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From $316 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 $316 per night (USD)
VRBO
From $387 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 $387 per night (USD)
Expedia
From $280 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 $280 per night (USD)
VRBO
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
From $165 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 $165 per night (USD)
VRBO
From $403 per night (USD)
Expedia
SaltyLux16 Heated Saltwater Pool/Near Beach/Island
Bedrooms:
3
Bathrooms:
3
Sleeps:
17
Welcome to your Exquisite Florida Oasis 3/2 Home Retreat. Enjoy privacy w a fenced yard, a sun &mosquito-protected pool ...
From $403 per night (USD)
Expedia
From $697 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 $697 per night (USD)
VRBO
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
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
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
From $347 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 $347 per night (USD)
VRBO
From $581 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 $581 per night (USD)
Expedia
From $228 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 $228 per night (USD)
VRBO
From $103 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 $103 per night (USD)
VRBO
$Endless amenities & great location condo in Palm Harbor.\n\n\n\n$
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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
$Clearwater Beach, Dunedin, Caladesi Island Getaway\n$
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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
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
From $305 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 $305 per night (USD)
Expedia
From $1361 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 $1361 per night (USD)
VRBO
From $494 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 $494 per night (USD)
Expedia
From $180 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 $180 per night (USD)
VRBO
From $260 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 $260 per night (USD)
VRBO
From $296 per night (USD)
VRBO
Heated Pool in Private 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 $296 per night (USD)
VRBO
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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 ...
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Expedia
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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
From $137 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 $137 per night (USD)
VRBO
From $250 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 $250 per night (USD)
VRBO
From $668 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 $668 per night (USD)
Expedia
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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 ...
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VRBO
From $258 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 $258 per night (USD)
Expedia
From $1663 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 $1663 per night (USD)
VRBO
From $516 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 $516 per night (USD)
Expedia
From $176 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 $176 per night (USD)
VRBO
From $162 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 $162 per night (USD)
Expedia
From $237 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 $237 per night (USD)
VRBO
From $110 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 $110 per night (USD)
Expedia
From $1753 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 $1753 per night (USD)
VRBO
$Clearwater 5 minutes from Blue Jays Training Camp !\n Romy's Coastal Cottage$
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
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
From $682 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 $682 per night (USD)
Expedia
From $226 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 $226 per night (USD)
VRBO
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
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
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
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
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
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
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
From $2082 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 $2082 per night (USD)
VRBO
From $1446 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 $1446 per night (USD)
Expedia
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
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
From $1928 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 $1928 per night (USD)
VRBO
$4bd/2br Tiki Bar, King bed, & Pool... amenities galore!\n$
From $437 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 $437 per night (USD)
Expedia
From $526 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 $526 per night (USD)
VRBO
From $491 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 $491 per night (USD)
Expedia
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
From $340 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 $340 per night (USD)
VRBO
From $429 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 $429 per night (USD)
VRBO
From $221 per night (USD)
VRBO
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 $221 per night (USD)
VRBO
From $496 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 $496 per night (USD)
VRBO
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
From $137 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 $137 per night (USD)
VRBO
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
From $360 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 $360 per night (USD)
VRBO
From $199 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 $199 per night (USD)
Expedia
From $216 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 $216 per night (USD)
VRBO
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
From $258 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 $258 per night (USD)
VRBO
From $335 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 $335 per night (USD)
Expedia
From $265 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 $265 per night (USD)
VRBO
From $241 per night (USD)
Expedia
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)
Expedia
From $144 per night (USD)
VRBO
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 $144 per night (USD)
VRBO
From $241 per night (USD)
Expedia
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)
Expedia
From $558 per night (USD)
VRBO
The Oaks at Keene Estate
Bedrooms:
3
Bathrooms:
6
Sleeps:
10
This beautiful estate 6112 sq/ft home is set on over one acre of landscaped grounds. Some features include a swimmin ...
From $558 per night (USD)
VRBO
From $635 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 $635 per night (USD)
VRBO
From $221 per night (USD)
VRBO
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)
VRBO
From $414 per night (USD)
Expedia
3BR Oasis | Sleeps 11 | Heated Pool | Ping Pong!
Bedrooms:
2
Bathrooms:
3
Sleeps:
11
*****AVAILABLE TODAY - (OCTOBER 5, 2025) - BOOK NOW!!! 5⭐⭐⭐⭐⭐ Service & Accommodations! Welcome to our fully remodeled ...
From $414 per night (USD)
Expedia
From $239 per night (USD)
VRBO
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 $239 per night (USD)
VRBO
From $239 per night (USD)
Expedia
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 $239 per night (USD)
Expedia
From $592 per night (USD)
VRBO
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 $592 per night (USD)
VRBO
From $115 per night (USD)
Expedia
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)
Expedia
From $122 per night (USD)
VRBO
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 $122 per night (USD)
VRBO
From $121 per night (USD)
Expedia
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 $121 per night (USD)
Expedia
From $120 per night (USD)
VRBO
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 $120 per night (USD)
VRBO
From $130 per night (USD)
Expedia
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 $130 per night (USD)
Expedia
From $135 per night (USD)
VRBO
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 $135 per night (USD)
VRBO
From $122 per night (USD)
Expedia
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 $122 per night (USD)
Expedia
From $121 per night (USD)
VRBO
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 $121 per night (USD)
VRBO
From $138 per night (USD)
Expedia
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 $138 per night (USD)
Expedia
From $89 per night (USD)
VRBO
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)
VRBO
From $111 per night (USD)
Expedia
8 · Seaside Artisan Apartment 8
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)
Expedia
Click For Pricing
VRBO
Movie Theater |Bowling + Putt Putt|Resort Yard
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Summary: This Luxe house with a resort style backyard has everything you need for a dream vacation in FL! Just mins away ...
Click For Pricing
VRBO
From $190 per night (USD)
Expedia
Mango Tree Cottage on a bike trail
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Have fun with the whole family at this private luxury 1 bedroom house called the Mango Tree cottage, named after the lar ...
From $190 per night (USD)
Expedia
From $500 per night (USD)
VRBO
Luxury Beachfront, Clearwater Beach, Stunning Views, Private Wrap-Around Balcony
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Premium 3-bedroom / 2-bathroom highly sought-after luxury condo directly on Clearwater Beach. Sleeps six. A slice of hea ...
From $500 per night (USD)
VRBO
From $294 per night (USD)
Expedia
Backyard Oasis with only steps to the beach - Comfy, cozy cottage - 3bed/2bath
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Quiet, Comfy and Cozy 3 Bedroom/2 Bath Cottage steps away from the beach. Close enough to bicycle to restaurants and liv ...
From $294 per night (USD)
Expedia
From $215 per night (USD)
VRBO
Sea Board Pool Home - Monthly Vacation Rental
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Unwind in Paradise: Your Clearwater Beach Escape Awaits at Sea Board! Immerse yourself in the Florida sunshine at Sea B ...
From $215 per night (USD)
VRBO
From $1154 per night (USD)
Expedia
Fall Escape - Luxury Private 7BR Lakeside Villa with heated Pool, Putting Green
Bedrooms:
5
Bathrooms:
7
Sleeps:
18
Discover luxury living in this unique lakeside estate. This 7BR spacious villa boasts a large pool deck, outdoor dining ...
From $1154 per night (USD)
Expedia
From $509 per night (USD)
VRBO
Family Paradise: Salt Pool, Hot Tub, XBox & Nature Views!
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Prime Location, Location, Location & Family-Friendly Comfort! All you need is sunscreen! Location, Location, Location & ...
From $509 per night (USD)
VRBO
From $147 per night (USD)
Expedia
Stunning 1/1 Beachfront Oasis at Regatta Beach Club - Gulf Views Galore!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Welcome to your beachfront paradise at the Regatta Beach Club! This updated 1/1 condo on the 3rd floor offers breathtaki ...
From $147 per night (USD)
Expedia

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