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Results: 799 Rentals

  • Enchanted Inn Suite #4 w/ View of the Intra-costal water-way Pool, Fishing Dock,
    From $226 per night (USD)

    VRBO

    Enchanted Inn Suite #4 w/ View of the Intra-costal water-way Pool, Fishing Dock,

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Summary: This rental property is located on North Clearwater Beach on the Intra-Coastal Waterway. Located within a quick ...

    From $226 per night (USD)

    VRBO

    Details
  • Enchanted Inn Suite #2 w/ View of the Intra-costal water-way Pool, Fishing Dock,
    From $223 per night (USD)

    Expedia

    Enchanted Inn Suite #2 w/ View of the Intra-costal water-way Pool, Fishing Dock,

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Summary: This rental property is located on North Clearwater Beach on the Intra-Coastal Waterway. Located within a quick ...

    From $223 per night (USD)

    Expedia

    Details
  • Beachside Retreat 15B / Steps to Clw Beach!
    From $249 per night (USD)

    VRBO

    Beachside Retreat 15B / Steps to Clw Beach!

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Summary: Welcome to our STUDIO Cottage where you are just steps away from the sandy shores of Clearwater Beach! You will ...

    From $249 per night (USD)

    VRBO

    Details
  • Enchanted Inn Suite #6 w/ View of the Intra-costal water-way Pool, Fishing Dock,
    From $208 per night (USD)

    Expedia

    Enchanted Inn Suite #6 w/ View of the Intra-costal water-way Pool, Fishing Dock,

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Summary: This rental property is located on North Clearwater Beach on the Intra-Coastal Waterway. Located within a quick ...

    From $208 per night (USD)

    Expedia

    Details
  • Clearwater Beach Cottage 24 / Walk to the beach!
    From $261 per night (USD)

    VRBO

    Clearwater Beach Cottage 24 / Walk to the beach!

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Summary: Welcome to our Cottage where you are just steps away from the sandy shores of Clearwater Beach! You will be wit ...

    From $261 per night (USD)

    VRBO

    Details
  • Enchanted Inn Suite #3 w/ View of the Intra-costal water-way Pool, Fishing Dock,
    From $208 per night (USD)

    Expedia

    Enchanted Inn Suite #3 w/ View of the Intra-costal water-way Pool, Fishing Dock,

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Summary: This rental property is located on North Clearwater Beach on the Intra-Coastal Waterway. Located within a quick ...

    From $208 per night (USD)

    Expedia

    Details
  • Enchanted Inn Deluxe Suite #8 w/ View of the Intra-costal water-way Pool, Fishin
    From $253 per night (USD)

    VRBO

    Enchanted Inn Deluxe Suite #8 w/ View of the Intra-costal water-way Pool, Fishin

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Summary: This rental property is located on North Clearwater Beach on the Intra-Coastal Waterway. Located within a quick ...

    From $253 per night (USD)

    VRBO

    Details
  • Beachside Cottage 22 / Steps to the beach!
    From $296 per night (USD)

    Expedia

    Beachside Cottage 22 / Steps to the beach!

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Summary: Welcome to our Cottage where you are just steps away from the sandy shores of Clearwater Beach! You will be wit ...

    From $296 per night (USD)

    Expedia

    Details
  • Beachside Courtyard Retreat 15A / Steps to Clearwater Beach!
    From $298 per night (USD)

    VRBO

    Beachside Courtyard Retreat 15A / Steps to Clearwater Beach!

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    3

    Summary: Welcome to our Cottage where you are just steps away from the sandy shores of Clearwater Beach! You will be wit ...

    From $298 per night (USD)

    VRBO

    Details
  • WOW! Fully remodeled 2 bed/2 bath! Only a 5 min walk to the beach! Great views!
    From $356 per night (USD)

    Expedia

    WOW! Fully remodeled 2 bed/2 bath! Only a 5 min walk to the beach! Great views!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Indulge in the perfect cozy getaway, away from the high-rises, but still close enough for all the fun! Charm and comfort ...

    From $356 per night (USD)

    Expedia

    Details
  • Key West Style Apartment - with pool/hot-tub
    From $130 per night (USD)

    VRBO

    Key West Style Apartment - with pool/hot-tub

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    This apartment features two double beds, free wifi, a private bathroom, a mini fridge as well as a freezer. Unwind in t ...

    From $130 per night (USD)

    VRBO

    Details
  • SaltyLux16 Heated Saltwater Pool/Near Beach/Island
    From $357 per night (USD)

    Expedia

    SaltyLux16 Heated Saltwater Pool/Near Beach/Island

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    16

    Welcome to your Exquisite Florida Oasis 3/2 Home Retreat. Enjoy privacy w a fenced yard, a sun &mosquito-protected pool ...

    From $357 per night (USD)

    Expedia

    Details
  • Heated POOL- 2 Houses to BEACH- Coastal MAIN House
    From $494 per night (USD)

    VRBO

    Heated POOL- 2 Houses to BEACH- Coastal MAIN House

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    8

    Enjoy your next vacation in our tastefully updated coastal beach home! Interior of main home features 4 well appointed b ...

    From $494 per night (USD)

    VRBO

    Details
  • Regatta C610 '90 Day min'
    From $282 per night (USD)

    VRBO

    Regatta C610 '90 Day min'

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Welcome to your idyllic retreat at the prestigious Regatta Beach Club. Situated on the 6th floor, this 2-bedroom, 1-bath ...

    From $282 per night (USD)

    VRBO

    Details
  • One Bedroom Cozy Condo One Year Lease,,Downtown Dunedin, Gate Community
    From $186 per night (USD)

    VRBO

    One Bedroom Cozy Condo One Year Lease,,Downtown Dunedin, Gate Community

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Snow Bird Seasonal Rate December through April $ 160.00 per night 30 night’s minimum contract. $1500.00 security depos ...

    From $186 per night (USD)

    VRBO

    Details
  • cozy and cheerful 2 bedroom home minutes to the beach!
    From $171 per night (USD)

    Expedia

    cozy and cheerful 2 bedroom home minutes to the beach!

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    This vacation home is located in Clearwater. Relax with the whole family at this peaceful place to stay. Want to see the ...

    From $171 per night (USD)

    Expedia

    Details
  • Beachy Bungalow in the heart of Dunedin; 5 minute walk to downtown
    From $317 per night (USD)

    VRBO

    Beachy Bungalow in the heart of Dunedin; 5 minute walk to downtown

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    7

    Are you looking for a perfect vacation spot? Look no further! The Larimar House is the perfect rental for you! 🤩 This ...

    From $317 per night (USD)

    VRBO

    Details
  • Bohemian Tropical Paradise Palm Harbor. Pool Home. 10mins to Honeymoon Island.
    From $475 per night (USD)

    Expedia

    Bohemian Tropical Paradise Palm Harbor. Pool Home. 10mins to Honeymoon Island.

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    10

    Welcome to your slice of Bohemian Paradise! This home, on the Cul-de-sac accentuated by soaring high ceilings that add a ...

    From $475 per night (USD)

    Expedia

    Details
  • Family and pet friendly. Dedicated work station with local attractions.
    From $222 per night (USD)

    VRBO

    Family and pet friendly. Dedicated work station with local attractions.

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    10

    Welcome to Villa Florentina: Your Clearwater Escape! Discover luxury and relaxation at Villa Florentina in Clearwater, ...

    From $222 per night (USD)

    VRBO

    Details
  • Dunedin Causeway Waterfront Community Completely Remodeled 2Bed/2Bath Pool/Bikes
    From $112 per night (USD)

    VRBO

    Dunedin Causeway Waterfront Community Completely Remodeled 2Bed/2Bath Pool/Bikes

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    5

    LOCATION!! This beautiful waterfront condominium community is the prime location of Dunedin. Dolphin Pointe is located ...

    From $112 per night (USD)

    VRBO

    Details
  • Endless amenities & great location condo in Palm Harbor.\n\n\n\n
    Click For Pricing

    VRBO

    Endless amenities & great location condo in Palm Harbor.\n\n\n\n

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    This condo community checks all the boxes. This 1st floor end unit has 2 bedrooms and 2 full baths. It is fully furnis ...

    Click For Pricing

    VRBO

    Details
  • Clearwater Beach, Dunedin, Caladesi Island Getaway\n
    Click For Pricing

    Expedia

    Clearwater Beach, Dunedin, Caladesi Island Getaway\n

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Newly remodeled Clearwater Beach Family friendly getaway with a Gameroom, 20 minutes from Clearwater Beach and only a ve ...

    Click For Pricing

    Expedia

    Details
  • Water View Condo on the causeway to Honeymoon Island
    From $117 per night (USD)

    VRBO

    Water View Condo on the causeway to Honeymoon Island

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    LOCATION.LOCATION.LOCATION.. It's all here. Beautiful View of the water. On the causeway to Honeymoon Island. One bl ...

    From $117 per night (USD)

    VRBO

    Details
  • Waterfront Resort 1Bed/2Baths Condo/Beaches Sunset/Free Bikes
    From $226 per night (USD)

    Expedia

    Waterfront Resort 1Bed/2Baths Condo/Beaches Sunset/Free Bikes

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    4

    A Self check-in private condo (1 bedroom & 2 bathrooms) in the resort/Free bikes. Heated waterfront swimming pool and ho ...

    From $226 per night (USD)

    Expedia

    Details
  • Key West Style Apartment - with pool/hot-tub
    From $1146 per night (USD)

    VRBO

    Key West Style Apartment - with pool/hot-tub

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    This apartment features a queen bed, free wifi, a private bathroom, a mini fridge as well as a freezer. Unwind in the b ...

    From $1146 per night (USD)

    VRBO

    Details
  • Only 4 bedroom with a view of Main Street located in the Downtown Core District
    From $478 per night (USD)

    Expedia

    Only 4 bedroom with a view of Main Street located in the Downtown Core District

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    8

    Completely remodeled home in the Historic Downtown Core of Dunedin! Enjoy sunshine and beaches in charming Dunedin! Th ...

    From $478 per night (USD)

    Expedia

    Details
  • Dunedin Causeway Honeymoon Caladesi Island 1/1 Pool 316
    From $120 per night (USD)

    VRBO

    Dunedin Causeway Honeymoon Caladesi Island 1/1 Pool 316

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Enjoy this gorgeous 3rd floor, west end unit with spectacular gulf and intercoastal views! Located in Dunedin's Waterfro ...

    From $120 per night (USD)

    VRBO

    Details
  • Clearwater Beach Retreats at Bayside View 4
    From $261 per night (USD)

    VRBO

    Clearwater Beach Retreats at Bayside View 4

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Summary: Bayside View 4 is a delightful bayside getaway offering big water views of the Mandalay Channel. Enjoy 2 bedro ...

    From $261 per night (USD)

    VRBO

    Details
  • Private Pool Setting
    From $308 per night (USD)

    VRBO

    Private Pool Setting

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    10

    Relax with the whole family at this peaceful place to stay near Clearwater Beach, sporting venues, Dunedin, and many oth ...

    From $308 per night (USD)

    VRBO

    Details
  • Luxury 3 Beds 2 Bath Clearwater
    Click For Pricing

    Expedia

    Luxury 3 Beds 2 Bath Clearwater

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    About this space SUPER LUX HOUSE! 3 Beds 2 baths perfect location just 13 minutes from the beach! Going to Clearwater? D ...

    Click For Pricing

    Expedia

    Details
  • Heart of Dunedin - Bay Suite: walk&ride everywhere
    Click For Pricing

    VRBO

    Heart of Dunedin - Bay Suite: walk&ride everywhere

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Comfortable new construction apartment. Great for a quick getaway, or a longer vacation rental hideaway. Located in down ...

    Click For Pricing

    VRBO

    Details
  • NEW - Beachy Vibes & Golf Cart Rides in the Heart of Dunedin!
    From $184 per night (USD)

    VRBO

    NEW - Beachy Vibes & Golf Cart Rides in the Heart of Dunedin!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    NEW! Available Oct 15, 2025-Jan 15, 2026. for a 90-day stay or longer, it's the perfect seasonal or transitional rental. ...

    From $184 per night (USD)

    VRBO

    Details
  • Downtown Dunedin Hideaway
    From $194 per night (USD)

    VRBO

    Downtown Dunedin Hideaway

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Summary: Welcome to our Brand New Downtown Dunedin Hideaway located within walking distance to the heart of Downtown! Ev ...

    From $194 per night (USD)

    VRBO

    Details
  • Downtown Dunedin B&B/Sleeps 12!
    From $610 per night (USD)

    Expedia

    Downtown Dunedin B&B/Sleeps 12!

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    12

    Summary: Welcome to our brand new Coastal Casa & Cabin Combo Unit located within walking distance to downtown Dunedin! T ...

    From $610 per night (USD)

    Expedia

    Details
  • Stunning Clearwater Beach Home
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    VRBO

    Stunning Clearwater Beach Home

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    12

    Carlouel beach home just steps away from the sand. This home has been updated and ready for Fall tenants. Magnificent ...

    Click For Pricing

    VRBO

    Details
  • Nautical Landings West-Honeymoon Island
    From $197 per night (USD)

    Expedia

    Nautical Landings West-Honeymoon Island

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    This is one of 4 suites inside Nautical Landings, our Gulf-front fourplex in Dunedin, Florida. It's on the second floor, ...

    From $197 per night (USD)

    Expedia

    Details
  • Beach House on the water with dock, pool & everything to enjoy the beach life.
    From $1653 per night (USD)

    VRBO

    Beach House on the water with dock, pool & everything to enjoy the beach life.

    Bedrooms:
    3
    Bathrooms:
    5
    Sleeps:
    16

    Have fun with the whole family at this private waterfront Beach House. Take a dip in the heated Have fun with the whole ...

    From $1653 per night (USD)

    VRBO

    Details
  • Luxe Private Waterfront Getaway with Pool in Ozona
    From $430 per night (USD)

    Expedia

    Luxe Private Waterfront Getaway with Pool in Ozona

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    10

    Luxurious Intracoastal Waterfront Retreat with Private Pool and Boat Dock Experience the ultimate Florida getaway in thi ...

    From $430 per night (USD)

    Expedia

    Details
  • Bright, Clean and Cozy Coastal Cottage in Ozona
    From $156 per night (USD)

    VRBO

    Bright, Clean and Cozy Coastal Cottage in Ozona

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    7

    Discover Old Florida Charm with Modern Luxury in Ozona! Escape to this hidden gem in Palm Harbor's quaint village of Oz ...

    From $156 per night (USD)

    VRBO

    Details
  • Quaint, Clean and Bright Cottage in Ozona
    From $138 per night (USD)

    Expedia

    Quaint, Clean and Bright Cottage in Ozona

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    6

    Charming Modern Cottage in Ozona, Palm Harbor Experience the best of Florida's Gulf Coast in this beautifully renovated ...

    From $138 per night (USD)

    Expedia

    Details
  • Renovated duplex near Honeymoon/Caladesi Island with patio, AC, & W/D
    From $239 per night (USD)

    VRBO

    Renovated duplex near Honeymoon/Caladesi Island with patio, AC, & W/D

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Islander's Outpost Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...

    From $239 per night (USD)

    VRBO

    Details
  • La Casita Solar
    From $108 per night (USD)

    Expedia

    La Casita Solar

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    3

    Welcome to "La Casita Solar", a healthy and clean energy experience: solar panels and high-end water/air purification sy ...

    From $108 per night (USD)

    Expedia

    Details
  • Sunset Breeze - Beachfront Pool Home - Monthly Rental
    From $1703 per night (USD)

    VRBO

    Sunset Breeze - Beachfront Pool Home - Monthly Rental

    Bedrooms:
    3
    Bathrooms:
    5
    Sleeps:
    14

    Welcome to the epitome of beachfront luxury: Sunset Breeze! Step into a world where the sunsets are spectacular, the poo ...

    From $1703 per night (USD)

    VRBO

    Details
  •  Clearwater 5 minutes from Blue Jays Training Camp !\n  Romy's Coastal Cottage
    From $100 per night (USD)

    VRBO

    Clearwater 5 minutes from Blue Jays Training Camp !\n Romy's Coastal Cottage

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    2

    Special offer for 4 adults/one must be 55 or over, 1,600/month for the four of you , price is in US dollars. Come fo ...

    From $100 per night (USD)

    VRBO

    Details
  • Bright & open home with private pool, screened lanai, enclosed yard, & W/D
    From $444 per night (USD)

    VRBO

    Bright & open home with private pool, screened lanai, enclosed yard, & W/D

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Tropical Vibe Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desi ...

    From $444 per night (USD)

    VRBO

    Details
  • Dunedin Lux 5BR Villa w/heated saltwater pool & spa, patio, putting green & BBQ
    From $666 per night (USD)

    Expedia

    Dunedin Lux 5BR Villa w/heated saltwater pool & spa, patio, putting green & BBQ

    Bedrooms:
    3
    Bathrooms:
    5
    Sleeps:
    10

    Explore this luxury 5 BR /3 BA villa, perfect for family vacations or gatherings with friends. Featuring a cozy pool pa ...

    From $666 per night (USD)

    Expedia

    Details
  • Charming, dog-friendly home with lanai & washer/dryer - near downtown, beach
    From $212 per night (USD)

    VRBO

    Charming, dog-friendly home with lanai & washer/dryer - near downtown, beach

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Parkside Bliss Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...

    From $212 per night (USD)

    VRBO

    Details
  • 601 A Newly Renovated 1 Bedroom with Kitchen
    From $172 per night (USD)

    VRBO

    601 A Newly Renovated 1 Bedroom with Kitchen

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    This newly renovated one bedroom/one bath is in the heart of Downtown Dunedin. In Dunedin, you will find a charming and ...

    From $172 per night (USD)

    VRBO

    Details
  • 603 Newly Renovated 1 Bedroom with Kitchen
    From $172 per night (USD)

    VRBO

    603 Newly Renovated 1 Bedroom with Kitchen

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    This newly renovated one bedroom/one bath is in the heart of Downtown Dunedin. In Dunedin, you will find a charming and ...

    From $172 per night (USD)

    VRBO

    Details
  • 1156 Angle Rd - One-Year Lease
    From $62 per night (USD)

    VRBO

    1156 Angle Rd - One-Year Lease

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    This charming 1 bed/1 bath is located in the heart of Downtown Dunedin. Great location. Quiet Easily. Walk to the water, ...

    From $62 per night (USD)

    VRBO

    Details
  • 1158 Angle Rd - One-Year Lease
    From $62 per night (USD)

    VRBO

    1158 Angle Rd - One-Year Lease

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    This charming 1 bed/1 bath is located in the heart of Downtown Dunedin. Great location. Quiet Easily. Walk to the water, ...

    From $62 per night (USD)

    VRBO

    Details
  • 519-B Casita with Kitchenette
    From $111 per night (USD)

    VRBO

    519-B Casita with Kitchenette

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    This charming fully remodeled casita is located in the heart of Downtown Dunedin. *Easily walk to the water, shops, an ...

    From $111 per night (USD)

    VRBO

    Details
  • 519-C Casita with Kitchenette
    From $129 per night (USD)

    VRBO

    519-C Casita with Kitchenette

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    This charming fully remodeled casita is located in the heart of Downtown Dunedin. *Easily walk to the water, shops, an ...

    From $129 per night (USD)

    VRBO

    Details
  • Lakeview Chic 3BD House for golf/beach lovers
    From $244 per night (USD)

    Expedia

    Lakeview Chic 3BD House for golf/beach lovers

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    6

    This unique place has a style all its own. Spacious 3BR, 1.5BA house only 15min drive from Clearwater Beach! Ideal vacat ...

    From $244 per night (USD)

    Expedia

    Details
  • Enchanted Inn/7 Private King Suites/Waterfront
    From $1779 per night (USD)

    VRBO

    Enchanted Inn/7 Private King Suites/Waterfront

    Bedrooms:
    7
    Bathrooms:
    7
    Sleeps:
    16

    Summary: This listing is for larger groups who would like to rent all 7 private suites. Each Suite come with a full kitc ...

    From $1779 per night (USD)

    VRBO

    Details
  • Clearwater Beach Cottages/Sleeps 16
    From $1288 per night (USD)

    Expedia

    Clearwater Beach Cottages/Sleeps 16

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    16

    Summary: Welcome to our Cambria Cottages Combo Listing (Sleeps up to 16 people), where you are just steps away from the ...

    From $1288 per night (USD)

    Expedia

    Details
  • Clearwater Beach! Waterfront Modern Villa 4BD/2openLoft/4BT Pool /Boat Deck. 14p
    From $495 per night (USD)

    VRBO

    Clearwater Beach! Waterfront Modern Villa 4BD/2openLoft/4BT Pool /Boat Deck. 14p

    Bedrooms:
    4
    Bathrooms:
    6
    Sleeps:
    13

    Clearwater Beach Waterfront Modern Villa Experience the ultimate beach vacation at our stunning Clearwater Beach villa ...

    From $495 per night (USD)

    VRBO

    Details
  • Rustic Cottage in Dunedin FL
    From $137 per night (USD)

    Expedia

    Rustic Cottage in Dunedin FL

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    3

    Completely furnished, tile and bamboo floors, gas oven, dishes and cookware.. Close to downtown with great restaurants ...

    From $137 per night (USD)

    Expedia

    Details
  • Dunedin Tiny House Combo/Sleeps 26
    From $1396 per night (USD)

    VRBO

    Dunedin Tiny House Combo/Sleeps 26

    Bedrooms:
    6
    Bathrooms:
    8
    Sleeps:
    26

    Summary: Welcome to Our Dunedin Tiny House Combo Listing. Six individual units located on the Pinellas Trail and within ...

    From $1396 per night (USD)

    VRBO

    Details
  • 4bd/2br Tiki Bar, King bed, & Pool... amenities galore!\n
    From $526 per night (USD)

    Expedia

    4bd/2br Tiki Bar, King bed, & Pool... amenities galore!\n

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    10

    Kick up your feet and relax at our updated home by the world renown beaches of Clearwater! Enjoy our diverse set of ame ...

    From $526 per night (USD)

    Expedia

    Details
  • Spacious Beach Oasis
    From $516 per night (USD)

    VRBO

    Spacious Beach Oasis

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    8

    Welcome to the island living lifestyle here on North Clearwater Beach in the exclusive Carlouel neighborhood. Enjoy your ...

    From $516 per night (USD)

    VRBO

    Details
  • 1 Mile to Beach~ Private Pool Oasis!~Volleyball
    From $423 per night (USD)

    Expedia

    1 Mile to Beach~ Private Pool Oasis!~Volleyball

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    10

    Summary: Step into our charming oasis in Palm Harbor, Florida! Packed with a variety of amenities, it guarantees a memo ...

    From $423 per night (USD)

    Expedia

    Details
  • Regatta Beach Club S613 Beachfront Property in Regatta Beach Club S613
    From $135 per night (USD)

    VRBO

    Regatta Beach Club S613 Beachfront Property in Regatta Beach Club S613

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Please read House Rules and Special Requirements below before booking. The location is perfect for a beach vacation wi ...

    From $135 per night (USD)

    VRBO

    Details
  • Luxury Belle Harbor Condo on Clearwater Beach. Perfect location and amazing view
    From $344 per night (USD)

    VRBO

    Luxury Belle Harbor Condo on Clearwater Beach. Perfect location and amazing view

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Located just steps from the pristine white sands and clear tranquil water of Clearwater Beach, Belle Harbor offers a lux ...

    From $344 per night (USD)

    VRBO

    Details
  • FREE Heated Pool• 3mi to beach•W/D•Game Room• King bed• Bikes•Lake View
    From $376 per night (USD)

    VRBO

    FREE Heated Pool• 3mi to beach•W/D•Game Room• King bed• Bikes•Lake View

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    10

    Welcome to your tranquil 1,400 sq. ft. escape—perfect for families, friends, and pets! Unwind in the free heated pool, s ...

    From $376 per night (USD)

    VRBO

    Details
  • Centrally Located Clearwater Home w/ Outdoor Pool!
    From $206 per night (USD)

    Expedia

    Centrally Located Clearwater Home w/ Outdoor Pool!

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    8

    A fun-filled extended stay in Clearwater is just a click away! This tropical gem is nestled in a quiet, tree-lined neigh ...

    From $206 per night (USD)

    Expedia

    Details
  • Heated salt water pool Spacious 4BR,3BR
    From $458 per night (USD)

    VRBO

    Heated salt water pool Spacious 4BR,3BR

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    10

    Welcome to Cerulean Cottage, our newly renovated home centrally located in Dunedin, Florida. Whatever brings you to this ...

    From $458 per night (USD)

    VRBO

    Details
  • Beachview 4 bedroom Townhome! 30 second walk from the beach! Free parking!
    From $494 per night (USD)

    VRBO

    Beachview 4 bedroom Townhome! 30 second walk from the beach! Free parking!

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    6

    The white sands of Clearwater Beach are calling! Bring your loved ones on an unforgettable trip to this coastal 4-bedroo ...

    From $494 per night (USD)

    VRBO

    Details
  • Regatta Beach Club C808 '90 day min stay with 2 week lead time'
    From $129 per night (USD)

    VRBO

    Regatta Beach Club C808 '90 day min stay with 2 week lead time'

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Welcome to your idyllic retreat at the prestigious Regatta Beach Club. Situated on the 8th floor, this 2-bedroom, 1-bath ...

    From $129 per night (USD)

    VRBO

    Details
  • Awesome 2 bedroom condo only 2 miles to Honeymoon Island on the water!
    From $148 per night (USD)

    VRBO

    Awesome 2 bedroom condo only 2 miles to Honeymoon Island on the water!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Dunedin Condo - Completely renovated in 2022. Unique floor plan with kitchen, open dining/living room, bath and laundry ...

    From $148 per night (USD)

    VRBO

    Details
  • Sunny Retreat in Clearwater by RedAwning
    From $337 per night (USD)

    VRBO

    Sunny Retreat in Clearwater by RedAwning

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    5

    Welcome to your dream getaway in the heart of the Greenbriar community in Clearwater, Florida! Our charming vacation r ...

    From $337 per night (USD)

    VRBO

    Details
  • Cozy 3 BR home 10 min away from beach and close to downtown
    From $228 per night (USD)

    Expedia

    Cozy 3 BR home 10 min away from beach and close to downtown

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Perfect place for a family vacation at this beautiful newly renovated home. Close to clearwater beach. Enjoy your day at ...

    From $228 per night (USD)

    Expedia

    Details
  • Cozy 3 bedroom family friendly home close to clearwater beach and downtown
    From $342 per night (USD)

    VRBO

    Cozy 3 bedroom family friendly home close to clearwater beach and downtown

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Bring the whole family to this great place with lots of room for fun. About 10 min from clearwater beach. 3 min away fro ...

    From $342 per night (USD)

    VRBO

    Details
  • In the Heart of Downtown Dunedin One Bedroom Apt
    From $167 per night (USD)

    Expedia

    In the Heart of Downtown Dunedin One Bedroom Apt

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Historic Home in the heart of Downtown Dunedin, known by locals as the Yellow House. First floor 1 bedroom apartment is ...

    From $167 per night (USD)

    Expedia

    Details
  • Cozy Apartment Overlooking Downtown Dunedin
    From $189 per night (USD)

    VRBO

    Cozy Apartment Overlooking Downtown Dunedin

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Historic Home in the heart of Downtown Dunedin, known by locals as the Yellow House. Second floor 1 bedroom apartment i ...

    From $189 per night (USD)

    VRBO

    Details
  • NEW Listing! 1 bed/1 bath Apartment! Only a 5 min walk to beach! Great views!
    From $265 per night (USD)

    Expedia

    NEW Listing! 1 bed/1 bath Apartment! Only a 5 min walk to beach! Great views!

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Indulge in the perfect cozy getaway, away from the high-rises, but still close enough for all the fun! Charm and comfort ...

    From $265 per night (USD)

    Expedia

    Details
  • NEW Listing! Waterfront 1 bed/1 bath Apt! Only a 5 min walk beach! Great views!
    From $266 per night (USD)

    VRBO

    NEW Listing! Waterfront 1 bed/1 bath Apt! Only a 5 min walk beach! Great views!

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Indulge in the perfect cozy getaway, away from the high-rises, but still close enough for all the fun! Charm and comfort ...

    From $266 per night (USD)

    VRBO

    Details
  • NEW Listing! 2 bed/2 bath CONDO-1000sq ft! Only a 5 min walk beach! Great views!
    From $349 per night (USD)

    Expedia

    NEW Listing! 2 bed/2 bath CONDO-1000sq ft! Only a 5 min walk beach! Great views!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Indulge in the perfect cozy getaway, away from the high-rises, but still close enough for all the fun! Charm and comfort ...

    From $349 per night (USD)

    Expedia

    Details
  • NEW Listing! 1 bed/1 bath Apartment! Only a 5 min walk to beach! Great views!
    From $273 per night (USD)

    VRBO

    NEW Listing! 1 bed/1 bath Apartment! Only a 5 min walk to beach! Great views!

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Indulge in the perfect cozy getaway, away from the high-rises, but still close enough for all the fun! Charm and comfort ...

    From $273 per night (USD)

    VRBO

    Details
  • Ozona on the Gulf of Mexico. Bikes Provided. Honeymoon Island. Pinellas Trail.
    From $187 per night (USD)

    Expedia

    Ozona on the Gulf of Mexico. Bikes Provided. Honeymoon Island. Pinellas Trail.

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Greetings! Welcome to beautiful Ozona, Florida. Gulf of Mexico at your front door! Gulf of Mexico viewing bench a ...

    From $187 per night (USD)

    Expedia

    Details
  • NEW Listing! 1 bedroom/1 bath Apartment! Only a 5 min walk beach! Great views!
    From $241 per night (USD)

    VRBO

    NEW Listing! 1 bedroom/1 bath Apartment! Only a 5 min walk beach! Great views!

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Indulge in the perfect cozy getaway, away from the high-rises, but still close enough for all the fun! Charm and comfort ...

    From $241 per night (USD)

    VRBO

    Details
  • Coastal Retreat & Biking Bliss
    From $131 per night (USD)

    Expedia

    Coastal Retreat & Biking Bliss

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Discover the beautiful butterfly murals that adorn this cozy tiny home nestled conveniently between Clearwater Beach and ...

    From $131 per night (USD)

    Expedia

    Details
  • NEW Listing! 1 bedroom/1 bath Apartment! Only a 5 min walk beach! Great views!
    From $241 per night (USD)

    VRBO

    NEW Listing! 1 bedroom/1 bath Apartment! Only a 5 min walk beach! Great views!

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Indulge in the perfect cozy getaway, away from the high-rises, but still close enough for all the fun! Charm and comfort ...

    From $241 per night (USD)

    VRBO

    Details
  • The Oaks at Keene Estate
    From $454 per night (USD)

    VRBO

    The Oaks at Keene Estate

    Bedrooms:
    4
    Bathrooms:
    6
    Sleeps:
    10

    This beautiful estate 6112 sq/ft home is set on over one acre of landscaped grounds. Some features include a swimming ...

    From $454 per night (USD)

    VRBO

    Details
  • Chateaus on White Sands 302 Beachfront Condo
    From $659 per night (USD)

    VRBO

    Chateaus on White Sands 302 Beachfront Condo

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    8

    Background checks are required for all adults. See House Rules below before booking. Your million-dollar condo in exclu ...

    From $659 per night (USD)

    VRBO

    Details
  • Cozy Nest in Clearwater/Palm Harbor area
    From $221 per night (USD)

    Expedia

    Cozy Nest in Clearwater/Palm Harbor area

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Discover comfort and cleanliness in our charming 3-bedroom, 2-bathroom retreat nestled between Clearwater and Palm Harbo ...

    From $221 per night (USD)

    Expedia

    Details
  • 3BR Oasis | Sleeps 11 | Heated Pool | Ping Pong!
    From $342 per night (USD)

    VRBO

    3BR Oasis | Sleeps 11 | Heated Pool | Ping Pong!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    11

    5⭐⭐⭐⭐⭐ Service & Accommodations! Welcome to our fully remodeled 3-bedroom, 2-bathroom oasis in Dunedin, Florida! Dive i ...

    From $342 per night (USD)

    VRBO

    Details
  • Cozy Cottage Downtown + near Waterfront
    From $194 per night (USD)

    Expedia

    Cozy Cottage Downtown + near Waterfront

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Summary: Citrus Cottage is a modern, single-level cottage that blends coastal comfort and convenience. Enjoy a fully eq ...

    From $194 per night (USD)

    Expedia

    Details
  • Downtown Dunedin Cottage Near Beaches + Breweries
    From $193 per night (USD)

    VRBO

    Downtown Dunedin Cottage Near Beaches + Breweries

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Summary: Experience coastal comfort in this charming Downtown Dunedin cottage, steps from Main Street and a short strol ...

    From $193 per night (USD)

    VRBO

    Details
  • 1 Mile to Honeymoon Island ~Pool ~Putt Putt
    From $547 per night (USD)

    Expedia

    1 Mile to Honeymoon Island ~Pool ~Putt Putt

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    12

    Summary: This house has everything you need for your dream paradise vacation! ~1 Mile to Honeymoon Island ~Indoor Slide ...

    From $547 per night (USD)

    Expedia

    Details
  • Sky Blue Bungalow near the Beach
    From $115 per night (USD)

    VRBO

    Sky Blue Bungalow near the Beach

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    Escape to our charming sky blue bungalow nestled in the heart of Dunedin, where vintage charm meets modern comfort for a ...

    From $115 per night (USD)

    VRBO

    Details
  • 6 · Seaside Artisan Apartment 6
    From $132 per night (USD)

    Expedia

    6 · Seaside Artisan Apartment 6

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    This Airbnb offers a unique experience to stay at a mom and pop style retro motel. The property has total of 10 airbnb’s ...

    From $132 per night (USD)

    Expedia

    Details
  • 9 · Seaside Artisan Apartment 9
    From $93 per night (USD)

    VRBO

    9 · Seaside Artisan Apartment 9

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    This Airbnb offers a unique experience to stay at a mom and pop style retro motel. The property has total of 10 airbnb’s ...

    From $93 per night (USD)

    VRBO

    Details
  • 1 · Sea Side Artisan Apartment 1
    From $101 per night (USD)

    Expedia

    1 · Sea Side Artisan Apartment 1

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    This Airbnb offers a unique experience to stay at a mom and pop style retro motel. There is no lobby for the guests, how ...

    From $101 per night (USD)

    Expedia

    Details
  • 4 · Seaside Artisan Apartment 4
    From $111 per night (USD)

    VRBO

    4 · Seaside Artisan Apartment 4

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    This Airbnb offers a unique experience to stay at a mom and pop style retro motel. The property has total of 10 airbnb’s ...

    From $111 per night (USD)

    VRBO

    Details
  • 7 · Seaside Artisan Apartment 7
    From $91 per night (USD)

    Expedia

    7 · Seaside Artisan Apartment 7

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    This Airbnb offers a unique experience to stay at a mom and pop style retro motel. The property has total of 10 airbnb’s ...

    From $91 per night (USD)

    Expedia

    Details
  • 5 · Seaside Artisan Apartment *Dog Friendly* 5
    From $98 per night (USD)

    VRBO

    5 · Seaside Artisan Apartment *Dog Friendly* 5

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    This Airbnb offers a unique experience to stay at a mom and pop style retro motel. The property has total of 10 airbnb’s ...

    From $98 per night (USD)

    VRBO

    Details
  • 3 · Seaside Artisan Apartment 3
    From $88 per night (USD)

    Expedia

    3 · Seaside Artisan Apartment 3

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    This Airbnb offers a unique experience to stay at a mom and pop style retro motel. There is no lobby for the guests, how ...

    From $88 per night (USD)

    Expedia

    Details
  • 10 · Sea Side Artisan Apartment 10
    From $127 per night (USD)

    VRBO

    10 · Sea Side Artisan Apartment 10

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    This Airbnb offers a unique experience to stay at a mom and pop style retro motel. The property has total of 10 airbnb’s ...

    From $127 per night (USD)

    VRBO

    Details
  • 2 · Seaside Artisan Apartment 2
    From $89 per night (USD)

    Expedia

    2 · Seaside Artisan Apartment 2

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    This Airbnb offers a unique experience to stay at a mom and pop style retro motel. There is no lobby for the guests. How ...

    From $89 per night (USD)

    Expedia

    Details