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Luxury Vacation Rentals in St. Petersburg

(71 rentals)
Anna Maria Island House
Sleeps 8, 4 bedrooms, 4 bathrooms
2 reviews

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Island Escape by Beach Retreats Vacation Rentals 307 65th St, Holmes Beach, FL 34217 VRC18-000047 Your dream getaway awaits on Anna Maria Island! This stunning 4-bedroom (+ bonus room), 4-bath luxury vacation home is just steps from the beach and close to the best dining, shopping, and island attractions....

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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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$875
avg per night
Anna Maria Island House
Sleeps 8, 4 bedrooms, 3 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Mermaid's Crossing by Beach Retreats Vacation Rentals 210 65th St, Holmes Beach, FL 34217 VRC17-000007 4 Bedrooms | 3 Bathrooms | Sleeps 8 | Heated Pool & Hot Tub This home can park up to 3 vehicles Quiet hours at 10p-7a: please respect neighbors No cancellation fees! Cancel 60+...

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Featured review

"Yearly family vacation"

Location was good with only a short walk to the beach and in a quiet location. House was clean and there was plenty of room for the group. Lots of pool and beach toys for us and the kids. The pool needed...

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$711
avg per night
Anna Maria Island House
Sleeps 8, 4 bedrooms, 4.5 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Hot tub
  • Pet friendly
  • Private pool
  • WiFi

About this property

Surf Side Beach House – Gulf Views Hosted by Beach Retreats Vacation Rentals 6605 Gulf Drive, Holmes Beach, FL 34217 VRC19-00290 4 Bedrooms | 4.5 Bathrooms | Sleeps 8 | Heated Pool & Hot Tub This home can park up to 4 vehicles Quiet hours at 10p-7a: please respect neighbors Welcome...

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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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$1,027
avg per night
Bradenton House
Sleeps 19, 8 bedrooms, 6 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

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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$921
avg per night
Anna Maria Island House
Sleeps 8, 4 bedrooms, 4.5 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Pet friendly
  • Private pool
  • WiFi

About this property

6 PERSON GOLF CART INCLUDED ON ALL NEW RESERVATIONS! All Drivers must be over the age of 21. Drivers must provide valid Driver's License and Vehicle Insurance. To drive the golf cart, non-US driver license holders are required to pay an additional $25 per day instead of providing vehicle insurance....

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$971
avg per night

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Bradenton House
Sleeps 19, 5 bedrooms, 5 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Hot tub
  • Pet friendly
  • Private pool
  • WiFi

About this property

Welcome to Retreat at Palma Sola Bay your Waterfront Oasis! 150+ Feet of Direct Palma Sola Bay Waterfront Private Heated Pool & Spa (Pool Heat Included) Private Dock – Fish, Kayak, Paddleboard or Bring Your Boat Separate Guest House + Game Room Sleeps 19 Guests Comfortably Walk...

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Featured review

"Perfect"

We were a group of soccer moms (and one dad) there for a few days for a tournament. This house was everything we could have wanted! Clean, well appointed, excellent location, I can't say enough!Nights...

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$1,019
avg per night
Anna Maria Island House
Sleeps 8, 4 bedrooms, 5 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Hot tub
  • Pet friendly
  • Private pool
  • WiFi

About this property

Just Beachy – Your Luxury Island Retreat on Anna Maria Island 128 49th Street Holmes Beach FL 34217 VRC21-000019 4 Bedrooms + nanny suite | 6 Bathrooms | Sleeps 10 | Heated Pool & Hot Tub | This home can park up to 4 vehicles Quiet hours at 10p-7a: please respect neighborsEscape...

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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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$1,005
avg per night
Anna Maria Island House
Sleeps 8, 4 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

Footprints in the Sand 114 48th Street Holmes Beach FL 34217 VRC19-000156 4 Bedrooms | 3 Bathrooms | Sleeps 8 | Heated Pool & Hot Tub | Pet Friendly This home can park up to 3 vehicles Quiet hours at 10p-7a: please respect neighbors Welcome to FootPrints in the Sand, a stunning vacation...

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$760
avg per night
Anna Maria Island House
Sleeps 8, 4 bedrooms, 5.5 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Located in the heart of Holmes Beach on Anna Maria Island, this 4-bedroom, 5.5-bath coastal getaway is your dream vacation home — perfect for families, friends, or group trips.Short walk to the beach Private mini putt-putt + game room Heated pool + spa oasis Close to bars, dining, and...

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$1,046
avg per night
Anna Maria Island House
Sleeps 10, 5 bedrooms, 4.5 bathrooms
7 reviews

Key Amenities

  • Air conditioning
  • 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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$790
avg per night
Anna Maria Island House
Sleeps 8, 4 bedrooms, 4 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • Rentals by owner
  • WiFi

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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$791
avg per night
Anna Maria Island House
Sleeps 12, 6 bedrooms, 3.5 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Hot tub
  • Pet friendly
  • Private pool
  • WiFi

About this property

Angel Sea by Beach Retreats Vacation Rentals VRC19-000188 4118 5th Ave, Holmes Beach, FL 34217 6 Bedrooms | 3.5 Bathrooms | Sleeps 12 | Elevator | Heated Pool & Hot Tub This home can park up to 4 vehiclesWelcome to Angel Sea—a stunning 6-bedroom, 3.5-bathroom vacation home designed...

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Featured review

"Family vacation"

House was very comfortable. Everything was as advertised. Pool heater was not working when we checked in. They offered us the use of the pool next door. It was very kind and made our trip perfect.

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$895
avg per night
Anna Maria Island House
Sleeps 12, 6 bedrooms, 6.5 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Paradise Beach House – Luxury 5-Bedroom Retreat with Pool & Jacuzzi 403 42nd Street, Holmes Beach, FL 34217 VRC 5 Bedrooms | 6.5 Bathrooms | Sleeps 12 | Heated Pool & Hot Tub This home can park up to 4 vehicles Quiet hours at 10p-7a: please respect neighbors Welcome to Paradise...

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$897
avg per night
Anna Maria Island House
Sleeps 12, 6 bedrooms, 6.5 bathrooms
2 reviews

Key Amenities

  • Air conditioning
  • Hot tub
  • Pet friendly
  • Private pool
  • WiFi

About this property

Paradise Found - with Pool & Hot Tub 401 42nd Street, Holmes Beach, FL 34217 VRC17-000010 5 Bedrooms | 6.5 Bathrooms | Sleeps 12 | Heated Pool & Hot Tub ​​​​​​​ Pet Friendly This home can park up to 4 vehicles Quiet hours at 10p-7a: please respect neighbors No cancellation...

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Featured review

"Paradise Found"

We rented this home for time with our kids and grandkids. It worked great! The rooms were spacious and it was great that every room had a bathroom. We had no issues. The kitchen was well stocked. The backyard...

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$855
avg per night
Clearwater Beach House
Sleeps 12, 4 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • Beachfront
  • Pet friendly
  • Rentals by owner
  • WiFi

About this property

Experience coastal luxury at this one-of-a-kind beachfront retreat with breathtaking, unobstructed views of the shoreline. This beautifully appointed home features four spacious bedrooms and three well-designed bathrooms, comfortably accommodating guests with five queen beds and one king bed. Every bedroom...

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$1,088
avg per night
Anna Maria Island House
Sleeps 17, 7 bedrooms, 7.5 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Pet friendly
  • Private pool
  • WiFi

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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$983
avg per night
Anna Maria Island House
Sleeps 12, 4 bedrooms, 4.5 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

6 PERSON GOLF CART INCLUDED ON ALL NEW RESERVATIONS! All Drivers must be over the age of 21. Drivers must provide valid Driver's License and Vehicle Insurance. To drive the golf cart, non-US driver license holders are required to pay an additional $25 per day instead of providing vehicle insurance....

View all property information

$1,008
avg per night
Anna Maria Island House
Sleeps 14, 5 bedrooms, 4 bathrooms
17 reviews

Key Amenities

  • Air conditioning
  • Hot tub
  • Pet friendly
  • Private pool
  • WiFi

About this property

Welcome to Breathe Inn, your island escape where the sea breeze is plentiful and the relaxation comes naturally. This beautifully renovated 5-bedroom, 3.5-bath duplex with 2 kitchens invites you to exhale and settle into vacation mode. With two fully private units under one roof, it's the perfect...

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Featured review

"Breathe Inn"

Wonderful property and perfect for families with kids. The house was clean, well appointed with everything you could possibly need, and comfortable for everyone. The pool was always clean and well maintained....

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$796
avg per night
Anna Maria Island House
Sleeps 16, 7 bedrooms, 6 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

6 PERSON GOLF CART INCLUDED ON ALL NEW RESERVATIONS! All Drivers must be over the age of 21. Drivers must provide valid Driver's License and Vehicle Insurance. To drive the golf cart, non-US driver license holders are required to pay an additional $25 per day instead of providing vehicle insurance....

View all property information

$1,327
avg per night
Anna Maria Island Condo
Sleeps 10, 4 bedrooms, 2.5 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Welcome to Sunset Penthouse at Bradenton Beach Club, where top-floor luxury meets picture-perfect Gulf views. Step into the family room and be greeted by sweeping panoramas of Bradenton Beach.This 4-bedroom, 2.5-bathroom penthouse is thoughtfully designed for comfort, style, and effortless coastal...

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$900
avg per night
Clearwater Beach Villa
Sleeps 15, 4 bedrooms, 4 bathrooms

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pet friendly
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Clearwater Beach Waterfront Modern VillaExperience the ultimate beach vacation at our stunning Clearwater Beach villa, where Beuity meets the sea! This beautifully renovated 4-bedroom, 2-loft, 4-bath home is designed for comfort and style, offering everything you need for an unforgettable getaway.Property...

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$700
avg per night
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