Luxury Vacation Home Rentals by Owner
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Sarasota Florida Vacation Rentals
3708 Island Paradise
Location Beds Baths Sleeps Weekly Low Weekly High Weekly Peak
Holmes Beach 2 2 6 $2,595 Inquire$3,495
3708 Island Paradise Vacation Rentals

3708 Island Paradise is just that- the best view on Anna Maria Island. Panoramic views of the beautiful blue waters of the Gulf of Mexico and the white sand beaches. And don't forget the legendary sunsets. It simply does not get any better than this. It is like you are sitting on the deck of a cruise ship- just in more luxury!

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Serenity
Location Beds Baths Sleeps Weekly Low Weekly High Weekly Peak
Gulf Front 3 1.5 6 $4,375 InquireInquire
Serenity  Vacation Rentals

GULF FRONT HOME - "Serenity" - Just as its name implies: "Peacefulness."! Enjoy coastal living at its best. Newly renovated private home that still embraces that "Old Florida" charm with high end quality decor and furnishings

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Tropical Oasis
Location Beds Baths Sleeps Weekly Low Weekly High Weekly Peak
Holmes Beach 3 2 8 $1,350 Inquire$4,100
Captiva Island Vacation Rentals

Nestled in lush tropical landscaping is Tropical Oasis, a ground level 3 bedroom, 2 bathroom island delight. At only a short 2-3 minute walk over to the beautiful Gulf beach, this home is a great value for the family vacation. It has it's own private, heated pool with hot tub

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Beach Club C
Location Beds Baths Sleeps Weekly Low Weekly High Weekly Peak
Bradenton Beach 3 2.5 6 $2,595 InquireInquire
Beach Club C Anna Maria Vacation Rentals

With Beach Club (Gulf Breeze), you will get exactly what the name says - outstanding breezes right off the crystal blue waters of the Gulf of Mexico. This luxury 3 bedroom, 2.5 bathroom water front condo has it all

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White Sands
Location Beds Baths Sleeps Weekly Low Weekly High Weekly Peak
Anna Maria 3 2.5 6-8 Inquire InquireInquire
Captiva Island Vacation Rentals

White Sands is a truly breathtaking direct beachfront, one of a Kind, Holiday Rental in Anna Maria Florida. It’s beyond what you would expect, truly a wonderful escape. Take your shoes off and just put your toes through the sands, really spectacular.

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LaPlage Beach Condo 9
Location Beds Baths Sleeps Weekly Low Weekly High Weekly Peak
Holmes Beach 3 3 6 $2,795 Inquire$4,890
LaPlage Beach Condo 9 Vacation Rentals

LaPlage Beach Condo 9 is the cream of the crop. Direct Gulf Front, high-floor views make this one of the most spectacular luxury condo's on all of Anna Maria Island. What you get on the inside is no less outstanding. The deep cherry wood island style furniture is the finest around.

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LaCasa Beach
Location Beds Baths Sleeps Weekly Low Weekly High Weekly Peak
Holmes Beach 3 3 6 $2,295 Inquire$3,495
LaCasa Beach Vacation Rentals

You will be hard-pressed to find something more luxurious than LaCasa Beach. These high-end condominiums are in demand year around. One step inside and you will immediately know why. This luxury property has all the touches- crown molding, granite, deluxe kitchen, oversized balcony, lush tropical landscaping and exquisite island decor are just a few of the many features.

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LaPlage Beach Condo
Location Beds Baths Sleeps Weekly Low Weekly High Weekly Peak
Holmes Beach 4 3 8 $2,795 Inquire$4,890
LaPlage Beach Condo Vacation Rentals

LaPlage Beach Condo is Island luxury at its finest! An exquisite example of Mediterranean architecture nestled right on the sands of the Gulf of Mexico, this beachfront enclave will exceed all your expectations. Relax in the tropical splendor of this ultra-luxurious beachfront property on Anna Maria Island in a gated community that features expansive verandas for sunbathing

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Beach Escapade
Location Beds Baths Sleeps Weekly Low Weekly High Weekly Peak
Anna Maria 4 3 10 $2,050 Inquire$4,500
Beach Escapade Captiva Island Vacation Rentals

New rental property with heated pool and dock, north end of the island. Newly remodeled and several renovations

 

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Oceans Break
Location Beds Baths Sleeps Weekly Low Weekly High Weekly Peak
Anna Maria 4 3 10 $2,200 Inquire$5,600
Oceans Break Captiva Island Vacation Rentals

This exquisite 4 bedroom, 3.5 bath home defines luxury. From the deep, rich cherry wood flooring and cabinetry throughout the house to the lush tropical pool, this home has it all. There are beautiful crown moldings, classic looking ceiling fans, beautiful tiles and an elevator that travels from the bottom floor garage up to the third floor lookout tower

 

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Blue Bird Villa
Location Beds Baths Sleeps Weekly Low Weekly High Weekly Peak
Holmes Beach 4 3.5 8 $2,800 Inquire$6,500
Captiva Island Vacation Rentals

Blue Bird Villa is a fanciful and lovely accommodation offering 4 bedrooms and 3.5 bathrooms for your next holiday stay. Walk to beaches and enjoy the local culture and nightlife, truly a great space. The house is one of the newest partner collections through dreamexoticrentals.com and makes for a great escape.

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Sandy Lane
Location Beds Baths Sleeps Weekly Low Weekly High Weekly Peak
Holmes Beach 4 4 8 $2,282 InquireInquire
Sandy Lane Vacation Rentals

Sandy Lane is a beautiful beach house that is only 3 houses away from the stunning Gulf of Mexico. Offering a fantastic location, private heated pool, lots of amenities including a gourmet and fully stocked kitchen and much more!

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Villa Playa
Location Beds Baths Sleeps Weekly Low Weekly High Weekly Peak
Holmes Beach 4 4 10 $3,200 Inquire$8,500
Captiva Island Vacation Rentals

Villa Playa is a luxury home in Holmes Beach near Anna Maria Island, with lovely views, amazing pool and luxury amenities. This luxury 4 bedroom, 4 bathroom are simply out-of-this-world! The floors are done in travertine, custom hard wood, premium fixtures and furniture you would find at a Ritz-Carlton- it just does not get any better than this on Holmes Beach.

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Lazy Daze
Location Beds Baths Sleeps Weekly Low Weekly High Weekly Peak
Anna Maria 4 4 8 $3,300 Inquire$11,200
Captiva Island Vacation Rentals

Lazy Daze may well be one of the most exquisite private homes available for rent on all. Enjoy the amazing amenities is 4+ bedroom/4 bathroom 5300 sq. ft. custom home has all the fine touches and professional craftsmanship one would expect in a high-end custom home.

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Whispering Seas
Location Beds Baths Sleeps Weekly Low Weekly High Weekly Peak
Anna Maria 5 3.5 16 $4,025 Inquire Inquire
Whispering Seas  Florida Vacation Rental

Whispering Seas is a beautiful, bright and airy 5 bedroom and 3.5 bathroom private home, located on the prestigious North-end of Anna Maria. Only a block away from the stunning white sand beaches, this newly renovated canal front home offers a private pool with spa, a fantastic location, private dock, large screened in porch, game room with pool table and so much more

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Sunflower Beachfront
Location Beds Baths Sleeps Weekly Low Weekly High Weekly Peak
Anna Maria 5 4 10-14 $5,200 Inquire Inquire
Sunflower Beachfront Florida Vacation Rental

This home is one of a handful of very select rental properties on the island- direct Gulf front with a private heated pool! It has all the perfect ingredients for a wonderful vacation. Enjoy your front row seat to spectacular sunsets from this newly remodeled 5 bedroom 4 bath direct gulf front home

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Oyster Pearl
Location Beds Baths Sleeps Weekly Low Weekly High Weekly Peak
Anna Maria 5 4.5 12 $2,297 Inquire Inquire
Oyster Pearl Florida Vacation Rental

Oyster Pearl is a stunning brand new elevated and luxury Island home located on the prestigious Northern end of Anna Maria Island. This lovely home is located West of Gulf Drive and just 1 minute stroll down the street from a direct beach access to the Gulf of Mexico and beaches

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Southern Oaks Estate
Location Beds Baths Sleeps Weekly Low Weekly High Weekly Peak
Osprey 5 7 10 Inquire Inquire Inquire
Osprey Florida Vacation Rental

A stunning Georgian estate – exquisitely furnished multi-million dollar estate, available for short term rentals and long term stays.  Relax on the terrace beside the beautiful infinity pool, wet bar and BBQ. 

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Casa de Ferias
Location Beds Baths Sleeps Weekly Low Weekly High Weekly Peak
Holmes Beach 6 3.5 12-14 $2,500 InquireInquire
Casa de Ferias Vacation Rentals

This home is just the sort of place where relaxing will become second nature, and enjoying the company of family and friends is made so easy. An ideal place to stage a family reunion in glamorous surroundings, or simply to catch up with old acquaintances in a fabulous spacious home.

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Bay Living
Location Beds Baths Sleeps Weekly Low Weekly High Weekly Peak
Brandenton Beach 6 4 17 $2,780 Inquire$11,290
Captiva Island Vacation Rentals

The Bay Front is a luxury island water-front home that has it all. This home has 6 bedrooms and 4 full bathrooms. There are also 2 full gourmet kitchens- one on the first level and one on the second level. There is a new screened-in porch on the second level overlooking the pool which will has full direct views of Anna Maria Sound and the skyline of downtown Sarasota.

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Island Oasis
Location Beds Baths Sleeps Weekly Low Weekly High Weekly Peak
Holmes Beach 6 5 14 $2,630 InquireInquire
Island Oasis Vacation Rentals

This is it- the pinnacle of Anna Maria Island luxury! Island Oasis is a brand new luxury home that combines comfort, class and convenience. Spacious, with 6 bedrooms and 5 full bathrooms

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Vista Azul
Location Beds Baths Sleeps Weekly Low Weekly High Weekly Peak
Holmes Beach 6 5 12 $2,700 Inquire$11,300
Captiva Island Vacation Rentals

A fantastic Opportunity to be amazing by the Beautiful Vista Azul, named for the gorgeous Holmes Beach waters, which seem to glisten with turquoise colors and blue hues throughout the year. A beach location that is sure to knock your socks off from the moment you walk through the door.

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Casa Cortez
Location Beds Baths Sleeps Weekly Low Weekly High Weekly Peak
Anna Maria 6 6.5 12-14 $3,375 Inquire$8,750
Casa Cortez Captiva Island Vacation Rentals

Casa Cortez is a unique and special vacation "luxury compound" that provides all the exceptional amenities that a discriminating vacationer is looking for in a unique setting. This outstanding 6 bedroom, 5.5 bathroom property has an amazing 500+ feet of water frontage!

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Villa Earnest
Location Beds Baths Sleeps Weekly Low Weekly High Weekly Peak
Anna Maria 6 6.5 16 $2,625 Inquire$7,245
Villa Earnest Vacation Rentals

Villa Earnest is a gorgeous, brand new elevated Island house that is tucked away on a quiet residential street and only a short one minute stroll to the Gulf beaches. This 6 bedroom and 6.5 bathroom luxury home is equipped with a private heated pool, spa, BBQ grill and multiple balconies and a rooftop deck! Professionally decorated

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Island Retreat
Location Beds Baths Sleeps Weekly Low Weekly High Weekly Peak
Holmes Beach 7 3 20 $3,250 Inquire$12,500
Captiva Island Vacation Rentals

Island Retreat is a spectacular example of high architecture, fine design and custom finishing at its best. This home was designed by the award winning Gene Leedy combining the use of pre-stressed concrete, contemporary architecture and a splash of British East Indies Island flavor

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Rendez View
Location Beds Baths Sleeps Weekly Low Weekly High Weekly Peak
Holmes Beach 7 6 15 2,555 Inquire$12,500
Rendez View  Vacation Rentals

What if we told you there was a place where luxury comes as standard, where quality, comfort and style converge in the most magnificent villa you can imagine, and where you are just steps from the soft, white sand of Anna Maria Island’s famous shoreline? It sounds like a lot to wish for, but it is all here in Rendez View, Anna Maria one of our most spectacular rental properties.

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Jewel of the Sea
Location Beds Baths Sleeps Weekly Low Weekly High Weekly Peak
Holmes Beach 8 5.5 16 $2,900 InquireInquire
Jewel of the Sea Vacation Rentals

Jewel of the sea is the pinnacle of Holmes Beach Coastal Living. This palatial 8 bedroom, 5.5 bathroom is something out of your dreams. A home that truly has it all with beautiful hardwood floors, crown moldings, fine fixtures, granite counter and so much more. And that is just the construction. This home real beauty is what it brings to you.

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Villa Verano
Location Beds Baths Sleeps Weekly Low Weekly High Weekly Peak
Holmes Beach 8 6 16 $4,375 InquireInquire
Villa Verano  Vacation Rentals

Villa Verano is a brand new 8 bedroom and 6 bathroom rental home just completed and rental ready! The rental home has so many fun options for everyone- close to the beach, Gulf and Bay water views, table games, water slide, spa, roof top deck with hot tub (coming soon), video games, bikes- something for everybody

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Sea View Play
Location Beds Baths Sleeps Weekly Low Weekly High Weekly Peak
Holmes Beach 8 6 16 $4,375 InquireInquire
Sea View Play Vacation Rentals

Sea View Play is a newly constructed custom luxury home that is now ready for your large family gathering. The home is lavish and bold- it offers everything you would expect out of a luxury home and more!! Enjoy the private heated pool, waterslide, spa, swim-up Tiki table, rooftop deck with hot tub (coming soon) that offers Gulf and Bay water views and so much more

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Bradenton Horizons
Location Beds Baths Sleeps Weekly Low Weekly High Weekly Peak
Bradenton Beach 9 7.5 22 Inquire Inquire Inquire
Osprey Florida Vacation Rental

A newly finished 9 bedroom, 7.5 baths compound- this one will have it all! Two separate homes sleeping a total of 22. Both with unbelievable views of the Gulf of Mexico. With a deluxe heated pool and all the amenities of a luxury property. Wedding parties are allowed (with an additional surcharge). Please contact the office for more details.

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Visiting Sarasota, Florida

Most people choose a destination for their travels based on their preferences for the type of trip they are planning.  The Gulf Coast and Central Florida Regions have long been known as the areas to travel for such places as: Disney, Universal Studios, Busch Gardens, SeaWorld, Islands of Adventure and the Newest Water Parks offered by Disney.  Villas are a great way to stay in the area while enjoying all the comforts of home.  You can visit a theme park and we can accommodate your entire family in one location.  If you want to bring a pet, inquire about our pet friendly selections.