Vacation Rentals By Owner In Siesta Key, FL

Experience Siesta Key in this lovely island condo! Conveniently located above one of our island’s grocery stores, this 3-bedroom, 2-bathroom condo is directly in the heart of the vibrant South Siesta Key Village. With 13 public beach access points, great food, shopping, and plenty of activities, Siesta Key promises amazing experiences for everyone who visits. Take advantage of the tranquil waters, soft sand, and warm sun as you explore all the island has to offer and unwind at the end of a fantastic day in this beautiful condo.brbrMaster Bedroom: KingbrBedroom 2: QueenbrAdditional Space: Twin BunkbrLiving Room: Sofa Bedbrbr*This unit is located on the second floor, must be able to climb stairs**brbrAdded Amenities Included in Your Stay:brComplimentary Bicycles Rentals,brOne Complimentary Parking Space,brWifi,brBeach Chairs,brBeach Towels,brBeach Wagon,brBeach Cooler,brPartner Property Pool/Hot tub Access,brAccess to Siesta Beach Pickleball Courts,brSiesta Key Trolley - Free-Rides Around Siesta Key,brA 7-day week, Beachside Management office for your convenience and guest needs!brbr*Minimum Age to Book: 23br*To book a Beachside Managed Property Between February 1st and April 15th, the booker must be 27 years old or older. br*Security Authorization Hold taken upon check-in. Amount: $500

Perfect Cozy Island Get-Away on Siesta Key!

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$796.65

Contact the host to inquire about discounts for longer stays! We offer 25% off stays longer than 14 nights, 30% off 21 nights, and 35% off of 28 nights or more. The 28 night discount shows in the listing, but please inquire for 14 or 21 night discounts.brbrThis 4 bedroom, 3.5 bathroom serene, lakefront oasis with a private pool is a short walking distance from Siesta Key Village. With a bathroom on each of the 3 floors and 4 king, 3 twin, and 1 full beds, this home sleeps 13 and is the perfect retreat for multiple families, 4 couples, or a multigenerational family vacation.brbrOutside the home you will find several areas of enjoyment around the property including a lakefront firepit, a private, heated salt-water pool, a covered lanai area with a ping pong table and a large HDTV and seating area, and a bike storage area. If you enjoy nature, we recommend getting biodegradable turtle food to throw into the lake to see the wildlife up close. brbrInside, the home is laid out over three stories with a full bathroom on each level for optimum privacy. In the lower level, which has it's own separate entrance, there is a bedroom with a king sized bed and additionally a full bed in the laundry room/kitchenette just outside the bedroom. This level also houses a large washer and dryer, a Keurig, a full sized refrigerator, outdoor dining supplies, and a sink/countertop area for food prep. The second level of the home consists of a full sized kitchen, dining room, living room with a large HDTV, an enclosed porch that overlooks the lake, a half bathroom, and the primary bedroom with a full ensuite bathroom. The third level of the home has two bedrooms, each containing a king sized bed, and a shared full bathroom. All bedrooms have a large HDTV.brbrThe home also has several beach cruiser bikes and two closets full of beach and pool accessories including a wagon, beach chairs, sand toys, pool toys, and many floaties. The driveway has room for 3-4 cars (if you don't mind parking each other in).brbrThe free Siesta Breeze trolley picks up within a block of the house and loops between downtown Sarasota and Turtle beach on the south side of the island. You can ride the trolley a few blocks to get to the village or beach access points or easily walk or ride bikes. brbrYou will not regret staying in this tropical paradise just minutes away from Siesta Key Beach and Siesta Key Village!

Island Sol: Secluded 4 BR Paradise with Salt Water Pool, Walk to the Village

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$279.79

Looking for quick easy access to the #1 beach in America You've found the place! Enjoy the excellent location of the Siesta Key Beachside vacation rental condo. Just a few 100 feet from private beach access allows our guests to enjoy some fun and relaxation in the sun. The community offers free access to its heated pool, picnic style charcoal grills, and laundry facilities. The community in general is located just 1/4 mile from Siesta Key public beach which offers addition amenities such as tennis courts, pavilion, picnic areas, playground, and is host to many of the areas festivals such as the seafood festival and sandy castle festival to name a couple. Utilize many of the islands free ride services or island shuttle to visit Siesta Key Village; offering a myriad of dining and entertaining venues. brbrArrive at this unit at the designated parking spot and check right in, no keys to pickup or lines to wait in. Entering the unit you arrive in the living room furnished with lounge seating and flat screen TV. Within the living area you will find the dining area with seating for 3 and addition 2 at the breakfast off the kitchen. The kitchen is equipped with 4 piece major appliance set among other small kitchen appliances and stocked for light to medium cooking needs. Towards the back of the unit you will find the master bedroom furnished with king-size bedroom set and ample closet space. Next you will find the guest bedroom furnished with a queen and twin size beds. The two bedrooms share a common bathroom just off the hall equipped with stall shower.

Siesta Beach Condo Rental with direct beach and pool access

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$346.05

Sea Angel | 400 Ft to Beach + Dog Friendly + Shared Patiobrbr Why You'll Love This HomebrPerched on the top left corner of CJ's on Siesta, Sea Angel offers cozy privacy and bright natural light just steps from Siesta Key Beach. With fresh interiors, a king suite, and a relaxing outdoor patio shared with just five other units, it's the ideal beach hideaway for couples or small families.brbr ‍ ‍ Perfect ForbrCouples, solo travelers, or a small family seeking a walkable, pet-friendly retreat near the beach and Village fun.brbr ️ Imagine ThisbrStart your morning with a fresh cup of coffee as the sunlight pours through your corner-unit windows. Slip on sandals and stroll just 400 feet to the world-famous sands of Siesta Key Beach. After soaking up the sun, stop by Siesta Key Village for a fish taco or cold drink, then return to your tranquil unit to unwind. Fire up the shared grill, stretch out on a lounger under the palms as the evening breeze rolls in.brbr Where You'll Sleepbr• Bedroom 1: King Bed, Ensuite Bath, Second Floor (Top Left Unit), TVbr• Living Area: Modular Sleeper Sofa, Open Concept Living Room, TVbrbr Explore the Areabr• 0.1 miles to Siesta Key Beach (400 feet)br• 0.1 miles to Siesta Key Village – Walkable to Restaurants, Shops, and Nightlifebr• Tucked in a Vibrant, Coastal Neighborhood with Local Energy and Beachside Charmbr• Easy Access to Water Sports, Ice Cream Spots, and Sunset Strollsbrbr⌛ Don't Wait—This Home Books FastbrYour stay at Sea Angel includes peace of mind with a 6-hour deep clean and 35-point inspection before every arrival. Bonus: Furry friends welcome! This unit allows 1 dog (up to 25 lbs) with an applicable pet fee.brbr Need to Know: Starter packs of kitchen and toiletry essentials provided for a seamless first couple of nights. One designated parking space is available. Free High-Speed WiFi in the unit. Shared on-site laundry available. One dog allowed (max 25 lbs) with a pet fee. If any guest has difficulty with stairs, please contact us for alternative accommodations. Your listing is part of a multi unit complex and is a distinct unit—with its own private entrance, kitchen, and living areas—with no interior connection. As a multi-unit complex, it could share a dividing wall, floor, ceiling, outdoor space, and/or amenities with another unit(s). Contact us directly for more information regarding any shared space for this vacation home.

Sea Angel - Pet Friendly, Located in Siesta Key Village, Steps to Siesta Key Beach!

Siesta Key, Florida, United States

1

Bed

1

Bath

4

Sleeps

$2497.38

CJ's on Siesta | 400 Ft to Beach + Shared Patio & Grillbrbr Why You'll Love This HomebrSteps from Siesta Key Beach and nestled in the heart of the Village, CJ's on Siesta offers the rare flexibility of six private, stylish units all in one place. A spacious shared patio with chaise loungers, table with chairs, and grill sets the stage for unforgettable moments between dips in the ocean and sunset cocktails.brbr ‍ ‍ Perfect ForbrMulti-family groups, wedding guests, reunions, or corporate retreats seeking connected-yet-private accommodations right by the beach.brbr ️ Imagine ThisbrWake up and sip coffee just 400 feet from the powder-soft sands of Siesta Key Beach. Everyone has their own space—each unit offering a king suite, cozy lounge with sleeper sofa, and full bath. Meet in the shared patio for morning plans under the palms, then stroll into Siesta Key Village for brunch or boutique browsing. Evenings bring beachside sunsets followed by BBQs on the grill, laughter on the chaise lounges, and starry-night chats in your private outdoor retreat.brbr Where You'll SleepbrEach of the 6 private units includes:br• Bedroom 1: King Bed, Ensuite Bath, First or Second Floor, TVbr• Living Area: Modular Sleeper Sofa, Shared Living Space, TVbr Note: All units are similar in layout. Three are on the first floor, three on the second, with shared interior walls.brbr Explore the Areabr• 0.1 miles to Siesta Key Beach (400 feet)br• 0.1 miles to Siesta Key Village – Dining, Shops, Nightlifebr• Walkable, Vibrant Coastal Neighborhood with a Laid-back Tropical Vibebr• Quick Access to Water Sports Rentals, Beach Yoga, and Casual Eatsbrbr⌛ Don't Wait—This Home Books FastbrCJ's on Siesta provides everything needed for effortless group travel. Your reservation includes peace of mind with a 6-hour deep clean and 35-point inspection prior to your arrival.brbr Need to Know: Starter packs of kitchen and toiletry essentials provided for a seamless first couple of nights. 6 parking spaces available. Free High-Speed WiFi in each unit. Shared on-site laundry available to all guests. If any guest has difficulty with stairs, please contact us for alternative accommodations. This listing is a multi unit complex and has distinct units. Each of the six units has their own private entrance, kitchen, and living areas—with no interior connection. As a multi-unit complex, it could share a dividing wall, floor, and ceiling. As the entire complex the outdoor space is private. Contact us directly for more information regarding any shared space for this vacation home.

CJs - Pet Friendly, Located in Siesta Key Village, Steps to Siesta Key Beach!

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$301.34

FULL BAY VIEWS FROM THIS 1ST FLOOR UNIT. brYOU CAN’T GET ANY CLOSER TO THE BAY THAN THIS. brbrSit on your screened in Lanai while you watch the boats and wildlife. The versatile layout boasts one spacious bedroom, and a smaller guest bedroom. Washer and dryer in unit. Newer Hurricane windows & sliding door. brbrIn addition to beautiful views & fabulous location the Amenities include a community fishing pier with great views up and down the inter-coastal waterway, picnic and grilling area, clubhouse, covered parking, tennis courts, heated pool. A short walk puts you on the sugar-fine quartz white sands of the World-Famous Siesta Key Beach or jump on the trolley to all the other attractions Siesta offers. brbrIt's time to create memories that will last a lifetime in your own little piece of paradise. brThis condo is Florida resort-style living at its finest!

Siesta Key Direct Water Views - A

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$299.84

The Anchorage Resort on Siesta Key - includes resort amenity 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.br* Anchorage Resort Condo br* 2 bedrooms / 2 bathroomsbr* Spacious Balcony overlooking Southern Siesta Keybr* Third Floor Condo overlooks the canal and Southern Siesta Keybr* Fully equipped Kitchen with seating for 4 at the dining tablebr* Beach Supplies include- Chairs, Umbrella, Cooler, Raft/Float Items, Beach Towelsbr* Community Pool- Largest pool on the Key!br* Gated Communitybr* Siesta Key Trolley- free pickup in front of the resort entrancebr* Private Beach access to Crescent Beach across the streetbr* 25-year minimum age to rent restrictionbrbrBEDROOMS (Third Floor Condo)brBedroom 1: One King Bed and One Queen(Attached Bathroom) / Balcony AccessbrBedroom 2: Two Queen Beds / Balcony AccessbrbrPool Information:br- Community Poolbr- Heated brbrResort Parking Rules:brThe resort allows a maximum of 2 cars.brVehicles must be registered with the front office during office hoursbrbrHOA Rules:brLead guest must be age 25 or older. ID is checked upon registration at the resort.brNo petsbrJanuary 1- April 16 Rentals are 7-nights beginning and ending on Saturday onlybrbrThe Anchorage Resort Amenity Access Included with Rental:br* Olympic-Size poolbr* 3 Lighted Tennis/Pickleball Courts br* 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 brDistances 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 toilet paper per bathroombr- 1 hotel-size bar soap per bathroombr- 1 hotel-size shampoo/conditioner per full bathroombr- 1 roll paper towelbr- 2 packet 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 with us $250.00. $1,250.00 will be refunded.brIf canceled between 61 and 89 days prior to arrival, we keep with us the $1,500.00 deposit.brNo cancellation or modification 60 days or less prior to arrival.

Anchorage Resort 3rd Floor Two Bedroom Condo with Beach Access

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$565.82

Welcome to Siesta Sunset, a breathtaking beachfront rental home located right on the pristine shores of Siesta Key Beach. This gorgeous condo not only offers direct beach access but also stunning panoramic views of the Gulf of Mexico, ensuring your island getaway is nothing less than spectacular!brbrAs you step inside Siesta Sunset, you'll be greeted by the magnificent beach views that can be enjoyed from three different rooms, allowing you to soak in the beauty of the coastline throughout your stay. The spacious balcony offers a prime vantage point for witnessing breathtaking sunsets and provides a comfortable lounge space where you can relax and unwind while being mesmerized by the tranquil Gulf views.brbrSiesta Sunset features three bedrooms and two full baths, including a master bedroom for added privacy and comfort. With two king beds, one queen bed, and one twin bed, this home comfortably accommodates up to six guests. Linens are provided, ensuring a cozy and restful night's sleep for everyone.brbrFor your convenience, Siesta Sunset offers a starter pack of toiletry essentials, including shampoo, conditioner, hand/face soap, body lotion, and makeup wipes. A starter pack of home essentials, such as dish soap, a dish sponge, dishwasher tablets, laundry tablets, and cleaning wipes, is also provided. Beach towels, chairs, a cooler, and a caddy are available in the bottom-level storage space, ensuring you have everything you need for a day at the beach. And if you're in the mood for a delicious BBQ, a gas grill is conveniently located on the side of the building.brbrThe amenities at Siesta Sunset cater to your every need. Two private carports provide convenient parking options, and free WiFi and four HDTVs keep you connected and entertained throughout your stay. The gourmet kitchen includes regular and Keurig coffee makers, a dishwasher, a washer and dryer, and all the kitchen essentials you need to prepare meals with ease. A pellet ice maker adds a special touch, providing cool refreshments for those warm beach days. The kitchen effortlessly merges with the adjoining living room and dining area, creating an open concept design. This allows you to enjoy breathtaking views of the water while seated comfortably in the heart of the home.brbrWith Siesta Key Beach just steps away, you have the convenience of easily accessing the soft powdery sands, crystal-clear waters, and endless beach activities. Spend your days sunbathing, building sandcastles, or taking refreshing dips in the ocean. The direct beach access ensures that you can fully embrace the beach lifestyle and enjoy the soothing sound of the waves throughout your stay.brbrLocated less than 0.5 miles from Siesta Key Village, Siesta Sunset offers the perfect balance between beachfront tranquility and the vibrant energy of the village. Explore the charming shops, indulge in delectable dining options, and immerse yourself in the local culture. Whether you're seeking a lively nightlife scene or a leisurely stroll through the village, the close proximity makes it convenient to experience all that Siesta Key has to offer.brbrIndulge in the ultimate beachfront experience at Siesta Sunset, where stunning sunsets, direct beach access, and a prime location combine to create an unforgettable vacation. Book your stay today and experience the best of Siesta Key!brbrExclusive Amenities Include:br• Direct Beach Access with Panoramic Beach Views From 3 Roomsbr• Spacious Balcony With Breathtaking Gulf Views & Lounge Spacebr• Siesta Key Beach Just Steps Awaybr• Less Than 0.5 miles to Siesta Key Villagebr• 3 Bedrooms, 2 Full Baths (1 Master Bedroom)br• 2 King Beds, 1 Queen Bed, & 1 Twin Bed (Sleeps 6) with linens providedbr• 2 Private Carportsbr• Free WiFi & 4 HDTV'sbr• Regular & Keurig Coffee Maker, Dishwasher, Washer & Dryer, and Kitchen Essentials Providedbr• Starter Pack of Toiletry Essentials Included - Shampoo, Conditioner, Hand / Face Soap, Body Lotion, & Makeup Wipesbr• Starter Pack of Home Essentials Included - Dish Soap, Dish Sponge, Dishwasher Tablets, Laundry Tablets, & Cleaning Wipesbr• Pellet Ice Makerbr• Beach Towels, Chairs, Cooler, & Caddy Provided - located in bottom level storage spacebr• Gas Grill - Located On Side Of Buildingbr• Enhanced cleaning protocols provided by our CottageClean Teambr• Island Shuttle Transportation AvailablebrbrSiesta Sunset can accommodate up to 6 guests with a bedding configuration as follows:brbr• Bedroom # 1: King Bed (1)br• Bedroom # 2: King Bed (1)br• Bedroom # 3: Queen Bed (1) & Twin bed (1)brbrWe go above and beyond the industry standard for cleanings with our multi-tiered cleaning protocol within our CottageClean Program. After our six hour in-depth cleaning of your home, we complete a 35 point property inspection to ensure that you feel tremendously safe and happy with this amazing home. This allows you to vacation worry free regarding the cleanliness of your home and truly relax as soon as you arrive. Our goal is to have you feel like you are walking into a brand new vacation home that no one has ever stayed at before!brbrNEED TO KNOW: This home is a part of a duplex unit, meaning that it could share a dividing wall, floor, ceiling, outdoor space, and/or amenities with another unit(s). When renting this unit, you will have access to the 1st floor covered parking area labeled PH. This unit is a 3rd floor unit with no elevator; however, if you need assistance bringing large items up the stairs, let us know and our team would be happy to assist! Contact us directly for more information regarding any shared space for this vacation home.

Siesta Sunset | Luxurious Beach Front Penthouse w/ Views of Gulf, Minutes to Siesta Key Village

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$2342.88

Step into the luxurious embrace of Luxe Lagoon, where Siesta Key's charm blends seamlessly with unparalleled sophistication. This exclusive, 7-bedroom, 7-bathroom estate accommodates up to 20 guests and promises a vacation experience like no other—one where elegance and comfort meet every desire. Whether you're gathering with family, friends, or colleagues, Luxe Lagoon is the perfect haven for your getaway.brbrAs you enter the private backyard oasis, a tropical paradise unfolds. Surrounded by lush, swaying palms, the heated pool and spa invite you to unwind and immerse yourself in pure relaxation. For added enjoyment, the manicured putting green and ping pong table offer entertainment and leisure without ever leaving the property. A convenient half-bath is located on the first floor, ensuring easy access for all guests.brbrThe second floor welcomes you with lavish accommodations. Three king bedrooms, each with their own en-suite bath, offer a restful retreat for your group. The spacious kitchen area, with its sprawling island, 8-seat dining table, and 5 barstools, is perfect for meal prep and socializing. Cooking here is a joy with the top-of-the-line gas range elevating every culinary creation.brbrVenture up to the third floor, where comfort and style continue. Four beautifully appointed bedrooms include three king suites, each with en-suite bathrooms, and a charming bunk room featuring two sets of Full-over-Full beds—ideal for families or groups. The spacious living area, with ample seating and a sophisticated wet bar, opens onto a wraparound balcony with tropical views that instantly soothe the soul. Here, you'll hear the sound of the hot tub waterfall and the gentle rustling of palm leaves—perfect for unwinding after a day of adventure.brbrFor an elevated experience, take the spiral staircase up to the rooftop terrace, where panoramic views of Siesta Key Beach and Village await. Watch the sun set over the sparkling Gulf Coast and indulge in moments of tranquility that are uniquely Siesta Key.brbrLuxe Lagoon is more than a home—it's a luxury experience, where every detail has been carefully considered to offer you the ultimate vacation. From the stunning interior design to the lush outdoor spaces, this is a place where you'll feel deeply connected to the serene beauty of Siesta Key. Whether you're here for a relaxing retreat or an adventure-filled vacation, Luxe Lagoon delivers a blend of elegance, comfort, and unforgettable moments.brbrBook your stay at Luxe Lagoon today and make memories in this breathtaking Siesta Key paradise.brbrbrExclusive Amenities Include:br• Private Heated Pool & Spabr• Breathtaking Sunset and Partial Gulf Views on Rooftop Terracebr• Less than 500 ft to Siesta Key Villagebr• Less than a 3 Minute Walk to Siesta Key Beachbr• 7 Bedrooms (7 Master Bedrooms), 7 Full Baths, 2 Half Bathsbr• 6 King Beds & 2 Full Over Full Bunk Beds (Sleeps 20) with linens providedbr• Multiple Spacious Balconiesbr• Three Story Convenience Elevator for luggage, groceries and personal gearbr• Private parking for 2 vehicles in drivewaybr• Free WiFi & 11 HD Smart TV'sbr• Wolf / Subzero Kitchen Appliances, Regular & Keurig Coffee Maker, Dishwasher, Washer and Dryer, and Kitchen Essentials Providedbr• Starter Pack of Toiletry Essentials Included - Shampoo, Conditioner, Hand / Face Soap, Body Lotion, & Makeup Wipesbr• Starter Pack of Home Essentials Included - Dish Soap, Dish Sponge, Dishwasher Tablets, Laundry Tablets, & Cleaning Wipesbr• Beach Towels, Chairs, Cooler, & Caddy Providedbr• Outdoor Lounge Area Includes Ping Pong, Wooden Bar with HD Smart TV, Dining Table, Gas Grill, & Poolside Showerbr• Enhanced cleaning protocols provided by our CottageClean Teambr •Island Shuttle Transportation Availablebr• Dog-Friendly with a Fee (1 dog up to 25lbs)brbrLuxe Lagoon can accommodate up to 20 guests with a bedding configuration as follows:brbr• Bedroom # 1: King Bed (1) - Sleeps 2 - Private Bathroom 1br• Bedroom # 2: King Bed (1) - Sleeps 2 - Private Bathroom 2br• Bedroom # 3: King Bed (1) - Sleeps 2 - Private Bathroom 3br• Bedroom # 4: King Bed (1) - Sleeps 2 - Private Bathroom 4br• Bedroom # 5: King Bed (1) - Sleeps 2 - Private Bathroom 5br• Bedroom # 6: King Bed (1) - Sleeps 2 - Private Bathroom 6br• Bedroom # 7: Full Bunk Beds (2) - Sleeps 8 - Private Bathroom 7brbrWe go above and beyond the industry standard for cleanings with our multi-tiered cleaning protocol within our CottageClean Program. After our six hour in-depth cleaning of your home, we complete a 35 point property inspection to ensure that you feel tremendously safe and happy with this amazing home. This allows you to vacation worry free regarding the cleanliness of your home and truly relax as soon as you arrive. Our goal is to have you feel like you are walking into a brand new vacation home that no one has ever stayed at before!brbrPLEASE NOTE: This pool is heated from November 15th to April 15th.brbrThis home has stairs. If any member of your party has difficulty with stairs, please contact us to discuss alternative accommodations.

Luxe Lagoon | Located in SK Village! Private Pool & Spa, Rooftop, Pet Friendly ️☀️

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$543.47

This is a spacious, two story, 4 bedroom home with 3 master suites that have their own on-suite bathrooms. Two of these masters have king size beds and TV's, the other Master has a queen bed and a TV as well. The 4th bedroom has 2 twin beds and a TV with a Sony play station and games for the kids. There is also a small play area on the balcony for kids with books, chairs and toys to play with. The kitchen is very spacious newly remodeled with stainless steel appliances, a new stove and dishwasher. All kitchen utensils are supplied and all linens as well. The laundry is conveniently located on the second level with a brand new front load washer and dryer and a utility sink -beach towels are in the laundry room as well. The home also has an attached 2 car garage with pool toys, beach chairs, 4 bicycles, a surf board,fishing poles, tennis rackets, beach umbrella, and cooler as well as other items for your beach pleasure.brbr We also have a spacious patio/lanai with stairs leading to our wonderful lap pool! On the lanai and/or pool deck we have patio chairs, 2 recliners, a table and a BBQ grill for you to enjoy family time. br Come and make memories in our home..enjoy the Florida lifestyle and re-energize your mind and soul! We look forward to your stay!You can always reach us by calling 941 626 2625 for any other questions as well

A Private Secluded Retreat In Great Neighborhood -Sleeps 8 Near Beach

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$261.27

Amazing private villa location, steps away from all the action. Newly remodeled 2025, ready to rent. Seven minute walk to beach, restaurants, grocery store, and boat rentals. This place will feel like your home away from home. Large, fully stocked kitchen and 65-inch TV in living room. Enter this single family, one story, 1200 SF house from your private carport. Two bedroom/2 bathroom home sleeps 7. Master bed has a king bed and full bath with a walk-in closet. Second bedroom has a queen bed and bunk beds (twin over double). Second bathroom has a large walk-in shower with handicap bar. In-unit laundry with beach chairs, towels, cooler, wagon and umbrella. You will have your own gas grill with large patio set to enjoy outdoor eating in the beautiful Florida sun. Grass area available for kids to run around. Community pool with a clubhouse and shuffleboard. Free trolley service available.

Villa

2025 completely remodeled private villa, 7 min walk to beach, entertainment

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$338.2

Welcome to Whispering Palms: Your Siesta Key Villa Escape! brbr brbrCheck out this serene 3-bedroom, 2-bath villa in Polynesian Gardens just minutes from Siesta Key’s famous beaches. Enjoy spacious indoor-outdoor living with a sunroom, fully equipped kitchen, and access to a large community pool and private dock. Perfect for families or groups, this peaceful villa offers comfort, privacy, and all the amenities needed for an unforgettable beach getaway. brbr brbrLOCATION HIGHLIGHTS: brbr- Nestled in the serene Polynesian Gardens community on the Intracoastal Waterway side of Siesta Key brbr- Lush tropical landscaping and tree-lined streets brbr- Large community pool and private dock for fishing or sunsets brbr- Public Siesta Key Beach just a 15-minute walk away brbr- Peaceful, family-friendly neighborhood brbr brbrPROPERTY FEATURES: brbr- Standalone 3-bedroom, 2-bathroom villa (1842 sq ft) brbr- Open floor plan designed for relaxation and connection brbr- Fully enclosed, air-conditioned sunroom—a rare find in Siesta Key brbr- Private backyard with charcoal smoker and chiminea brbr- High-speed WiFi and smart TVs in every room brbr- Washer, dryer, and high-quality linens included brbr- Large community pool access brbr- Private dock for fishing or scenic views brbr- Cozy outdoor backyard for sunbathing and relaxing brbr brbrLIVING ROOM: brbr- Spacious living area with seating for five brbr- 65” smart TV for streaming your favorite shows brbr- Opens directly to the sunroom for seamless indoor-outdoor living brbr brbrKITCHEN AND DINING: brbr- Large galley kitchen fully equipped with high-end appliances brbr- Formal dining table seats six brbr- Breakfast nook seats four for casual meals brbr brbrBEDROOMS AND BATHROOMS: brbr- Master Suite: King-size bed, plush bedding, private bathroom with walk-in shower, direct access to sunroom brbr- Guest Bedroom 1: King-size bed, smart TV brbr- Guest Bedroom 2: Queen-size bed, smart TV brbr- Guest bathroom: big vanity with walk-in shower brbr brbrEXTRA PERKS brbr- Beach supplies included: a couple of chairs, an umbrella, cart brbr brbrLOCAL FAVORITES brbr- Enjoy strolling the shaded streets of Polynesian Gardens brbr- Visit nearby Siesta Key Village for dining, shopping, and entertainment brbr- Take advantage of water activities in the Intracoastal Waterway or at Siesta Key Beach brbr brbrIMPORTANT INFO brbr- Family- and adult-friendly property brbr- No smoking or pets allowed brbr- No parties brbr- Maximum occupancy and usage per house rules brbr- No boats, trailers, jet skis, or oversized vehicles. Resident parking limited to passenger vehicles only brbr brbr brbrCLICK BOOK NOW AND RELAX INTO COASTAL LIVINGbrbrWe help make the most of your vacation by providing Xplorie's Free Admission to some of the area’s top attractions each and every day including a choice of a free bike rental, kayak rental, a dolphin cruise tour, or admission to the Ringling Museum ! Round-trip airport transportation provided for up to 3 passengers from SRQ or TPA with advance reservation. The fare is free but please tip the driver. Limited to one activity for just one person each day (other members of the group can partake but will need to pay). Create exciting memories, have more fun, and truly experience the Beaches of Sarasota! Book now for an amazing vacation experience! Activities are subject to change and based on availability; non-cumulative and non-transferrable.brbrbrbrimg src=https://admin.itrip.net/upload/360/marketingimageitripsarasota.1718820503.jpg alt=marketing /brbrbrbrFeel free to book for a month or longer but Xplorie is not available for booking 25 days or longer.brbrThis property does not allow Emotional Support Animals in addition to their no pet policy.brbrIMPORTANT: The min age to rent is 25 years old. No parties, large gatherings. Please reach out if you have any questions.

Private Lanai | Shared Pool | Brand-New Rental by Top-Rated Host | Siesta Villa Whispering Palms

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$559.7

Spend your vacation relaxing in this lovely 3-bedroom, 2.5-bathroom townhome. On the ground level, you will find covered parking for up to 2 cars, and storage. The second level hosts an open concept for the living room, dining, and kitchen areas. The spacious living room features rattan ceiling panels for a casual coastal vibe. The kitchen offers plenty of storage and stainless countertops. On this floor, you will also find a powder room and a balcony for enjoying the fresh island breeze. The 3 bedrooms and 2 full bathrooms are located on the third level. The master bedroom features a king and an area with two twins and privacy doors for separations. Located within walking distance to Siesta Key Village, this home is adjacent to beach access #10 – perfect for taking a trip down to Siesta Beach! br*This property is stairs only; all guests must have the ability to use stairs.brbrBedroom 1 – 1 King, 2 Twin beds, and 1 Twin TrundlebrBedroom 2 – QueenbrBedroom 3 – Two DoublesbrLivingroom – Queen Sleeper SofabrbrAdded Amenities Included in Your Stay:brComplimentary Bicycles Rentals,brOne Complimentary Parking Space,brWifi,brBeach Chairs,brBeach Towels,brBeach Wagon,brBeach Cooler,brPartner Property Pool/Hot tub Access,brAccess to Siesta Beach Pickleball Courts,brSiesta Key Trolly - Free-Rides Around Siesta Key,brA 7-day week, Beachside Management office for your convenience and guest needs!brbr*Minimum Age to Book: 25 br*To book a beachside managed Property Between February 1st and April 15th, the booker must be 27 years old or older. br*Security authorization Hold taken upon check-in. Amount: $1,000

Stunning 3 Bedroom/ 3 Bath Adjacent to Siesta Key Beach Access!

Siesta Key, Florida, United States

3

Bed

Bath

13

Sleeps

$264.57

2 BR - 2 BA - 4 Person Max - Bay-side Garden - Bay-front View brbrThis property is a 30 night minimum. brbrThis 2 bedroom, 2 bath is a first floor garden condo on the bay side of Midnight Pass. brThe master bedroom has a King bed, a ceiling fan, a 32 inch smart TV, and windows for natural light. The master bathroom has updated granite counters and a walk-in shower with a sliding glass door and a removable shower head. brThe guest bedroom has a king bed, a ceiling fan and a 32 inch smart TV. The guest bathroom has granite counter tops and a tub/shower combination. brThe dining table has 6 seats and windows for natural light. The dining room has an open flow into the living room and out to the lanai. brThe living room has a lot natural light and beautiful views of the bay, comfortable couch seating, a ceiling fan, and a TV. The living room opens right up to the lanai. The lanai has a ceiling fan, comfortable couch seating for the entire family to enjoy while you soak up the fresh bay air and bay views.br brThis unit has no access to park a car in the garage and requires outdoor stair access to enter the unit. It also has an in-unit washer and dryer. brPets or smoking are not permitted

6039 EPW - Premium - Bright and Airy Coastal Escape

Siesta Key, Florida, United States

Bed

Bath

4

Sleeps

$208.11

2 BR -- 2 BA -- 6 person Max -- Large Garden -- Greenbelt ViewbrbrThis property is a 30 night minimum.brbr6030 is a small garden unit, located on the Bayside of Midnight Pass Ground Floor unit. brbr2 bedroom, 2 bath unit . Approx. 1250 Sq. Ft. (1350 including the lanai).brbrBedding:brMaster bedroom: KingbrGuest Bedroom: QueenbrbrElectronics:brLiving room: 32 inch Flat PanelbrMaster Bedroom: 20 inch brGuest Bedroom: 12 inchbrbrBathrooms:brMaster: ShowerbrGuest: Tub/ShowerbrbrRecessed lighting in kitchen, 6 person dinning area table. T.V. in the guest bedroom is wall mounted, open porch lanai. These specific units include access to a private garage.

6030 EPW - Standard Plus - Cozy Bay Side Garden Paradise

Siesta Key, Florida, United States

Bed

Bath

6

Sleeps

$188.96

2 BR - 2 BA - 4 person Max - Large Garden - Greenbelt View brbrThis property is a 30 night minimum. br6026 EPW is a Large garden unit, located on the Bay-side of Midnight Pass.brOpen porch lanai. This specific unit has a garage. brLocated about 35 yards away from the Bay. brApprox. 1250 Sq. Ft. (1350 including the lanai). brbrCondo Summary: brBedding: Master bedroom: King - Guest Bedroom: 2 Twins brElectronics: Living room: 70 inch Flat Screen - Master Bedroom: 40 inch Flat Screenbr Guest Bedroom: N/A brBathrooms: Master: Walk-in Shower - Guest: Tub/Shower (removable shower head)

6026 Bayside 1st Floor Large garden unit

Siesta Key, Florida, United States

Bed

Bath

4

Sleeps

$200.19

30 night minimum required brbrEnjoy Gulf of Mexico views from our recently renovated penthouse apartment on Siesta Key. You will have access to the #1 beach in the US with white powder sand and warm gulf waters. Enjoy beautiful views of the gulf from our full-length lanai and both bedrooms. brThe condominium offers multiple heated swimming pools, beach side and bay side grills, fishing pier, and a recently renovated exercise room. The condo comes with one reserved covered parking space right next to the elevators. There is ample non reserved outside parking available. There is free wireless internet access in all rooms and pool areas! brThere are 2 bedrooms/2 full baths, with a pull out queen couch accommodating 6 to sleep comfortably. The master bedroom has a King size bed, en suite bathroom and walk-in closet. The 2nd bedroom has two twin beds and a large closet. Both bedrooms have direct access to the lanai. The lanai includes a comfortable seating area, a desk for computer use, and an additional dining table. The kitchen is fully equipped.

1255-602 - Standard - Enjoy this Seaside Paradise

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$320.32

The Anchorage Resort on Siesta Key - includes resort amenity access!brOur 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 Condobr* 2 bedrooms / 2 bathroomsbr* Spacious Balcony overlooking Southern Siesta Keybr* Top Floor Condo with amazing views, including the Gulf of America from the balconybr* Community Pool- Largest pool on the Key!br* Pickleball & Tennis Courtsbr* Gated Communitybr* Siesta Key Trolley- free pickup in front of the resort entrancebr* Private Beach access to Crescent Beach across the streetbr* Fully equipped Kitchen with seating for 6 at the dining tablebr* Beach Supplies include- Chairs, Cooler, Beach Towelsbr* 25-year minimum age to rent restrictionbrbrBEDROOMS (Top Floor Condo)brBedroom 1: One King Bed (Attached Bathroom)brBedroom 2: Two Queen BedsbrbrPool Information:br- Community Poolbr- Heated brbrResort Parking Rules:brThe resort allows a maximum of 2 cars.brVehicles must be registered with the front office during office hoursbrbrHOA Rules:br* No Hanging Towels over the Balconybr* Lead guest must be age 25 or older. ID is checked upon registration at the resort.br* January 1- April 16 Rentals are 7 nights, beginning and ending on Saturday onlybr* No Pets AllowedbrbrThe 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/Seawall br*Coin-Operated Washer/Dryer on Each FloorbrbrDistances 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 toilet paper per bathroombr- 1 hotel-size bar soap per bathroombr- 1 hotel-size shampoo/conditioner per full bathroombr- 1 roll paper towelbr- 2 packet dishwasher detergentbr- Size 13-gallon Trash bagsbrAny supplies beyond this are up to the guest to replenish, we do not restock these items. 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 with us $250.00. $1,250.00 will be refunded.brIf canceled between 61 and 89 days prior to arrival, we keep with us the $1,500.00 deposit.brNo cancellation or modification 60 days or less prior to arrival.

Anchorage Resort Top Floor 2 Bedroom Condo with Gulf Views

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$320.32

The Anchorage Resort on Siesta Key - includes resort amenity 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 br* 2 bedrooms / 2 bathroomsbr* Eighth Floor Condo with balcony overlooks South-Western Siesta Keybr* Fully equipped Kitchen with seating for 4 at the dining tablebr* Beach Supplies include- 2 Chairs, Beach Cart, 2 Boogie Boards, Pool Noodles and toys, Beach Towelsbr* Community Pool- Largest pool on the Key!br* Gated Communitybr* Siesta Key Trolley- free pickup in front of the resort entrancebr* Private Beach access to Crescent Beach across the streetbr* 25-year minimum age to rent restrictionbrbrBEDROOMS (Eighth Floor Condo)brBedroom 1: One King Bed (Ensuite Bathroom) / Balcony Access / 42 TVbrBedroom 2: Two Queen Beds / 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 FloorbrbrPool 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:brLead guest must be age 25 or older. ID is checked upon registration at the resort.brNo petsbrJanuary 1- April 16 Rentals are 7-nights beginning and ending on Saturday onlybrbr brDistances 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 toilet paper per bathroombr- 1 hotel-size bar soap per bathroombr- 1 hotel-size shampoo/conditioner per full bathroombr- 1 roll paper towelbr- 2 packet 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 with us $250.00. $1,250.00 will be refunded.brIf canceled between 61 and 89 days prior to arrival, we keep with us 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 private beach access, pool, boat dock!

Siesta Key, Florida, United States

Bed