Vacation Rentals By Owner In Siesta Key, FL

Relaxing lake view, 2-bedroom, 2-bath home on Siesta Key! This home is a spacious unit, featuring a king bed in the master and 2 twin beds in the second bedroom. This home sleep up to 6 guests. Outside your living room is a 20 ft long deck with a stunning full-length view of the lake! A brief walk from the condo to sand, is the beautiful Siesta Key Beach! This location has something for everyone, Our House at the Beach offers guests a heated pool, tennis courts and a covered pavilion with grilling area. Relax on our world-famous Siesta Beach, or take a trip to Siesta Key Village, which offers endless boutique shopping, live entertainment, and dining, making this condo the perfect place for you to enjoy your island getaway vacation! brbrBedding and Televisions:brBedroom 1: King, TVbrBedroom 2: 2 Twins, TVbrLiving Room: Sleeper Sofa, TVbrbrAdded 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: 25br*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

Lovely 2 Bedroom Lake View Home on Siesta Key!

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$327.59

Welcome to Crescent Arms unit 405NbrThis 4th floor unit, with an elevator, is steps from the beach and a short walk to several restaurants, a Tiki bar, an island grocery store and water sports/ boating. Welcome to Crescent Arms on beautiful siesta key Florida. If you are looking for your vacation to be on the best beach and have the most beautiful sunsets, then you are in luck.br There are two separate bedrooms, each with their own bathroom and flat screen TV. The master bedroom has a King bed and the 2nd bedroom has a queen bed plus a double bed. The kitchen is fully stocked with dishes/pots and pans/utensils/appliances and has everything you need. Beach chairs and umbrellas are provided for your beach comfort and enjoyment. The lanai has a gulf view and there is a laundry room conveniently located on the 4th floor. The condo has a designated, covered parking spot on site, BBQ grills, a heated pool and is truly a beach paradise.brBook now and get ready to view the beautiful sunsets from your own slice of Siesta Perfection!brThis unit Features:brBeach front property! Easy access on and off the Island! No loading up a car or crossing streets just walk out of the building onto the sand! 2 Bedroom 2 bathroom . Sleeps up to 6 people. Screened in lanai with patio furniture. Full kitchen, dining area, Tv in each room with free Wi-Fi. brShared resort amenities:br Heated pool, Private Beach, BBQ area with gas grills. Beach chairs provided. Beach personnel you can rent an umbrella from. Beach towels included. Bed linens and bath towels included. We do not have a linen service if you would like fresh linen you will have to wash them. Coin operated laundry in the tower buildings, Villas have washers and dryers in the garage. NO GOLF CARTS, Trailers, motorcycles, mopeds, boats If you want to enjoy the sugar-white sand of Crescent Beach, shop or just relax by the pool, located directly on the beach side of Midnight Pass Road, we offer something for everyone: Wi-Fi, cable television, generous closet space, a lanai or glassed-in porch and a fully furnished kitchen.brCrescent Arms features: Fully Furnished, Gated Condominiums Private Beach Access with Chairs No smoking and no pets, please!brThere is a seven-night minimum stay Saturday to Saturday. Check in: 4 PM Check out: 10 AM We strongly encourage you to get rental insurance in case of any problems that may occur. Your Florida Vacation Awaits You.

Crescent Arms Vacation Rentals 405N Siesta Key Florida

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$348.15

Welcome to Crescent Arms unit CA 505SbrweeksbrApril 11-18th 2026 25% offbrApril 18-18th 2026 25% offbrApril 25- May 1 2026 15% offbrMay9-16th 2026 15% offbrMay 16-23rd 15% offbrFully equipped, 5th-floor, 2 bedroom/2 bath condo in Crescent Arms Towers, Gulf views. The fifth floor 505s beachfront condo is steps away from the sugar-white sand of Crescent Beach. Its screened in lanai offers a direct Gulf view as well as a sneak peak of the bayside looking East. If you are looking for your vacation to be on the best beach and have the most beautiful sunsets, then you are in luck.brThis unit Features:brBeach front property! Easy access on and off the Beach! No loading up a car or crossing streets just walk out of the building onto the sand! 2 Bedroom 2 bathroom Sleeps up to 6 people. Screened in lanai with patio furniture. Full kitchen, dining area, Tv in each room with free Wi-Fi. brShared resort amenities:brHeated pool, Private Beach, BBQ area with gas grills. Beach chairs provided. Beach personnel you can rent an umbrella from. Beach towels included. Bed linens and bath towels included. We do not have a linen service if you would like fresh linen you will have to wash them. Coin operated laundry in the tower buildings. Villas have washers and dryers in the garage. NO GOLF CARTS, Trailers, motorcycles, mopeds, boats If you want to enjoy the sugar-white sand of Crescent Beach, shop or just relax by the pool, located directly on the beach side of Midnight Pass Road, we offer something for everyone: Wi-Fi, cable television, generous closet space, a lanai or glassed-in porch and a fully furnished kitchen.brCrescent Arms features: Fully Furnished, Gated Condominiums Private Beach Access with Chairs No smoking and no pets, please! brThere is a seven-night minimum stay Saturday to Saturday. Check in: 4 PM Check out: 10 AM We strongly encourage you to get rental insurance in case of any problems that may occur. Your Florida Vacation Awaits You.

Crescent Arms Vacation Rentals 505S Siesta Key Florida DISCOUNTS on selected dates

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$411.16

Welcome to Crescent Arms Unit CA 202S - This unit is Located on the southwest corner of the south building. It features a lanai that is directly overlooking the Gulf of Mexico. The living room and kitchen offer a breathtaking view of the beach and the amazing sunsets .Our second floor, gulf-front apartment offers a spectacular, uninterrupted view down beautiful Crescent Beach., its screened lanai provides a sunny front-row seat for beach and sunset watching with shelter from the occasional north breeze.brThe bedrooms are located down the hall. The first bedroom has 2 twin beds with a hall bathroom. The second bedroom has a king bed and is located at the back of the unit making this room separated from the main living area, offering a quiet room for the kids during nap times or the adults needing a couple of extra minutes to sleep in without being disturbed by the people in the living room.brThe living room contains soft leather couches and a recliner chair, three reading lamps, and a 46-inch, flat-screen remote-control cable television. One couch is a queen-sized sleeper sofa. The elegant glass dining table seats six. The kitchen, with its beautiful granite countertops, is open to the living area and the beach view. Each bedroom has its own flat screen TV. Both bathrooms have beautifully designed walk-in showers with built-in seats and sliding glass doors. brCrescent Beach, with its three miles of white, sugar-like sand, is rated as one of the most beautiful beaches in the world. Its smooth, fine sand and gentle slope are perfect for walking, jogging, even pushing strollers. Look for shells, watch for dolphins, or just watch the people as you stroll along this inviting Gulf shore. On the street side, it is an easy walk or a short drive to shops, stores, and restaurants. Decorated in neutral sand colors with coral accents, our condo provides contemporary, comfortable furniture and handsome ceramic tile floors throughout. If you are looking for your vacation to be on the best beach and have the most beautiful sunsets, then you are in luck.brThis unit Features:brBeach front property! Easy access on and off the Island! No loading up a car or crossing streets just walk out of the building onto the sand! 2 Bedroom 2 bathroom. Sleeps up to 4 people. Screened in lanai with patio furniture. Full kitchen, dining area, Tv in each room with free Wi-Fi. brShared resort amenities:brHeated pool, Private Beach, BBQ area with gas grill. Beach chairs provided. Beach personnel you can rent an umbrella from. Beach towels included. Bed linens and bath towels included. We do not have a linen service if you would like fresh linen you will have to wash them. Coin operated laundry in the tower buildings, Villas have washers and dryers in the garage. brNO GOLF CARTS, Trailers, motorcycles, mopeds, boats If you want to enjoy the sugar-white sand of Crescent Beach, shop or just relax by the pool, located directly on the beach side of Midnight Pass Road, we offer something for everyone: Wi-Fi, cable television, generous closet space, a lanai or glassed-in porch and a fully furnished kitchen. Crescent Arms features: Fully Furnished, Gated Condominiums Private Beach Access with Chairs No smoking and no pets, please!brThere is a seven-night minimum stay Saturday to Saturday. Check in: 4 PM Check out: 10 AM We strongly encourage you to get rental insurance in case of any problems that may occur. Your Florida Vacation Awaits You.

Crescent Arms Vacation Rentals 202S Siesta Key Florida

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$328.96

Beautiful lake view, 2-bedroom, 2-bath home on Siesta Key! Our townhouse is a spacious unit located on the second floor, featuring a king bed in the master, a queen and twin in the second bedroom, and a sleeper sofa in the living room, sleeping up to 7 guests. Outside your living room is a long deck with southern sun exposure, perfect for early more coffee over looking the lake! A brief walk from the townhouse to sand, is the beautiful Siesta Key Beach! This location has something for everyone, Our House at the Beach offers guests a heated pool, tennis courts and a covered pavilion with grilling area. Relax on our world-famous Siesta Beach, or take a trip to Siesta Key Village, which offers endless boutique shopping, live entertainment, and dining, making this condo the perfect place for you to enjoy your island getaway vacation! brbrBedroom 1- KingbrBedroom 2- Queen, TwinbrLiving Room- 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 Trolley - Free-Rides Around Siesta Key,brA 7-day week, Beachside Management office for your convenience and guest needs!brbr*Minimum Age to Book: 25br*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

Beautiful Lake View Condo Near Siesta Beach!

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$327.59

403 N brSPECIALS!! brSPRING BREAK 4/11-25th $2,300 per weekbrMay special 5/9-16, 5/23-30 $1,400 per weekbrbrPlease call the office for the discount.brbr Please call the office for the discount. Seven day minimum Saturday to Saturday We strongly advise taking rental insurance in case of any unforeseen. Please call the office and they will enter the discount. 941 349-4171.brCome and enjoy the sun and moon light on the Gulf and feel the powder white sands of Siesta Key between your toes, where the sand never gets hot, steps away from your condo. We are located on the 4th-floor DIRECTLY ON THE WORLD FAMOUS BEACH IN SIESTA KEY! Crescent Beach, is famous for its crescent shape with pure white powder sand that is 99% pure quartz. Enjoy your morning coffee or perhaps a refreshing mimosa overlooking the sparkling Gulf in your spacious, screened lanai. Dolphins and stunning sunsets can be viewed from the beach or lanai. Leave your car parked in the shade under our covered parking and enjoy all this area has to offer.brFrom sitting on the beach, in loungers and chairs provided free of charge to our guests, to strolling to the South Village of Siesta Key. Here you'll find restaurants, shopping, clothing shops, grocery and drug stores. The Daiquiri Deck is a new addition to the South Village, steps from our condo. The Siesta Key Village is a short drive or long walk where you'll find an assortment of shops, entertainment, pubs, bars and restaurants. After souvenir shopping, enjoy an ice cream or refreshing drink. Rental equipment (bikes, canoes, kayaks, boats, jet skis, etc.) are also conveniently available.brOur 4th floor condo boasts granite countertops in the kitchen and both bathrooms. The kitchen has everything you'll need to prepare meals and drinks if you choose to stay in and relax. Sleep comfortably in our king sized beds, along with their own private bathrooms and showers. TVs are located in each bedroom and the living room. The living area has a new leather pull out sofa (queen sized) and loveseat for relaxing and entertaining. Cable HD, LCD TV, DVD/VCR combo and FREE WIFI are also included in the unit, as well as all linens, bath and beach towels, air-conditioning and ceiling fans in all rooms. Each room also has an individual access by sliders to the lanai. Washers/dryers are located just a few steps away near the elevator. No smoking and no pets, please! brbrThere is a seven night minimum stay Saturday to Saturday. Check in: 4 PM Check out: 10 AM Please consider purchasing independent trip/rental insurance to protect against any loss of payments. Come and enjoy the gentle surf of the ocean, the sugar white, powdery sand of Siesta Key. Start making your memories here and continue vacationing here as we have.brCrescent Arms features: Fully Furnished, Gated Condominiums 2 Bedrooms/2 Baths Private Wireless Internet in Unit Private Beach Access with Chairs Steps to the beach 1-Week, Saturday to Saturday, Minimum Required Stay

Crescent Arms Vacation Rentals 403 N Siesta Key Florida

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$460.79

201N brbrSPECIALS!!!brbrbrbrWe strongly advise you purchase travel insurance. 7 day minimum stay, Saturday to Saturday. Please call the office for the discount. We strongly recommend getting vacation insurance in case of any unforeseen circumstances. Come and enjoy the sun and moon light on the Gulf and feel the powder white sands of Siesta Key between your toes, where the sand never gets hot, steps away from your condo. We are located DIRECTLY ON THE WORLD FAMOUS BEACH IN SIESTA KEY WITH A MILLION DOLLAR VIEW. Crescent Beach, is famous for its crescent shape with pure white powder sand that is 99% pure quartz. Enjoy your morning coffee or perhaps a refreshing mimosa overlooking the sparkling Gulf in your spacious, screened lanai. Dolphins and stunning sunsets can be viewed from the beach or lanai. Leave your car parked in the shade under our covered parking and enjoy all this area has to offer. From sitting on the beach, in loungers and chairs provided free of charge to our guests, to strolling to the South Village of Siesta Key. Here you ll find restaurants, shopping, clothing shops, grocery and drug stores. The Daiquiri Deck is a new addition to the South Village, steps from our condo. The Siesta Key Village is a short drive or long walk where you ll find an assortment of shops, entertainment, pubs, bars and restaurants. After souvenir shopping, enjoy an ice cream or refreshing drink. Rental equipment (bikes, canoes, kayaks, boats, jet skis, etc.) are also conveniently available. Our 2nd floor condo boasts an updated kitchen with a new pantry and quartz countertops and peninsula. The kitchen has everything you ll need to prepare meals and drinks if you choose to stay in and relax. Sleep comfortably in our bedrooms; one with a king-sized bed and private completely renovated bathroom and shower and the other bedroom with two full beds with private completely renovated bathroom with shower. You can view and listen to the waves of the ocean from each bedroom as they lull you to sleep. TVs are located in each bedroom and the living room. The living room area has a couch and loveseat with built in recliners for relaxing as you enjoy the breathtaking views of the gulf or have fun entertaining. Cable HD, LCD TV, DVD/VCR combo and FREE WIFI are also included in the unit, as well as all linens, bath and beach towels, air-conditioning and ceiling fans in all rooms. Each room also has an individual access by sliders to the lanai for magnificent views of the gulf. Washers/dryers are located just a few steps away near the elevator. No smoking and no pets, please! Rules: There is a seven night minimum stay Saturday to Saturday. Check in: 4 PM Check out: 10 AM Please consider purchasing independent trip/rental insurance to protect against any loss of payments. Crescent Arms features: Fully Furnished, Gated Condominiums 2 Bedrooms/2 Baths Private Wireless Internet in Unit Private Beach Access with Chairs Steps to the beach 1-Week, Saturday to Saturday, Minimum Required Stay

Crescent Arms Vacation Rentals 201N Siesta Key Florida

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$251.09

Welcome to Crescent Arms unit CA 705SbrbrThis is Crescent Arms only 1 bedroom 1 bath unit. It is the perfect size for a individual, A couple, or even a small family sleeping up to 4 people. New HALO induct air purifying system for the whole condo. New items include, two living room chairs, coffee table, lamps with USB outlets, lanai table, bedroom fan, TVs, and linens and bedspread. Bright and cheery, freshly painted, new linens and some new furniture! Brand new Murphy Bed! Living room has a flat screen TV. Bedroom has a king bed, large chair and light for reading. Flat screen TV Lanai has a gulf view of world famous Crescent Beach. Put your toes in its unique 99% quartz sand that has been judged the world's finest and whitest!brTake the free trolley to the village or to the south end of the island! It stops right in front of the complex! So much to see and do and very relaxing!brCrescent Arms features: Easy access on and off the Island! brFully Furnished, Gated Condominiums & Villas 1 Bedroom/ 1 Bath Private Wireless Internet in Unit Private Beach Access with Chairs Steps to the beach Villas with Attached Garagesbr1-Week, Saturday to Saturday, Minimum Required Stay We strongly advise taking rental insurance in case of any unforeseen circumstances.

Crescent Arms 705 N Siesta Key Florida

Siesta Key, Florida, United States

1

Bed

1

Bath

4

Sleeps

$533.43

Enjoy automatic discounts based on your stay length, no codes needed, and the price you see already includes your savingsbrbrExperience the ultimate Siesta Key stay at Mermaid Cove, an expansive 4-bedroom retreat designed for families who love the outdoors. Located just 1.5 miles from the quartz sands of Siesta Key Beach, this home is a private playground featuring a heated pool, a backyard putting green, a custom fire pit, and an outdoor bar area. Whether you're staying for a month or a season, this is the perfect coastal home for work, play, and relaxation. brbr brbrThe Highlights brbr- Prime Location: Just 1.5 miles to Siesta Key Beach and to the Village. brbr- Outdoor Entertainment: Private heated pool, putting green, and fire pit with Adirondack seating. Pool heat is extra. brbr- Florida Living: Screened-in lanai with a covered bar, outdoor TV, and dining area. brbr- Spacious Layout: 4 Bedrooms / 3 Bathrooms, including two King suites. brbr- Work-from-Home Friendly: Dedicated desk space and a second living area for quiet focus. brbr- Chef’s Kitchen: Granite countertops, stainless appliances, and breakfast bar seating. brbr brbrThe Outdoor Experience brbrThe backyard at Mermaid Cove is where vacation memories are made. The screened-in patio houses a sparkling heated pool and a dedicated bar area with a TV - ideal for catching the game while grilling. Step outside the screen to practice your short game on the private putting green, or gather around the landscaped fire pit as the sun goes down. It’s a private resort experience right in your own backyard. brbr brbrInterior & Living brbr- The home features a bright, open-concept floor plan that seamlessly connects the kitchen, dining, and main living areas. brbr- Main Living: Plush seating and a large Smart TV for movie nights. brbr- Flex Space: A second lounge area provides extra room for kids to hang out or for you to catch up on emails at the desk. brbr- Kitchen: Fully stocked with everything needed for family feasts, featuring ample counter space and a convenient laundry room nearby. brbr brbrBedroom & Bathroom Configuration brbr- Primary Suite: King bed, private ensuite bathroom with double vanity and walk-in shower. brbr- Bedroom 2: King bed with easy access to a full hall bath. brbr- Bedroom 3: Comfortable Queen bed. brbr- Bedroom 4: Two Twin beds with Twin trundles - the ultimate kids space! brbr- Bathrooms: Three full bathrooms ensure no one is waiting in line after a day at the beach. brbr brbrEssential Amenities brbr- BBQ Grill for easy island cookouts. brbr- High-Speed Wi-Fi & Smart TVs throughout. brbr- Parking: Driveway space for 3 vehicles. brbr brbrOther information: brbr- No smoking property brbr- Pool heat extra - reach out for details. brbr- No parties or large gatherings - This home is in a quiet residential neighborhood. We kindly ask that all guests treat the home and surrounding community with the same care and respect as they would their own. brbr- Per Sarasota ordinance, this home is limited to 1 rental per 30 day period. brbr brbrThe Neighborhood brbrMermaid Cove is nestled in a quiet residential neighborhood, offering a peaceful escape while remaining walking or biking distance to the best of Siesta Key. Enjoy easy access to world-class dining, boutique shopping, and the legendary sunsets that make this island famous. brbr brbrRare is the home that offers a putting green, a fire pit, and a poolside bar all in one private backyard. Mermaid Cove isn't just a place to stay, it’s your own private island club. Perfect for those seeking an extended escape, you're close enough to feel the Gulf breeze but tucked away enough to enjoy total backyard bliss!brbrIMPORTANT: The min age to rent is 25 years old. No parties, large gatherings. Please reach out if you have any questions.

Mermaid Cove | Family Oasis with Putting Green & Heated Pool

Siesta Key, Florida, United States

4

Bed

3

Bath

10

Sleeps

$291.49

Beautiful Siesta Key 3-bedroom pool home on the island, just minutes to the village and beach. Spacious and comfortable, sleeps up to 10 guests with multiple living areas, fully equipped kitchen, and private outdoor oasis. Enjoy sunny days by the pool, dining al fresco, and easy access to shops, restaurants, and nightlife. Perfect for families or groups.

Siesta Key 3BR pool home village/beach sleeps 10

Siesta Key, Florida, United States

3

Bed

Bath

10

Sleeps

$323.45

Gulf and Bay Club B604 by Tropical Sands AccommodationsbrbrCondo in Sarasota, FL 34242brbrGulf and Bay Club B604 offers a serene escape with two bedrooms, two baths, and a stunning screened-in balcony. Marvel at panoramic views of the beach, lake, and shared pool while dining al fresco or laughing with friends and family over a glass of wine and appetizers.brbrHighlightsbrbr• Private beach accessbrbr• Shared poolsbrbr• Tennis, pickleball, racquetball, basketball, and shuffleboard courtsbrbr• Fitness Centerbrbr• Community electric vehicle chargersbrbrInside is a coastal-inspired living space with a complete seating area, TV, and a formal dining room table. The kitchen has every cooking essential you’ll need to prepare favorites, and there is even a kitchen table.brbrThe primary bedroom is adorned with a premium King bed, a walk-in closet, and an ensuite bathroom with two vanities and a shower and tub combo. In the guest bedroom, there are two full beds, and each room has a television. Additionally, a washer and dryer are provided in this unit to add convenience to your stay.brbrGulf and Bay is a fabulous beachfront condominium complex with private beach access to Siesta Key Beach and its world-famous white sands and warm waters. This complex features three heated pools, saunas, a hot tub, activity courts for tennis, pickleball, racquetball, and shuffleboard, a fitness center, and numerous tiki-themed BBQ areas surrounding the lakes. Pack your sunscreen and your sense of adventure – because at Gulf and Bay Club B604, the fun never takes a vacation!

Gulf and Bay Club B604

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$226.49

Welcome to your perfect beachside retreat! This charming off-the-beach condo is ideally located just a short walk from the shoreline, offering all the perks of coastal living. Enjoy easy beach access, ocean breezes, and a relaxed gulf side vibe.brbrInside, the condo features a bright, open layout with comfortable living spaces designed for easy living and relaxation. Whether you’re sipping morning coffee on the back patio to unwinding after a day in the sun, this home is the condo escape. Ideal for a couples vacation getaway, this condo puts you right where you want to be—near the beach, but away from the crowds.

Jamaica Royale Unit #19: Comfy Condo just a short walk to the beach

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$359.61

Enjoy automatic discounts based on your stay length, no codes needed, and the price you see already includes your savingsbrbrWELCOME TO JAMAICA ROYALE BEACH VILLA brbr brbrRelaxation and fun await just steps from Siesta Key Beach! This charming one-bedroom villa combines modern comfort with unbeatable convenience. Guests enjoy three heated swimming pools, beautifully landscaped grounds, and a private walkway to Siesta Key’s famous white sand. brbr brbrPROPERTY HIGHLIGHTS brbrSleeps up to 6 guests with a king bed, queen bed, and queen sleeper sofa in the spacious living area brbrLess than a 5-minute walk to Siesta Key Beach via the complex’s private walkway brbrRecently renovated with new flooring, updated furnishings, and a modern kitchen with stainless steel appliances brbrPrivate patio with two dining tables, perfect for outdoor meals under the umbrella brbrIn-unit washer and dryer for added convenience brbrUncovered parking with one reserved space brbrBeautiful courtyard views from the villa brbr brbrSLEEPING ARRANGEMENTS brbrBedroom: King bed + Queen bed brbrLiving room: Queen sleeper sofa brbrAccommodates up to 6 guests brbr brbrINSIDE THE VILLA brbrSpacious open-plan living and dining area with updated furnishings brbrFully equipped kitchen with new cabinetry, stainless steel appliances, and cookware brbrPrivate laundry with washer and dryer brbrPatio dining area with seating for al fresco meals brbrKeyless entry for easy check-in brbr brbrRESORT AMENITIES brbrThree heated swimming pools, including one close to the Gulf brbrPrivate beach access with outdoor showers brbrTennis and shuffleboard courts brbrBBQ grilling areas brbrLandscaped walkways and gardens brbr brbrLOCATION brbrJust steps to Siesta Key Beach brbr1.5 miles to Siesta Key Village with shopping, dining, and live music brbrFree local ride services available for easy transportation around the island brbr brbrADDITIONAL DETAILS brbrNon-smoking and pet-free complex brbrBeach essentials provided, including towels, chairs, and accessories brbrPhotos reflect recent renovations; additional updates are ongoing to enhance guest stays brbrRepairs on the sliders are scheduled for May 13, 2026 between 9 - 11 am. brbr brbrEXTRA PERKS brbrComplimentary Xplorie activities for stays under 28 days, including bike rentals, dolphin cruises, kayak rentals, and admission to The Ringling Museum brbrOne complimentary round-trip airport transfer for up to 3 guests from SRQ or TPA with advance reservation (tips appreciated) brbr brbrBOOK YOUR STAY AT JAMAICA ROYALE BEACH VILLA TODAY brbr brbrEnjoy modern comfort, private beach access, and the perfect Siesta Key location for your next tropical getaway.brbrNext door complex is under construction. Unfortunately, we don't have any say in the matter.brbrWe 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.brbrIMPORTANT: The min age to rent is 25 years old. No parties, large gatherings. Please reach out if you have any questions.

Hello, Sunshine! Jamaica Royale Condo: Steps to Private Beach, Pools, & Free Daily Activities!

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$1483.38

The Hummingbird | 6BR/6BA | Sleeps 20 | Private Heated Pool | Heart of Siesta Key Villagebrbr Why You'll Love This HomebrThe Hummingbird is a rare, full-property rental comprised of four charming units—Lantana, Mimosa, Plumbago, and Vinca—creating the ultimate retreat for large families or groups. Featuring 6 private bedrooms, 6 full bathrooms, 4 full kitchens, and your very own private heated pool, this home is steps from both the beach and Siesta Key Village's best restaurants and shops.brbr☀️ Perfect ForbrMulti-family reunions, wedding groups, retreats, or any large gathering looking for the perfect balance of privacy and togetherness in an unbeatable walkable location.brbr Imagine ThisbrStart your day sitting on one of three private balconies or the screened front lanai. Then walk just 0.2 miles to sink your toes into the soft sands of Siesta Key Beach—ranked #1 in the U.S. After a beachside lunch, retreat to your tropically landscaped private pool and relax under swaying palms. With four kitchens and six bedrooms, your group can spread out or come together with ease, creating shared memories without sacrificing personal space.brbr Where Everyone Sleeps (Sleeps 20 Total)br Lantana - Lower Unit (2BR/2BA):br • Bedroom 1: King Bed – Sleeps 2, TVbr • Bedroom 2: King Bed – Sleeps 2, TVbr • Living Room: Queen Sleeper Sofa – Sleeps 2brMimosa - Lower Unit (1BR/1BA):br • Bedroom 1: King Bed – Sleeps 2, TVbr • Living Room: Queen Sleeper Sofa – Sleeps 2brPlumbago - Upper Unit (2BR/2BA):br • Bedroom 1: King Bed – Sleeps 2, TVbr • Bedroom 2: King Bed – Sleeps 2, TVbr • Living Room: Queen Sleeper Sofa – Sleeps 2brVinca - Upper Unit (1BR/1BA):br • Bedroom 1: King Bed – Sleeps 2, TVbr • Living Room: Queen Sleeper Sofa – Sleeps 2brbr Location Highlightsbr • 3-Minute Walk (0.2 mi) to Siesta Key Beachbr • 1-Minute Walk to Siesta Key Village (across from Gilligan's)br • Walkable to live music, cafés, boutiques & bike rentalsbr • 15-Minute Drive to Downtown Sarasotabrbr Home Featuresbr • 6 Bedrooms, 6 Full Bathroomsbr • 4 Full Kitchensbr • 3 Private Balconies + Screened-In Lanaibr • Private Heated Pool (Nov 15–Apr 15)br • 4 Living Rooms w/ Queen Sleeper Sofasbr • In-Unit Laundry in All Unitsbr • Pet-Friendly (Lower Floor Units Only – Confirm When Booking)br • 4 Dining Areas, Outdoor Lounge Furniturebr • Smart TVs, Free WiFibrbrNEED TO KNOW:br The Hummingbird is a combination of 4 individual units:br• Lantana (5251A)br• Mimosa (5251B)br• Plumbago (5251C)br• Vinca (5251D)brbrThese units do not share interior space and are accessed by separate exterior entrances unless the upper and lower access doors are opened between those units. All share access to the private heated pool, screened lanai, and outdoor lounging areas. Your stay is protected by our CottageClean Program, featuring a 6-hour deep clean, 35-point property inspection, and enhanced sanitization to give you full peace of mind. We aim for every guest to walk into a home that feels brand new. pool is heated from November 15 to April 15.

The Hummingbird | Located in Siesta Key Village w/ Private Pool, Walk to Beach!

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$602.8

Plumbago | 2 King Suites + Balcony | 0.2 Miles to Siesta Key Beachbrbr Why You'll Love This HomebrPerched above Siesta Key Village, Plumbago offers a peaceful second-floor retreat with two private king suites, a balcony for breezy mornings, and a shared heated pool just steps from white-sand beaches.brbr ‍ ‍ Perfect ForbrSmall families, couples, or close friends seeking comfort, privacy, and walkability in a beachside location.brbr ️ Imagine ThisbrStart your day on the private balcony with fresh coffee and ocean air, then stroll just 0.2 miles to Siesta Key Beach for swimming, shell hunting, or sunbathing on the powder-soft sand. After exploring the Village's local shops and eateries, cool off in the shared heated pool nestled among tropical landscaping. Back home, prep dinner in the full kitchen, stream a movie in the cozy living room, and retreat to two spacious king bedrooms for a restful night.brbr Where You'll Sleepbr- Bedroom 1: King Bed, Ensuite Bath, Second Floor, TVbr- Bedroom 2: King Bed, Shared Bath, Second Floor, TVbr- Living Room: Queen Sleeper Sofabrbr Explore the Areabr- 0.2 miles to Siesta Key Beachbr- 0.1 miles to Siesta Key Villagebr- Steps to dining, beach bars, and boutique shoppingbr- Easy access to bike rentals, live music, and sunset viewsbrbr Don't wait—this home books fast. Every stay is backed by our CottageClean™ Program, including a 6-hour deep clean and 35-point inspection before check-in—so you can arrive stress-free.brbr Need to Know: Starter packs of kitchen and toiletry essentials provided for a seamless first couple of nights. This home is part of a duplex and may share walls, floor/ceiling, or outdoor spaces. Located on the second floor with front-facing stair access. Heated pool available November 15 – April 15. If any guest has difficulty with stairs, please contact us for alternative accommodations.

Plumbago | Prime Location in Siesta Key Village w/ Heated Pool, Walk to Beach!

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$408.86

SHORT WALK TO THE FAMOUS SIESTA WHITE SAND BEACH & QUAINT ISLAND VILLAGE. brbrEnjoy this ‘Old Florida Charm’ beach cottage. It has two bedrooms (one king and one queen) and two bathrooms (stall shower in one and tub/shower in the other.) The large living room has French doors leading onto a screened-in porch, which overlooks the brick walkway in the gardens. It has a large kitchen and bright dining room surrounded by windows, which have a view of the canal. The master suite has a beautiful bay window for gorgeous views of the gardens and a separate additional entrance for privacy that leads to the outdoor shower. Across the street is the canal and a dock for boating, kayaking, and fishing. It is only a short walk to the famous Siesta Key beach and village for all your shopping needs.brbrPets are welcome with a refundable pet deposit.brbrFor additional availability on Siesta Key please see our other listings:brBlue Lagoon VRBO#1043727 (2B/2B)brFern Haven VRBO#1044027 (Studio)brGarden Terrace VRBO#1043802 (Studio)brTropical Hideaway VRBO#1044034 (2B/1.5B)brLily Patch VRBO#10056 (2B/2B)

Canal Place Tropical Bungalow -Walk To Siesta Beach & Village - Bring your Pets!

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$202.56

Enjoy the best of Siesta Key from this beautifully renovated canal-front vacation home that blends modern comfort with relaxed Old Florida charm. Fully updated throughout, the home features a well-equipped kitchen, stainless steel appliances, quartzite countertops, terrazzo floors, ceiling fans in every room, central air conditioning, a washer and dryer, two televisions, high-speed internet, and updated furnishings throughout.brbrThe home offers two comfortable bedrooms, each with a queen bed. The primary suite overlooks the garden and includes a private ensuite bath with a spacious walk-in shower, along with direct access to a convenient outdoor shower. The second bedroom overlooks the canal, includes a television, and shares a guest bath that also features a walk-in shower. An additional built-in bunk nook provides sleeping space for two more guests.brbrOutdoor living is a highlight, with multiple inviting spaces including a screened front patio, a large screened lanai with grill and dining table overlooking the canal, and a backyard with artificial turf — ideal for relaxing, dining outdoors, or simply enjoying the peaceful waterfront setting.brbrBoating enthusiasts will appreciate the private dock with fishing access and an electric boat lift accommodating vessels up to approximately 25 feet or 13,000 lbs. Guests also have access to bikes, paddleboards, and surfboards for exploring the surrounding area.brbrLocated just minutes from world-famous Siesta Key Beach and vibrant Siesta Key Village, you’ll enjoy easy access to renowned restaurants, live music, shopping, and local events while still returning to a quiet residential setting.brbrSmall pets may be considered with owner approval.brbrImportant Note:brPer Sarasota County ordinance, this property allows one rental per 30-day period.

Coastal Canal Retreat- Peaceful Waterfront Stay On Siesta Key

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$452.0

- Kitchen includes large island with cook top stove and seating for four. br- Spacious living room with Ethan Allen furniture.br- Dining room seats four. br- Paneled den includes two couches and flat screen TV with sliding doors to balcony.br- Master Bedroom includes Ethan Allen king size bedroom set, flat screen TV, en suite bathroom with a walk in shower, walk in closet and sliding door to balcony.br- Bedroom #2 has a queen size bed, flat screen TV with a sliding door to balcony.br- Bedroom #3 has a queen size bed with sliding doors to balcony.br- Large heated pool, shuffleboard, workout room, private tennis courts which include pickle ball, boat docks with direct access to the intracoastal waterway. Private beach access just steps from Siesta Key beach. br- Coin-op washers and dryers are located on each end of every floor.br- Beach towels, toys, chairs, cooler, umbrellas and tennis rackets/balls provided.br- Reserved parking spot under building for two standard vehicles. Overflow parking available in front and back of building.

Newly renovated 2400 sq. ft (5th floor) condo w/ gulf views and 70 ft balcony

Siesta Key, Florida, United States

3

Bed

Bath

6

Sleeps

Select Dates for Price

Gulf and Bay Club C204 by Tropical Sands AccommodationsbrCondo in Sarasota, FloridabrbrWelcome to Gulf and Bay Club C204! This beautiful two bedroom and two bath condo features a screened-in lanai with a dining table overlooking the condominiums lake, community pool, and you might just catch a glimpse of the Gulf of Mexico.brbrHighlights br• Private Beach Access br• Shared pools br• Tennis, pickleball, Racquetball, basketball, and shuffleboard courts br• Fitness Center br• Community electric vehicle chargers brbrInside is a gorgeous, fully equipped kitchen, a wicker and glass dining set, and a large sectional couch with a TV. The main bedroom is a true oasis of comfort, featuring a king-sized bed adorned with plush bedding and tropical decor. The attached bathroom is equally impressive, boasting two vanities, a walk-in shower, and a walk-in closet. The second bedroom is charmingly decorated with Florida-style furnishings and has easy access to the hall bath, which includes a shower and tub combo. To ensure your utmost convenience, each room has a television, and a washer and dryer are readily available for use.brbrGulf and Bay is a fabulous beachfront condominium complex with private beach access to Siesta Key Beach and its world-famous white sands and warm waters. This complex features three heated pools, saunas, a hot tub, activity courts for tennis, pickleball, racquetball, and shuffleboard, a fitness center, and numerous tiki-themed BBQ areas surrounding the lakes. Gulf & Bay Club C204 is a true gem and we cannot wait to have you as our guest and provide you and your loved ones with an incredible stay.

Gulf and Bay Club C204

Siesta Key, Florida, United States

Bed