Luxury Vacation Rentals in Longboat Key

(5 rentals)
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Longboat Key House
4 BR | 3 BA | Sleeps 10 | Quick View
Sleeps 10, 4 bedrooms, 3 bathrooms

Distance to beach: 0.5 miles to Longboat

$1066

avg/night

$1,066
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Private pool

About this property

Imagine waking up to dolphins playing just beyond your window. This exquisitely renovated Longboat Key luxury waterfront home offers breathtaking "Big Bayfront" views and unparalleled access to the Gulf of Mexico. Boater's Dream: • Direct access to the Gulf for fishing or cruising • Private ...

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Property Type

Longboat Key House

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Bradenton House
5 BR | 4 BA | Sleeps 18 | Quick View
Sleeps 18, 5 bedrooms, 4 bathrooms
1 review

$1121

avg/night

$1,121
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool
  • Rentals by owner

About this property

(Hurricane repair: only outside fence repair) The Sweet Escape is a new vacation home that celebrates beach life in Bradenton, Florida. Reimagined in early 2023, our three-story home is great for families, friends and retreats. You’ll enjoy all-new interiors, sun-filled living spaces and five bedrooms ...

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Property Type

Bradenton House

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Anna Maria Island House
6 BR | 4 BA | Sleeps 12 | Quick View
Sleeps 12, 6 bedrooms, 4 bathrooms
3 reviews

$850

avg/night

$850
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Private pool

About this property

110 11th Street South - Bradenton Beach - FL 34217 Book with confidence: You may cancel your reservation up to 60 days before check-in for a full refund minus a $495 processing fee and less 3rd party travel insurance fees, if applicable. The refund will be made to the original payment method. After ...

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Property Type

Anna Maria Island House

Featured review

"Anna Maria week long get away"

The home was lovely. The pool and whirl pool were fabulous. Strong recommendations: TV by pool never worked. Multiple lightbulbs in lamps, etc. need to be replaced. Two blow dryers need to be replaced. ...

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Anna Maria Island House
8 BR | 5 BA | Sleeps 18 | Quick View
Sleeps 18, 8 bedrooms, 5 bathrooms
3 reviews

$947

avg/night

$947
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

Looking for a relaxing island retreat just steps from the soft white sand and turquoise waters in Bradenton Beach on Anna Maria Island? Look no further for your perfect vacation home for the whole family. Island Oasis is a custom-built spacious 8 bedroom/5 bathroom was professionally furnished to provide ...

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Property Type

Anna Maria Island House

Featured review

"Nice"

Very clean nice home enjoyed it...would consider renting again..thank you...talked with the owner and manager next door Great people

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Anna Maria Island House
7 BR | 6 BA | Sleeps 16 | Quick View
Sleeps 16, 7 bedrooms, 6 bathrooms

$1107

avg/night

$1,107
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

6 PERSON GOLF CART INCLUDED ON ALL NEW RESERVATIONS WITH A CHECK-IN DATE BETWEEN ! All Drivers must be over the age of 21. Driver's must provide valid US Driver's License and US Vehicle Insurance. Endless Summer is the latest addition to SeaBreeze Vacation's portfolio. Pristine, newly ...

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Property Type

Anna Maria Island House

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Anna Maria Island House
4 BR | 4.5 BA | Sleeps 12 | Quick View
Sleeps 12, 4 bedrooms, 4.5 bathrooms
4.9 rating on other travel sites

$917

avg/night

$917
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

6 PERSON GOLF CART INCLUDED ON ALL NEW RESERVATIONS All Drivers must be over the age of 21. Driver's must provide valid US Driver's License and US Vehicle Insurance Summer Retreat is an absolutely amazing, new, custom luxury home nestled in the quiet residential area in the heart of Bradenton ...

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Property Type

Anna Maria Island House

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Anna Maria Island House
7 BR | 7.5 BA | Sleeps 17 | Quick View
Sleeps 17, 7 bedrooms, 7.5 bathrooms

$1500

avg/night

$1,500
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Private pool

About this property

Welcome to Ocean Star! .01 Miles to Amazing Gulf Coast Beaches Private Heated Pool/Spa with Outdoor Seating & BBQ Beach Equipment Available for Use Every Bedroom Has a Private Bathroom Fully stocked kitchen for all of your favorite home-cooked meals High-speed Wi-Fi, Smart lock for Self Check-in ...

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Property Type

Anna Maria Island House

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Anna Maria Island House
8 BR | 8.5 BA | Sleeps 18 | Quick View
Sleeps 18, 8 bedrooms, 8.5 bathrooms
4.8 rating on other travel sites

$1154

avg/night

$1,154
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Private pool

About this property

Welcome to “On the Rocks”! This professionally designed nautical themed home hosts 8 bedrooms and 8.5 bathrooms, plenty of space for large families or friends. This property has an elevator and is also pet-friendly. Bring your boat and fishing gear because On the Rocks is a waterfront home ...

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Property Type

Anna Maria Island House

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Anna Maria Island House
8 BR | 6.5 BA | Sleeps 18 | Quick View
Sleeps 18, 8 bedrooms, 6.5 bathrooms
1 review

$1739

avg/night

$1,739
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Private pool

About this property

Paradise Beach lives up to its name! Nestled directly on the pristine soft white sands of Bradenton Beach, this remarkable property boasts 8 bedrooms, 6.5 bathrooms, and is pet-friendly. Complete with an elevator, it comfortably accommodates up to 18 guests. Bring your family and friends along to experience ...

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Property Type

Anna Maria Island House

Featured review

"Margaritaville Themed Paradise with 2 King Beds & Incredible Lanai!"

Truly an amazing resort and we loved staying in Sunset Seacret! Our family enjoyed every minute! We looked hard to find a beautiful, safe, clean, beachy condo with 2 king beds, as we were vacationing with ...

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Bradenton House
5 BR | 5 BA | Sleeps 18 | Quick View
Sleeps 18, 5 bedrooms, 5 bathrooms

$1030

avg/night

$1,030
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Private pool

About this property

Welcome to Palma Sola Bay House your Water Front Oasis! Short drive to the World Class Beaches of Anna Maria Island Private Heated Pool/Spa, Game Room, Boat Dock, & more! Walk to the Palma Sola Causeway/ Jet Ski Rentals, Kayak rentals, and Horseback Riding! Close proximity to Lakewood Ranch, ...

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Property Type

Bradenton House

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Bradenton House
7 BR | 6 BA | Sleeps 19 | Quick View
Sleeps 19, 7 bedrooms, 6 bathrooms

$1170

avg/night

$1,170
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

Welcome to "The Plantation House"! Short drive to the World Class Beaches of Anna Maria Island Private Enclosed Heated Pool/Spa, Game Room, Boat Dock, & more! Walk to the Palma Sola Causeway/ Jet Ski Rentals, Kayak rentals, and Horseback Riding! Close proximity to Lakewood Ranch, ...

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Property Type

Bradenton House

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Anna Maria Island House
4 BR | 4.5 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 4.5 bathrooms
1 review

$877

avg/night

$877
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

Be one of the very first to stay in this LUXE, newly constructed custom home. Heated pool & spa, rooftop deck with GULF VIEWS. Grill, custome kitchen, wet bar on thrid level. ALL THE BELLS AND WHISTLES! This stunning 4 bedroom + bonus room (2 additional twin beds), 5 bathroom home only 2-minute ...

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Property Type

Anna Maria Island House

Featured review

"Holmes beach"

This is an amazing property! Location and pool and lanai were awesome! Private and close to everything! There was a Publix right up the road also. We rented golf carts from zoom around and we could easily ...

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Anna Maria Island House
4 BR | 4 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 4 bathrooms

$713

avg/night

$713
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool
  • Rentals by owner

About this property

Breathtaking sunset views atop your own expansive and elevated deck await at this spacious single story home on gorgeous Anna Maria Island! This home features 4 large bedrooms, each with its own private en suite bathroom, a large kitchen, living room, additional sitting area plus two separate dining spaces. ...

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Property Type

Anna Maria Island House

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Anna Maria Island House
5 BR | 4.5 BA | Sleeps 10 | Quick View
Sleeps 10, 5 bedrooms, 4.5 bathrooms
5 reviews

$737

avg/night

$737
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Private pool

About this property

This luxurious property offers a perfect blend of indoor and outdoor living, with spacious accommodations for large groups or families, all while staying steps from the pristine white sand beaches and centrally located on Anna Maria Island! As you step through the front door, you enter a bright and ...

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Property Type

Anna Maria Island House

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Anna Maria Island House
4 BR | 4.5 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 4.5 bathrooms
1 review

$1159

avg/night

$1,159
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Private pool

About this property

128 49th St Holmes Beach VRC You may cancel your reservation up to 60 days before check-in for a full refund minus a $495 processing fee and less 3rd party travel insurance fees, if applicable. The refund will be made to the original payment method. After that time, or for reservations made on or less ...

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Property Type

Anna Maria Island House

Featured review

"Great Thanksgiving Vacation!"

We spent Thanksgiving week at Sunset and Sand and it delivered on all our expectations. The home is clean, beautifully decorated and functional. The kids absolutely loved the heated pool and Spa and Its ...

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Anna Maria Island House
6 BR | 4.5 BA | Sleeps 12 | Quick View
Sleeps 12, 6 bedrooms, 4.5 bathrooms
4.8 rating on other travel sites

$817

avg/night

$817
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

Prime Location! VERY CLOSE TO BEACH!!! Luxurious ground level home located at 124 50th Street, Holmes Beach, in the „Golden Triangle" of Anna Maria Island, FL, only few steps to the beach. 6 Bedrooms, 4,5 Bathrooms. Accommodates up to 12 people. Beds: 2 Kings, 2 Queen, 4 Twins, 1 Queen Sleeper ...

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Property Type

Anna Maria Island House

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Bradenton House
8 BR | 7.5 BA | Sleeps 23 | Quick View
Sleeps 23, 8 bedrooms, 7.5 bathrooms

$1044

avg/night

$1,044
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Private pool

About this property

Welcome to 75 Palms! Short drive to the World Class Beaches of Anna Maria Island Private Pool, Hot Tub, Game Room, 3 Hole Putting Green, & more! Close proximity to Lakewood Ranch, Sarasota, and Tampa Fully stocked kitchen, Exterior Kitchen and BBQ Grill 2 Houses, 1 Lot, 8 Bedrooms Pool ...

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Property Type

Bradenton House

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Anna Maria Island House
4 BR | 4.5 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 4.5 bathrooms

$779

avg/night

$779
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool
  • Rentals by owner

About this property

What You'll Love About This Home: Location! 3 Blocks to the Beach! 4 Bedrooms / 4 Bathrooms 3 King Beds, Two Sets of Bunk Beds with Twin Bed over Full Bed Lagoon Style Heated Pool w/ sundeck & Spa In Pool Umbrellas Pool Deck Lounge Chairs Poolside Covered Lounge with Patio Furniture, ...

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Property Type

Anna Maria Island House

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Anna Maria Island House
6 BR | 5.5 BA | Sleeps 14 | Quick View
Sleeps 14, 6 bedrooms, 5.5 bathrooms
14 reviews

$1047

avg/night

$1,047
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Private pool
  • Rentals by owner

About this property

ASK US ABOUT MULTI WEEK DISCOUNTS!! Featuring 6 bedrooms 5.5 baths (sleeps 14) and a fantastic location - just a 1 minute walk to the white sands of the 65th St Beach Access! This vacation home offers a huge heated pool with spa, rock water slide and grotto waterfall. Covered outdoor entertaining ...

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Property Type

Anna Maria Island House

Featured review

"Perfect!"

This place was perfect for our family! The 4 bedrooms with King size beds and en suite baths made it so convenient for each couple. The bunk beds were perfect for the kids. The children (and adults) loved ...

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Anna Maria Island House
4 BR | 4 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 4 bathrooms
3 reviews

$764

avg/night

$764
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

VRC If Guest needs to shorten their stay or change to a different property, the normal cancellation policy applies. No changes are permitted during the stay. This stunningly built and decorated 4 bedroom + Bunk Den 4 bath home is just steps from the sparkling white sandy beaches of the Gulf of Mexico ...

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Property Type

Anna Maria Island House

Featured review

"Pleasantly surprised"

We rented this house for a family vacation. This house is everything you see & more. We found it to be perfectly located from beach/stores/restaurants in a quite neighborhood. The house was perfectly ...

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Anna Maria Island House
9 BR | 10 BA | Sleeps 18 | Quick View
Sleeps 18, 9 bedrooms, 10 bathrooms

$1577

avg/night

$1,577
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Private pool

About this property

Gather your family and friends and head to Swanky Bubbles! Swanky Bubbles can accommodate 18 people! This exquisite 9-bedroom, 11-bathroom, pet-friendly with an elevator residence is ideally situated. Just steps away from the beach and within walking distance of shopping and restaurants, you'll have ...

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Property Type

Anna Maria Island House

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Anna Maria Island House
4 BR | 4.5 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 4.5 bathrooms
1 review

$984

avg/night

$984
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Private pool

About this property

6605 Gulf Drive Holmes Beach, FL 34217 VRC19-00290 Right across the street from the beach and the Beach Bistro! Gulf Views available from this beautiful home. This custom 4 bed 4.5 bath home was built with no expense spared! Custom kitchen with gas stove, wine bar, roof top deck with sweeping views ...

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Property Type

Anna Maria Island House

Featured review

"Ideal family vacation home!"

The property was great, and worked really well with our family-which includes a 4 year old and a 9 month old, so having the bedrooms in different areas and private baths, made everything much easier. Centrally ...

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Anna Maria Island House
4 BR | 5 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 5 bathrooms
5.0 rating on other travel sites

$1049

avg/night

$1,049
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

Slice of Paradise VRC 216 68th St - Holmes Beach - FL - 34217 This stunning custom built and decorated 4 bedroom 5.5 bath home is just steps from the sparkling white sandy beaches of the Gulf of Mexico. Located in prime Holmes Beach you are with in walking distance to the award winning Beach Bistro ...

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Property Type

Anna Maria Island House

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Anna Maria Island House
4 BR | 3 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 3 bathrooms
2 reviews

$758

avg/night

$758
avg per night
View Details

About this property

Welcome to "Luana Breeze" located at 208 68th Street, Holmes Beach. Find ease and relaxation the moment you arrive, this property is about 100 steps to the Gulf of Mexico and one of the best beaches on the West Coast of Florida. This ground level beach house offers 4 bedrooms, 3 bathrooms ...

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Property Type

Anna Maria Island House

Featured review

"A True Retreat"

This is a true retreat any time of the year. The backyard and pool area is well designed and an oh so private area that includes a hot tub, a pool, ping pong table, mini golf and hammocks for relaxing. ...

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Anna Maria Island House
6 BR | 4.5 BA | Sleeps 12 | Quick View
Sleeps 12, 6 bedrooms, 4.5 bathrooms

$1086

avg/night

$1,086
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Private pool
  • Rentals by owner

About this property

Big Luxury 6 bdrm, Pool, Spa, Bikes, Kayak, Reviews, Beach! Come enjoy a large family and friends gathering at this spacious luxury home just a few minutes stroll to the beach. One of the larger homes on the island, with 6 bedrooms and 4.5 bathrooms and 3400 sq. ft, this home has plenty of room for ...

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Property Type

Anna Maria Island House

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Anna Maria Island Townhome
5 BR | 4 BA | Sleeps 10 | Quick View
Sleeps 10, 5 bedrooms, 4 bathrooms
1 review

$712

avg/night

$712
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

202 69 th Street - Holmes Beach - FL 34217 VRC Book with confidence: You may cancel your reservation up to 60 days before check-in for a full refund minus a $495 processing fee and less 3rd party travel insurance fees, if applicable. The refund will be made to the original payment method. After that ...

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Property Type

Anna Maria Island Townhome

Featured review

"Lovely stay"

Another family and ourselves rented the property. We found it very clean and equipped to a high standard. The pool and jacuzzi were great and well used especially by the kids. The management company were ...

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Anna Maria Island House
4 BR | 2.5 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 2.5 bathrooms
4.9 rating on other travel sites

$788

avg/night

$788
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

6 PERSON GOLF CART INCLUDED ON ALL NEW RESERVATIONS WITH A CHECK-IN DATE AFTER SEPTEMBER 5, 2023! All Drivers must be over the age of 21. Driver's must provide valid US Driver's License and US Vehicle Insurance Located just steps away from the sugary, soft sand and clear ocean water, Salty ...

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Property Type

Anna Maria Island House

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Anna Maria Island House
4 BR | 6.5 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 6.5 bathrooms

$756

avg/night

$756
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Private pool

About this property

6 PERSON GOLF CART INCLUDED ON ALL NEW RESERVATIONS MADE AFTER April 29, 2024! All Drivers must be over the age of 21. Drivers must provide valid US Driver's License and US Vehicle Insurance Surfer's Dream boasts 4 bedrooms, 6 full bathrooms, and 1 half bath, and is also pet-friendly! This ...

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Property Type

Anna Maria Island House

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Anna Maria Island House
4 BR | 6.5 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 6.5 bathrooms
1 review

$737

avg/night

$737
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Private pool

About this property

6 PERSON GOLF CART INCLUDED ON ALL NEW RESERVATIONS WITH A CHECK-IN DATE AFTER SEPTEMBER 5, 2023! All Drivers must be over the age of 21. Driver's must provide valid US Driver's License and US Vehicle Insurance This gorgeous, custom-built, professionally designed, private home is a 4 bedroom/6.5 ...

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Property Type

Anna Maria Island House

Featured review

"Better than i expected."

Wonderful house. Very clean and well stocked. The pool was clean and big. Very close to a very nice beach. Would stay here again.

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Anna Maria Island House
5 BR | 2 BA | Sleeps 10 | Quick View
Sleeps 10, 5 bedrooms, 2 bathrooms
2 reviews

$856

avg/night

$856
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Private pool
  • Rentals by owner

About this property

One of the highest rated vacation homes on Anna Maria Island with more than 150 five-star ratings from Airbnb/VRBO! Stay at the home of a NY Times best-selling food writer! Big 5-bedroom house, pet friendly, lots of space and charm, great location (5-min walk to beach) with private lagoon-style heated ...

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Property Type

Anna Maria Island House

Featured review

"Hidden paradise"

We were attending a beach wedding and made a vacation out if it. I connected with the owner Kath immediately. She was generous, attentive, available and without a doubt the best host we have ever met. ...

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Sarasota House
4 BR | 4 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 4 bathrooms
2 reviews

Distance to beach: 0.1 miles to Lido

$989

avg/night

$989
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

St. Armand's Canal-Front Pool Home steps to the beach! This gem, ranch style home estate has been completely rebuilt and remodeled in 2015 from the frame including all new finishes inside and out. With fresh, coastal Old-Florida decor, it is in one of the most desirable locations on the west ...

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Property Type

Sarasota House

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Sarasota House
3 BR | 3 BA | Sleeps 8 | Quick View
Sleeps 8, 3 bedrooms, 3 bathrooms
5 reviews

Distance to beach: 0.1 miles to Lido

$800

avg/night

$800
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

This fabulous canal-front home located on famous Lido Key is a boater's dream. This home is well appointed with outdoor fire pit, pool, recliners, chairs, and a dining table. Please note that the front gate has been removed and a new picture is will be posted. The kitchen is equipped with an extra ...

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Property Type

Sarasota House

Featured review

"Everything superb"

Lovely home! Spacious, spotlessly clean, all the supplies were well stocked and the kitchen had everything I needed, it was a pleasure to cook in. We will be booking again next year. Sue

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Anna Maria Island House
2 BR | 4 BA | Sleeps 8 | Quick View
Sleeps 8, 2 bedrooms, 4 bathrooms

$1953

avg/night

$1,953
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Private pool

About this property

LimeFish is a luxurious newly remodeled 3 bedroom (1 king-sized, 1 queen-sized, and a bunk room)/3 bathroom single level home right on the sands of Anna Maria Island. Additional sleeping accommodations can be added with the sleeper sofa in the living room. It is a perfect destination for a trip with family ...

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Property Type

Anna Maria Island House

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Lido Key House
5 BR | 4.5 BA | Sleeps 10 | Quick View
Sleeps 10, 5 bedrooms, 4.5 bathrooms
2 reviews

Distance to beach: 80 feet to Lido Beach

$2132

avg/night

$2,132
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Private pool

About this property

Sophisticated, modern and elegant home located in the heart of it all. This home is LEED Platinum Certified! A short walk to St Armand's Circle and only steps to the wonderful Lido Beach. Rooftop deck with 360 degree view and two level pool. his home is very spacious at 4,617 square feet and features ...

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Property Type

Lido Key House

Featured review

"Special vacation"

We have been renting near St. Armand’s Circle for the past 6 years and this was by far our best experience. From my first phone call to Rick B. until our last day, everything was first class. The customer ...

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Sarasota House
5 BR | 5 BA | Sleeps 12 | Quick View
Sleeps 12, 5 bedrooms, 5 bathrooms
1 review

Distance to beach: 0.1 miles to Lido

$800

avg/night

$800
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

Lovely remodeled and refurbished 5 bedroom 5.5 bath pool home on desirable St. Armand's Circle! This 3,000 s.f. home comfortably sleeps (8) in beds, and has T.V.'s in the family room and living room for when the family is not enjoying the caged pool and spa. Professionally decorated, quality ...

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Property Type

Sarasota House

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Sarasota House
4 BR | 3 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 3 bathrooms

$724

avg/night

$724
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Pet friendly
  • Private pool

About this property

Very inviting home with pool, fenced yard and simple walk to St Armand's Circle. A Jewel on St. Armands Circle! The location makes this spacious 3BR+Casita/3BA with a private pool in a botanical setting a perfect month long vacation spot. This residence has it all for those who want to be right ...

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Property Type

Sarasota House

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Anna Maria Island House
4 BR | 4 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 4 bathrooms

$2041

avg/night

$2,041
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Private pool

About this property

Private Beachfront Home - one block from Pine Avenue and the City Pier. Watch dolphins and manatees swim by from your back deck. Bike or take the golf cart (included) to explore the island and boutique shops and restaurants. Ground floor has a beachfront king bedroom with en-suite bathroom, second king ...

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Property Type

Anna Maria Island House

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Anna Maria Island House
4 BR | 4 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 4 bathrooms

$1619

avg/night

$1,619
avg per night
View Details

Key Amenities

  • Kid friendly
  • Kitchen
  • Pet friendly

About this property

Mintfish is a tropical hideaway that blends high-end decor with natural beauty. This 4 bedroom, 4 bath ground-level luxury vacation home has recently been remodeled to combine natural and sustainable materials with decadent living. The single-floor layout makes the home easily accessible to people of ...

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Property Type

Anna Maria Island House

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Anna Maria Island House
5 BR | 6 BA | Sleeps 12 | Quick View
Sleeps 12, 5 bedrooms, 6 bathrooms
1 review

$807

avg/night

$807
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

A 6-person electric golf cart is included with any new reservation for this property! You must be 21 years old and show proof of US driver's license and vehicle insurance. You'll fall in love with this incredible bay front 5 bedroom/6 full bathrooms home with a separate suite, having 2 full-size ...

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Property Type

Anna Maria Island House

Featured review

"Great getaway !"

A time much needed . We so enjoyed our stay at 2311 ave.c that we hope to return every year . We just felt like we were at home .

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Anna Maria Island House
9 BR | 8.5 BA | Sleeps 8 | Quick View
Sleeps 8, 9 bedrooms, 8.5 bathrooms

$1275

avg/night

$1,275
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Private pool

About this property

Get ready to be swept off your feet by the charm and luxury of Winding Waves, your dream vacation spot right on the beautiful Anna Maria Island. This dazzling nine-bedroom, eight-and-a-half bathroom beachfront home is all about fun in the sun and upscale relaxation! Splash and Play Outdoors: Dive ...

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Property Type

Anna Maria Island House

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Anna Maria Island House
9 BR | 8.5 BA | Sleeps 8 | Quick View
Sleeps 8, 9 bedrooms, 8.5 bathrooms
2 reviews

$1256

avg/night

$1,256
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Private pool

About this property

Compass Rose, a captivating residence offering deluxe amenities including a lazy-river-style pool with a hot tub, a game room, an elevator and a rooftop deck boasting amazing views of the Gulf of Mexico. This 9 bedroom, 8.5 bathroom, pet-friendly abode is an ideal beach retreat suitable for multiple families ...

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Property Type

Anna Maria Island House

Featured review

"Great location"

Very clean and comfortable. Easy walk to everything you need and want to do. I would stay there again and highly recommend.

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Sarasota House
8 BR | 8 BA | Sleeps 20 | Quick View
Sleeps 20, 8 bedrooms, 8 bathrooms

$1968

avg/night

$1,968
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly

About this property

Gillespie Park includes 10 acres of trails, playground, basketball, pickleball courts, tennis courts, pond & 2 public dog parks and is just a 7-10 minute drive to Lido Key Beach & International renowned St. Armands Circle. Come home to this charming and spacious compound with a total of 8 ...

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Property Type

Sarasota House

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Sarasota Condo
3 BR | 3 BA | Sleeps 8 | Quick View
Sleeps 8, 3 bedrooms, 3 bathrooms

$875

avg/night

$875
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Pool

About this property

exquisite furnishings, Ritz Managed building, Ritz membership access included. This home is brand new to our rental options so book quickly before its filled. Ritz-Carlton Managed "The Beach Residences" southeast corner residence is desirably positioned to capture the stunning Sarasota Bay ...

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Property Type

Sarasota Condo

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Sarasota Condo | On the beach
4 BR | 3.5 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 3.5 bathrooms

$1259

avg/night

$1,259
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Pool
  • Rentals by owner

About this property

Immerse yourself in beachfront bliss at Lido Bliss: Imagine stepping off the elevator into your private sanctuary. Breathtaking panoramic views of the Gulf of Mexico greet you from your expansive balcony, setting the scene for an unforgettable stay. This meticulously kept, 4-bedroom 3.5 bath haven exudes ...

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Property Type

Sarasota Condo

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Anna Maria Island House
4 BR | 4 BA | Sleeps 12 | Quick View
Sleeps 12, 4 bedrooms, 4 bathrooms
4.6 rating on other travel sites

$740

avg/night

$740
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

About this property

Come enjoy this 4 bedroom/4 bath duplex that can sleep up to 12 people with the add-on of the sleeper sofas. Blue Lagoon is located on North Shore which is just a few blocks from the renowned shopping and dining of Pine Avenue and features a large, shared heated pool, and an EV Charger. Upon entry in ...

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Property Type

Anna Maria Island House

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Anna Maria Island House
5 BR | 6.5 BA | Sleeps 8 | Quick View
Sleeps 8, 5 bedrooms, 6.5 bathrooms
4.8 rating on other travel sites

$876

avg/night

$876
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Private pool

About this property

Anna Maria Beach House offers a 5 bedroom and 6.5 bathroom, pet-friendly property, making it a perfect vacation retreat for your whole family. Situated close to the beach, shops, and restaurants, this property is an ideal choice. Just a brief stroll away from the beach, the house boasts a pool and hot ...

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Property Type

Anna Maria Island House

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Anna Maria Island House | On the beach
5 BR | 5 BA | Sleeps 14 | Quick View
Sleeps 14, 5 bedrooms, 5 bathrooms
1 review

Distance to beach: 0.1 miles to Bayside Beach

$805

avg/night

$805
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Private pool
  • Rentals by owner

About this property

Just updated 2021, with state of the art finishes! 5 BR + 2 King Sleep Sofas, 1.5 Chaise Lounger, 5 BA Duplex can sleep many with direct views of Skyway Bridge and Tampa Bay in front and at canal end in back with frequent visits from Manatees!! Email owner about our other property that sleeps 6 for smaller ...

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Property Type

Anna Maria Island House

Featured review

"Family holiday"

Fabulous location and spotlessly clean family villa with every conceivable convenience to hand. Fitted our purposes exactly and the addition of the kayaks, boat and bikes/golf cart if you wanted them was ...

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Anna Maria Island House
4 BR | 3 BA | Sleeps 10 | Quick View
Sleeps 10, 4 bedrooms, 3 bathrooms
4.7 rating on other travel sites

$783

avg/night

$783
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

If you're looking for the perfect spot to drop anchor on Anna Maria Island— look no further than this spacious four-bedroom oasis. Located on the idyllic north end, Anchor Splash is a short stroll from the white sandy beaches and warm, aquamarine gulf waters. It's also within walking distance ...

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Property Type

Anna Maria Island House

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Anna Maria Island House
4 BR | 4 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 4 bathrooms
1 review
owner special
Owner special: Perfect location! Rates are the best of the year!!!

Distance to beach: 0.1 miles to Tampa Bay

$891

avg/night

$891
avg per night
Owner special:
Perfect location! Rates are the best of the year!!!

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Private pool

About this property

Views, views, views! Experience all the best of the North end of Anna Maria from this waterfront home with pool, spa and mini golf. *Features include* * Ultimate Bay front vacation home * Private heated pool and full Putt-putt course * Paddleboards, kayak * Standalone Hot Tub * Gas grill ...

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Property Type

Anna Maria Island House

Featured review

"Sandtrap house with Beach Boutique"

Beautiful home, fantastic location and incredible service. Everything was perfect. Live the area, restaurants, biking, atmosphere and people. Super friendly. We will be back using Beach Boutique again!

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Anna Maria Island House
5 BR | 5.5 BA | Sleeps 8 | Quick View
Sleeps 8, 5 bedrooms, 5.5 bathrooms
1 review

$981

avg/night

$981
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Private pool

About this property

Come stay at From Dusk 'Til Dune! This home is a recently built beach residence offering rooftop water views just one block away from the Gulf of Mexico beaches. This 5 bedroom, 5.5 bathroom, pet-friendly vacation haven is brimming with amenities. Its stunning backyard features a private pool, hot ...

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Property Type

Anna Maria Island House

Featured review

"Serenity on the Water"

The condo was only surpassed by the view, which included a nightly explosion of sunset glory over the sound. If one wanted to be closer to the sun from the beach, the club directly on the gulf was only ...

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