Monthly Vacation Rentals
Siesta Key, Sarasota FL

Beautiful 5th floor condo with stunning panoramic Gulf views from the wall of windows spanning the entire width of the unit. Office area w/2 desks. Private beach, bay access, gated community. Sleeps 4

Beautiful 5th floor condo with private beach and stunning water views from every room! Spacious, open-concept 2 bedroom, gourmet kitchen, large lanai. Sleeps 4 w/king beds in both bedrooms.

Spacious 3 Bedroom, 2.5 bath Gulf Front with gorgeous water views and private beach. Updated gourmet kitchen, large screened lanai. Located on the quieter Southern end of Siesta Key. Heated pool & bay access. Sleeps 6

Spacious waterfront condo overlooking Turtle Beach Inlet with private beach and bay access. Relax on the large enclosed lanai while watching boats, kayaks & paddle boarders float by on the bay. Sleeps 4

Beautifully remodeled townhouse with 2 floors of living space, 2 lanais and a porch. Spacious unit with views of tropical landscaping and mature trees. Large BBQ/Picnic area and fishing piers on the bay. Watch for dolphin in the bay waters! Sleeps 7

Great location, 2 blocks to the beach! Walk to, shopping, restaurants, and night time entertainment. Recently remodeled with updated kitchen & baths. New bed in master, new queen bed in guest bdrm. Heated pool. 2 bdrm/2 bath, sleeps 5

Relax and enjoy your own piece of paradise at this luxurious Casarina condominium on beautiful Siesta Key! Casarina complex is located in a very private setting just south of the public beach. Enjoy the lush tropical garden view from your lanai, a w

2 bdrm, 2 bath condo with screened lanai located at Bay Oaks resort on Siesta Key. Beautiful bayside waterfront picnic area where dolphins can be seen passing by. 2 large fishing piers w/fish cleaning station. Sleeps 4

Gorgeous 2 bedroom Siesta Key waterfront condo right on the beach with spectacular views from every room! Large 7th floor unit at Fisherman's Haven on the quieter southern end of the island. Sleeps 6

5th floor at Peppertree Bay resort in the heart of Siesta Key directly on Crescent Beach. Large lanai with gulf views. Heated pool, fishing pier, exercise room & more. 2 bdrm, sleeps 6

Spacious Gulf Front condo with private beach & Gulf Views from every room. Large screened & glassed lanai spans the entire width of the unit. 2 bdrm/2 bath on the quieter Southern end of Siesta Key. Sleeps 6

Waterfront condo at Fisherman’s Haven overlooking Turtle Beach Inlet with private beach & bay access. Relax on the large lanai while watching boats, kayaks & paddle boarders float by on the bay. Sleeps 6

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 lanai. Bay access, gated. Sleeps 4

Beautifully decorated 4th floor condo with private beach and stunning water views from every room! Spacious 2 bedroom, gourmet kitchen, large screened/glassed lanai. Sleeps 6

Spacious 6th floor 2 bedroom condo overlooking the Gulf of Mexico with stunning Gulf views and private beach plus bay access and heated pool. Large lanai. Quiet, peaceful & relaxing. Sleeps 4

Luxurious 6th floor, 3 bedroom Gulf Front condo with gorgeous water views and private beach at Fisherman's Haven. Located on the quieter Southern end of Siesta Key. Sleeps 6

Beautiful 5th floor beachfront condo at Fisherman’s Haven with private beach and stunning water views from every room! Fish from the bay at the rear of the complex. Heated pool. Sleeps 4

Large 7th floor condo at Fisherman's Haven with stunning Gulf views, private beach, bay access, heated pool. Large lanai overlooking the Gulf of Mexico. Sleeps 6

First Time Renting and Everything is NEW! This custom home is being offered for rent for the first time and everything inside is new including all furniture, beds, linens, dishes, TV’s etc. Private courtyard with heated pool. Sleeps 13!

Gorgeous 3 bedroom, 2 story Siesta Key home with private pool, close to the north bridge for easy access on and off the island. Full size washer & dryer. 2 patio areas. Bicycles, beach toys, and many more extras provided. Sleeps 8.

Spacious 2 bedroom, 3rd floor condo at The Anchorage with private deeded beach access to Crescent Beach. Great location, walk to shopping & restaurants. New furnishings, many amenities. Sleeps 6

Charming 2 bdrm in great location just 2 blocks to the Beach. 5 minute walk to many shopping & dining options. Easy access on & off the island. Heated pool. Sleeps 4

Gorgeous waterfront condo on Blind Pass Lagoon in Siesta Key just a short 3-5 minute walk from Turtle Beach. Relax and enjoy peaceful surroundings, fish from the docks, take a dip in the pool. Sleeps 6

Siesta Key vacation rental at Cozy Cove on the quieter Southern end of the island. Located waterfront on Blind Pass Lagoon with Docks provided. 5 minute walk to Turtle Beach, restaurants & entertainment. 2 bedroom, sleeps 4

Stunning views of everything from the Gulf of Mexico & Siesta Key Beach to fantastic sunsets & downtown Sarasota. Located just across from world-famous Siesta Key Beach. Walk to Siesta Key Village by sidewalk or beach. Sleeps 6

Watch the sunset from the wrap around balconies in this beautifully decorated 2 bedroom condo directly across from Siesta Key Beach. Spacious and inviting with ceiling to floor sliders on two entire walls for incredible views. Sleeps 6

Enjoy gorgeous Bay views from the balcony of this beautifully appointed third floor condo located in the heart of Siesta Key! Enjoy private beach access as well as bay access. 2 heated pools, custom hot tub overlooking the Bay, fishing pier, boat doc

2 bedroom, ground floor, waterfront condo on Turtle Beach Inlet in Siesta Key where you can fish, swim, or boat just steps from your door. Heated pool. Large screened, glassed lanai. Located on the quieter Southern end of Siesta Key. Short walk to Tu

2 bedroom condo located on world famous Crescent Beach in Siesta Key! Private beach area with loungers provided. Enjoy the tiki hut BBQ/picnic area on the beach. Nicely furnished and close to dining, shopping, and night time entertainment.

Enjoy spectacular million dollar views from this gorgeous gulf front condo! All new furnishings & appliances. Located at the desirable Tortuga complex on the quieter southern end of Siesta Key. Private beach area exclusively for Tortuga guests. Indoo

Siesta Key Gulf Front Living at it's Finest! Juust 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 Gulf & Bay Club has to offer. Private beach, 3 pools,

Fabulous 2nd floor gulf front condo overlooking the beautiful Gulf of Mexico! Located in the desirable Island Reef complex on Siesta Key, this spacious condo features extraordinary views of the beach and sunsets from the front room, the lanai.

Recently renovated 2 bedroom condo in the heart of Siesta Key at Harbor Towers. Beautiful views & just a short walk to Siesta Key beach. Watch dolphin in the bay, fish off the dock, enjoy the heated pools, tennis courts & sauna.

Completely renovated and beautifully decorated 3rd floor condo on the quieter southern end of Siesta Key. Everything in this condo is new! Waterfront unit on Turtle Beach Inlet. Walk to the beach, restaurants, entertainment.

2 bedroom waterfront condo located directly on Turtle Beach Inlet where you can fish, swim, and boat just steps from your door. Large covered, screened glassed in Lanai. Perfect location to relax and enjoy your Siesta Key vacation or get away from th

Affordable 2 bedroom Siesta Key condo located on the quieter, southern end of the island directly onTurtle Beach Inlet where you can fish, swim, and boat just steps from your door.

Recently renovated Siesta Key townhouse decorated in charming Florida décor. Picnic on the water as you watch dolphin in the bay. Kitchen completely updated with new appliances, new counters, new fixtures & lighting. 2 floors of living space featuri

Charming 2 bedroom condo overlooking the heated pool, beautifully appointed and immaculately clean. Watch dolphin from the beautiful waterfront area on the Bay where you can BBQ, picnic, or fish from the piers!

Ground Floor, nicely furnished condo located in the popular Bay Oaks resort on Siesta Key. Covered parking just steps from the unit. Comfortable leather seating in living room. Waterfront bayside picnic area where dolphins can be seen passing by. Fis

3rd Floor at popular Vista Hermosa in Siesta Key. Great location close to Crescent Beach access 13. Walk to the beach, dining, shopping and night time entertainment. Heated pool, BBQ grills, clubhouse & more. 2 bedroom, 2 bath

Large 2nd floor condo at Ashton Lakes, just 2 miles from the white sand beaches of Siesta Key! Screened & glassed lanai overlooking the lake. Enjoy all the amenities that Ashton Lakes has to offer: Two pools (1 heated), 2 tennis courts, RV/Boat stora

Beautiful 2 bedroom Polynesian Gardens villa in the heart of Siesta Key. The owners have just redone this property and it is gorgeous! New furnishings, new linens, new BBQ grill, and beautifully decorated in Florida style. Heated pool, private pier o

Enjoy luxurious resort style living in this beautifully furnished 2 bedroom, 2 bath penthouse condo on the white powder sands of Crescent Beach. Located on the 9th, floor this home offers incredible views of the Gulf of Mexico and the lush landscapin

Everything is NEW and the views are fantastic! Attention to detail shows in this gorgeous gulf front condo located at the desirable Tortuga complex on the quieter southern end of Siesta Key. Siesta Key's only indoor/outdoor heated pool.

Large private waterview condo located far from the busy areas of the island, yet just a short walk from Crescent Beach, shopping & restaurants. Relax on your private enclosed lanai overlooking a private lagoon. 2 bdrm, 2 bath, and a lower bonus room

Very nice and comfortable 3 bedroom home in the established neighborhood of Cedar Creek. This home is surrounded by beautiful trees and landscaping. Exceptionally private backyard with large, beautiful pool and patio area that is caged. Backs up to l

Address:

6623 Midnight Pass Road Siesta Key, FL 34242

Phone:

941-349-8100
Toll Free: 1-888-607-5181

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