Category Archives: Rental Listings

Stunning 12th floor Penthouse located directly on Siesta Key Beach with Spectacular Full Gulf Views! Whispering Sands is a friendly 55+ community with a private 850-feet section of the white sands of world famous Siesta Key Beach. This gorgeous 2 bedroom, 2 bath unit has been recently and totally renovated. The open kitchen features white wood cabinets, white granite countertops, stainless steel appliances, a closet pantry and a corner desk. Both contemporary bathrooms feature wood vanities, stone countertops and designer fixtures. The large lanai stretches across the back of the unit and provides a great space to relax and enjoy the view. Expansive sliders both on the exterior and interior at the lanai allow for an abundance of light and, combined with the open floor plan, present amazing views from virtually everywhere in the unit. Sunshade blinds are remotely controlled. Free WiFi & Cable are provided, laundry facilities are on each floor, and parking is covered & assigned.

Located just a minutes walk to shopping and dining in Siesta Village, Whispering Sands features beautifully manicured grounds, a large natural lagoon, a beautiful white-sand private beach, 2 pools, fitness room, clubhouse, beach-front tiki hut with grills for entertaining, shuffleboard, and on-site security. A social committee gets busy with the start of the season organizing card games, movie nights, happy hours and trips to local arts events. Gorgeous unit with incredible views in the ideal location!

A 2-month minimum is required to rent at Whispering Sands. Contact us about discounted rates for stays of 3 or more months.

  • Bedrooms: 2
  • Beds : King in master, Queen & Full in guest
  • Bathrooms : 2
  • Other rooms : Screened/Glassed lanai
  • Laundry : On-site, each floor
  • Furnished : yes
  • Pets : No
  • Smoking : No
  • Pool : 2 Heated pools
  • Minimum rental period : 2 Months
  • Parking : Free, assigned, covered

Two Month Minimum

January: $7000 Monthly

Feb & March: $7500 Monthly

April: $6500 Monthly

May – November: $4800 Monthly

December: $5500 Monthly

Condo Application Fee: $175

Contact us about discounted rates for stays of 3 or more months.

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Available

Booked

Charming, modern condo just 2 blocks from the beach & a short stroll to shopping, restaurants, and night time entertainment. This 3rd floor condo is nicely furnished with coastal decor and features an open concept design with 2 bedrooms, 2 baths, large kitchen & screened/glassed lanai. Comfortable master bedroom has king size sleep number bed & ensuite bath with large shower. Guest bedroom is located near the guest bath and has queen bed (sleeper sofa is provided in the living room for overnight guests). Washer/dryer are furnished in the unit for your convenience. Free WiFi & cable are provided and TV’s are in the living room as well as both bedrooms. Free covered parking is assigned, and parking space is near the elevator.

Enjoy all of the on-site amenities including the heated pool, shuffleboard, picnic tables for socializing, BBQ grills & clubhouse. Beach towels & beach chairs are provided for your use. Walk to market, drug store, restaurants, night clubs, etc. Hop on the free Siesta Key Breeze Trolley in front of the complex and explore the entire island including the Siesta Key Beach Pavilion, Siesta Key Village and Turtle Beach.

  • Bedrooms: 2
  • Beds : King sleep number, queen, sleeper sofa
  • Bathrooms : 2
  • Other rooms : Lanai
  • Laundry : In unit
  • Furnished : yes
  • Pets : no
  • Smoking : No
  • Pool : on-site, heated
  • Minimum rental period : 2 weeks
  • Parking : assigned, covered

Jan: $3700 Monthly, $1100 Weekly (2 week minimum)

Feb. 1 to March 30: $4000 Monthly

March 30 to April 13: $1300 Weekly (2 week minimum)

April 14 to Dec. 13: $800 Weekly (2 week minimum)

Dec. 14 to Dec. 31: $1200 Weekly (2 week minimum)

Condo Application Fee: $25 for 2 weeks, $50 monthly

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Available

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Welcome you to your own tropical paradise! This unique custom home is being offered for rent for the first time and everything is new including all furniture, beds, linens, dishes, cooking utensils, TV’s, patio furniture, BBQ grill, etc. Located in a very nice neighborhood near the North bridge for easy access on and off the island. Walled & gated for privacy with a courtyard featuring a large heated pool and beautiful exotic plants. Custom French doors wrap around the entire first floor creating a “walls of glass” feeling. The large cooks kitchen features a gourmet gas range with dual ovens, 2 vegetable sinks, wine cooler, and plenty of counter space.

Bring your family and friends! The home will sleep 13 in beds, but also has a warm and cozy atmosphere for smaller groups. The main living area of the home is on the first level, with the living room, dining area, kitchen, master bedroom w/ensuite bath, bonus room and additional bathroom. Master bedroom has a king bed, and ensuite master bathroom features a jetted tub, large shower, dual sinks & bidet. The bonus room is near the additional bathroom and has a queen sleeper sofa and desk. Dining area will seat 8 (we still have chairs coming that are not reflected in the photos). (room for 4 in beds downstairs)

Upstairs are 3 bedrooms, 2 bathrooms plus a den/entertainment room with new TV, games, and queen sleeper sofa. 2 upstairs bedrooms have queen beds, and one of those bedrooms has an ensuite bathroom. The other upstairs bedroom has a bunk bed plus additional twin bed. The additional upstairs bathroom is centrally located. (room for 9 in beds upstairs)

Plenty of outdoor space is provided for your friends and family to relax by the pool or cook out (BBQ grill is also provided). Large dining table & chairs for 6, 2 separate conversation areas with patio furniture & tables, plus additional loungers.

Free WiFi and cable are provided and home has 5 new TV’s (living room, master bedroom, den/entertainment room, and 2 upstairs bedrooms). Washer & dryer are in the garage so you can pack light.

Shell Beach (a local favorite) is 3 blocks from the home, and the public beach is about a 10 minute drive. Siesta Key Village is about a 5 minute drive. Beach towels, beach chairs, umbrella & coolers are provided for your use.

  • Bedrooms: 4
  • Beds : King, 2 queens, bunk beds + extra twin, 2 queen sleeper sofas
  • Bathrooms : 4
  • Other rooms : Bonus room w/sleeper & den/entertainment room w/sleeper –
  • Laundry : Full size washer/dryer in garage
  • Furnished : yes
  • Pets : No pets
  • Smoking : No
  • Pool : Built-in, heated
  • Minimum rental period : 1- week
  • Parking : Garage, carport + 1 additional

One Week Minimum

JANUARY: $2000 Weekly up to 6 people, $5 per person per day over 6.
$7500 Monthly

FEB 1 – SPRING BREAK: $2500 Weekly up to 6 people, $5 per person per day over 6.
$9000 Monthly

APRIL 15 – JUNE 30: $1490 Weekly up to 6 people, $5 per person per day over 6.

JULY 1 – JULY 8: $1600 Weekly up to 6 people, $5 per person per day over 6.

JULY 9 – AUGUST 31: $1490 Weekly up to 6 people, $5 per person per day over 6.

SEPT 1 – DEC 22: $1350 Weekly up to 6 people, $5 per person per day over 6.

THANKSGIVING WEEK: $1490 up to 6 people, $5 per person per day over 6

CHRISTMAS WEEK: $1700 up to 6 people, $5 per person per day over 6.

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Tortuga is truly a special Siesta Key property, and only a few units are available for rent. Expect a casual, friendly atmosphere, and impeccable facilities and grounds.

This luxury condo is located on the 5th floor and offers excellent views of the Gulf, the indoor/outdoor pool, and the gorgeous tropical landscaping. Inside, you will be delighted to find an updated kitchen with new cabinets, granite counter tops and upper end appliances. Sleeps 6 comfortably with 2 large bedrooms plus a sleeper sofa on the re-claimed lanai. Shuttered sliders allow for privacy on the lanai. Features 2 dining areas; a dining area near the kitchen as well as a dining area on the lanai with a Gulf view. Both bedrooms have beautifully updated en-suite bathrooms. A washer & dryer are provided in the unit, and free WiFi & cable are provided as well.

The private beach area for Tortuga is just a short stroll from the condo. On-site amenities include the only heated indoor/outdoor heated pool on Siesta Key, secure parking garage, secure building, newly remodeled clubhouse, library & movie room. Across the street at Turtle Bay, there are boat docks along with full access to Turtle Bay’s tennis facilities.

Many social activities are planned and everyone is welcome to attend. These range from pool aerobics to dominoes to monthly movie and other social events. If just watching the sun set is what you love, then Tortuga is the place to be with regular gatherings on the beach for cocktails.

Hop on the free Siesta Key Breeze Trolley in front of the complex and explore the island. Take a ride to Siesta Key Village, Crescent Beach, Siesta Key Public Beach Pavilion, and everywhere in between.

  • Bedrooms: 2
  • Beds : King, 2 twins, sleeper sofa Sleeps 6
  • Bathrooms : 2
  • Other rooms : –
  • Laundry : Washer/dryer in unit
  • Furnished : yes
  • Pets : no
  • Smoking : No
  • Pool : on-site, heated, indoor/outdoor
  • Minimum rental period : 1 month
  • Parking : secure parking garage

One Month Minimum – Tortuga only allows 3 rentals per year so we prefer at least 2 month rentals. Contact us for discounted rates for 3 or more months.

January: $5200 per month

Feb & March: $5500 per month

April: $4000 per Month

May – November: $2800 per month

December: $3000 per month

Condo Application Fee: $100

Tortuga #501C

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Siesta Key Gulf Front Living at it’s Finest! Just steps from Crescent Beach, you are sure to fall in love with this beautiful, spacious 2 bedroom, 2 bath ground floor unit with all the amenities the Gulf & Bay Club Resort has to offer.  Step out the door of the enclosed lanai and stroll the beautifully landscaped path right down to the beach, where you will have over 780 square feet of private beach dedicated to Gulf & Bay Club guests. This gorgeous condo has been completely renovated and updated with new tile floors, new designer kitchen with stainless steel appliances, new desk/workspace in kitchen, new dining set, new recliner in living room, new designer bathrooms, new bunk bed in guest bedroom, and new patio furniture on the lanai. Living room and both bedrooms have flat screen TV’s with free cable, and free WiFi is provided.

The Gulf & Bay Club is unrivaled in amenities provided for your enjoyment, including:
3 large heated pools (including 1 lap pool)
780ft Private soft white sandy beach on world famous Siesta Key beach
8 Tennis courts including 1 Har-Tru court
Organized tennis from November to May
Basketball/racquetball court
Shuffleboard court
Organized seasonal golf for men and women
Sate of the art fitness center, including free weights and yoga room
6 Dry saunas, hot tub
2 Clubhouses- library with books, bar, pool table and TV’s
Numerous social activities during season
2 Freshwater lakes, numerous barbeque areas and beautiful picnic island

Sleeps 8 with a king bed in the master, 2 full size beds + bunk bed in the guest room and a comfortable full size sleeper sofa in the living room.

  • Bedrooms: 2
  • Beds : king, 2 fulls, bunk bed w/twin & full, full sleeper sofa
  • Bathrooms : 2
  • Other rooms : Lanai
  • Laundry : washer/dryer in unit
  • Furnished : yes
  • Pets : no
  • Smoking : No
  • Pool : 3 community, heated
  • Minimum rental period : Call 941-349-8100
  • Parking : covered, assigned

One Month Minimum

January: $6500 Monthly

Feb & March: $7600 Monthly

April: $5000 Monthly

May – December: $4000 Monthly

Condo Application Fee: $100

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Available

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Bright and Airy 4th floor condo at Fisherman’s Haven with private beach and stunning water views! Spacious, open-concept 2 bedroom featuring a roomy kitchen with breakfast bar, large bedrooms, and nicely furnished oversized living room with Bay views. King beds and large closets are provided in both bedrooms, and both have gorgeous views of the Gulf of Mexico, the Bay, and the pool. Bathrooms are beautifully upgraded with large walk-in showers. Master bath is ensuite, and guest bathroom is located near the guest bedroom. TV’s are in the living room & both bedrooms, and free WiFi and cable are provided. Laundry room with free washers & coin-operated dryers are in the hall. Unit is well stocked with beach chairs, beach towels, umbrella & coolers for the beach.

Fisherman’s Haven is a friendly community located directly on the Gulf of Mexico and nestled on the quieter southern end of Siesta Key just south of Turtle Beach. Direct beach front property with the Gulf on one side and the Bay on the other side. Enjoy long walks & beautiful sunsets from the private beach, take a dip in the heated pool, or fish from the bay waters at the rear of the property (on-site fish cleaning is station provided). A bbq grill is also provided on-site. Secure gated community close to restaurants, shopping and night time entertainment. Turtle’s Restaurant and Ophelia’s on the Bay are both very close & you can dine on the water. Hop on the free Siesta Key Breeze trolley at Turtle Beach and ride to Siesta Key Village, Crescent Beach, and other points of interest on the island.

  • Bedrooms: 2
  • Beds : 2 Kings + 2 Roll-aways for guests
  • Bathrooms : 2
  • Other rooms :
  • Laundry : Across the hall
  • Furnished : yes
  • Pets : No
  • Smoking : No
  • Pool : On-site, heated
  • Minimum rental period : 1 Month
  • Parking : Free, assigned

One Month Minimum

January: $5400 Monthly

Feb & March: $5600 Monthly

April: $3800 Monthly

May & June: $2600 Monthly

July: $2800 Monthly

August – November: $2600 Monthly

December: $3000 Monthly

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Beautiful 5th floor condo at Fisherman’s Haven with private beach and stunning panoramic Gulf views from the wall of windows spanning the entire width of the unit. Spacious 2 bedroom open concept floor plan featuring a large updated gourmet kitchen with granite counters, large bedrooms with gulf views, and office area. Master bedroom features a king bed, large ensuite bathroom with walk in shower, walk in closet, and beautiful Gulf views. The guest bedroom offers 2 twin beds and also has beautiful gulf views. Guest bathroom located near the guest bedroom has a shower/tub combo. A great feature of this condo is the office area tucked in beside the guest bedroom. This area has 2 desks and shutters that can be closed if you want to keep it private, or open if you wish to see the gulf view. Laundry room with free washers & coin-operated dryers are across the hall. TV’s are in the living room & both bedrooms & free WiFi and cable are provided.

Fisherman’s Haven is a friendly community located directly on the Gulf of Mexico and nestled on the quieter southern end of Siesta Key just south of Turtle Beach. Direct beach front property with the Gulf on one side and the Bay on the other side. Enjoy long walks & beautiful sunsets from the private beach, take a dip in the heated pool, or fish from the bay waters at the rear of the property (on-site fish cleaning is station provided). A bbq grill is also provided on-site. Secure gated community close to restaurants, shopping and night time entertainment. Turtle’s Restaurant and Ophelia’s on the Bay are both very close & you can dine on the water. Hop on the free Siesta Key Breeze trolley at Turtle Beach and ride to Siesta Key Village, Crescent Beach, and other points of interest on the island.

  • Bedrooms: 2
  • Beds : King, 2 twins
  • Bathrooms : 2
  • Other rooms : Office w/2 desks
  • Laundry : Across the hall
  • Furnished : yes
  • Pets : No
  • Smoking : No
  • Pool : On-site, heated
  • Minimum rental period : 1 Month
  • Parking : Free, assigned

One Month Minimum

January: $5400 Monthly

Feb & March: $5600 Monthly

April: $3800 Monthly

May & June: $2600 Monthly

July: $2800 Monthly

August – November: $2600 Monthly

December: $3000 Monthly

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Fabulous 6th floor waterfront condo with private beach located in the gulf-front complex of Fisherman’s Haven. Enjoy gorgeous bay views from the large screened lanai that spans the entire width of the unit. Beautifully decorated, spacious 2 bedroom featuring an updated gourmet kitchen with granite counters & stainless appliances and large bedrooms. Nicely furnished throughout with comfortable seating in the living room, which leads out to the relaxing lanai. Master bedroom features a king bed, ensuite bathroom with shower, lanai access, and beautiful gulf & bay views from 2 large windows. The guest bedroom has gorgeous beach views and offers 2 twin beds. Guest bathroom is located near the guest bedroom and has a shower/tub combo. Laundry room with free washers & coin-operated dryers are across the hall. TV’s are in the living room & master bedroom, and free WiFi and cable are provided.

Fisherman’s Haven is a friendly community located directly on the Gulf of Mexico and nestled on the quieter southern end of Siesta Key just south of Turtle Beach. Direct beach front property with the Gulf on one side and the Bay on the other side. Enjoy long walks & beautiful sunsets from the private beach, take a dip in the heated pool, or fish from the bay waters at the rear of the property (on-site fish cleaning is station provided). A bbq grill is also provided on-site. Secure gated community close to restaurants, shopping and night time entertainment. Turtle’s Restaurant and Ophelia’s on the Bay are both very close & you can dine on the water. Hop on the free Siesta Key Breeze trolley at Turtle Beach and ride to Siesta Key Village, Crescent Beach, and other points of interest on the island.

  • Bedrooms: 2
  • Beds : King, 2 twins
  • Bathrooms : 2
  • Other rooms : Large screened lanai
  • Laundry : Across the hall
  • Furnished : yes
  • Pets : No
  • Smoking : No
  • Pool : On-site, heated
  • Minimum rental period : 1 Month
  • Parking : Free, assigned

One Month Minimum

January: $5300 Monthly

Feb & March: $5500 Monthly

April: $3800 Monthly

May & June: $2600 Monthly

July: $2800 Monthly

August – November: $2600 Monthly

December: $3000 Monthly

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Booked

Spacious waterfront condo at Fisherman’s Haven overlooking Turtle Beach Inlet with private beach & bay access. Relax on the large enclosed lanai while watching boats, kayaks & paddle boarders float by on the bay. Decorated in true Florida style with comfortable rattan furniture in the living room. The kitchen is well stocked, light & bright. The lanai spans the entire width of the unit and is accessible from the living room & from both bedrooms. Open-concept floor plan with bedrooms separated by living area for privacy. Master bedroom w/ensuite bathroom has a king bed, large walk-in closet and water views. Guest bedroom with 2 full beds also offers bay views. Ensuite master bath has large shower, and guest bathroom has shower/tub combo. Laundry room with free washers & coin-operated dryers are across the hall. TV’s are in the living room & master bedroom, and free WiFi and cable are provided.

Fisherman’s Haven is a friendly community located directly on the Gulf of Mexico and nestled on the quieter southern end of Siesta Key just south of Turtle Beach. Direct beach front property with the Gulf on one side and the Bay on the other side. Enjoy long walks & beautiful sunsets from the private beach, take a dip in the heated pool, or fish from the bay waters at the rear of the property (on-site fish cleaning is station provided). A bbq grill is also provided on-site. Secure gated community close to restaurants, shopping and night time entertainment. Turtle’s Restaurant and Ophelia’s on the Bay are both very close & you can dine on the water. Hop on the free Siesta Key Breeze trolley at Turtle Beach and ride to Siesta Key Village, Crescent Beach, and other points of interest on the island.

  • Bedrooms: 2
  • Beds : King, 2 Full size
  • Bathrooms : 2
  • Other rooms : Large screened
    lanai
  • Laundry : Across the hall, free washers
  • Furnished : yes
  • Pets : No
  • Smoking : No
  • Pool : On-site, heated
  • Minimum rental period : 1 Month
  • Parking : Free, assigned

One Month Minimum

January: $5300 Monthly

Feb & March: $5500 Monthly

April: $3800 Monthly

May & June: $2600 Monthly

July: $2800 Monthly

August – November: $2600 Monthly

December: $3000 Monthly

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Available

Booked

Spacious Gulf Front condo with private beach and gorgeous Gulf Views from every room. Relax on the large screened & glassed lanai which spans the entire width of the unit. Comfortably furnished unit with 2 bedrooms plus sleeper sofa in the living room for extra sleeping accomodations. The eat-in kitchen is well stocked, light & bright. Open-concept floor plan with bedrooms separated by living area for privacy. Master bedroom w/ensuite bathroom has a king bed, large walk-in closet and gulf views. Guest bedroom with 2 twin beds also offers gulf views. Shower/tub combos are in both bathrooms. Laundry room with free washers & coin-operated dryers are across the hall. TV’s are in the living room & both bedrooms, and free WiFi and cable are provided.

Fisherman’s Haven is a friendly community located directly on the Gulf of Mexico and nestled on the quieter southern end of Siesta Key just south of Turtle Beach. Direct beach front property with the Gulf on one side and the Bay on the other side. Enjoy long walks & beautiful sunsets from the private beach, take a dip in the heated pool, or fish from the bay waters at the rear of the property (on-site fish cleaning is station provided). A bbq grill is also provided on-site. Secure gated community close to restaurants, shopping and night time entertainment. Turtle’s Restaurant and Ophelia’s on the Bay are both very close & you can dine on the water. Hop on the free Siesta Key Breeze trolley at Turtle Beach and ride to Siesta Key Village, Crescent Beach, and other points of interest on the island.

  • Bedrooms: 2
  • Beds : King, 2 Twins, Sleeper sofa
  • Bathrooms : 2
  • Other rooms : Large screened & glassed
    lanai
  • Laundry : Across the hall, free washers
  • Furnished : yes
  • Pets : No
  • Smoking : No
  • Pool : On-site, heated
  • Minimum rental period : 1 Month
  • Parking : Free, assigned

One Month Minimum

January: $5300 Monthly

Feb & March: $5500 Monthly

April: $3800 Monthly

May & June: $2600 Monthly

July: $2800 Monthly

August – November: $2600 Monthly

December: $3000 Monthly

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Available

Booked