Vacation Rentals By Owner In Siesta Key, FL

$882.4

Private house steps from the beach and village.

Siesta Key, Florida, United States

Beautiful 3 bedroom 3 bath home with pool facing thebrcanal. It is all surrounded by a high privacy wall. The pool is heated and surrounded by palms and other floweringbrplants.brbrThe location, is a step from town and a couple of blocks to the beach, make it the perfect place for a relaxing fun-filled vacation.

3

Bed

3

Bath

6

Sleeps

$438.62

/ Nightly

Private Vacation Home

NEW! Sea Turtle Bungalow | Private Unit in Duplex, Walk to Crescent Beach & Community Pool

Siesta Key, Florida, United States

NEW! Sea Turtle Bungalow | Private Unit in Duplex Walk to Crescent Beach & Community PoolbrNow Welcoming Guestsbrbr Why You'll Love This HomebrSea Turtle Bungalow offers a relaxed Siesta Key stay just 0.1 miles from Crescent Beach, combining walkable beach access with a comfortable, private unit within a duplex setting. This two-bedroom home is ideal for smaller groups looking for convenience. Guests can enjoy a private patio along with access to a shared backyard featuring hammocks, outdoor dining areas, and a grill. The nearby heated community pool and beach access provide additional options for time in the sun, all within a short distance from the home. Inside, the bungalow includes an updated kitchen with a brand new stainless Samsung refrigerator and glass cooktop, along with inviting living spaces and an in-unit laundry area for everyday convenience.brbr ‍ ‍ Perfect ForbrCouples, friends, or small families looking for a Siesta Key stay close to the beach with shared outdoor space and easy access to island amenities.brbr ️ Imagine ThisbrEase into your morning with coffee outside before taking a short walk to Crescent Beach. Spend the day along the shoreline, then head back to rinse off and recharge. In the afternoon, take a quick trip to the nearby community pool or relax back at the property, whether that's unwinding in a hammock, sharing a meal outdoors, or stepping inside for a break from the sun. The trolley stop just steps away makes it easy to explore without needing to drive. As the day winds down, head over to South Village for dinner or bring something back to enjoy on the patio before settling in for the evening.brbr Where You'll Sleepbr• Bedroom 1: King Bedbr• Bedroom 2: Queen Bedbr• Living Room: Queen Sleeper SofabrbrAccommodates up to 6 guests.brbr Explore the Areabr• 0.1 Miles to Crescent Beach – Quick Walk to Sand and Gulf Watersbr• 1 Building Away to South Village & Trolley Stop – Dining, Bars, and Easy Island Transportationbr• 2.9 Miles to Siesta Key Village – Shopping, Restaurants, and Nightlifebr• Nearby Community Beach Access & Pool – Heated Pool, Lockers, Changing Rooms, and Beachside Facilitiesbr• 1 Block to Local Park & Shuffleboard Court – Casual Outdoor Activitiesbrbr⌛ Don't WaitbrYour reservation includes peace of mind with our CottageClean™ program, featuring a six-hour deep clean and a detailed 35-point inspection prior to arrival.brbr Need to KnowbrSea Turtle Bungalow is one unit within a duplex property and will share walls, the backyard area, and the HOA pool with the neighboring unit. Interior spaces are fully private.This property includes access to a heated community pool and beach access located nearby, which also features restrooms, changing rooms, and lockers for guest use. Starter packs of kitchen and toiletry essentials are provided for your first couple of nights. Free high-speed WiFi is included.

3

Bed

1

Bath

6

Sleeps

$843.23

/ Nightly

Private Vacation Home

NEW! Beachside Bungalow | Entire Duplex, Walk to Crescent Beach, and Community Pool

Siesta Key, Florida, United States

NEW! Beachside Bungalow | Entire Duplex Walk to Crescent Beach and Community PoolbrNow Welcoming Guests brbr Why You ll Love This HomebrBeachside Bungalow offers a unique Siesta Key setup with two private bungalow-style units on one property, ideal for groups who want to stay together while maintaining their own space. The two bungalows adjoin and can be opened to one another, allowing the home to function as a single, larger space or remain separate for added privacy as needed. Located just 0.1 miles from Crescent Beach, this property combines walkable beach access with a quiet, tucked away setting. The outdoor space creates a central place to gather, with a private yard, hammocks, patio dining areas, and grills for shared meals. The nearby heated community pool and beach access provide additional options for relaxing and spending time outdoors. Inside, both units feature updated kitchens with brand new stainless Samsung refrigerators and glass cooktops, along with comfortable living areas and in-unit laundry for convenience during your stay.brbr Perfect ForbrFamilies, multi-family groups, and friends traveling together who want a private, flexible setup with walkable beach access and shared outdoor space.brbr ️ Imagine ThisbrYou arrive on Siesta Key and settle into your own private bungalow setup. Mornings begin with coffee on the patio before a short walk to Crescent Beach, where the day starts with time on the sand and in the water. Afternoons are spent between the beach and the nearby community pool, with easy access to restrooms, changing rooms, and shaded areas. Back at the property, the private yard becomes a place to gather. Relax in the hammocks, grill dinner, or enjoy time together at the outdoor tables. As the evening sets in, take a quick walk to South Village for a casual meal or hop on the trolley just steps away. End the night back at the property, where each group can retreat to their own space while still being close together.brbr Where You ll SleepbrCrabby Bungalow - Bungalow 1brBedroom 1: King BedbrBedroom 2: Queen BedbrLiving Room: Queen Sleeper SofabrbrSea Turtle Bungalow - Bungalow 2brBedroom 3: King BedbrBedroom 4: Queen BedbrLiving Room: Queen Sleeper SofabrbrAccommodates up to 12 guests.brbr Explore the Areabr0.1 Miles to Crescent Beach Quick Walk to Sand and Gulf WatersbrSouth Village Trolley Stop Just 1 Building Away Dining, Bars, and Easy Island TransportationbrNearby Community Beach Access Pool Heated Pool, Lockers, Changing Rooms, and Beachside Facilitiesbr1 Block to Local Park Shuffleboard Court Casual Outdoor Activitiesbr2.9 Miles to Siesta Key Village Shopping, Restaurants, and Nightlifebrbr⌛ Book TodaybrYour reservation includes peace of mind with our CottageClean program, featuring a six-hour deep clean and a detailed 35-point inspection prior to arrival.brbr Need to KnowbrBeachside Bungalow is a duplex property made up of two separate units. When reserving the full property, you will have exclusive access to both interiors, along with the private yard, patios, and parking areas. The two bungalows adjoin and can be opened to one another, allowing the home to function as a single, larger space or remain separate. This property includes access to a heated community pool and beach access located nearby, which features restrooms, changing rooms, and lockers for guest use. Starter packs of kitchen and toiletry essentials are provided for your first couple of nights. Free high-speed WiFi is included.

Bed

Bath

Sleeps

$516.31

/ Nightly

Private Vacation Home

Siesta Key Waterfront Oasis - Heated Pool, Dock, Walk to Village & Beach

Siesta Key, Florida, United States

Wade n' Sea | Siesta Key Canal-Front Home with Heated/Cooled Saltwater Pool, Walkable to the Beach + Siesta Key Village & Pet Friendly brbr Why You'll Love This HomebrThis luxurious retreat offers direct boating access, a private saltwater pool, and a short stroll to the white sands of America's #1 beach. Picture yourself poolside under café lights as dolphins glide through the canal just beyond the seawall. With a heated + cooled saltwater pool, boat tie-up, and screened lanai with two TVs and NFL Sunday Ticket, this waterfront retreat blends island ease with immersive coastal living—all just 0.3 miles to Siesta Beach and 0.4 miles to Siesta Village. This Siesta Key Waterfront Oasis blends tropical tranquility with modern elegance in one of the island's most desirable neighborhoods.brbr ‍ ‍ Perfect ForbrCouples, families, boaters, or anyone who wants sun, sand, and walkability—with plenty of space to spread out indoors and out.brbr ️ Imagine ThisbrYour morning begins on the screened lanai lounge, flipping between NFL games on two outdoor TVs , savoring breakfast in the soft morning light while palm trees sway over the canal. Slide open the patio doors and step into a sun-washed lanai as the smell of salt air mixes with fresh-ground coffee. brbrAfter a short walk to Siesta Beach, return for a dip in your private, heated saltwater pool, relax on the cabana-style double lounger, or grill fresh seafood while the kids splash. After dinner, pour a drink, tie up the paddleboard, and head out to your private canal dock with a cocktail as underwater lights illuminate the canal and the sky turns pink just as the sun dips beyond.brbrInside, you'll find restored terrazzo floors, coastal touches, and a layout made for comfort and conversation. Whether you're cooling off after a beach day or hosting happy hour, this home surrounds you with style, convenience, and Siesta charm. Whether it's beach days, boat rides, or quiet evenings at home, every detail of this oasis is designed for unforgettable moments.brbr Where You'll Sleepbr• Bedroom 1: King Bed, Ensuite with Shower, Lanai Access, TVbr• Bedroom 2: King Bed, Shared Hall Bath with Tub/Shower, TVbr• Bedroom 3: Queen Bed, Shared Hall Bath with Tub/Shower, TVbrbr Explore the Areabr• 0.5 Miles to Siesta Key Beach Access 4 or 5br• 0.4 Miles to Siesta Key Village (Shops, Restaurants, Nightlife)br• 0.2 Miles to Avenida Messina Park + Gulf viewsbr• Easily Walk or Bike to Coffee Shops, Boutiques, and Beach Barsbr• Located in Quiet Siesta Manor Cul-de-sac—Low Trafficbrbr⌛ Don't wait—Book Your Stay at Siesta Key Waterfront Oasis Today this home books quickly. This is more than a vacation rental—it's your personal sanctuary on the water. Whether you're here to reconnect with family, relax with friends, or explore the best of Siesta Key, this canal-front escape makes every day feel like paradise. Your reservation includes peace of mind with a 6-hour deep clean and 35-point inspection prior to every arrival. The home is well stocked with everyday essentials, including foil, plastic wrap, spices and seasonings, along with a full supply of paper products, soaps, laundry detergent, shampoo, conditioner, and more.brbr Need to Know: The property offers direct canal access with 75 feet of frontage, Sea Wall Docking and a 10,000 lb boat lift*, and underwater lighting, making it perfect for boating, fishing and waterfront lounging. Adjustable pool heating per guests preferences is available. The home is equipped with free high-speed WiFi, a washer/dryer, and starter packs of kitchen and toiletry essentials to make settling in easy. Important Note: Bedroom 3 has a window security camera facing the driveway/entry. *Boat lift usage must be approved in advance—contact us for details.

Bed

Bath

Sleeps

$491.06

/ Nightly

Private Vacation Home

100 FEET TO THE BEACH! SIESTA KEY VACATION !!!

Siesta Key, Florida, United States

brTHE BEST VALUE IN SIESTA KEY AMAZING LOCATION!brThis home offers a true beach house atmosphere and one of the best locations you can find directly across from the beach and within walking distance to restaurants, bars, shops, and the Village.brBeing only 100 feet from the beach, you can easily walk back to the house anytime to take a break from the sun or restock your cooler. The location is perfectly positioned between Siesta Key Village and the main entrance to Siesta Key Beach.brIdeal for vacations, family trips, and even wedding stays the beach is just steps away through the access point right across the street. The neighborhood is safe, walkable, and full of fun things to do.brNo car needed everything is within walking distance!brFREE parking on site.brThis 2-bedroom, 2-bath home accommodates up to 8 guests and includes:br • Comfortable bedsbr • Beach chairsbr • Beach towelsbr • Plenty of bath towelsbr • Fully equipped home for large groupsbrRestaurants, shopping, nightlife, live music, and entertainment are all just a short walk away in the Village.brIf you have any questions, I’m happy to help!brSleeping arrangements:br • Bedroom #1: Queen Bed (sleeps 2) + Sofa Bed (sleeps 2) – Total: 4br • Bedroom #2: King Bed (sleeps 2) + Sofa Bed (sleeps 2) – Total: 4

2

Bed

2

Bath

7

Sleeps

$385.6

/ Nightly

Private Vacation Home

NEW! Crabby Bungalow | Duplex Unit Walk to Crescent Beach & Community Pool

Siesta Key, Florida, United States

Crabby Bungalow | Duplex Unit Walk to Crescent Beach & Community Poolbrbr Why You'll Love This HomebrCrabby Bungalow offers a private slice of Siesta Key living within a charming duplex setup, just 0.1 miles from Crescent Beach. This two-bedroom unit is ideal for smaller groups looking for walkable beach access while still enjoying a relaxed, residential setting. The home features a relaxing patio space along with access to a shared backyard complete with hammocks, outdoor dining areas, and a grill. Guests also have access to a nearby heated community pool and beach access, adding even more ways to spend time outdoors. Inside, the bungalow includes an updated kitchen with a brand new stainless Samsung refrigerator and glass cooktop, along with comfortable living spaces and an in-unit laundry room for added convenience.brbr ‍ ‍ Perfect ForbrCouples, small families, or friends looking for a walkable Siesta Key stay with beach access and shared outdoor amenities.brbr ️ Imagine ThisbrStart your morning with coffee on the patio before taking a short walk to Crescent Beach, where the day begins with time on the sand and in the water. After the beach, head to the nearby community pool for a swim or return to the property to relax in the backyard hammocks. Spend the afternoon at your own pace, grill lunch, unwind in the shaded outdoor areas, or hop on the trolley just steps away to explore the island. As evening sets in, walk over to South Village for a casual dinner or bring food back to enjoy outdoors before settling in for the night.brbr Where You'll Sleepbr• Bedroom 1: King Bedbr• Bedroom 2: Queen Bedbr• Living Room: Queen Sleeper SofabrbrAccommodates up to 6 guests.brbr Explore the Areabr• 0.1 Miles to Crescent Beach – Quick Walk to Sand and Gulf Watersbr• South Village & Trolley Stop Just 1 Building Away – Dining, Bars, and Easy Island Transportationbr• Nearby Community Beach Access & Pool – Heated Pool, Lockers, Changing Rooms, and Beachside Facilitiesbr• 1 Block to Local Park & Shuffleboard Court – Casual Outdoor Activitiesbr• 2.9 Miles to Siesta Key Village – Shopping, Restaurants, and Nightlifebrbr⌛ Don't WaitbrYour reservation includes peace of mind with our CottageClean™ program, featuring a six-hour deep clean and a detailed 35-point inspection prior to arrival.brbr Need to KnowbrCrabby Bungalow is one side of a duplex and will share walls, the backyard area, and the HOA pool with the neighboring unit. Interior spaces are fully private. This property includes access to a heated community pool and beach access located nearby, which also features restrooms, changing rooms, and lockers for guest use. Starter packs of kitchen and toiletry essentials are provided for your first couple of nights. Free high-speed WiFi is included.

Bed

Bath

Sleeps

$300.66

/ Nightly

Condo

Renovated 3 bed & 2.5 bath condo just steps away from private Siesta Key beach

Siesta Key, Florida, United States

Stunning Siesta Key Condo Steps from the BeachbrbrWelcome to our completely remodeled, 1600 sq. ft. condo nestled just a few steps away from America’s best beach on scenic Siesta Key. With three bedrooms and two-and-a-half baths, this stylish retreat offers a perfect blend of comfort and convenience.brbrKey Features:brbr- Masterful Remodel: Immerse yourself in modern luxury. Our condo boasts all-new glassed-in shower installations, pristine toilets, elegant counters, and sleek sinks.br- Gourmet Kitchen: The remodeled kitchen features stainless steel appliances, quartzite countertops, and ample cabinet space.br- Bright and Airy: Fresh tile and paint adorn both floors, seamlessly connected by a charming spiral staircase.br- Main Bedroom: The master bedroom suite is a sanctuary. Enjoy a king-size bed, dressing area, walk-in closet, and a spacious master bathroom with a dual-head shower enclosure.br- Accessibility: We’ve widened all door openings in the master suite for easy wheelchair access. The toilet, sink and shower are ADA compliant, with the exception of a shower threshold, which necessitates a transfer.br- Second Bedroom: A queen-size bed awaits in the second bedroom, which also has direct access to a full bathroom.br- Third Bedroom: Ascend the spiral staircase to discover the upper-level third bedroom, complete with twin beds and its own half bathroom.br- Spacious Living/Dining Area: Vaulted ceilings create an open, inviting ambiance. Step out onto the newly installed, glassed-in lanai for serene views.br- Modern Comforts: Control the air conditioning, heating, and humidity levels right from the condo unit. New overhead fans with dimmable light fixtures enhance every room.br- Entertainment Hub: Stay connected with wireless Internet access throughout the unit. Enjoy Sharp/Roku TVs in the living room, main bedroom, and second bedroom.br- Convenience: A stacked washer and dryer are tucked away in the second bathroom.br- Tranquil Setting: Our quiet, third-floor end unit offers partial Gulf views and overlooks a peaceful courtyard.br- Excelsior Amenities: Located in the prestigious Excelsior Beach to Bay Condominiums, our condo grants access to elevators, ample parking, and luggage carts. Explore the beautifully landscaped grounds, featuring two heated pools with Jacuzzis, tennis and pickle-ball courts, and an exercise room.br - Gas Grills and Veranda: Savor outdoor meals on the bayside veranda equipped with gas grills.br - Friendly Service: The Excelsior on-site office is staffed by knowledgeable and welcoming professionals in the event you need anything.brbrAdditional Highlights:brbr- Full-Time Maintenance Crew: Rest easy knowing that our property benefits from a dedicated maintenance team available around the clock. Any issues will be promptly addressed.br- Gated Beach Access: You’re just steps away from a private section of Siesta Key’s Crescent Beach, consistently voted America’s #1 beach. Enjoy miles of cool, crystal quartz sands and warm Gulf waters.br - Explore Siesta Key Village: Take a leisurely stroll or hop on the free transfer to Siesta Key village, where you’ll find charming shops, great dining options, and vibrant bars.brbrBook your stay today and experience Siesta Key’s premier condo living at its finest! We are looking forward to welcoming you!

3

Bed

2

Bath

8

Sleeps

$337.45

/ Nightly

Private Vacation Home

Just Breathe | Your Private Canal front Escape with Pool & Dock on Siesta Key

Siesta Key, Florida, United States

Discover your perfect slice of ,Island Time, at Just Breathe, a serene 3 bedroom, 2.5 bathroom home nestled directly on a peaceful Siesta Key canal. From the moment you arrive, you'll feel the world melt away as you step into this ultimate beach house getaway designed for relaxation and fun. Imagine sipping your morning coffee on the private dock, watching for playful manatees and jumping fish, or simply basking in the sunshine by your private pool. With ample outdoor space for lounging, dining, or even trying your hand at fishing, this backyard oasis is your personal paradise. Inside, the home offers a beautifully appointed, light-filled space. The primary bedroom boasts a comfortable King bed and an en-suite bathroom, while the second bedroom features a Queen bed, and the third provides flexible sleeping with two Twin/Single beds. The fully equipped kitchen is ready for family dinners, though with the vibrant Siesta Key Village near, you might prefer to explore the array of locally owned restaurants, cafes, and lively bars. The unbeatable location means you're not only steps from delicious dining and entertainment, but also just a short 3-minute drive (or a fun bike/golf cart ride, a local favorite!) to the world-famous Siesta Key Beach, consistently ranked among the best in the USA. Please note: If you are bringing a pet, there is a $250 pet fee (per pet). We encourage you to inquire about the specific pet policy applicable to your reservation for clarification, including how and when the pet fee will be collected.

3

Bed

2

Bath

6

Sleeps

$2396.02

/ Nightly

Private Vacation Home

Historic Gulf-Front Charm, Gulf Views, House Suite + Direct Beach Access on Siesta Key

Siesta Key, Florida, United States

The Original Beach House | Beachfront Home on Siesta Key with Gulf Views + In-Law SuitebrbrWhy You'll Love This HomebrStep into the charm of Old Florida with this private 5 Bedroom/4 Bath 3642 square foot beachfront home nestled directly on Siesta Key's legendary Point of Rocks, a diver/snorkeling paradise & marine life habitat on the world-famous Siesta Key Beach. Surrounded by tropical landscaping and panoramic Gulf views, this vintage 1940s beach retreat evokes warmth, nostalgia, and pure coastal serenity. brbrPerfect ForbrIdeal for extended families, friend groups, or multi-generational stays seeking space, privacy, and direct beachfront access just 50 steps from the Gulf. brbrWhere You'll SleepbrMain Housebr• Bedroom 1 (First Floor): 1 King Bed, Main Floor Full Bath (shower stall), TVbr• Bedroom 2 (Second Floor): 2 Twin Beds, Hall Full Bath (shower stall), TVbr• Bedroom 3 - Primary Suite (Second Floor): 1 Queen Bed, Sitting Area, Balcony with Gulf Views, Ensuite Bath (Jetted Tub, Shower Stall, Private Commode, Bidet), TVbr• Bedroom 4/Den off of Primary Suite (Second Floor): 1 Queen Sofa Bed, Hall Full Bath, Adjacent to Bedroomsbr• Den (First Floor): 1 Queen SofabrbrDetached Guest House Suite (Above Garage – Stair Access Required)br• Bedroom 5: 1 Queen Bed, Private Full Bath (Shower Stall), Full Kitchenette, 2-seat Table, TVbrbrExplore the Areabr• Direct Private Beachfront Location on Siesta Key's Famed Point of Rocksbr• Just 3 Blocks to South Siesta Key Village Grocery, Shopping, Restaurants, Cafes, Live Music and Tiki Barsbr• 2.5 Miles to Siesta Key Village – Local Shops, Live Music, and Coastal Cuisinebr• 2.7 Miles to Turtle Beach and Kayak Launchesbr• 7 Miles to Downtown Sarasota's Galleries, Museums, and GardensbrbrIt has a 100% walkability score for everything you need for a perfect vacation! If you want to explore further, without the hassle of driving, you'll find multiple stops nearby for the free trolley that provides transportation service to the entirety of Siesta Key. You're also just a quick drive or Uber/Lyft (10-15 minutes) to downtown Sarasota for access to the amazing Sarasota Performing Arts scene, and numerous fantastic restaurants, shops, marinas, bars, entertainment, and more. Day trips to iconic Lido Key are only 20 minutes away. Be sure to check out Anna Maria Island, 40 minutes away, as well as the amazing theme parks of Tampa and Orlando that are all just 1-2 hours away!brbrDon't wait—homes on Point of Rocks rarely become available, let alone on the beach, as there are only 4 of them in this private enclave of Siesta Key Beach. Experience historic coastal charm with modern comforts in one of Siesta's most exclusive beachfront locations.brbr Need to Know: Starter packs of kitchen and toiletry essentials provided for a seamless first couple of nights. Free High-Speed WiFi. This unit has stairs and is handicap accessible. If any guest has difficulty with stairs, please contact us for alternative accommodations.brbr*Don't forget to check out our Matterport 3D Tour for this home*

Bed

Bath

Sleeps

$896.57

/ Nightly

Private Vacation Home

Cast A Waves 1 Block from beach.

Siesta Key, Florida, United States

Enjoy Siesta Key with luxury! This beautiful Townhouse is located just 3 blocks from Siesta Key Village (with shops and restaurants) and only 1 block from the beach! This great home greets you with solid surface floors and a beautiful chefs kitchen! With sleeping up to 9 guests you will be able to bring your whole family with plenty of room and beds! Once you have enjoyed to beach for the day you can relax by the private pool out back located on a canal!

Bed

Bath

Sleeps

$303.84

/ Nightly

Condo

Stunning Gulf Views 2 Bed 2 Bath at Siesta Key Beach Walk to Beach

Siesta Key, Florida, United States

Welcome to Condo 4A, an exquisite tropical paradise that will undoubtedly leave you in awe! Situated at the Crescent Royale Condominiums, this luxurious vacation home stands out as one of the properties’ crown jewels, boasting stunning beachfront views of America's #1 beach, Siesta Key Beach, from every angle.brbrWith a living space of 1220 sq ft, this unit offers two cozy bedrooms, two full bathrooms, and a screened-in lanai where you can relax and take in the breathtaking sunsets. The master bedroom features two queen-sized beds, while the guest room offers another queen bed, providing ample space for all.brbrThis unit is a foodie's haven, with a fully stocked kitchen that has everything you need to prepare your favorite meals. And, if you prefer to unwind indoors, we've got you covered with three TVs equipped with basic cable and WIFI, so you won't have to miss out on any of your favorite shows.brbrBut the icing on the cake is the screened-in lanai, where you can enjoy your morning coffee while taking in the stunning view. Keep an eye out for dolphins and snap some pictures that will make your friends envious on Instagram.brbrNot to mention, we've got all your beach essentials covered, including chairs, towels, and umbrellas, ensuring that you have everything you need for a perfect day at the beach. If you feel like lounging around, Crescent Royale offers a heated pool, gym, BBQ area, shuffleboard court, and plenty of chairs to relax in.brbrLocated in the heart of Siesta Key, this condo is a quick walk or a free trolley ride away from Siesta Key Village, where you can indulge in world-class dining, entertainment, and souvenir shopping, all with a cool Florida vibe.brbrAnd if you need anything, our on-site management team is just a phone call away. Don't delay any longer; book now and experience the ultimate Siesta Key dream! We adore this unit, and we are certain you will too. Book with us today!

Bed

Bath

Sleeps

$679.29

/ Nightly

Private Vacation Home

Chic Siesta Retreat – Pool, Hot Tub & Water Views

Siesta Key, Florida, United States

Summary:brbrPink Pineapple Properties Presents – Siesta Key Sanctuary.brbrbrbrA chic four-bedroom haven on Siesta Key featuring a private pool, soothing hot tub, and beautiful water views. Guests can enjoy relaxing by the water or fishing from the dock (bring your own poles). Just a short walk to Siesta Key Village and a quick drive to world-famous Siesta Key Beach, this retreat blends comfort and style for an unforgettable stay.brbrbrbrThe Space:brbrWelcome to Siesta Key Sanctuary, a luxurious four-bedroom retreat crafted for an exceptional Siesta Key experience. Let's unveil the spaces:brbrbrbrBedrooms (x4): Each bedroom presents a plush king-size bed, promising serene nights. These private havens are designed with comfort and tranquility in mind, featuring high-quality linens and ample closet space.brbrbrbrBathrooms (x3): Indulge in the convenience of three full bathrooms, ensuring ample space and privacy. Each bathroom is exquisitely appointed with a modern aesthetic, including walk-in showers and premium toiletries.brbrbrbrLiving Room: A spacious and inviting area, ideal for relaxation and socializing. The living room is designed with comfort in mind, featuring comfortable seating, a large television, and abundant natural light.brbrbrbrKitchen: Fully equipped with modern appliances, including a refrigerator, oven, stove, microwave, and dishwasher. It's a chef's dream, facilitating effortless meal preparation. The kitchen also includes a coffee maker, and all necessary cookware and utensils.brbrbrbrDining Area: A dedicated dining space, perfect for enjoying meals together. The dining area is designed to create a warm and inviting atmosphere, with seating for all guests.brbrbrbrOutdoor Pool Area: Step into your private oasis, featuring a sparkling pool and a soothing hot tub. It's the perfect spot for sunbathing, swimming, or simply unwinding. The outdoor space also includes a BBQ grill and comfortable seating, perfect for al fresco dining.brbrbrbrPatio: Savor the Florida sunshine and fresh air on your private patio, offering a serene setting to relax and take in the views. The patio or balcony is furnished with comfortable outdoor furniture.brbrbrbrWater Views & Fishing Dock: The property offers beautiful waterfront views and the opportunity to fish right from the dock. Guests are welcome to bring their own fishing poles. The water behind the home is not deep enough to safely accommodate boats, ensuring a quiet and serene environment.brbrbrbrWe've designed Wild Palm to be your home away from home, providing everything you need for a perfect vacation.brbrbrbrGuest Access:brbrWe will provide you with a Personalized access code a few days prior to arrival. Use your unique 4-digit code to enter the home. The code is active starting at 4pm on check in day and automatically deactivates at 10am on check out day.brbrbrbrThe Neighborhood:brbrNestled in the heart of Siesta Key, our home offers unparalleled access to the best of the island. A short walk will take you to the vibrant North Village, where you'll find a variety of dining options, from casual cafes to upscale restaurants. Explore unique boutiques and shops, or simply stroll along the charming streets. The world-famous Siesta Key Beach is also within easy reach, offering pristine white sands and crystal-clear waters. Experience the relaxed island lifestyle, with everything you need just steps away.brbrbrbrGetting Around:brbrGetting around Siesta Key and beyond is a breeze from Siesta Key Sanctuary. While the island is easily navigable by car, golf carts are a popular and fun way to explore. Parking is readily available at the property and in the Siesta Key Village, but can be limited during peak season. Enjoy the convenience of accessing all that Siesta Key has to offer!brbrbrbrOther Things to Note:brbrHere are answers to some of our most commonly received questions!brbrbrbr Is there a minimum age requirement to make a reservation brbrYes, the minimum age required to make a reservation is 21 years old.brbrbrbr Is the property pet-friendly brbrWe are ONLY dog friendly. To ensure a comfortable and enjoyable stay for all guests a non-refundable fee of $150 per reservation will be charged. Pet fees are NOT included in the original reservation price or nightly rate provided. Any applicable pet fees will be added to your reservation MANUALLY and charged AFTER booking. If you do not honor our pet policy and bring an unapproved pet, there is a $500 fine.brbrbrbr Is the pool heated brbrThe pool is open year-round and can be heated in the winter for a fee of $25 per day. Due to the nature of the heating system we can only offer it for the entirety of your stay and not on an ad hoc basis. brbrbrbr Is smoking allowed brbrWe have a strict NO SMOKING policy. If you smoke inside, there is a $250 fine plus the cost of remediation.brbrbrbr If I leave something it be sent back to me brbrWe are not responsible for items left behind by guests. If you leave an item behind and you want it to be sent back to you. We charge $50 for that item to be shipped plus the shipping costs.brbrbrbr What kind of coffee machine do you have brbrWe have a kurig in the home.brbrbrbr Can I book for less than 5 nights brbrUnfortunately not, due to the amount of wear and tear on the homes from frequent turnovers we have a 5 night minimum across our portfolio.brbrbrbr What is the nearest beach brbrWe are 1.8 miles from Siesta Key Beach. It is a 5 minute drive. Guest's usually rent golf cars to drive around the island. brbrbrbr What beach equipment do you provide brbrWe provide beach chairs for our guests. If there is additional equipment you need you would either need to bring it or rent it.brbrInteraction with guests.brbrbrbr Is it possible to have a late check-out brbrUnfortunately, we’re not able to accommodate a late checkout. Our cleaning team works on a scheduled timeline and has an agreed arrival time to prepare the property properly for the next guests. Thank you very much for your understandingbrbrbrbrInteraction with Guests:brbrOur 24/7 dedicated support team is always available to ensure your stay is smooth, comfortable, and five-star-worthy. If there’s anything you need—questions, recommendations, or assistance—please don’t hesitate to reach out. We're just a message away and happy to help.

Bed

Bath

Sleeps

$303.07

/ Nightly

Condo

Stunning Siesta Key Gulf Views 2 Bed 2 Bath Top Floor Steps to Beach

Siesta Key, Florida, United States

Discover Condo 505 at Crescent Royale – Your Siesta Key EscapebrbrLooking for the perfect beachfront getaway Condo 505 at Crescent Royale Condominiums offers stunning views of Siesta Key’s world-famous white sand beach, right from your private screened-in lanai.brbrThis beautifully updated 2-bedroom, 2-bath unit features:br• A spacious lanai with unobstructed Gulf viewsbr• King bed in the primary suite, two twins (convertible to a king) in the guest roombr• A fully stocked kitchen with stainless steel appliancesbr• Cable, Wi-Fi, and 3 TVs for your conveniencebr• All the beach gear you’ll need – just bring your swimsuitbrbrThe gated complex includes a large heated pool, fitness center, BBQ grills, shuffleboard, and on-site management. Just a short walk to Siesta Key Village, where you’ll find great dining, shopping, and live music.brbrWhether you're watching the sunset from the lanai or relaxing by the pool, Condo 505 has everything you need for a comfortable and memorable stay.

2

Bed

2

Bath

4

Sleeps

$280.66

/ Nightly

Condo

Serene Gulf View Living Spacious 2 Bed 2 Bath Siesta Key Beach Condo

Siesta Key, Florida, United States

Your Beachfront Escape Awaits at Unit 106!brEnd your vacation rental search—paradise is calling! Welcome to Unit 106, a stylish and spacious 2-bedroom, 2-bathroom ground-floor condo with over 1,250 sq. ft. of beautifully curated comfort, just steps from the soft, white sands of Siesta Key Beach.brbrStart your mornings with a coffee on the screened-in lanai, where the Gulf views and ocean breeze set the tone for a perfect day.brbrInside, you’ll enjoy:brbrA fully equipped kitchenbrbrBright, beachy living spacesbrbrFlat-screen TVs & free WiFibrbrThoughtful touches that make it feel like homebrbrThis condo also includes beach equipment for your convenience: beach chairs, a beach umbrella, beach towels, and a beach wagon.brbrWhether you're lounging by the heated pool, hitting the beach, or exploring the best of Siesta Key Village, adventure and relaxation are always within reach.brbrWith a friendly on-site management team ready to assist, your only job is to unwind.brbr Unit 106 has everything you need for an unforgettable stay—book now and make your dream vacation a reality!

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Bath

Sleeps

$267.97

/ Nightly

Condo

Steps to the Beach 1 Bed 1 Bath at Siesta Key with Views and Sunsets

Siesta Key, Florida, United States

Condo 205 is an exquisite 1 bedroom, 1 bathroom, second-floor unit that offers over 820 square feet of comfortable living space. The fully stocked kitchen featuring full-size appliances provides the perfect opportunity to showcase your culinary skills. brbrWith a king-sized bed, the bedroom is designed to ensure maximum comfort and relaxation. The screened-in lanai provides breathtaking views of the gulf, and our world-class sunsets are not to be missed. This unit is perfect for a romantic getaway, providing everything you could wish for. brbrLocated just a few steps from Siesta Key Beach, you can immerse yourself in our world-renowned white quartz sands in no time. The unit comes equipped with beach gear, making your beach experience seamless. brbrLess than a mile away from The Village, take a romantic stroll or hop on the free trolley to enjoy the best restaurants, shopping, and nightlife in the area. Honestly, this unit offers everything you need for a memorable stay, except for you.brbrOur onsite management team is available to make sure your beach vacation is one to remember. Book today!

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Bath

Sleeps

$315.93

/ Nightly

Condo

Siesta Key Stunner Endless Gulf Views from Your 2 Bed 2 Bath Top Floor Escape

Siesta Key, Florida, United States

Prepare to be awestruck by the sheer beauty of Siesta Key Beach - your perfect vacation destination. The breathtaking panoramic view of the beach from unit 502 at Crescent Royale Condominiums will transport you to a paradise-like setting.brbrRecently renovated, this unit exudes a modern and relaxed beach vibe that'll make you feel like royalty. With over 1,250 square feet of living space, this 2 bedroom, 2-bathroom gem accommodates up to four guests comfortably. The master bedroom features a king-sized bed, while the second bedroom has two twin beds that can be converted to a king. For additional guests, the living room comes equipped with a double sized sofa sleeper (with an additional per night charge) and a supersized flat screen.brbrWe know you're here to soak up the sun, and we've got you covered with all the beach essentials you need - chairs, umbrellas, mats, and coolers! brbrThe cherry on top Siesta Key Beach is just a hop, skip, and a jump away, so you'll have your toes in the sand in no time.brbrBut wait, there's more! The Village is just a complimentary trolley ride away, with endless options for shopping, dining, and people-watching. So, pack your bags, grab your crew, and get ready for your new beachy paradise. We can't wait to welcome you!brLong description of amenities and featuresbrbrCrescent Royale offers a range of amenities for your enjoyment, including a heated pool, workout gym, BBQ area, and shuffleboard. The onsite management team is always available to ensure your vacation goes smoothly. Don't wait - book your stay at this highly sought-after Condo. It's a fan favorite.

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Bath

Sleeps

$259.54

/ Nightly

Condo

Siesta Key Beach 2 Bed 2 Bath with Gulf Views Steps to Beach

Siesta Key, Florida, United States

Attention beach lovers! You're in for a treat with our Condo 211, where relaxation is the order of the day. With 1220 sq. ft. of space, 2 bedrooms, and 2 baths, this condo is a slice of heaven. And its location Just a hop, skip, and jump away from Siesta Key beach!brbrSleep like royalty in either of the spacious bedrooms, furnished with super comfortable king-sized beds. The guest room has two twin beds that can be joined to form another king-sized bed. And if that isn't enough, there's also a sleeper sofa. The kitchen is a modern marvel, with state-of-the-art amenities and a fancy kitchen island. Whip up a tasty beach meal without breaking a sweat!brbrNo need to carry heavy beach gear - we've got it all sorted! The condo comes equipped with towels, linens, beach chairs, and even umbrellas! Pack your beach essentials: swimsuit, sunglasses, sunscreen, and flip flops, and you're good to go!brbrAfter a day of sunbathing and sandcastle-building, enjoy breathtaking sunsets while sipping wine from our screened-in lanai. Alternatively, take a free trolley ride to the Village, where you'll find a plethora of dining, shopping, and nightlife options.brbrFitness enthusiasts will love our beach-facing suites and heated pool, while beach bums can soak up the sun. We also have an on-site gym for those who can't do without a workout. Our on-site management team is dedicated to making your stay stress-free.brbrThis condo is the ultimate beach vacation dream come true. The only thing missing You! Book now and make it a reality!brbrLeave your footprints on Siesta Beach and create memories of a lifetime.

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Bath

Sleeps

$346.16

/ Nightly

Condo

Siesta Key Beach Stunning Gulf Views 2 Bed 2 Bath Steps to Beach

Siesta Key, Florida, United States

Stunning views of the Gulf of Mexico's Siesta Key Beach. Dr. Beach's #1 rated beach in the U.S. and its world renowned white quartz sand is only steps from vacationing at Crescent Royale's Unit 5A! This newly renovated and refurnished 2 bedroom/2 bath Beachy condo is an end unit that features a wrap around screened lanai that offers panoramic views and sunsets not to be found but in a few of the units throughout the property. Enjoy both fun on the spectacular beach or in the beautiful heated swimming pool with newly renovated restrooms and adjoining fitness center.br brThe Condo is equipped with wireless high-speed internet, 2 DVD players, a 50 HD smart TV for streaming movies etc. There is also a 42 smart HD TV in the master bedroom and a 32 flat panel in the guest bedroom. The kitchen has a Keurig Duo Plus Single Serve K-Cup and/or 12 cup Carafe Coffee Maker along with all new high-end LG appliances.br brAfter a day of fun-n-sun on the beach or at the pool, you can discover Siesta Key Village, which is just a short walk away. The village features numerous open air style restaurants, many featuring live music. There are also numerous shops, a full grocery store, post office and drug store.brbrThe public beach features lifeguards, tennis courts, children's playground, gift shops and concessions. Don't forget the famous drum Sunday prior to sunset. FREE instructor lead Yoga every Monday, Wednesday, Friday and Saturday at the public beach along with nightly sunsets that are second to none!

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Bath

Sleeps

$297.8

/ Nightly

Condo

Vacation Ready 2 Bed 2 bath Siesta Key Beach with Gulf Views Steps to Beach

Siesta Key, Florida, United States

Welcome, beach enthusiasts! Prepare to indulge in a slice of paradise by booking our Condo 302,, located in a beachy wonderland adjacent to Siesta Key beach. With ample space of 1220 sq. ft., 2 bedrooms, and 2 baths, there's plenty of room for you to relax and unwind.brbrOur super comfortable king-sized beds and guest room with twin beds that can be joined together to provide the ideal sleeping arrangements. The kitchen is equipped with everything you need to cook up a storm.brbrDon't worry about lugging your beach gear - we've got you covered! The condo comes fully stocked with towels, linens, beach chairs, and even umbrellas. All you need to bring is your beach essentials, including a swimsuit, shades, sunscreen, and flip flops.brbrEnd your day of sunbathing and sandcastle building by admiring the sunset with a glass of wine on our screened-in lanai. Additionally, our free trolley can transport you to the Village, where you'll find plenty of dining, shopping, and nightlife options.brbrFor the fitness enthusiasts, our beach-facing suites, heated pool, and on-site gym provide ample opportunities to stay active. Our team is dedicated to making your stay worry-free and enjoyable.brbrThis condo is the ultimate beach vacation dream - all that's missing is you. Book now to make it a reality!

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Bath

Sleeps

$308.59

/ Nightly

Condo

Siesta Key 2 Bed 2 Bath Gulf View 100 Steps to White Sand Beach

Siesta Key, Florida, United States

Pack your bags and prepare to be swept off your feet by the jaw-dropping magnificence of Siesta Key Beach - ranked numero uno for its powder-soft quartz sand and sunset spectacles! Nestled on the third-floor corner, Unit 301 is a luxurious haven, boasting two bedrooms, two full bathrooms, and over 1220 sq. ft of living space, fit for all your needs.brbrTaking a dip in the Gulf is just a hop, skip, and jump from your door, while the lanai and master bedroom offer unbeatable views of the beach. With plenty of space to host six guests comfortably, the unit boasts two queen beds in the master bedroom, and a king-sized bed in the guest room, all with adjustable frames that add to your comfort.brbrThe unit features all-new tiles and flooring, with a fully equipped kitchen sporting stainless steel appliances, perfect for your culinary experiments. You can enjoy new large flat-screen TVs in the living room and each bedroom, and free Wi-Fi keeps you connected with the world. With luxury sheets and towels at your disposal, your stay will be nothing short of a dreamy float in the clouds.brbrOur unit provides beach towels, toys, and beach chairs with built-in cooler pouches, so you can make the most of your beach trips. And after a day of relaxing in the sun, refresh yourself in the heated pool, fire up the BBQ grill, or work out in the gym. You can even challenge your friends to a game of shuffleboard on the court available for guests.brbrSituated in the heart of Siesta Key, the Village is a stroll or trolley ride away, where you can explore restaurants, nightlife, and shopping. And here's the cherry on top: the enclosed lanai offers panoramic gulf views, presenting some of the world's most beautiful sunsets.brbrTo ensure you have the best vacation experience, our onsite management team is ready to assist you. So, pack your bags and book your stay today - paradise awaits you at Siesta Key!

2

Bed

2

Bath

6

Sleeps

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