, exploring the local area, or enjoying water sports, this beach rental condo in Siesta Key is the ideal choice for your next vacation.brPlease note: This unit requires a minimum stay of 2 weeks. Weekly rentals are not permitted.brLocated at beautiful Casa Mar on Siesta Key, this unit offers access to a wide range of community amenities including:br Two sparkling swimming poolsbrbr Private beach access with complimentary beach chairsbrbr Four picnic areas featuring gas BBQ grillsbrbr Tennis/pickleball court, shuffleboard, and a basketball hoopbrbr One covered parking space for your conveniencebrbr Pet-free unit — no animals allowed

Casa Mar - Unit 17 1 Bedroom 1 Bath

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$321.6

This one-bedroom condo is a cozy retreat located in a great spot on the property, just a short walk from the beach. The bedroom features a king-sized bed and a screened-in lanai perfect for relaxing and taking in the breeze. With a maximum occupancy of two guests, this unit is ideal for a romantic getaway or a small group of friends. Unit is on the ground floor. The condo complex offers a range of amenities, including two swimming pools, picnic areas with gas BBQs, beach chairs, a tennis/pickleball court, and shuffleboard courts. Plus, there's one covered parking space for added convenience.

Casa Mar - Unit 26 1 Bedroom 1 Bath Pool View

Siesta Key, Florida, United States

Bed

Bath

Sleeps

Exceptional(3)

$304.7

Welcome to Casa Mar Unit 25, a newly remodeled 1-bedroom, 1-bath condo on beautiful Siesta Key, thoughtfully updated to provide a bright and comfortable beach retreat just steps from the sand.brbrThe interior features a fresh coastal design with modern finishes throughout. The fully renovated kitchen showcases updated cabinetry, sleek countertops, stainless steel appliances, and a stylish backsplash, all complemented by warm wood-beam ceiling accents that add character and charm to the space. The open living area offers comfortable seating and a sofa sleeper, making it easy to accommodate additional guests.brbrThe bedroom provides a peaceful escape with a comfortable king-size bed and clean, airy décor designed for restful nights after a day at the beach. A screened lanai extends the living space and creates the perfect spot to enjoy morning coffee or evening breezes overlooking the tropical surroundings.brbrGuests of Casa Mar enjoy access to two heated swimming pools, private beach access with complimentary beach chairs, picnic and BBQ areas, and recreational amenities including tennis, pickleball, and shuffleboard. Covered parking is included for convenience.brbrLocated in the heart of Siesta Key, this updated condo combines modern comfort with classic coastal charm, making it an excellent choice for couples or small families looking for a relaxing and well-appointed beach getaway.

Casa Mar - Unit 25 1 Bedroom 1 Bath

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$315.47

Welcome to this charming beach condo in Siesta Key! This one-bedroom unit is the perfect retreat for a relaxing beach vacation.brAs you enter, you'll be greeted by a beautifully updated kitchen, complete with appliances and all the necessary amenities to prepare delicious meals. The open-concept living area features a comfortable couch that can be converted into a pull-out sofa bed, allowing the unit to accommodate up to four guests.brThe unit also offers a screened-in lanai, where you can unwind and enjoy the peaceful surroundings. Located at the front of the property, this quiet location provides a serene atmosphere for relaxation.brJust steps away from the condo, you'll find the grill and pool area, perfect for enjoying outdoor meals and taking a refreshing dip in the pool. And when you're ready to hit the beach, it's just a short distance away, allowing you to easily soak up the sun and enjoy the beautiful white sands and turquoise waters of Siesta Key.brWhether you're looking for a romantic getaway or a fun-filled family vacation, this beach condo in Siesta Key offers the perfect combination of comfort, convenience, and relaxation.brLocated at beautiful Casa Mar on Siesta Key, this unit offers access to a wide range of community amenities including:br Two sparkling swimming poolsbrbr Private beach access with complimentary beach chairsbrbr Four picnic areas featuring gas BBQ grillsbrbr Tennis/pickleball court, shuffleboard, and a basketball hoopbrbr One covered parking space for your conveniencebrbr Pet-free unit — no animals allowed

Casa Mar - Unit 4 1 Bedroom 1 Bath

Siesta Key, Florida, United States

Bed

Bath

Sleeps

Exceptional(4)

$297.26

pEscape to this cozy one-bedroom, one-bath condo on Siesta Key, where comfort and convenience meet. This charming retreat features two full beds and a sleeper sofa, providing ample sleeping space for up to four guests. A screened-in porch is the perfect spot to enjoy the tropical breeze. Just steps away from the beach, this condo is also close to a tennis court and grill, making it easy to stay active and entertained. Plus, you're just a short walk from the bus line, making it simple to explore the surrounding area. With access to two swimming pools, shuffleboard courts, tennis/pickleball courts, basketball, and four grill and picnic areas, you'll have everything you need for a relaxing and enjoyable getaway./p

Casa Mar - Unit 73 ; Courtyard 1 Bedroom 1 Bath

Siesta Key, Florida, United States

Bed

Bath

Sleeps

Exceptional(6)

$250.2

Escape to a tropical oasis in this renovated studio condo on Siesta Key! This beach retreat features a queen-sized murphy bed, perfect for a romantic getaway or relaxing escape. With its bright and airy vibe, you'll feel like you're already on island time. Plus, enjoy access to the resort's amazing amenities, including two swimming pools, shuffleboard, tennis/pickleball court, basketball, and four grill and picnic areas. Just steps from the beach, you'll have the perfect blend of relaxation and activity. Book your vacation today!

Casa Mar - Unit 67 Studio Pool View

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$310.53

Escape to a tropical oasis in this completely remodeled 1 bedroom condo on Siesta Key! This beachy retreat features a spacious king sized bed, perfect for a romantic getaway or relaxing escape. The extended living room is bathed in natural light and offers plenty of space to unwind. With its bright and airy vibe, you'll feel like you're already on island time. Plus, enjoy access to the resort's amazing amenities, including two swimming pools, shuffleboard, tennis/pickleball court, basketball, and four grill and picnic areas. Just steps from the beach, you'll have the perfect blend of relaxation and activity. Book your dream vacation today!

Casa mar - Unit 62 ; 1 Bedroom 1 Bath Courtyard

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$310.53

Escape to paradise in this roomy 1 bedroom condo on Siesta Key! Enjoy the serenity of the Gulf Coast just steps from your door, with direct access to the soft white sands and crystal-clear waters. This cozy retreat features a comfortable king sized bed, perfect for a relaxing getaway. The recently updated kitchen and bathroom ensure a touch of modern luxury, while the extended living room provides ample space to unwind. Take advantage of the resort's fantastic amenities, including four grill and picnic areas, two swimming pools, shuffleboard, tennis/pickleball, and basketball. Book your dream vacation today!

Casa Mar - Unit 55 ; 1 Bedroom 1 Bath Courtyard

Siesta Key, Florida, United States

Bed

Bath

Sleeps

Exceptional(1)

$244.45

Escape to the tranquil oasis of Siesta Key in this charming 1 bedroom condo, boasting a cozy king-sized bed and a lovely screened-in porch perfect for sipping coffee or enjoying the warm Florida breeze. This beautifully updated retreat is conveniently located near laundry facilities, a sparkling pool, grills, and the stunning white sand beach. With a relaxing atmosphere and thoughtful amenities, this condo is the perfect hideaway for a romantic getaway or solo retreat. Enjoy access to two swimming pools, four grill and picnic areas, tennis/pickleball courts, shuffleboard courts, and basketball - all just steps from your front door. Book your dream vacation today!

Casa Mar - Unit 51 ; 1 Bedroom 1 Bath Pool View

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$393.25

Escape to the sun-kissed shores of Siesta Key in this beautifully renovated 2 bedroom, 1 bathroom condo! This cozy retreat features a spacious king-sized bed in one bedroom and a comfortable double bed in the other, perfect for couples or small families. The newly furnished interior is bright and airy, with a modern kitchen boasting fresh appliances and stylish finishes. Just steps from the beach, you'll have direct access to the soft white sands and crystal-clear waters of the Gulf of Mexico. When you're ready to unwind, enjoy resort amenities like tennis and pickleball courts, shuffleboard, two swimming pools, basketball, and four grill and picnic areas. Book your dream getaway today!

Casa Mar - Unit 46 ; 2 Bedroom 1 Bath Pool View

Siesta Key, Florida, United States

Bed

Bath

Sleeps

Exceptional(4)

$434.92

Step into your dream getaway with this stunning 2-bedroom, 1.5-bath condo, freshly remodeled from top to bottom. brDesigned with comfort and style in mind, this coastal haven is the perfect blend of modern luxury and relaxed beach vibes.brbrInside, you’ll find a bright, open living space with plenty of natural light, a fully equipped kitchen for home-cooked meals, and thoughtful touches throughout to make your stay effortless. The primary bedroom offers a plush king bed, while the second bedroom is ideal for families or groups with a queen and twin bed—comfortably sleeping up to 5 guests.brBest of all, you’re literally just steps away from the sugar-white sands of Siesta Key Beach, world-famous for its soft quartz sand and turquoise waters. Whether you’re catching a sunset, enjoying a morning beach walk, or spending the whole day by the shore, paradise is right at your doorstep.brbrTo make beach days even easier, the condo comes stocked with beach supplies, including a beach wagon, umbrellas, toys, chairs, and more—just pack your sunscreen and you’re ready to go!brbrWhen you’re ready for a break from the beach, the property offers fantastic amenities:brGated Property with private beach accessbrTwo sparkling swimming poolsbrTennis & pickleball courts, basketball, and shuffleboardbrFour outdoor grill and picnic areas, perfect for evening cookoutsbrbrFrom sunrise to sunset, this condo has everything you need for a memorable vacation. Whether you’re traveling as a family, with friends, or enjoying a romantic retreat, this is your perfect home base on Siesta Key.brbrDon’t wait—book your slice of paradise today!

Casa Mar - Unit 43 ; 2 Bedroom 1.5 Bath Steps Away From the Beach

Siesta Key, Florida, United States

Bed

Bath

Sleeps

Exceptional(5)

$574.63

Welcome to Casa Mar Unit 41, a fully renovated 2 bedroom, 2 bathroom beachfront condo on Siesta Key, located within a private gated community.brbrThis second-floor unit features a screened-in balcony with beautiful Gulf views, perfect for enjoying morning coffee or evening sunsets. Inside, the condo offers a bright, modern coastal design with an open living space and a fully equipped kitchen.brbrbrbrThe primary bedroom includes a king bed, while the guest bedroom offers two twin beds, comfortably accommodating up to four guests.brbrYou will enjoy two new full size bathrooms updated with sea themed tiles and plenty of storage. brbrThe kitchen is fully stocked with your every need, new appliances and accessories including cookware and baking sets.brbrYou will be mesmerized by the ocean and Siesta Key beach views. The unit includes gorgeous artwork by local Sarasota artists with water vistas and beach paths, with the sensation of hearing the roar of the ocean. You are surrounded by the tranquility of life on the Key.brbrbrbrGuests enjoy private beach access with complimentary beach chairs, along with two heated pools, tennis and pickleball courts, shuffleboard, and outdoor grill areas.brbrConveniently located just minutes from Siesta Key Village, you’ll enjoy easy access to dining, shopping, and entertainment while staying right on the beach.

Casa Mar - Unit 41 ; 2 Bedroom 2 Bath Beach Front

Siesta Key, Florida, United States

Bed

Bath

Sleeps

Exceptional(7)

$541.78

Wake up to the sound of gentle waves and endless views of the Gulf of Mexico in this beautifully updated 2-bedroom, 2-bath beachfront condo — the perfect setting for your next Florida getaway. brbrStep inside this bright and inviting space, where you’ll find a king-sized master bedroom and a second bedroom with two cozy single beds, ideal for families, couples, or friends traveling together. Both bathrooms were recently enlarged and modernized, adding a touch of luxury and comfort to your stay. brbrRelax on your spacious private balcony with breathtaking panoramic ocean views — perfect for your morning coffee or evening sunset cocktails. Just steps from your door, soft white sand and crystal waters await, along with exclusive beach access and a heated pool for leisurely afternoons. brbrThis condo offers thoughtful amenities including free Wi-Fi, beach chairs, BBQ grill, and on-site parking, making it an easy and comfortable choice for your Siesta Key escape. brbrWhether you’re here to unwind by the sea, explore local dining and shopping, or simply enjoy time with loved ones, Casa Mar Unit #35 delivers a beachfront experience you’ll remember.

Casa Mar - Unit 35 ; 2 Bedroom 2 Bath Beach Front

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$426.9