Welcome to Florida, land of perpetual sunshine! Here you'll find sandy beaches, crystal springs, Walt Disney World, and sun-soaked vacation rentals to call home. A weekend on Panama City Beach could be just the ticket and we have vacation homes/condos galore. Use the blue location links below to select the region you'd like to explore or filter your preferences using the panel to the side. RedAwning offers easy, instant, hotel-style reservations and a simplified booking process that will have your vacation buttoned up in no time!
Photo Credit Ann Caron

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  1. HOUSE
    35 Pine Cone House

    35 Pine Cone House

    Davenport, FL

    4 Bedroom / 2 Bathroom (1,654 sqft)Single StorySouth Facing Private Pool Electric Pool Heat is an additional cost.Living Room 1 (Front): Sleeper Sofa / Stereo-CD PlayerLiving Room 2 (Back): TV / VCR-DVD Player / Cable BoxDining Area - Seats...

    Pool
    FREE CANCELLATION

    $101 to $148/night

  2. HOUSE
    40 Montego House

    40 Montego House

    Kissimmee, FL

    3 Bedroom / 2 Bathroom (1,565 sqft)Single Story Electric Pool Heat is an additional cost.South Facing PoolLiving Room (Front)Living Room (Back): TV / DVDDining Area - Seats 6Breakfast Table - Seats 4Master Bedroom 1: Queen / TV / Pool AccessBedroom...

    Pool
    FREE CANCELLATION

    $89 to $113/night

  3. HOUSE
    Gladiolus House

    Gladiolus House

    Anna Maria, FL

    Welcome to Gladiolus House and what a location, north of Pine Avenue! An old style florida two bedroom/two bathroom cottage on the north end of the Island! Not enough room for all the family, Gladiolus House is right behind Hibiscus House so why...

    $128 to $271/night

  4. CONDOMINIUM
    Westbay Point Moorings 268

    Westbay Point Moorings 268

    Holmes Beach, FL

    Beautiful second floor end unit fully furnished vacation condominium in Holmes Beach Florida with fabulous view of dolphins splashing in Bimini Bay and the incredible Gulf Coast sunsets from the screened lanai. Take a short walk to the white sandy...

    Pool

    $94 to $203/night

  5. CONDOMINIUM
    Cayman Cay 107

    Cayman Cay 107

    Holmes Beach, FL

    Just right across the street from the white sandy beaches of Anna Maria Island!!!! Cayman 107 is a spacious ground floor condo with a pool side view! Nicely updated, spacious and comfortable 2 bedroom, 2 bath condo. Cayman 107 overlooks the heated...

    Pool

    $137 to $271/night

  6. HOUSE
    Surfer's Paradise

    Surfer's Paradise

    Holmes Beach, FL

    Welcome to Surfer's Paradise. Stay at this adorable, fully renovated duplex offering 3 bedrooms and a private pool and spa! With its West of Gulf Drive location and only 5 houses away from the beach this retreat features 2 units. The separate sides...

    Pool

    $284 to $588/night

  7. CABIN
    The Terrace 3

    The Terrace 3

    Holmes Beach, FL

    This beautiful, newly renovated 2-bedroom, 2-bath townhouse-style condo with garage sleeps up to 6. The townhouse is located on the west side of Gulf Drive, so there are no busy streets to cross on the short walk to the beach. After a day at the...

    Pool

    $171 to $348/night

  8. CONDOMINIUM
    Gulf Watch 204

    Gulf Watch 204

    Bradenton Beach, FL

    Gulf Watch #204 is a 2 bedroom condo across from the beach!  The condo has a screened balcony with views of the Gulf a great place to enjoy your morning coffee.  Living room has plenty of seating with large flat screen and open plan dining area. ...

    Pool

    $156 to $271/night

  9. CABIN
    Minnow 1

    Minnow 1

    Anna Maria, FL

    The Minnow is a ground level, beautiful, tastefully decorated, polished terrazzo throughout, one bedroom, one bathroom bungalow offering a secluded and private screened in patio! It is only a short 2 minute stroll over to the beautiful white sandy...

    $118 to $235/night

  10. HOUSE
    Red Rose Beach House

    Red Rose Beach House

    Holmes Beach, FL

    Nestled right in the midst of Anna Maria Island is this lovely 3 bedroom 2 bath single family home with private pool (this is not a heated pool). The pool area is very inviting with sun on it throughout the day. This island home offers a comfortable...

    Pool Pets OK

    $235 to $441/night

  11. CONDOMINIUM
    Nautilus-117

    Nautilus-117

    Holmes Beach, FL

    The Nautilus-117 - Gulf front and west of Gulf Drive! The Nautilus condominiums occupy one entire block on the Gulf of Mexico. The Condo is steps from the white sands and blue water! With a pool right out side your door and tennis courts, all day...

    Pool

    $179 to $255/night

  12. HOUSE
    Hibiscus House

    Hibiscus House

    Anna Maria, FL

    Welcome to Hibiscus House!  This is a four bedroom, three bathrom vacation rental home which is spacious and family friendly. Located directly across from the bay with views of the intercoastal and children's playground, you'll love this location....

    $235 to $460/night

  13. APARTMENT
    Beach Walkers Sidekick

    Beach Walkers Sidekick

    Holmes Beach, FL

    Cute as a button duplex! Walk only 130 steps to one of the most beautiful beaches you will ever see. When the sun sets you will be amazed at the colors you are beholding. Smell the burgers cooking on the charcoal grill, hear the soothing sounds of...

    $128 to $235/night

  14. HOUSE
    Lazy Daisy Three

    Lazy Daisy Three

    Bradenton Beach, FL

    Lazy Daisy Three is a duplex with a 2 bedroom downstairs and a one bedroom upstairs set up. So cute and just 25 steps from the sugar white sand of Gulf of Mexico! Newly updated, enjoy a great island getaway for up 10 people together but in separate...

    Pets OK

    $272 to $519/night

  15. HOUSE
    Westbay Point Moorings 274

    Westbay Point Moorings 274

    Holmes Beach, FL

    A vacation rental that has it all from intercoastal views to tennis courts! Westbay Point & Moorings is a three bedroom, two bath with fabulous Bay & Intracoastal views on Anna Maria Island. This unit has a spacious, open, split floor plan and...

    Pool

    $140 to $268/night

  16. HOUSE
    Pleasant Palms

    Pleasant Palms

    Holmes Beach, FL

    Nestled right in the midst of Anna Maria Island is this 3 bedroom 2 bath single family home with private pool. The pool area is very inviting with sun on it throughout the day... Enjoy evening cocktails in the large screened in poolside patio. Enjoy...

    Pool

    $193 to $316/night

  17. HOUSE
    Pier To Pier Paradise

    Pier To Pier Paradise

    Anna Maria, FL

    Welcome to Pier to Pier Paradise! This beautiful brand new luxury home is one of a kind!  Three stories high and ideally situated on Anna Maria's North end, the property is tucked into a quiet little neighborhood across the street from the beach...

    Pool

    $392 to $1,176/night

  18. HOUSE
    Mermaids Watch

    Mermaids Watch

    Anna Maria, FL

    Less than a half a block from the gorgeous gulf side beaches. This 1945 built home has the original pine wood floors, and high ceilings making it feel very quaint and perfect for your family's vacation. There's also lots of windows and natural light...

    $217 to $475/night

  19. HOUSE
    PalmaSolaParadise

    PalmaSolaParadise

    Bradenton, FL

    Palma Sola Paradise is the next best thing to being on the island!  This spacious property sits right on the waters edge of Palma Sola Bay and only 5 short miles to Holmes Beach.  This well appointed 7 bedroom / 4 bathroom property has 5,500 sq ft...

    Pool

    $385 to $667/night

  20. HOUSE
    Redfish Cottage

    Redfish Cottage

    Holmes Beach, FL

    Redfish Cottage is on a quiet street in Holmes Beach and within walking distance to all restaurants and shops. Recently updated, this three bedroom, two bath home features a king bed in the master bedroom, queen bed in the guest room, and full bed...

    $185 to $230/night

  21. HOUSE
    Wrights Retreat

    Wrights Retreat

    Holmes Beach, FL

    Enjoy a spacious three bedroom vacation home with the beach barely a block away! This three bedroom/two bathroom home is west of Gulf Drive. Wrights Retreat is within easy walking distance to Gulf beaches, barely a block away! It features a...

    $162 to $265/night

  22. HOUSE
    Playa Encantada 214

    Playa Encantada 214

    Holmes Beach, FL

    Access that leads to one of the best beaches on the West Coast. Anna Maria Island gulf front complex with an elevator offers a recently remodeled 2BD/2BA with large lanai, covered parking and storage. This well maintained complex offers heated pool...

    Pool

    $150 to $372/night

  23. VILLA
    Lazy Daisy Too

    Lazy Daisy Too

    Bradenton Beach, FL

    Lazy Daisy Too is the cutest footprint by the sand! Located 25 steps from the sugar white sand of Gulf of Mexico with a view of the beach, Lazy Daisy Too is a bright one bedroom. What you see is a cheerful space with a full kitchen, private bedroom...

    Pets OK

    $103 to $204/night

  24. HOUSE
    Manatee Cottage

    Manatee Cottage

    Anna Maria, FL

    Manatee Cottage is a newly remodeled two bedroom, two bathroom private home with a pool and spa. This fabulous house is only a short walk to the white sand beaches of Anna Maria and also a short walk to Bay Front park.  Stroll down to Pine Avenue...

    Pool

    $274 to $411/night

  25. CABIN
    Sunkissed

    Sunkissed

    Holmes Beach, FL

    Sunkissed is a beautiful elevated home that is located in Holmes Beach-just a short 4 minute stroll to the gorgeous white sandy beaches of the Gulf of Mexico. This great property offers more than just a fantastic and central location but also...

    Pool

    $213 to $470/night

  26. CABIN
    Latitude Adjustment

    Latitude Adjustment

    Anna Maria, FL

    Latitude Adjustment! Here it is: that stress-free attitude you've been wishing for in the "Old Florida" at Latitude Adjustment. This super-walkable villa is within steps of beach, bay, restaurants, bars, shops, piers, and more. A charming 2...

    Pets OK

    $118 to $265/night

  27. VILLA
    Blue Water Escape

    Blue Water Escape

    Bradenton Beach, FL

    The beautiful Blue Water Escape! Experience its panoramic rooftop deck views with a location in the heart of Bradenton Beach around the corner from Bridge Street! This three-story duplex begins with a walk up to the first floor above a garage...

    $274 to $539/night

  28. VILLA
    Beach Breeze Hideaway

    Beach Breeze Hideaway

    Holmes Beach, FL

    Welcome to Beach Breeze Hideaway! This cute island property is just perfect for your laid-back Anna Maria Island retreat! Newly updated throughout, this 2 bedroom/2 bathroom beach duplex is just a short walk  to the fabulous Gulf beaches of Anna...

    Pets OK

    $167 to $293/night

  29. HOUSE
    Westbay Point Moorings 214

    Westbay Point Moorings 214

    Holmes Beach, FL

    Enjoy a canal view from this lovely 2 bedroom condo equipped with a heated pool, jacuzzi and tennis courts.~ A lovely two bedroom, two bathroom, canal front condominium at Westbay Point and Moorings on Holmes Beach. Enjoy the large lanai overlooking...

    Pool

    $171 to $192/night

  30. CONDOMINIUM
    Amelia Landings #8A

    Amelia Landings #8A

    Fernandina Beach, FL

    2 Bed/2 Bath 1st floor condo sleeps 6. Wrap around screen porch, short walk to beach. New to our Rental Program! This is a great first floor unit at Amelia Landing ! Enjoy your morning coffee on a beautiful wrap around screen porch with a very...

    Pool
    FREE CANCELLATION

    $205 to $217/night