Siesta Key Vacation Rentals

Looking for a tropical getaway, a place to leave the everyday grind behind? Look no further than Siesta Key! It's white sandy beaches, clear waters, spectacular sunsets and a wide range of restaurants, bars and other activities makes it the perfect place to spend your vacation. Take a look through our collection of Siesta Key area rental property information to help you decide which property suits your vacation best. Good luck and we hope you enjoy your stay.

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Siesta Key Vacation Rentals

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Siesta Key Village Area Rentals

The Terrace

Terrace Condominiums has to be one of the best locations on Siesta Key if proximity of the Village and sweeping Gulf views are on you “must have” list. Located at the corner of Beach Rd. and Ocean Blvd at 5400 Ocean Blvd, this 17-story 70-unit building features include a private raised second floor heated pool, under-building parking, and sweeping Gulf and/or Key views. Of course, it’s just a few steps to the pure white Siesta Key beaches known throughout the world as one of the best.

Ringling Beach House

Featuring a Spanish hacienda-style exterior, this circa-1920 Siesta Key beach house accommodations feature free Wi-Fi, flat-screen TVs and full kitchens. Options range from cozy efficiency rooms to 3-bedroom suites. Amenities include 2 outdoor pools, patios with gazebos and grills, and free parking, as well as a fitness center.

Sea Village

Sea Village Condos on Siesta Key is located directly on the Gulf of Mexico near the world famous Siesta Key Beach at 4660 Ocean Blvd. Sea Village is a 42 unit complex that features 2 swimming pools, a fishing pier and is a short walk to the Siesta Key Village.

Tivoli by the Sea

The closest weekly rental complex to the village! Nineteen two bedroom/two baths with washer/dryers in each unit, as well as, high-speed internet and a 26 foot open balcony with amazing gulf views. The property features Private beach, covered parking, heated pool, putt-putt golf course, ping-pong and more!

Sunset Royale

This charming mid-rise condominium is located on a well-manicured landscape with lush tropical foliage. It is located on the section of Beach Road, closest to Siesta Key Beach. Residents and guests of the Sunset Royale enjoy million dollar full Gulf views from every unit. Local shops, dining, and entertainment in Siesta Village are within walking distance or a short ride on the many tips only taxis that service the island. One of the popular streets in Siesta Key island is Ocean Boulevard, famous for its fresh seafood fare, restaurants and bars.

Crescent Royale

Crescent Royale Condominiums offer a variety of accommodation types ranging from one bedroom/one bath to four bedroom/three baths available for weekly and monthly stays. Crescent Royale has the right size condo for a romantic getaway, family vacation or business event. You can’t find better rooms on Siesta Key. From your lanai, enjoy an amazing sunset. Each fully furnished unit faces Siesta Public Beach and the Gulf of Mexico. At Crescent Royale, dreamy evenings will become cherished memories as sure as the sun will set where the ocean meets the sky.

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Siesta Key Vacation Rentals

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Siesta Key Public Beach Area Rentals

La Siesta

The closest condominium complex to Siesta Beach. Overlook the unique white quartz powder sands of this world famous beach. La Siesta offers tastefully furnished beach front vacation rental units with one or two bedrooms – each privately owned and maintained by their owners. Year-round vacation rentals require a minimum one week stay.


These condos are all about beachfront living. You’ll enjoy gorgeous beach views all day and sunsets every night. In addition to the beach, there’s shuffleboard and a swimming pool as well as shopping, dining and restaurants at nearby Village.

Our House At The Beach

Located directly across the street from the Siesta Public Beach, Choose from one of the two story Townhouse villas situated around the lake or one of the 7 floor towers overlooking Siesta Key. All units are 2 BR/ 2 Bths. This property offers tennis courts, swimming pool, BBQ area and more.

Gulf and Bay Club (Beach side)

Gulf and Bay Club Condos is a gated community built beside Siesta Public Beach. Guest of this condominium complex enjoy stunning views of the Gulf of Mexico as well as a resort ambiance enhanced by a charming courtyard and two freshwater lakes inside the property’s premises. Moreover, Gulf and Bay Club residents and guests have access to the property’s private beach. Other popular beaches are also a short stroll away.

Jamaica Royale (Beach side)

Create the perfect setting for the type of vacation you deserve with our studio, one and two bedroom condominium rentals. They have one story villas, two story Penthouses and two Bedroom Gulf View Tower Condos. You will be glad you came to Jamaica Royale. In addition to the beautiful beaches, the Jamaica Royale beautiful tropical grounds are very relaxing. You can enhance your stay further, by relaxing in one of the three heated swimming pools, enjoy playing shuffleboard, or have a BBQ at Beachside or on the Barbeque Island and patio.

Beach Haven (Beach side)

Experience Siesta Key’s premier community situated comfortably in the heart of beautiful Siesta Key. Walk along the pristine, powdery shoreline and see why Siesta Key is known for being #1 beach in US and top 10 in the world. Located just a short distance from the island’s quaint Siesta Key village district, Beachaven provides a peaceful setting with a beachside pool, picturesque roman style courtyard and community activities.

White Sands Village (Bay side)

White Sands Village Condominium is situated just a short walk from the world-renowned Siesta Key Public Beach, it’s a great place for a two-week vacation or for an extended stay. White Sands Village is a short 0.3 mile from Siesta Public Beach. No need to worry about Beach Parking. Please note: THE MINIMUM RENTAL PERIOD IS 14 DAYS.

Harbour Towers (Bay side)

In popular Harbor Towers Yacht & Racquet Club located in the heart of Siesta Key!! Close to both Siesta Key beach and Crescent beach (both less than a mile away) makes this property the perfect location for beach goers! A premier property with amenities such as heated (85 degrees!) pools, 3 Har-Tru Clay courts, fishing & boat docks, BBQ Grilling station, Clubhouse etc!

Gulf and Bay Club Bayside

Fall in love with charming Gulf and Bay Club Bayside, a Key West-inspired village located on the banks of the Intracoastal Waterway and directly across the street from world-famous Siesta Key Beach. Back on the bayside, you'll find a brand new dock stretching out into the Intracoastal Waterway, the perfect place for fishing or for watching the continuous parade of boats, people, and nature...a feast for the eyes!

Gulf Haven (Beach side)

Gulf Haven Condominiums are two-story villas, situated on the gulf side of beautiful Siesta Key. Each unit has a private entry, and is individually owned and decorated. The community includes full-time and seasonal owner/residents, and welcome rental guests, some of whom return year after year. Gulf Haven has private, direct access to wide, beautiful Crescent Beach.

Casarina (Beach side)

Casarina complex is located in a very private setting just south of the Siesta Public Beach. Enjoy the lush tropical garden view from your lanai, a wonderful peaceful setting and is particularly beautiful and lighted after dark. Amenities include a private beach and deck area, gated access to private pool and hot tub, lighted tennis courts, a lake, exercise equipment, bbq grills, a clubhouse with kitchen facilities. Walk to Siesta Key Village, restaurants and shopping.

Sarasota Surf and Racquet Club

Sarasota Surf and Racquet Club delivers the best of all worlds: The newly renovated condominiums have full amenities and include resort-like accommodations. Their customer service & satisfaction tops the charts and differentiates them from the many other choices you have when deciding on a vacation rental. Conveniently located close to fine dining and shopping and within minutes of area attractions, this is a perfect year-round island destination for travelers.

Sea Club II (Bay side)

This property is 2 minutes walk from the beach. Featuring an outdoor swimming pool, a garden as well as a private beach area, Sea Club II by Beachside Management is located in Siesta Key, within a 5-minute walk of Crescent Beach and 0.6 miles of Siesta Key Beach.

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Siesta Key Vacation Rentals

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Crescent Beach Area Rentals

Siesta Beach House (Beach side)

Relax on world-class white sand Crescent Beach, take a dip in the heated pool, play some shuffleboard, fish the Gulf, take in an opera or a club, go to a museum, shop, enjoy a quiet sunset, or have a fun family barbeque. The possibilities are endless on Florida’s Sun Coast. Siesta Beach House offer one and two bedroom condos, two bedroom townhouses and three bedroom cottages.

Palm Bay Club (Beach side)

This property is a 8-minute walk from the beach. Located in Siesta Key, a 3-minute walk from Crescent Beach and half a mile from Siesta Key Beach, Palm Bay Club provide accommodations with free WiFi, a garden with an outdoor swimming pool, garden views, and access to a fitness room and a hot tub.

Casa Mar (Beach side)

Stroll down palm lined walkway that lead to Siesta Key's fine white quartz sand and enjoy one of Florida's spectacular sunsets. Lounge chairs are conveniently located on the beach and a covered parking space is located outside of your door.

Horizons West (Beach side)

Horizons West offers an escape from the hustle and formality of commercialized vacation resorts. Their private section of beach is equipped with beach chairs and lounges for sunbathing; beach cabanas provide shade when you have had enough sun! Two swimming pools are located on the property and when you are weary after a hard day of shopping or playing, you can relax in our Jacuzzi.
The Horizons West high-rise offers an incomparable view of the Gulf of Mexico, complete with breathtaking sunsets! The high-rise has one, two and three bedroom apartments available. Or the villas are two bedroom single story homes that stretch from the Intracoastal Waterway to the beach. (Bay side)

Bay Oaks (Bay side)

Bay Oaks is a bayside, mid-rise condominium building complex in the middle of Siesta Key. It is located one half mile north of the Stickney Point Bridge, just a short walk from the world-famous Public Beach.

Aloha Kai (Beach side)

68 private villas on one of the best stretches of Siesta Keys famous Crescent Beach. Aloha Kai offers the largest heated pool on Siesta Key with studio, one, 2 and 3 bedroom units available. Most units offer high speed internet free of charge and are updated to the individual owners tastes. Value pricing with exceptional units.

Peppertree Bay (Beach side)

Peppertree Bay is the perfect monthly accommodation, check out the many amenities Peppertree Bay offers! Guests can enjoy the sparkling blue waters of Siesta Key beach in a comfortable lounge chair, or relax under the shade in one of the tiki huts right on the beach! Our long-term rental properties also have two beautiful tennis courts, a fitness center, two swimming pools nestled in their own garden paradise, and a wonderful fishing pier on Sarasota Bay! Plan the ultimate 4-week beach vacation and come rest and relax in the warm Florida sunshine and luxurious monthly vacation condo renta

Island House (Beach side)

Looking for a quiet vacation spot on the best beach in America? The Island House offers a variety of apartments and villas located on Siesta Key’s Crescent Beach, each with different features to meet your vacation needs. Overlooking the Gulf of Mexico, this vacation haven offers a serene place to stay with variety of activities. Full length heated swimming pool and Community House for games and recreational gatherings. Each villa and apartment reflects the mood of the beach and colorful evening sunsets, mirrored in the gulf water, enhance the serenity.

The Casa Blanca (Beach side)

The Casa Blanca offers a variety of accommodations from 1 bedroom 1 bathroom stand alone villas to 2 bedroom 2 bath gulf front view apartment. We are located on the beautiful Siesta Key Beach with quartz white sand. 100 steps to #1 beach in America. recreation room with pool and ping pong tables.

Siesta Dunes (Beach side)

Siesta Dunes Beachfront Condominiums offers our special guests a selection of over 90 Siesta Key vacation condo rentals. The beautiful sandy beaches of Siesta Key along the Florida Gulf Coast are right out your door, and you’ll also enjoy the pool and hot tub, beach deck and pavilion, tennis courts, club house, and plenty of restaurants and entertainment along Midnight Pass Road.

Polynesian Gardens (Bay side)

A relaxing and luxurious community located on Siesta Key, Florida, only steps from the world famous sugar soft white sands of Crescent Beach.

Excelsior (Beach to Bay)

Excelsior Condominiums’ luxury 2 and 3 bedroom condos are located on the beautiful, white sand beaches of world-famous Siesta Key. Experience Two Worlds: Your own private beach on world-famous Crescent Beach on Siesta Key and Classic Florida with tropical garden walkways, lakes and fountains. You can only find BOTH on one beautiful property. Our two large heated swiming pools, two heated whirlpools, shuffleboard, two pickle ball courts, and two tennis courts ensure you’ll have a fun and relaxing time.

Siesta Harbor (Bay side)

Beautiful property across the street from Crescent beach with canal views in peaceful Siesta Harbor with heated pool, hot tub, gym, BBQ's & gated private beach access to Crescent beach. Cornet unit with nice views. Highlights: Canal Water Views Throughout!! Heated Pool & Hot Tub, Private Gated Access Across the Street.

Midnight Cove II (Beach side)

Come and enjoy the island lifestyle on Siesta Key in this lovely condo. Enjoy your morning coffee or evening cocktail with views of the beautiful inter-coastal waterway from your balcony. Deeded beach access to Siesta Key’s famous quartz sand Crescent Beach is just a short stroll across the street. Enjoy the amazing community pool, boat basin, tennis courts, basketball courts, fitness room & BBQ area. Nearby restaurants and entertainment, Siesta Key village & convenient free Siesta Key trolley.

Crystal Sands (Beach side)

Luxury high rise apartments & ground floor villas directly on world famous Crescent Beach on Siesta Key Florida. Vacation rentals are 14 day minimum stay for the high rise apartments. The villas are a 14 day minimum stay except for the months of June through September when the minimum stay is 7 days. All high rise units are direct beach front with Gulf views. The property boasts a private beach, 2 heated pools (one with views of the Gulf).

Crescent Arms (Beach side)

If you want to enjoy the sugar-white sand of Crescent Beach, shop or just relax by the pool - Crescent Arms has what you need. Located directly on the Gulf of Mexico, Crescent Arms offers something for everyone, each 2-bedroom/2-bath vacation rental is individually owned and decorated. Each unit is equipped with WiFi, cable television, generous closet space, a lanai or glassed-in porch and a fully-furnished kitchen.

El Presidente (Beach side)

El Presidente Condominiums offer 38 spacious two and three bedroom fully furnished vacation rental condominiums, with 5 floor plans to choose from along with balconies to watch those majestic sunsets over the Gulf of Mexico. Our friendly staff and excellent facilities await you and your family!

Siesta Royal (Beach side)

A taste of "Old Florida" with modern amenities. Siesta Royale is a smoke-free gulf-front property with one- and two-bedroom units, as well as two efficiencies, all with full kitchens. Private beach, heated salt water pool, shuffleboard courts & BBQ grills. There is a laundry facility on-site. Sorry, no pets, motorcycles, scooters, trailers, boats or RVs. Parking is in front of your unit. Five night minimum.

Midnight Cove (Bay or Beach side)

Luxury two and three bedroom condominium and townhouse vacation rentals are individually owned, tastefully decorated, and furnished with all the conveniences of home to make your stay in paradise completely stress-free. (Also have a 4BR beachfront townhome that sleeps 8) Midnight Cove sits on 11 acres of lush, tropical and floral greenery that spans from the azure waters of the Gulf of Mexico on the west coast of Siesta Key to the serene and tranquil waters of Sarasota Bay/ Intercoastal Waterway on the east side of the island. Stay Gulfside for spectacular beachfront views & amazing Siesta Key sunsets or Bayside to enjoy the calm waters of the Bay and the tranquil setting of the Intercoastal Waterway.

Siesta Sun (Beach side)

Low Key and Peaceful The charming Siesta Sun Beach Villa has hosted guests from all over the world since 1958 and is comprised of twenty six individually owned units. The units include four 2-bedrooms, ten 1-bedrooms, and twelve studio/efficiencies. The villas have a wide variety of sleeping arrangements to accommodate guest’s needs. Ten of the units are located directly on the white sands of Crescent Beach, while the single story building is closer to the pool and just a few comfortable steps away from the beach. If you are searching for an old-fashioned Florida beach vacation Siesta Sun is your destination. Beach lounges, chairs, picnic tables and grills are provided for the guests. The swimming pool has been beautifully renovated and is heated.

Anchorage (Bay side)

The Anchorage is located in the Southern end of the Key. There is shopping and dining within walking distance and also a local grocery. There are many amenities, Olympic size pool, sauna, gym, shuffleboard, bocce ball, fishing, walking trail by the water and if you are a boater-you can dock your boat for an extra fee.1st come basis) Private beach access is also included-you will have an awesome time on Siesta Key and this place is the place to stay. Beautifully decorated, a home away from home.

Siesta Breakers

Beyond the entry gate to this luxury condominium resort, you will find everything you would want for an island retreat. From covered parking, deluxe accommodations & amenities to the soft, white sand of Crescent beach on beautiful Siesta Key. One visit to Siesta Breakers will undoubtedly result in your desire to return year after year like most of our clientele.

Sea Shell (Beach side)

Enjoy the beautiful private beach with palm trees and chaise lounges – Prepare your picnic at one of our outdoor tiki grills – Relax by the courtyard pool – Move in and out of your private condo via the open-air walkways.

Crescent (Beach side)

Crescent Siesta Key is Siesta Key’s newest luxury beachfront condominium building.(2006) A spacious, vacation-ready condominium awaits you. From fully-equipped gourmet kitchens to spacious living areas and bedrooms with a view of the gulf, a top of the line fitness room and an outdoor whirlpool spa. Dive into one of two outdoor pools overlooking the beach, walk the white sugar sand beaches that stretch for miles, create fabulous meals in the outdoor kitchen and dine al fresco with a view of the gulf amidst beautifully landscaped gardens or sink into a chaise lounge under the loggias with a great book.

House Of The Sun (Beach side)

House of the Sun features fully furnished two-bedroom, two-bathroom units with private balconies, full kitchens, and access to all on-site amenities. Why wait any longer for your beach getaway?

Sea Crest (Beach side)

SeaCrest on Siesta Key offers a variety of living arrangements, including one two-bedroom unit, one efficiency and 33 one bedroom units, at very affordable prices. All units have separate bedrooms, are fully furnished and equipped with cable TV, central heat and air. Linens are provided and each kitchen is fully stocked with dishes and cookware. FREE Wireless internet access available on Sea Crest grounds.

Ebb Tide (Beach side)

Ebb Tide On Siesta Key is 5 minutes' walk from Siesta Key Marina, and 10 minutes' drive from the fine white quartz sand "Siesta Key Beach". A kitchen and 1 bedroom are provided in the 1-bathroom vacation home as well as a dining area, a couch and iron/ironing board in the rooms.

Crescent Towers (Beach side)

Beautiful large studio or one bedroom apartments directly on the gulf of Mexico. Beautiful white sand and azure water. All units have full size eat in kitchens and large roomy area for enjoyment, and one bathroom. Screened in private lanais. Heated pool, grill area with ample seating. Views of beach and sunsets are spectacular.

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Siesta Key Vacation Rentals

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Point of Rocks Area Rentals

Siesta Sands (Beach side)

Siesta Sands Beach Resort is perfect vacation spot. Located directly on #1 beach the country, spend your days soaking up that sunshine and swimming in Gulf of Mexico or swimming that resorts two outdoor pools. They have gas grill by each of pools, an outdoor tiki/TV room, fitness area and fire pit… great spot for gathering with friends and family. Whether you looking for studio, one, two or three bedroom unit, Siesta Sands has you need.

Twin Palms

Twin Palms at Siesta provides accommodations with an outdoor swimming pool, free private parking, a garden and a private beach area. With free WiFi, this 3-star hotel has barbecue facilities and a terrace. Rooms come with a balcony.

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Siesta Key Vacation Rentals

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Turtle Beach Area Rentals

Turtle Beach Resort (Bay side)

Turtle Beach Resort located on Siesta Key in Sarasota, Florida, is the perfect family vacation getaway with spacious cottages that offer full kitchens, living, and dining areas. Enjoy the beautiful, private outdoor space of each cottage that includes a large hot tub with many facing the water. Our pet-friendly resort is a two-minute walk to Turtle Beach and offers complimentary use of kayaks, canoes, bicycles, fishing gear, beach chairs, and umbrellas.

Bay Tree Club (Bay and Beach side)

Located on both the Bay and the (Gulf) beach. Our residents and renters enjoy the serenity on both sides, the beach and the warm waters of the Gulf of Mexico and the Bay with soft breezes flowing through the gorgeous ancient Virginia oaks bordering the water. There is plenty of room for boats on our docks, whether a kayak or a yacht. Fishing is fabulous, both on the Gulf and on the Bay.

Sea Winds

Sea Winds is composed of thirty five condo units. This community is situated on the more secluded portion of the island. With its limited number of units and strategic location, residents/guest of Sea Winds will enjoy more privacy as compared to those staying in other communities.

Island Reef

Stretching from Gulf to Bay on picturesque southern Siesta Key, Island Reef is among the premier condominium complexes in the Sarasota area. Island Reef offers its guest a wide range of facilities and activities to enjoy year-round. Added to that are all of the great attractions of Siesta Key and the Sarasota area. Come join us at Island Reef for a month or more!!!

Cozy Cove

Cozy Cove is a small condominium complex of six total units, located on the south end of Siesta Key. The complex sits on the Gulf side of the Key along Blind Pass. The complex itself is on the inlet with a dock at the back of the property where you will often see fish jump and sometimes a manatee floating by. There is a 20' boat dock available for your use with the rental of this unit at no additional charge. They also do not rent to guests for shorter than one week rentals.

Fisherman's Cove (Beach side)

You have found Siesta Key's best kept secret - Fisherman's Cove at the south end of Siesta Key. The closest vacation rentals to the Gulf of Mexico on Siesta Key! Their location is unique! We are on the quiet south end where the locals come to get away from the crowds. You enter our relaxing property by coming through Turtle Beach Park and the road ends at our entrance gate. No traffic to disturb our guests - just the sound of waves and fun.

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Please be careful who you give your personal and financial information to. And please do your research before making ANY purchases online. All information on this site is provided by the following: VRBO, TripAdvisor,, Expedia and