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!
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  1. HOUSE
    6060S- Oceanfront Vacation Dream Home

    6060S- Oceanfront Vacation Dream Home

    New Smyrna Beach, FL

    Security Deposit: At the time of booking $500 will be collected and applied towards the rent. An additional $1,000 damage deposit will be collected. If no damage is found after your departure, this $1,000 security deposit will be refunded 14-days...

    $277 to $1,629/night

  2. 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

  3. 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

  4. 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

  5. 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

  6. 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

  7. 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

  8. 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

  9. 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

  10. 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

  11. 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

  12. 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

  13. 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

  14. 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

  15. 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

  16. 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

  17. 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

  18. 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

  19. 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

  20. HOUSE
    Tropical Daze Upper

    Tropical Daze Upper

    Bradenton Beach, FL

    Tropical Daze is the pinnacle of Anna Maria Island vacation rentals located at 2315 Gulf Drive North in the city of Bradenton Beach! This spacious home has been recently remodeled to combine comfort, class, and convenience. The unique home is...

    $256 to $463/night

  21. 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

  22. 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

  23. 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

  24. 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

  25. 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

  26. 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

  27. HOUSE
    The Lady Fish

    The Lady Fish

    Anna Maria, FL

    Nestled on the far north end of Anna Maria Island, three houses from beach access, is The Lady Fish, a newly remodeled three bedroom, two bathroom vacation home. Guests will enjoy a full gourmet kitchen with gas oven, cook top and ice maker,...

    Pets OK

    $216 to $460/night

  28. HOUSE
    Marmalade Mermaid

    Marmalade Mermaid

    Bradenton Beach, FL

    For true Southern Living and if only the best will do, this beautiful island vacation home is for you! Being only one house from the lovely beaches of Anna Maria Island and three houses to Tampa Bay you can enjoy all the waterways the island has to...

    Pets OK

    $265 to $735/night

  29. HOUSE
    Seagrass Retreat

    Seagrass Retreat

    Holmes Beach, FL

    This home is a ground level private home with five bedrooms, three full bathrooms, and private heated pool. One of the best values on the island with so much to offer! The bedrooms are perfectly situated with three on one end and two on the other....

    Pool Pets OK

    $293 to $694/night

  30. HOUSE
    Tarpon Pointe

    Tarpon Pointe

    Anna Maria, FL

    Tarpon Pointe is a gorgeous newly remodeled 2 bedroom 2 bath island home located on the north end of Anna Maria Island. You’ll enter the home from a large front deck with sliding glass doors into the living area. The living area features a large...

    Pool

    $235 to $465/night