Vacation Home Rentals By Owner In Sarasota, FL

Retreat to paradise in this charming 2-story, fully stocked, family friendly home located on Siesta Key. You'll only be a 2-minute bike ride to Shell Beach & an 8-minute drive to Siesta beach. You have everything you need here - beach equipment, firepit, full kitchen & large yard. Watch sunrise from the 2nd story deck & Lounge in the evening while you grill up dinner!brbrThe property is built on stilts, which means the main living area sits 1-story off the ground so the entrance to the house is up the front stairs (there is no elevator). The living room, kitchen, dining room, deck, queen bedroom and 1.5 bath is on the main floor living area and the other 3 bedrooms are on the second floor. brbrThere is a fire pit, adirondack chairs, hammock and swings located in the backyard for your enjoyment.brbrFor those of you with younger children, we have a high chair & playpen, but please be cognisant that there are two flights of stairs at the property.brbrPlease also be aware that the stairs to the bedrooms is up a narrow staircase inside (please see photos).brbrEntire PropertybrbrMessage me. I am always avilable!

Quiet Bohemian Home on Siesta Key

Sarasota, Florida, United States

Bed

Bath

Sleeps

$392.72

Peaceful and cozy resting on acres of space and tranquility. You will enjoy shooting stars at night and a pasture view while sipping on your coffee in the morning. Enjoy your space, your silence, and your privacy in this luxurious home. This is a 3 bedrooms home waiting for you with all necessary that you may need for your stay. Bedrooms have sheets and blankets, and more, + extra pillows from soft to firm. Bathrooms also are fully equipped with towels and all the necessary. The kitchen has it all, from crockpot to toaster, and cheese fondue. You like playing golf We do have a second that is located on a golf course, and its golf membership can be transferred to you at the cost of $300 for a month, payable to the country club of Stoneybrook.

Beautiful Home with Pool on 3 Acres of Privacy.

Sarasota, Florida, United States

Bed

Bath

6

Sleeps

$219.22

This Sarasota house boasts 3 welcoming bedrooms, including 2 queen beds and 1 full bed. Guests enjoy a tranquil space with Pool jacuzzi sauna in a private house private amenities m, perfect for relaxing after a day of exploring. The home features heating and air conditioning to keep you comfortable year-round. Whether you’re freshening up with the hair dryer or ironing your favorite outfit, you’ll find everything you need. This awesome retreat offers a cozy, inviting atmosphere that makes it easy to unwind. We look forward to welcoming you to our place.

Private Pool Sauna Jacuzzi 3 bedrooms 4 Beds

Sarasota, Florida, United States

Bed

Bath

Sleeps

$243.5

Welcome to your dream getaway! This stunning and impeccably clean 3-bedroom pool home offers the perfect blend of comfort and style, just a short 10-minute drive from the beautiful shores of Siesta Key.brbrKey Features:br3 spacious bedrooms – Perfect for families or small groupsbrQuiet location – Enjoy stunning views and peaceful surroundingsbrPool – Relax and unwind by the water with a refreshing dipbrClose to downtown Sarasota – Easy access to top dining, shopping, and attractionsbrFully equipped kitchen – Prepare meals in comfort and stylebrOutdoor seating areas – Ideal for enjoying the beautiful Florida weather and viewsbrbrThere are plenty of options for your grocery shopping, all within a convenient distance from the property, including Walmart, Target, Trader Joes, Whole foods, Publix and Aldi. brbrYou’ll find a variety of restaurants within the vicinity to suit different tastes, whether you’re looking for a casual meal or something a bit more upscale.brbrLocated on a quiet street in a desirable and private community, this villa offers convenient access to local amenities, parks, and recreational activities. Experience the ultimate in Florida living with this exceptional pool villa—your slice of paradise awaits!brbrIf you still have any questions concerning our homes, rates, availability calendar, amenities, policies, or otherwise, please contact our team and we will be happy to assist you. brbrGulf Coast Holiday Homes offer a wide range of services including: br- An any day arrival policy and length of stay requirements starting at just 7-nights.br- We have a professional property manager and maintenance systems meaning you’ll experience the service you deserve.br- Professional housekeeping pre-stay and during stay if requested. br- 'Guide Books' allowing you to be able to add experiences to your itinerary and see some of our recommendations. br- 'Preferred Vendors' meaning you can trust the company you use for rentals.brbrAll properties listed with Gulf Coast Holiday Homes benefit from an interactive 'Guide Book' which will be sent ahead of arrival and will include the house manual, check in instructions, preferred vendors and unique information about the home.brbrExperience the ultimate vacation in this exquisite 3-bedroom, 2-bathroom home, thoughtfully designed for relaxation and embracing the quintessential Florida lifestyle. Located just 3.5 miles from the world-renowned Siesta Key Beach, this property combines luxury and convenience for an unforgettable escape.brbrThe spacious living area features ample seating with brand-new furniture, perfect for lounging with family and friends. With 5 strategically placed TVs throughout the home, including one by the pool, entertainment is always at your fingertips.brbrStep into the fully equipped kitchen, a culinary haven ideal for whipping up delicious meals or enjoying takeout from the diverse array of nearby restaurants. The master bedroom, complete with a king bed, boasts an ensuite bathroom featuring a walk-in shower and a large closet to neatly stow away your belongings. The two additional bedrooms are located on the opposite side of the home, sharing a second bathroom with a convenient tub-shower combination that also includes a door to the pool area, making it perfect for poolside use. One of the bedrooms can double as an office, complete with a desk and chair for those needing a quiet space to work.brbrStep outside to discover your private outdoor lanai area, a highlight of the home, featuring a large pool that can be heated in the winter for an additional charge—just ask us, and we’ll be happy to assist! In the summer, enjoy refreshing dips or relax in the sun by the poolside TV, creating the ultimate outdoor living experience. The expansive backyard provides plenty of space for outdoor activities, whether playing games with the kids or simply soaking up the Florida sunshine. A new gas BBQ grill awaits you for cooking delicious meals for your family.brbrWith a washer and dryer in the laundry room, you can travel lightly with fewer clothes, making this home the perfect choice for your Florida getaway. brbrWhether you’re looking to relax by the pool or explore the nearby stunning beaches, this charming home is your ideal retreat. Book now and make unforgettable memories in this coastal paradise!brbrFrom I75 take exit 205 onto Clark Road, after 2.9 miles turn left onto S Beneva Rd., after 0.9 miles turn right onto Kingston Blvd. Follow the road keeping right for 0.6 miles. The home is on your right in a cul-de-sac. brbrParking is available on site for a maximum of 3 cars. One car can be parked in the garage and up to two cars can be parked on the driveway. Overnight parking on the street is not permitted. brbrThis property must be rented for a minimum of 90 nights. If the travel dates you are looking for don’t appear to be available, please contact our reservations team directly and we will see if we can accommodate your request at your property of choice, or another comparable home in our portfolio.brbrPrior to your stay, we require you to complete a pre-arrival form and sign & agree to our rental conditions. brbrAccidental Damage Insurance: Accidental Damage Insurance is included within all guest stays at Gulf Coast Holiday Homes. On this property, for stays greater than 29 nights, an additional $90 will be due as the current rates are for 29 nights or less. For additional blocks of 30 nights past 59 nights you, will be charged $71. brbrGuests must cancel at least 60 days before check-in to receive a full refund for all nights, minus a 10% processing fee.brGuests must cancel at least 30 days before check-in to receive a 50% refund for all nights.brIf a guest cancels less than 30 days before check-in, you’ll be charged 100% for all nights.brWe strongly recommend that you purchase your own travel insurance for your protection.brbrThis property is not available for instant booking due to the HOA application that is required. Lead time for this can vary from 7 days to 30 days. Enquire to find out more information.

The Kingston - 3 Bed Home in Sarasota with Pool by The Bay & Key Collection

Sarasota, Florida, United States

Bed

Bath

6

Sleeps

$457.2

Step into your own coastal escape. An inviting, beach-themed 3-bedroom home perfectly situated near Siesta Key, St. Armands Circle, and Lido Key. Bright, airy spaces, soft coastal colors, and relaxed décor set the tone the moment you arrive. Whether you’re planning family time, a friends’ getaway, or a peaceful retreat, this home offers room to spread out and unwind after sun-soaked days at some of the best beaches in Florida. Close to everything, yet far enough from the noise!

Bright Beach House with a Pool /Near the beaches

Sarasota, Florida, United States

Bed

Bath

Sleeps

$215.82

Escape to this house in picturesque Sarasota. With three queen bedrooms and two bathrooms featuring a jetted bathtub and shower, guests find plenty of space to relax. The home offers a soothing atmosphere where you can unwind after a day of exploring. Enjoy the comfort of air conditioning and heating, making every season enjoyable. Whether you’re curling up with a book or getting ready for a night out, this awesome retreat has you covered. You’re sure to make fantastic memories with a stay at our place.brIt is conveniently located at walking distance to grocery stores and restaurants, and it is within ten minutes drive to UTC Mall and twenty minutes to the beaches.

Lovely 3-bedroom house with AC in a quiet community of Sarasota

Sarasota, Florida, United States

Bed

Bath

Sleeps

$347.87

This modern coastal designed home will be your ultimate vacation retreat. Three spacious bedrooms, three bathrooms and a modern kitchen. The impeccable, stylish kitchen has stainless appliances and granite countertops. The master bedroom complete with walk-in closet and ensuite, ensures you will have your own private space. Outdoor lounge seating as well as a grill will complete your ideal vacation stay. Going to the beach Take the complimentary beach chairs, beach towels and umbrella with you.brCertificate Number: 25-VR-000002

Modern Coastal Home near Siesta Key and Downtown

Sarasota, Florida, United States

Bed

Bath

Sleeps

$435.29

Treat your family, friends, and beloved small dogs to an unforgettable oceanfront getaway in sunny Florida!brbrConveniently located near plenty of Sarasota's shopping and dining, your new home away from home is nice and isolated, surrounded by gorgeous views and just a quick walk from the waters of Sarasota Bay.brbrHigh-quality furnishings create a nice, pleasant atmosphere. Two couches await in the living room near the fireplace. Between internet browsing on the WiFi and cable on the flatscreen TV, you've got all you need to stay entertained.brbrThe brand new kitchen with granite counters and stainless steel appliances. Leave the dishwasher to work on cleaning up as you watch the sunset, before heading to one of the three bedrooms for bed. Between a king-size bed in the master bedroom, two twin-size beds in the second room, and a another king-size bed in the third bedroom, and sofa-bed in living room everyone will have a lovely place to sleep. There's also a laundry in garage for your convenience.brThe Sunshine State is waiting for you. Book today!brA security camera is positioned at the front of the house to monitor the driveway. Additionally, a second camera oversees the pool equipment to prevent unauthorized adjustments.brMINIMUM STAY REQUIREMENTS: 1 month minimum reservation required with the exception of 2 weeks minimum a maximum of 30 days in advance. Please contact host for details.

Oceanfront home w/sunset views of Sarasota Bay

Sarasota, Florida, United States

Bed

Bath

Sleeps

$337.67

Beautifully decorated and newly furnished Pool home in beautiful Palm Aire off University Blvd. brJust Minutes to the Mall, Airport, Downtown and the Beaches. brOne road in, one road out of our small subdivision. Great for walking and biking with very little traffic. brA luxurious home with 9 1/2-foot ceilings. Decor includes a new 70-inch flat screen TV in the family room. Sliders to lanai and large pool from the Family room, Kitchen, Living room and Master bedroom. brThe MBR has a king size bed, second TV and an ensuite bathroom with a walk-in shower and a large walk closet. brThe second bedroom has Queen bed and a walk-in closet. brThe third bedroom has 2 sets of twin bunk beds and walk in closet. brThe second bathroom has a tub and shower and door out to the pool. br*Pool can be heated in cooler months (December-April) for an additional charge of 25.00 a day. Please request before arrival so it's heated when you check-in*brThere is a full laundry room with new washer and dryer. brThe dining room has 6 chairs but can accommodate eight. The kitchen is well equipped with new appliances including a large fridge, stove, dishwasher, microwave, garburator, utensils, dishware, Keurig, toaster and blender. brThere is a 2-car garage to park your car(s). The home is fully air conditioned and equipped with beach chairs and coolers as it is only 20 Min. to the beach

Private Pool Home Hideaway in Palm Aire. Close to all Sarasota has to offer.

Sarasota, Florida, United States

Bed

Bath

8

Sleeps

$345.59

Escape to your private Sarasota retreat, perfect for families and friends, just 7 min from Siesta Key Beach! Behind a sliding gate, this stylish 3BR/2BA home sleeps 8 + 2 kids and offers a heated pool & spa under a screened lanai, cozy outdoor lounge and BBQ area. Inside — bright coastal décor, modern bathrooms with European fixtures, Smart TVs, Wi-Fi, and family comforts like a crib and high chair. Beach gear ready, groceries 2 min away, and exterior security cameras for peace of mind (no indoor cameras).

Private Coastal Retreat/Heated Pool • Family-Friendly• 7 min to Siesta Key Beach

Sarasota, Florida, United States

Bed

Bath

Sleeps

$359.83

Relax in this stylish Siesta Key retreat, just a 3-minute walk from the world-famous Siesta Key Beach and close to the Village’s top dining and nightlife. Enjoy sunny days by the shared swimming pool, fire up the BBQ grill, or unwind on the outdoor patio. This pet-friendly stay is perfect for romantic getaways, solo travelers, or families. Free parking included for your convenience. Comfort, location, and beach vibes come together here. Book your stylish Florida beach escape today!brbr☀ Beach Accessbr☀ Private Dockbr☀ Poolbr☀ BBQ Grillbr☀ Patiobr☀ Pet FriendlybrbrPlan the ultimate beach getaway at Siesta Retreats. Our welcoming, pet‑friendly villas offer spacious 1‑ and 2‑bedroom layouts, a guest‑only heated pool, and an unbeatable location just steps from world‑famous Siesta Key Beach and the Village’s shops and restaurants. Ideal for families with toddlers or teens, couples, and guests traveling with furry friends.brbr : Choose a 2‑bedroom villa with full kitchen and separate bedrooms or a 1‑bedroom unit with a sofa bed—comfortably sleeps small families.br : Guest‑only heated pool, outdoor grilling area, and poolside seating set in lush tropical landscaping.br : Private Grand Canal deck offers a rare chance to spot dolphins and manatees from shore.br ‑ : Complimentary towels, chairs, and wagons make beach days effortless.br : Off‑street parking and easy walkability to Siesta Village dining and nightlife.brbr :brbr☀ Heated pool open year‑round for guests only.br☀ Outdoor shower for rinsing off after the beach.br☀ BBQ area for family cookouts.br☀ Pet‑friendly accommodations—bring your well‑behaved companion (please check our pet policy when booking).brbr :brSteps from Siesta Key Beach and a short stroll to Siesta Village, you’ll be minutes from white sand, waterfront dining, local boutiques, and evening entertainment—no car required for most outings.brbr :brbr : Thoughtful amenities for kids and animals.br : Beach, cafes, and shops within minutes.br : Canal deck for wildlife viewing adds a memorable touch.br ‑ : We supply the gear so you can focus on fun.brbr to reserve your family‑friendly, pet‑friendly Siesta Key escape and create lasting coastal memories.brbr★ :br☀ Sarasota Beach: 4 min walkbr☀ Siesta Key Craft Festival: 7 min walkbr☀ Point of Rocks: 9 min drivebr☀ Sunset Beach: 10 min walkbr☀ Red Bug Slough Preserve: 15 min drivebr☀ St. Armands Circle: 15 min drivebr☀ Sarasota Art Museum: 15 min drivebr☀ TPC Prestancia (Golf Club): 20 min drivebr☀ Bayfront Park: 21 min drivebr☀ Quick Point Nature Preserve: 19–24 min drivebr☀ The John and Mable Ringling Museum of Art: 25 min drivebr☀ Ted Sperling Park Nature Trail: 25 min drivebr☀ South Lido County Park: 26 min drivebr☀ Ca` d`Zan (Historical Museum): 27 min drivebr☀ South Lido Key Beach Park on the Gulf: 28 min drivebr☀ Manatee Village Historical Park: 39 min drivebr☀ Palma Sola Botanical Park: 52 min drivebrbr★ :br ☀ Gilligan`s Island Bar & Grill: 5 min walkbr ☀Summer House Resturant: 5 min walkbr ☀ Lobster Pot Restaurant: 6 min walkbr ☀ Siesta Key Oyster Bar: 6 min walkbr ☀ The Cottage: 6 min walkbr ☀ Another Broken Egg Cafe: 7 min walkbr ☀ Sun Garden Cafe: 7 min walkbr ☀ The Old Salty Dog Siesta Key: 10 min walkbr ☀ Daiquiri Deck Siesta Key Village: 2 min drivebr ☀ Cafe Gabbiano: 2 min drivebr ☀ Clayton`s Siesta Grille: 8 min drivebr ☀ SPEARFISH GRILLE: 8 min drivebr ☀ The Toasted Yolk Cafe: 11 min drivebr ☀ Florence & The Spice Boys: 12 min drivebr ☀ Casa Masa - The Landings: 13 min drivebrbr★ :br ☀ Sarasota Memorial Hospital: 14 min drivebr ☀ Medical Center of Sarasota: 17 min drivebr ☀ HCA Florida Sarasota Doctors Hospital: 23 min drivebrbr★ :br ☀ Beach Rd @ Calle De La Siesta: 3 min walkbr ☀ Ocean Blvd @ Calle Miramar NB: 4 min walkbr ☀ Ocean Blvd @ Canal Rd SB: 6 min walkbr ☀ Explore every corner of the island with two hop-on hop-off companies offering free rides: 77 Siesta Islander and Bay Runner Trolley.br ☀ Get around stress-free with the Breeze Bus Service, serving both Downtown Sarasota and Siesta Key.brbr★ :br ☀ Sarasota Bradenton International Airport: 26 min drivebr ☀ Venice Municipal Airport: 32 min drivebr ☀ Hidden River Airport-22FA: 47 min drivebrbrb ★☆ Upcoming Events in Siesta Key Beach:/bbr☀ Thunder By The Bay Music & Motors Festival: Feb 13–15, 2026br☀ `Say I Do Again` Vow Renewal Ceremony: Saturday, Feb 14, 2026br☀ Elton John Tribute Concert: Feb 27, 2026br☀ Guns N` Roses Tribute Concert: Feb 28, 2026br☀ Sarasota Jazz Festival: Mar 9–14br☀ Sarasota County Fair: Mar 13–22br☀ Spring Break Season: All Monthbr☀ Siesta Key Drum Circle: March, 2026 Every Sunday in br☀ Siesta Key Farmers Market: March 2026, Every Sunday (9:00 AM – 1:00 PM) br☀ Embracing Our Differences (Outdoor Art Exhibit)—till April 13, 2026

Sleeps 8 • Steps to Siesta Key Beach • Pool • BBQ

Sarasota, Florida, United States

Bed

Bath

Sleeps

$367.04

Escape to our charming 1‑bedroom Siesta Key villa, just a 3‑minute walk to world‑famous Siesta Key Beach and steps from Village dining and nightlife. This airy, sunlit retreat is ideal for couples, solo travelers, or small families. Enjoy a fully equipped kitchen, modern bathroom with premium toiletries, high‑speed Wi‑Fi, and a private upper deck perfect for morning coffee or sunset lounging.brbr☀ Walk to Beachbr☀ Private Dockbr☀ Poolbr☀ BBQ Grillbr☀ Patiobr☀ Pet Friendlybrbr brbr : A leisurely 3‑minute walk to Siesta Key’s powder‑white quartz sand and minutes from Village shops, cafes, and restaurants.br : Outdoor dining and lounge furniture create a tranquil spot to soak up the Florida air.br ‑ : Relax year‑round in a lush, tropical pool setting.br ‑ : Wagon, chairs, and towels provided for effortless beach days.br : Fully equipped kitchen, 55‑inch Smart HDTV, high‑speed Wi‑Fi, and premium toiletries.br : Free off‑street parking and full, private access to the entire villa.brbrBright living area with comfortable seating and a 55‑inch Smart HDTV, a cozy bedroom with quality linens, and a clean, modern bathroom stocked with premium toiletries. The kitchen has modern appliances and everything you need to prepare meals. The upper deck extends your living space outdoors with peaceful canal or Village views.brbr brGuests have exclusive access to the villa and the guest‑only heated pool. We provide beach gear and an outdoor shower so you can rinse off after the beach. Free parking makes arrivals and day trips easy.brbr br☀ Walk to the beach and Village without the hassle of driving.br☀ Private outdoor space for quiet mornings and relaxed evenings.br☀ Thoughtful amenities for stress‑free beach days and comfortable stays.br☀ Ideal for couples, solo travelers, or small families seeking a convenient coastal escape.brbr to enjoy the perfect combination of comfort, convenience, and island charm in Siesta Key, FL.brbr★ :br ☀ Sarasota Beach: 4 min walkbr ☀ Siesta Key Craft Festival: 7 min walkbr ☀ Sunset Beach: 10 min walkbr ☀ Point Of Rocks: 9 min drivebr ☀ Red Bug Slough Preserve: 15 min drivebr ☀ Saint Armonds Circle: 15 min drivebr ☀ Sarasota Art Museum: 15 min drivebr ☀ TPC Prestancia (Golf Club): 20 min drivebr ☀ Bayfront Park: 21 min drivebr ☀ Quick Point Nature Preserve: 19–24 min drivebr ☀ The John and Mable Ringling Museum of Art: 25 min drivebr ☀ Ted Sperling Park Nature Trail: 25 min drivebr ☀ South Lido County Park: 26 min drivebr ☀ Ca` d`Zan (Historical Museum): 27 min drivebr ☀ South Lido Key Beach Park on the Gulf: 28 min drivebr ☀ Manatee Village Historical Park: 39 min drivebr ☀ Palma Sola Botanical Park: 52 min drivebrbr★ :br ☀ Gilligan`s Island Bar & Grill: 5 min walkbr ☀Summer House Resturant: 5 min walkbr ☀ Lobster Pot Restaurant: 6 min walkbr ☀ Siesta Key Oyster Bar: 6 min walkbr ☀ The Cottage: 6 min walkbr ☀ Another Broken Egg Cafe: 7 min walkbr ☀ Sun Garden Cafe: 7 min walkbr ☀ The Old Salty Dog Siesta Key: 10 min walkbr ☀ Daiquiri Deck Siesta Key Village: 2 min drivebr ☀ Cafe Gabbiano: 2 min drivebr ☀ Clayton`s Siesta Grille: 8 min drivebr ☀ SPEARFISH GRILLE: 8 min drivebr ☀ The Toasted Yolk Cafe: 11 min drivebr ☀ Florence & The Spice Boys: 12 min drivebr ☀ Casa Masa - The Landings: 13 min drivebrbr★ :br ☀ CVS Pharmacy: 12 min drivebr ☀ Sarasota Memorial Hospital: 14 min drivebr ☀ Medical Center of Sarasota: 17 min drivebr ☀ HCA Florida Sarasota Doctors Hospital: 23 min drivebrbr★ :br ☀ Beach Rd @ Calle De La Siesta: 3 min walkbr ☀ Ocean Blvd @ Calle Miramar NB: 4 min walkbr ☀ Ocean Blvd @ Canal Rd SB: 6 min walkbr ☀ Enjoy free rides to all major island attractions with two hop-on hop-off services: 77 Siesta Islander and Bay Runner Trolley.br ☀ Travel easily with Breeze, the local bus service, connecting Downtown Sarasota and Siesta Key.brbr★ :br ☀ Sarasota Bradenton International Airport: 26 min drivebr ☀ Venice Municipal Airport: 32 min drivebr ☀ Hidden River Airport-22FA: 47 min drivebrbrb ★☆ Upcoming Events in Siesta Key Beach:/bbr☀ Thunder By The Bay Music & Motors Festival: Feb 13–15, 2026br☀ `Say I Do Again` Vow Renewal Ceremony: Saturday, Feb 14, 2026br☀ Elton John Tribute Concert: Feb 27, 2026br☀ Guns N` Roses Tribute Concert: Feb 28, 2026br☀ Sarasota Jazz Festival: Mar 9–14br☀ Sarasota County Fair: Mar 13–22br☀ Spring Break Season: All Monthbr☀ Siesta Key Drum Circle: March, 2026 Every Sunday in br☀ Siesta Key Farmers Market: March 2026, Every Sunday (9:00 AM – 1:00 PM) br☀ Embracing Our Differences (Outdoor Art Exhibit)—till April 13, 2026

Waterfront Villa at Siesta Key • Pool • BBQ

Sarasota, Florida, United States

Bed

Bath

Sleeps

$295.32

Enjoy the ultimate Siesta Key getaway just a 3-minute walk from the beach and steps from the Village’s dining and shops. This cozy 1-bedroom retreat offers a shared pool, private dock access, BBQ area, and sun loungers for laid-back island living. Inside, enjoy a fully equipped kitchen and a comfortable living space to relax after beach days. Free parking is included, a rare find on Siesta Key. Perfect for couples, families, or solo travelers. Book your island escape today!brbr☀ Beach Accessbr☀ Private Dockbr☀ Poolbr☀ BBQ Grillbr☀ Patiobr☀ Pet FriendlybrbrStep into this newly renovated coastal villa, designed for travelers who want luxury, comfort, and unbeatable walkability. Enjoy a private balcony, access to a heated pool, and a location that puts Siesta Key Beach and Siesta Village just steps away.brbrIdeal for couples, families, and solo adventurers, this villa blends modern convenience with the relaxed charm of island living.brbr⭐ br : Only a 3‑minute walk to world‑famous Siesta Key Beach—renowned for its powder‑soft ‑ . : Restaurants, boutiques, cafés, and nightlife in . : Enjoy a guest‑only heated pool . : Relax in your own outdoor oasis with dining and . ‑ : Towels and wagons provided for effortless beach days. Bright & : Open‑concept living, a fully equipped kitchen, Smart TVs, and cozy bedrooms for . : Outdoor grilling area and convenient off‑street parking.brbr brSecure your dates and experience the ultimate Siesta Key getaway—where comfort, convenience, and coastal beauty come together.brbr★ :br ☀ Siesta key beach: 4 min walkbr ☀ Siesta Key Craft Festival: 7 min walkbr ☀ Sunset Beach: 10 min walkbr ☀ Point Of Rocks: 9 min drivebr ☀ Red Bug Slough Preserve: 15 min drivebr ☀ Saint Armonds Circle: 15 min drivebr ☀ Sarasota Art Museum: 15 min drivebr ☀ TPC Prestancia (Golf Club): 20 min drivebr ☀ Bayfront Park: 21 min drivebr ☀ Quick Point Nature Preserve: 19–24 min drivebr ☀ The John and Mable Ringling Museum of Art: 25 min drivebr ☀ Ted Sperling Park Nature Trail: 25 min drivebr ☀ South Lido County Park: 26 min drivebr ☀ Ca` d`Zan (Historical Museum): 27 min drivebr ☀ South Lido Key Beach Park on the Gulf: 28 min drivebr ☀ Manatee Village Historical Park: 39 min drivebr ☀ Palma Sola Botanical Park: 52 min drivebrbr★ : br ☀ Gilligan`s Island Bar & Grill: 5 min walkbr ☀Summer House Resturant: 5 min walkbr ☀ Lobster Pot Restaurant: 6 min walkbr ☀ Siesta Key Oyster Bar: 6 min walkbr ☀ The Cottage: 6 min walkbr ☀ Another Broken Egg Cafe: 7 min walkbr ☀ Sun Garden Cafe: 7 min walkbr ☀ The Old Salty Dog Siesta Key: 10 min walkbr ☀ Daiquiri Deck Siesta Key Village: 2 min drivebr ☀ Cafe Gabbiano: 2 min drivebr ☀ Clayton`s Siesta Grille: 8 min drivebr ☀ SPEARFISH GRILLE: 8 min drivebr ☀ The Toasted Yolk Cafe: 11 min drivebr ☀ Florence & The Spice Boys: 12 min drivebr ☀ Casa Masa - The Landings: 13 min drivebrbr★ :br ☀ Sarasota Memorial Hospital: 14 min drivebr ☀ Medical Center of Sarasota: 17 min drivebr ☀ HCA Florida Sarasota Doctors Hospital: 23 min drivebrbr★ :br ☀ Beach Rd @ Calle De La Siesta: 3 min walkbr ☀ Ocean Blvd @ Calle Miramar NB: 4 min walkbr ☀ Ocean Blvd @ Canal Rd SB: 6 min walkbr ☀ Enjoy free rides to all major island attractions with two hop-on hop-off services: 77 Siesta Islander and Bay Runner Trolley.br ☀ Travel easily with Breeze, the local bus service, connecting Downtown Sarasota and Siesta Key.brbr★ :br ☀ Sarasota Bradenton International Airport: 26 min drivebr ☀ Venice Municipal Airport: 32 min drivebr ☀ Hidden River Airport-22FA: 47 min drivebrbrb ★☆ Upcoming Events in Siesta Key Beach:/bbr☀ Thunder By The Bay Music & Motors Festival: Feb 13–15, 2026br☀ `Say I Do Again` Vow Renewal Ceremony: Saturday, Feb 14, 2026br☀ Elton John Tribute Concert: Feb 27, 2026br☀ Guns N` Roses Tribute Concert: Feb 28, 2026br☀ Sarasota Jazz Festival: Mar 9–14br☀ Sarasota County Fair: Mar 13–22br☀ Spring Break Season: All Monthbr☀ Siesta Key Drum Circle: March, 2026 Every Sunday in br☀ Siesta Key Farmers Market: March 2026, Every Sunday (9:00 AM – 1:00 PM) br☀ Embracing Our Differences (Outdoor Art Exhibit)—till April 13, 2026br• Full payment of all charges is due 30 days prior to arrival and will be charged automatically to same credit card use it at booking unless communicated otherwise. A full refund (minus a $100 cancellation fee) will be made for any cancellations made in writing with 30 days’ notice. There are no refunds for cancellations with less than 30 days prior to arrival.br• Check in time is any time after 4 PM.br• Check out time is 10 AM it is imperative that you be out promptly at 10 AMbrto allow our cleaners time to prepare the unit for the next guest. Unauthorized late check out may result in additional fee being charged to your credit card.br• Pets allowed. If unauthorized pet is discovered on premise, charge of up $200.00 plus damage may be assessed, as guest will be in breach of this agreement.br• No smoking allowed anywhere inside the unit (violation will result in forfeiture of full security deposit).br• Minimal rental age is 25. All persons under 25 years of age must be accompanied (staying in the unit wait them) by an adult (parent or guardian).br• Only the number of persons specified on the reservation sheet will be allowed. Any additional people will be charged $50 a day. This must be approved prior to arrival. The premises (room, pool area, common areas, etc.) are for the use and enjoyment of registered guess only.br• if you designated unit becomes unavailable due to unexpected circumstances, we reserve the right to assign you a comparable unit or cancel this agreement and refund all payments in full.br• Make sure chairs and wagons were returned to their place of origin. In case of loss this will be charged $30.00 per chair / $200.00 wagon.brbr• Security deposit: your credit card will be kept on file in lieu of a security deposit or a security deposit will be collect. Guess grants concerned for us to charge your credit card for damages, missing items, excessive cleaning, fines, additional occupants, etc.br• In order to maintain our high standards, we asked to our guest supervise the children all the times.br• If you have any problems or questions during your stay, please contact our supervisor (contact information provided on your checking instructions). You have 72 hours to report any dissatisfaction with your unit. NOTE: only urgent /emergency issues will be addressed after hours and Sundays.br• There is no daily maid or line service included except for cleaning after departure.br• If you like yourself out of your unit there is a $50 charge to have our maintenance manager, come and open the unit for you.br• The pool is heated during the winter months.br• POOL HOURS: 8AM - 9PM •br Noise Ordinance: There is a county noise ordinance in place that is in effectbr after dark and guest agrees to respect the ordinance and use commonbr sense in keeping noise volume low after dark and is aware that the sheriff’sbr department will be called if noise has not ceased by 10 PM. If this occursbr after one warning you will be asked to vacate the premises and there willbr be no refund. We are a family-oriented complex and hope you will respectbr your fellow guests. We do not allow loud parties, as it tends to disturb ourbr other guests and neighboring residents.br • You agree to abide by all condominium association rules and regulations. Parking is limited to passenger’s vehicles, motorcycles, and golf carts. Trailers (including boat trailers), motor homes and commercial trucks may not be parked at the premises.

Newly Renovated Beach-Side villa | Pool | Dock

Sarasota, Florida, United States

1

Bath

4

Sleeps

Exceptional(6)

$180.62

Perfect for couples or families looking for a comfortable and convenient vacation rental.brbrThis newly renovated duplex exudes beach vibes and is the perfect spot for a relaxing vacation. Located just a few blocks from Stickney Point bridge, which leads directly to the beautiful Siesta Key Beach, you`ll have easy access to all the fun and sun that Florida has to offer.brbrUpon arriving at the duplex, you`ll instantly feel at home with its stylish decor and updated amenities. The beach theme throughout will transport you to a state of relaxation, making it the perfect place to unwind after a day at the beach.brbrThe fenced yard is the perfect spot for outdoor dining and entertainment, with a gas grill, gas firepit, and a patio table with chairs. Relax and soak up the sun on the lounge chairs, or take a dip in the shared swim spa with the other side of the duplex.brbrPerfect for couples or families, this vacation rental has everything you need for a comfortable and convenient stay. Don`t miss out on your chance to make memories in this dreamy beach getaway. Book now and start counting down the days until your perfect Florida vacation.

Sarasota Duplex near Siesta Key

Sarasota, Florida, United States

Bed

Bath

5

Sleeps

$226.37

This Sarasota house boasts 2 inviting bedrooms, one with a queen bed and the other with a full bed. The bathrooms are equipped with showers for your convenience. Enjoy the soothing atmosphere of this delightful property, complete with amenities like a washing machine, AC, and WiFi. A great place to call homebase while you're away, we hope you enjoy your stay.

Charming 2-bedroom house with WiFi and AC in delightful Sarasota

Sarasota, Florida, United States

Bed

Bath

4

Sleeps

$288.77

This Sarasota house boasts 3 inviting bedrooms, including 1 king bed and 2 queen beds and is in a quiet residential area. There is a ONE MONTH MINIMUM. Only a 5-minute drive to Siesta Key Beach. It also has a large, heated saltwater pool for you to enjoy all year round. brKitchen is well equipped if you enjoy cooking or watch the beautiful sunsets on Siesta key Beach and enjoy any of the restaurants and music venues Siesta Key has to offer. There is a gas grill on the screened lanai.brGulf Gate Village is only minutes away and has many restaurants and shops to enjoy.brTVs are in all bedrooms and in both living areas.

3 Bedroom 2 Full Bath House near Siesta Key Beach

Sarasota, Florida, United States

Bed

Bath

Sleeps

$307.93

Welcome to Casa Trinidad — Your Coastal Oasis in Sarasota!brbrEscape to Casa Trinidad, a bright and stylish 4-bedroom coastal retreat located just minutes from world-famous Siesta Key Beach and vibrant Downtown Sarasota. Whether you’re planning a family getaway, a couples’ trip, or a relaxing retreat with friends, this home offers everything you need for the perfect Florida stay — a heated private pool, fire pit, BBQ area, game room, and all the cozy coastal touches that make it unforgettable.brbr⸻brbr Property OverviewbrbrStep inside and discover a spacious, sun-filled home designed with comfort, elegance, and functionality in mind. The open-concept living area blends beach-inspired décor with modern amenities to make you feel instantly at ease. Large windows and light tones create a calm, airy feel — perfect for relaxing after a day at the beach or a night in downtown Sarasota.brbrHighlights:br • 4 Bedrooms | 2 Bathrooms | Sleeps up to 13 guestsbr • Private heated pool surrounded by tropical landscaping.Pool heater is available at no extra cost. If you’d like the pool heated, please let us know at least 24 hours before your arrival (or before you’d like it turned on) so we can have it ready for you. ✨br • Outdoor fire pit and cozy seating areabr • Fully equipped kitchen with coffee bar & modern appliancesbr • Game room with pool table & family gamesbr • Outdoor dining patio with BBQ grillbr • Beach gear: chairs, umbrellas, and carts includedbr • Fast Wi-Fi + Roku smart TVs for all your streaming needsbr • Baby amenities (high chair, pack-and-play, and child-friendly dishes)br • Washer/dryer, driveway parking, and contactless entrybrbr⸻brbr Living Spaces — Relax, Entertain, and EnjoybrbrThe open-plan living area is perfect for gathering and creating memories. Sink into the plush sofas, turn on a movie night with Roku, or enjoy a drink from the coffee bar while you plan your next beach adventure.brbrThe game room is a favorite among guests — complete with a pool table, board games, and a smart TV for added fun. It’s an ideal space for families or groups to unwind after a sunny day outdoors.brbr⸻brbr Gourmet Kitchen & DiningbrbrLove to cook You’ll adore Casa Trinidad’s fully stocked kitchen — equipped with stainless steel appliances, cookware, bakeware, a Keurig and drip coffee machine, blender, toaster, and even a wine opener for sunset cocktails.brbrGather around the dining table for family meals or step outside to the patio dining area, where you can enjoy grilled favorites under the stars surrounded by twinkle lights and the gentle sound of palm trees swaying.brbr⸻brbr Comfortable Bedrooms for Restful NightsbrbrCasa Trinidad features four beautifully designed bedrooms, each offering cozy beds, premium linens, and plenty of storage.br • Bedroom 1: King bed, ensuite bath, smart TV, and serene coastal décorbr • Bedroom 2: Queen beds — smart Tv perfect for couples or siblingsbr • Bedroom 3: Queen beds and smart Tv with soft beach tonesbr • Bedroom 4: Fun bunk bed and twin bed setup ideal for kids or friendsbr • Plus a sofa bed in the common area for extra guestsbrbrAll rooms include blackout curtains, ceiling fans, and fresh linens to ensure a peaceful night’s sleep after your Florida adventures.brbr⸻brbr Outdoor ParadisebrbrStep outside and discover your private Sarasota oasis! The heated pool is surrounded by a lush tropical garden — perfect for sunbathing, floating, or sipping a drink poolside.brbrAt night, light up the fire pit and gather around with family or friends to share stories under the Florida stars. The BBQ grill and outdoor dining table make this area ideal for alfresco dinners.brbrThere’s even a tropical garden patio with cozy seating where you can enjoy your morning coffee or evening cocktail.brbr⸻brbrBeach Days Made EasybrbrYou’re just a short drive (8–10 minutes) from Siesta Key Beach, known for its powdery white sand and turquoise waters.brCasa Trinidad provides everything you need for stress-free beach days:br • Beach chairsbr • Umbrellasbr • Beach cartsbr • Towels and coolersbrbrYou can also explore nearby Lido Beach, Turtle Beach, or Venice Beach — all offering their own charm and unique coastal vibes.brbr⸻brbr Fun & EntertainmentbrbrWhen you’re not soaking up the sun or exploring Sarasota, Casa Trinidad keeps the fun going at home:br • Roku TVs with streaming apps (Netflix, Hulu, Prime Video)br • Board games for family nightsbr • Pool table for friendly competitionsbr • Wi-Fi strong enough for work or streamingbr • Outdoor Bluetooth speaker for poolside playlistsbrbr⸻brbr Perfect Location — Near Siesta Beach & Downtown SarasotabrbrYou’re right in the heart of Sarasota — a peaceful residential neighborhood close to everything:br • Siesta Key Beach – 8 minbr • Downtown Sarasota – 10 minbr • St. Armands Circle – 15 min (boutiques, dining, nightlife)br • Marie Selby Botanical Gardens – 10 minbr • Great restaurants – 5–10 minbr • Publix & Target – 3 min away for all essentialsbrbr⸻brbr Cleanliness & SafetybrbrYour comfort and safety are top priorities at Casa Trinidad.br • Professionally cleaned after every staybr • Fresh linens, sanitized surfaces, and stocked essentialsbr • Contactless check-in with smart lockbr • Pool maintained weeklybr • Exterior security camera for driveway safety (no indoor cameras)brbr⸻brbr Family-Friendly AmenitiesbrbrTraveling with little ones We’ve got you covered:br • High chair & pack ’n playbr • Plastic dishes & cupsbr • Step stool, nightlights, and children’s booksbr • Fenced backyard and plenty of open space for playbrbr⸻brbr Extras That Make It Specialbr • Fire pit nights under the starsbr • Coffee bar station with assorted pods & mugsbr • Outdoor string lighting and coastal décorbr • Dedicated workspace for remote work or studybr • Pet-friendly upon approval (ask before booking)brbr⸻brbrGuest AccessbrbrYou’ll have full access to the entire property — pool, patio, BBQ, and all indoor amenities.brPrivate driveway parking is available for up to 3 cars.brSelf-check-in with smart lock ensures an easy, flexible arrival.brbr⸻brbr Why Guests Love Casa Trinidadbrbr “Perfect location between Siesta and downtown!”br “Spotless, beautifully decorated, and stocked with everything.”br “Loved the fire pit nights and pool area — so peaceful.”br “The best family vacation house we’ve ever stayed in.”brbr⸻brbr Your Sarasota Home Away From HomebrbrWhether you’re chasing sunsets at Siesta Key, exploring Sarasota’s art and dining scene, or simply relaxing poolside with your favorite drink, Casa Trinidad is designed to make every moment special.brbrFrom the coastal décor to the thoughtful touches, this home combines resort-style amenities with true comfort — a place where you can recharge, reconnect, and make lasting memories.brbrBook your stay today and experience the magic of Sarasota’s coastal charm — Casa Trinidad awaits you!

4BR with Heated Pool , Fire Pit & Pool Table •Mins to Siesta & Downtown!

Sarasota, Florida, United States

4

Bed

Bath

12

Sleeps

$82.85

Enjoy this peaceful, affordable quiet room centrally located in south Sarasota. You’ll have a private entrance, comfy queen bed, private bath with shower, big screen TV, mini-fridge, micro-wave, and coffee pot at your room. Enjoy a beautiful private patio right outside your door. The entire space is newly finished. Your modern space adjoins a low-volume retail business right on the Tamiami Trail, putting you just a couple minute drive from shopping and restaurants. Sarasota's famous Siesta Beach is 16-minutes away.brbrYour room and patio are adjacent to a quiet low volume retail business on the Tamiami Trail, with easy access to everything Sarasota, Osprey, Nokomis, and Venice has to offer. A public bus stop (Breeze #17) is right out front. Several restaurants, Publix grocery, and a Target are a 10-minute walk on sidewalks.brbrPerfect for someone or couples that wants to explore different restaurants and outdoor activities.

Getaway Catfish Creek and Private Room Near Beaches

Sarasota, Florida, United States

Bed

Bath

Sleeps

$382.31

Welcome to this beautiful house in Sarasota!br With three bedrooms featuring a king, queen, and twin beds, as well as two family rooms, guests find plenty of space to relax in the bright and airy home. Open up the french doors to the screened-in pool with a large private area, featuring an outdoor sitting area and a grill. Perfect spot for your morning coffee!brbrWhether you’re unwinding after a day of exploring or going to the beach or golfing at the many courses nearby or biking the Legacy Trail, or enjoying quiet mornings, this peaceful retreat offers a marvelous setting for your vacation! Make your vacation one to remember with a stay at our place! *Please note- the vehicle in the garage is not for guest use. Also, the garage is not for guests to park their car*

Beautiful 3-bedroom pool home in Paradise! 4 miles to Siesta Key! Near Pinecraft

Sarasota, Florida, United States

Bed