
Pinellas Area Rentals

- From $334 per night (USD)
VRBO
Caprice 401 Awesome views|Great location|Walk to everything!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Stay more, SAVE more! We offer lower nightly rates on extended stays from Sept-Mar. No coupon code needed! Just enter yo ...
From $334 per night (USD)VRBO
- From $262 per night (USD)
Expedia
Beachfront location on Pass-A-Grille beach.Walking distance to great restaurants and downtown shops.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Stay right along the main beach area in historic, and beautiful, Pass-A-Grille beach. This beachfront complex has recen ...
From $262 per night (USD)Expedia
- From $269 per night (USD)
VRBO
Emerald Isle 204 Beautiful Updates|Beach Front|Corner Condo|Great location!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Stay more, SAVE more! We offer lower nightly rates on extended stays from Sept-Mar. No coupon code needed! Just enter yo ...
From $269 per night (USD)VRBO
- From $240 per night (USD)
Expedia
Land's End 202-11, Beach front, Close to Pool!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Stay more, SAVE more! We offer lower nightly rates on extended stays from Sept-Mar. No coupon code needed! Just enter yo ...
From $240 per night (USD)Expedia
- From $321 per night (USD)
VRBO
Sunset Villas 3 Million $ VIEWS|2 Balconies|BBQ|pool|Beachfront
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Stay more, SAVE more! We offer lower nightly rates on extended stays from Sept-Mar. No coupon code needed! Just enter yo ...
From $321 per night (USD)VRBO
- From $493 per night (USD)
Expedia
ENDLESS SUMMER! DIRECT BEACH FRONT 3 BEDROOM!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Get ready for a Beautiful Old Florida style vacation with all the conveniences of home! Fantastic 3 Bedroom 2 bath dire ...
From $493 per night (USD)Expedia
- From $220 per night (USD)
VRBO
Gulf and Intracoastal Views! WALK TO 4 OR 5 RESTAURANTS & MORE!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
The Marquise is located at the south end of the Indian Rocks Business triangle. Very easy walk to nearby restopaaurants ...
From $220 per night (USD)VRBO
- From $251 per night (USD)
Expedia
ENDLESS SUMMER! DIRECT GULF FRONT COTTAGE STYLE PROPERTY! UPDATED!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
***** EVERYTHING UPDATED AND NEW***** Fantastic 1 Bedroom direct Beach Front cottage style vacation rental! Beautifull ...
From $251 per night (USD)Expedia
- From $318 per night (USD)
VRBO
Trillium 5C Stunning beach front condo, beautifully remodeled w|amazing views
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
**NOTICE AS OF 9/26/25 - ELEVATOR CURRENTLY OUT OF SERVICE - NO ETA ON COMPLETION*** Stay more, SAVE more! We offer low ...
From $318 per night (USD)VRBO
- From $333 per night (USD)
Expedia
Sunset Villas 1 Amazing pool|Beachfront|BBQ|2 balconies-only 4 condos!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Stay more, SAVE more! We offer lower nightly rates on extended stays from Sept-Mar. No coupon code needed! Just enter yo ...
From $333 per night (USD)Expedia
- From $166 per night (USD)
VRBO
Premier unit on top floor w/ fantastic amenities! Land's End 1-404
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Stay more, SAVE more! We offer lower nightly rates on extended stays from Sept-Mar. No coupon code needed! Just enter yo ...
From $166 per night (USD)VRBO
- From $167 per night (USD)
Expedia
Land's End 203 bldg 1~ Cute, Coastal
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Stay more, SAVE more! We offer lower nightly rates on extended stays from Sept-Mar. No coupon code needed! Just enter yo ...
From $167 per night (USD)Expedia
- From $151 per night (USD)
VRBO
Land's End 204 building 1 Beautiful New Floors|Near Pool|Lounge chairs!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Stay more, SAVE more! We offer lower nightly rates on extended stays from Sept-Mar. No coupon code needed! Just enter yo ...
From $151 per night (USD)VRBO
- From $298 per night (USD)
Expedia
Villa Madeira 505 | Beach FRONT|Walk to John's Pass!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Stay more, SAVE more! We offer lower nightly rates on extended stays from Sept-Mar. No coupon code needed! Just enter yo ...
From $298 per night (USD)Expedia
- From $158 per night (USD)
VRBO
Land's End 304 building 1, Premier beautifully updated, Waterfront with view!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Stay more, SAVE more! We offer lower nightly rates on extended stays from Sept-Mar. No coupon code needed! Just enter yo ...
From $158 per night (USD)VRBO
- From $337 per night (USD)
Expedia
Villa Madeira 408 Beautifully updated, Walk to John's Pass, Beach front!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Stay more, SAVE more! We offer lower nightly rates on extended stays from Sept-Mar. No coupon code needed! Just enter yo ...
From $337 per night (USD)Expedia
- From $253 per night (USD)
VRBO
Land's End 303 building 6 Gorgeous 3rd floor remodeled beach front condo!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Stay more, SAVE more! We offer lower nightly rates on extended stays from Sept-Mar. No coupon code needed! Just enter yo ...
From $253 per night (USD)VRBO
- From $298 per night (USD)
Expedia
Trillium 4B Gulf Front Condo with Private Balcony|Amazing Beach Views|Pool!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
**NOTICE AS OF 9/26/25 - ELEVATOR CURRENTLY OUT OF SERVICE - NO ETA ON COMPLETION*** Stay more, SAVE more! We offer low ...
From $298 per night (USD)Expedia
- From $248 per night (USD)
VRBO
☀Top Floor🏖️Beachfront🌴 Emerald Isle 601🐬Heated Pool🌊Directly on the Sand
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Stay more, SAVE more! We offer lower nightly rates on extended stays from Sept-Mar. No coupon code needed! Just enter yo ...
From $248 per night (USD)VRBO
- From $319 per night (USD)
Expedia
Land's End 402 building 7 Top Floor Beach front with Awesome Views!!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Stay more, SAVE more! We offer lower nightly rates on extended stays from Sept-Mar. No coupon code needed! Just enter yo ...
From $319 per night (USD)Expedia
- From $236 per night (USD)
VRBO
Land's End 204 bldg 7~ Beachfront, Cute!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Stay more, SAVE more! We offer lower nightly rates on extended stays from Sept-Mar. No coupon code needed! Just enter yo ...
From $236 per night (USD)VRBO
- From $266 per night (USD)
Expedia
Land's End 404 bldg 9~ Next to Pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Stay more, SAVE more! We offer lower nightly rates on extended stays from Sept-Mar. No coupon code needed! Just enter yo ...
From $266 per night (USD)Expedia
- From $178 per night (USD)
VRBO
Sunset Chateau 506 ~Beach Front
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Stay more, SAVE more! We offer lower nightly rates on extended stays from Sept-Mar. No coupon code needed! Just enter yo ...
From $178 per night (USD)VRBO
- From $351 per night (USD)
Expedia
Trillium 1A South Corner|Amazing Remodel|Stunning View from balcony!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
**NOTICE AS OF 9/26/25 - ELEVATOR CURRENTLY OUT OF SERVICE - NO ETA ON COMPLETION*** Stay more, SAVE more! We offer low ...
From $351 per night (USD)Expedia
- From $427 per night (USD)
VRBO
COMPLETELY COASTAL! PRIVATE HEATED POOL! 3 BR 2 BA Close to John's Pass!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
*****************POOL AND POOL EQUIPMENT FUNCTIONING AND GATE REPAIRED/REPLACED******************* This COMPLETELY COAS ...
From $427 per night (USD)VRBO
- From $332 per night (USD)
Expedia
Arie Dam 202 - Beach Front|Amazing sunsets|Private balcony|Near John's Pass!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Stay more, SAVE more! We offer lower nightly rates on extended stays from Sept-Mar. No coupon code needed! Just enter yo ...
From $332 per night (USD)Expedia
- From $278 per night (USD)
VRBO
Emerald Isle 103 Beach Front Condo, Coastal décor, Pool, stunning views!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Stay more, SAVE more! We offer lower nightly rates on extended stays from Sept-Mar. No coupon code needed! Just enter yo ...
From $278 per night (USD)VRBO
- From $286 per night (USD)
Expedia
Land's End 306 building 8 Beach front corner condo, completely updated
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Stay more, SAVE more! We offer lower nightly rates on extended stays from Sept-Mar. No coupon code needed! Just enter yo ...
From $286 per night (USD)Expedia
- From $188 per night (USD)
VRBO
Land's End 303 building 8, Beautiful Gulf Front Condo With Private Balcony
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Stay more, SAVE more! We offer lower nightly rates on extended stays from Sept-Mar. No coupon code needed! Just enter yo ...
From $188 per night (USD)VRBO
- From $190 per night (USD)
Expedia
Land's End 202 building 9 Beachfront Condo w| balcony, close to pool!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Stay more, SAVE more! We offer lower nightly rates on extended stays from Sept-Mar. No coupon code needed! Just enter yo ...
From $190 per night (USD)Expedia
- From $259 per night (USD)
VRBO
Amadeus 5 Great water views|Central location|Walk to Beach!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Stay more, SAVE more! We offer lower nightly rates on extended stays from Sept-Mar. No coupon code needed! Just enter yo ...
From $259 per night (USD)VRBO
- From $277 per night (USD)
Expedia
Villa Madeira 307 Paradise! Many updates in this awesome Beach Front condo!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Stay more, SAVE more! We offer lower nightly rates on extended stays from Sept-Mar. No coupon code needed! Just enter yo ...
From $277 per night (USD)Expedia
- From $258 per night (USD)
VRBO
Land's End 302 building 10 Complete remodel|Beach front|close to pool!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Stay more, SAVE more! We offer lower nightly rates on extended stays from Sept-Mar. No coupon code needed! Just enter yo ...
From $258 per night (USD)VRBO
- From $204 per night (USD)
Expedia
Land's End 204 building 8 Complete Remodel, Beach Front, Amazing Views!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Stay more, SAVE more! We offer lower nightly rates on extended stays from Sept-Mar. No coupon code needed! Just enter yo ...
From $204 per night (USD)Expedia
- From $234 per night (USD)
VRBO
Inviting 4br 2ba Home, Large Screen Porch & Backyard, 2 miles from the Beach!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
This charming home features stylish terrazzo floors, an oversized screen porch, and a spacious backyard. This lovely ho ...
From $234 per night (USD)VRBO
- From $263 per night (USD)
Expedia
UPDATED OLD FLORIDA STYLE COTTAGE DIRECTLY ON THE BEACH!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
***** EVERYTHING UPDATED AND NEW***** Beautiful direct Beach Front cottage style property. This lovely 1 bedroom offer ...
From $263 per night (USD)Expedia
- From $165 per night (USD)
VRBO
3BR/2.5Bath, Award winning ARCHITECT designed Home Nr DOWNTOWN & Pier
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Our home is architect designed bungalow style home. Conveniently located in the center of town, right off I-275 with eas ...
From $165 per night (USD)VRBO
- From $382 per night (USD)
Expedia
3b 3b Beach View Balcony 1500 sq ft Crimson #103
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Crimson on the Gulf #103 - It doesn't get much better than this when visiting southern Madeira Beach! Enjoy first class ...
From $382 per night (USD)Expedia
- From $418 per night (USD)
VRBO
Spacious beachfront comfortable 3-bedroom 2-bath. Heated pool. Great location for a FL vacation.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Spacious, and completely outfitted condo for your Florida vacation. Walking distance to John's Pass Village. This outs ...
From $418 per night (USD)VRBO
- From $236 per night (USD)
Expedia
Harbor Mist - Fresh & Friendly in Marina District Private Oasis
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Bright, clean, and thoughtfully appointed, Harbor Mist brings new meaning to home-away-from-home. This Gulfport gem is t ...
From $236 per night (USD)Expedia
- From $362 per night (USD)
VRBO
Direct Beachfront - 3b 2b - Beach Place #411
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Beach Place #411 - Please note: The elevator in this building is scheduled to be out of service for maintenance starting ...
From $362 per night (USD)VRBO
- From $238 per night (USD)
Expedia
The Best View in the Building! Waterfront Resort in the Heart of Madeira Beach.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
A superb view from your private balcony in this new resort situated with easy walking distance to Johns Pass Village, an ...
From $238 per night (USD)Expedia
- From $404 per night (USD)
VRBO
Direct Beachfront Luxury 3b 2b - Beach Place #106
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Beach Place #106 - Please note: The elevator in this building is scheduled to be out of service for maintenance starting ...
From $404 per night (USD)VRBO
- From $270 per night (USD)
Expedia
Directly on the Beach. Walk to Shops, Dining & Activities. Heated Pool & Hot Tub. St Pete Beach!
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 4
Fantastic Location on Beautiful St. Pete Beach! Gulf Strand is situated on the sand in the heart of St. Pete Beach. Wal ...
From $270 per night (USD)Expedia
- From $301 per night (USD)
VRBO
Spacious corner unit on Pass-A-Grille Beach. Heated pool. Enjoy the best the area has to offer.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
This ground floor condo is located directly across from the beautiful award winning beaches of St. Pete Beach. At Pass- ...
From $301 per night (USD)VRBO
- From $426 per night (USD)
Expedia
Ocean Views - Updated 3/2 - Beach Place #207
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Beach Place #207 - Please note: The elevator in this building is scheduled to be out of service for maintenance starting ...
From $426 per night (USD)Expedia
- From $386 per night (USD)
VRBO
Beach Front Balcony - Beach Place #107
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Beach Place #107 - Please note: The elevator in this building is scheduled to be out of service for maintenance starting ...
From $386 per night (USD)VRBO
- From $278 per night (USD)
Expedia
Great Value, Great Location on Madeira Beach. Beachfront Building Across From Johns Pass Village.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Sandy Shores is located on the sugary sand beaches of Madeira Beach. Great swimming, fishing, and directly across from J ...
From $278 per night (USD)Expedia
- From $923 per night (USD)
VRBO
Breezy ‘White Sands House’ Steps to Gulf Shore!
- Bedrooms:
- 3
- Bathrooms:
- 7
- Sleeps:
- 18
Let your dream beach vacation become a reality when you book a stay at the 'White Sands House,' a 7-bedroom, 3-bath Clea ...
From $923 per night (USD)VRBO
- From $371 per night (USD)
VRBO
'Driftwood Beach Suite' - Walk to Clearwater Bch
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Sink your toes into the pristine white sands of Florida's Gulf Coast when you stay at 'Driftwood Beach Suite,' a 2-bedro ...
From $371 per night (USD)VRBO
- From $285 per night (USD)
VRBO
'Sea Turtle Suite' Condo w/ Clearwater Beach Views
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Find your own slice of Florida paradise at 'Sea Turtle Suite,' a 1-bedroom, 1-bath vacation rental nestled along the cal ...
From $285 per night (USD)VRBO
- From $312 per night (USD)
Expedia
Tarpon House - Center Street
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
The historic Tarpon House built over 100 years ago as the original Tarpon Inn. Spoil yourself with not only the home’s ...
From $312 per night (USD)Expedia
- From $174 per night (USD)
VRBO
Treasure Island Cottage, Near Boardwalk & Beach!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
This vibrant 1-bedroom, 1-bathroom cottage provides a seamless Treasure Island retreat for those looking to enjoy the be ...
From $174 per night (USD)VRBO
- From $290 per night (USD)
Expedia
Steps to Beach & Tranquility, #2 Quaint Apartment Steps Away from Beach
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
A charming Florida apartment, less than 100 yards to the gorgeous, white sand beaches of the Gulf of Mexico. Comfortably ...
From $290 per night (USD)Expedia
- Click For Pricing
VRBO
2/2 Condo on the intercoastal with beach access across the street
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Our condo is located at Golden Shores Condominiums in Indian Shores, Florida. It is available as a seasonal rental Janua ...
Click For PricingVRBO
- From $414 per night (USD)
Expedia
Fantastic Beachfront Location. Beachfront Heated Pool. Top Floor Balcony. Spacious and Comfortable.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
The Las Brisas Resort Condominiums are located alongside the sugary white sands of Madeira Beach, and are situated withi ...
From $414 per night (USD)Expedia
- From $262 per night (USD)
VRBO
John's Pass Updated 2B/2B - Beach Place #102
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Beach Place #102 - Remodeled, 2 bedroom, 2 bathroom condo complete with balcony view of popular John's Pass in southern ...
From $262 per night (USD)VRBO
- From $190 per night (USD)
Expedia
John's Pass - Beach Location - Beach Place #200
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Beach Place #200 - #200 is a spacious 1 bedroom, 1 bath rental property near everything, including popular John's Pass V ...
From $190 per night (USD)Expedia
- From $480 per night (USD)
VRBO
Stunning Views, Outstanding Location. Direct Beach Access. Plenty of Space For The Entire Family!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Walk into this beachfront paradise home and sail into another world. The Admirals Townhouse is a rare find on a pristine ...
From $480 per night (USD)VRBO
- From $252 per night (USD)
Expedia
Best Location on the Beach. Top Resort, Big Savings!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Location, Location! On The Beach and Across from John's Pass. Beautiful two bedroom condo in fabulous Madeira Norte. W ...
From $252 per night (USD)Expedia
- From $238 per night (USD)
VRBO
Poolside 2nd Floor 2b 2b - Surf Song #225
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Surf Song #225 - Warm and inviting with a tropical feel, this 2 bedroom, 2 bath condo at Surf Song Resort is ready for y ...
From $238 per night (USD)VRBO
- From $328 per night (USD)
Expedia
Beachfront Condo Directly Across from Johns Pass Village. Excellent Location!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Sandy Shores is located on the sugary sand beaches of Madeira Beach. Great swimming, fishing, and directly across from ...
From $328 per night (USD)Expedia
- From $160 per night (USD)
VRBO
1br 1b Beach View - King - Surf Song #333
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Surf Song #333 - Bright and spacious 1 bedroom, 1 bath condo with all the amenities right here at 333 Surf Song! Decorat ...
From $160 per night (USD)VRBO
- From $384 per night (USD)
Expedia
Luxury Unit - Top Floor Balcony - Crimson #302
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Crimson on the Gulf #302 - Memories are made here! | This beautiful condo boasts the best Gulf view in the complex! It's ...
From $384 per night (USD)Expedia
- From $274 per night (USD)
VRBO
5th Floor, Corner Penthouse w/ Amazing Beachfront Views! 2 King Beds, Ideal for Large Families.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Amazing beachfront views from this corner unit Penthouse Condo. Top floor penthouse condo features a wrap-around west f ...
From $274 per night (USD)VRBO
- From $292 per night (USD)
Expedia
Beach View - Balcony - 3b 2b - Beach Place #305
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Beach Place #305 - Please note: The elevator in this building is scheduled to be out of service for maintenance starting ...
From $292 per night (USD)Expedia
- From $281 per night (USD)
VRBO
Sea Breeze 602 is a Silver Tier 2 - bedroom 2 bath Gulf Front Condo!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Value Rated and Priced- Vacation Rental 602 is SILVER Tier WITH BRAND NEW RENOVATIONS. 602 is a spacious, two bedroom ...
From $281 per night (USD)VRBO
- From $329 per night (USD)
Expedia
Sea Breeze 207 is a Gold Tier 2 - bedroom 2 bath Gulf Front Condo
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Recently Updated-Home away from home- Vacation Rental 207 is Gold Tier. 207 is directly beachfront and located on the se ...
From $329 per night (USD)Expedia
- From $264 per night (USD)
VRBO
Free Daily Dolphin Show from your Private Balcony! Great Location. Great Condo!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Fantastic location, fantastic condo, and directly on the beach! This beachfront complex is located directly across th ...
From $264 per night (USD)VRBO
- From $492 per night (USD)
Expedia
Spectacular Four Bedroom Townhouse on the Beach. Incredible Views!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Walk into this beachfront paradise home and sail into another world. The Captains Townhouse is a rare find on a pristin ...
From $492 per night (USD)Expedia
- From $265 per night (USD)
VRBO
Exceptional View. Excellent Location. Heated Pool and Hot Tub. Close to Shopping and Restaurants.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Enjoy perfect sunset views from this large recently renovated Gulf front condo. Ocean Sands is located on the soft suga ...
From $265 per night (USD)VRBO
- From $385 per night (USD)
Expedia
Beachfront - Ocean Views - Beach Place #108
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Beach Place #108 - Please note: The elevator in this building is scheduled to be out of service for maintenance starting ...
From $385 per night (USD)Expedia
- From $180 per night (USD)
VRBO
Quiet Cottage < 1/2 Mi to Gulf Coast & Boardwalk!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
This 2-bedroom, 1-bath cottage provides a cozy Treasure Island getaway for 4 guests. A fully furnished interior, outdoor ...
From $180 per night (USD)VRBO
- From $181 per night (USD)
Expedia
Great Location on Sunset Beach. Private, Peaceful Accommodations. Full Interior Renovation.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Gulf Spray is located on the Southern end of Sunset Beach away from all the crowds and noise. The building sits across ...
From $181 per night (USD)Expedia
- From $312 per night (USD)
VRBO
Fantastic Beachfront Resort. Extra Roomy and Comfortable.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Fantastic Location in the Heart of Madeira Beach. Walking distance to shopping, restaurants, and watersports. The Las ...
From $312 per night (USD)VRBO
- From $377 per night (USD)
Expedia
Awesome Beach Place 3 Bedroom/2 Bath RIGHT ON THE BEACH-right next to Johns Pass
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Our 3BR at Beach Place Resorts (at John's Pass) is available along with our 2BR in the same complex! A FANTASTIC unit ...
From $377 per night (USD)Expedia
- From $324 per night (USD)
VRBO
Prime location, comfort, and sunset views – your perfect getaway awaits!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Fantastic Value in this Updated Beachfront Resort Sea Breeze Condominiums is located centrally on beautiful Madeira Bea ...
From $324 per night (USD)VRBO
- From $309 per night (USD)
Expedia
Spacious Corner Unit Overlooking the Pool, Parking. Free Fun & Great Location!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Our condo at the beautiful and modern Las Brisas resort delivers the perfect blend of home and vacation that you've been ...
From $309 per night (USD)Expedia
- From $413 per night (USD)
VRBO
Relaxation. Sunsets. Space. Perfect Vacation. Beachfront Balcony & Free Fun Activities!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
This large, beachfront, updated condo is setup perfectly for your Florida vacation. The master bedroom is furnished wit ...
From $413 per night (USD)VRBO
- From $294 per night (USD)
Expedia
Corner Unit Penthouse in Beachfront Ocean Sands Resort. Incredible View. Pool & Hot Tub. Near Shops.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
The Best on the Beach! The Ocean Sands complex is located conveniently at the North end of Madeira Beach, with easy a ...
From $294 per night (USD)Expedia
- From $261 per night (USD)
VRBO
Incredible View from Huge, Private Balcony! 2 King Bedrooms, Free Wifi, Upscale Building w/ Pool.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Incredible View from your Huge Private Balcony --Over 200 sq. ft. of balcony with plenty of room for lounging in the su ...
From $261 per night (USD)VRBO
- From $338 per night (USD)
Expedia
Comfortable Top Floor Unit Overlooking the Gulf. Incredible View. Great Resort.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Spend your vacation at this three bedroom top floor condo on the Beach! Furnishing updates 2023. The Villa Madeira Reso ...
From $338 per night (USD)Expedia
- From $292 per night (USD)
VRBO
Great Value in a Beachfront Condo. Walk Over to Johns Pass and Step Out the Door to the Beach.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Sandy Shores is located on the sugary sand beaches of Madeira Beach. Great swimming, fishing, and directly across from J ...
From $292 per night (USD)VRBO
- From $226 per night (USD)
Expedia
Great Value & Location. Pool & Tickets to Attractions.
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 4
This spacious top floor unit in Madeira Beach has been completely refurnished, and is fresh and ready for your Florida b ...
From $226 per night (USD)Expedia
- From $332 per night (USD)
VRBO
Sea Oats 403 is a 3- bedroom 2 bath Gulf Front Condo at a Great Price!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Value Rated and Value Priced- Home away from home- Vacation Rental Sea Oats 403 is a Bronze Tier condo located in Reding ...
From $332 per night (USD)VRBO
- From $415 per night (USD)
Expedia
Beachfront Condo Located In the Heart of Madeira Beach. All Updated. Stunning Views!!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Large Private Beachfront Balcony overlooking pristine Madeira Beach and Gulf of Mexico. Enjoy the daily Dolphin show, me ...
From $415 per night (USD)Expedia
- From $264 per night (USD)
VRBO
Tyn & Marty's Old-Fashioned Beach Cottage
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Clean, classic, uncluttered and one of the best locations in Gulfport! Retro original kitchen that has been tastefully u ...
From $264 per night (USD)VRBO
- From $312 per night (USD)
Expedia
Front Row Seat to World Class Sunsets. Beachfront and Across from Johns Pass Village.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Sandy Shores is located on the sugary sand beaches of Madeira Beach. Great swimming, fishing, and directly across from J ...
From $312 per night (USD)Expedia
- From $283 per night (USD)
VRBO
501S Sunset Vistas. Fantastic Beachfront Resort. Corner Unit with Double Balconies.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Corner Unit with Double Balconies. Beachfront Resort. Stay in one of the few units in Sunset Vistas with two balconies. ...
From $283 per night (USD)VRBO
- From $273 per night (USD)
Expedia
Direct Gulf View Upgraded Condo. Amazing Views! Pool, Amenities and Reserved Parking
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Relax and unwind in the peaceful and meticulously maintained grounds of the Lands End Resort in Treasure Island. With a ...
From $273 per night (USD)Expedia
- From $301 per night (USD)
VRBO
Great Location and Value! Private Balcony & Gulf View. Pools, Cafe, Bar, Fitness Center & Parking
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Luxury with All The Amenities. Beachfront Suite with Private Balcony. Sunset Vistas is located just south of John's Pas ...
From $301 per night (USD)VRBO
- From $293 per night (USD)
Expedia
Overlooking the Pool and Beach - Fantastic Value ~ Pool ~ Amenities Great Location
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Stay at one of the best updated locations along the beach. This beachfront condo has been beautifully upgraded througho ...
From $293 per night (USD)Expedia
- From $284 per night (USD)
VRBO
Beachfront Corner Unit ~ Pool ~ Private Balcony ~ Fully Equipped Kitchen ~ Heart of Treasure Island
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Located in the heart of Treasure Island, and on the edge of the widest and most picturesque stretch of beach in the area ...
From $284 per night (USD)VRBO
- From $284 per night (USD)
Expedia
Gulf Views from Balcony. Heated Pool. Beautiful Property Directly Across from the Beach!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Modern and Elegant Resort. This small (36 units), peaceful, and private building boasts some of the most outstanding vie ...
From $284 per night (USD)Expedia
- From $272 per night (USD)
VRBO
Treasure Island Premier Resort. Beautiful Pools. On Site Cafe. Gulf View. Great Value!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Gulf View Condo. Great Value! Experience the Ultimate Florida Gulf Vacation! Highlights: -- 2-bedroom condo in the Sunse ...
From $272 per night (USD)VRBO
- From $306 per night (USD)
Expedia
Amazing View from this Two Bedroom Beachfront Suite. Two Balconies! Great Value!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Stay at one of the only two bedroom suites at the Island Inn Resort. This large beachfront condo joins two separate sta ...
From $306 per night (USD)Expedia
- From $225 per night (USD)
VRBO
Hidden Oasis Guest Apt+Kg Bd 2bikes/close DT
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 3
Escape to the heart of St. Petersburg, where this stunning 2nd story 1.5 bedroom 1 bath guest rental awaits you. With it ...
From $225 per night (USD)VRBO
- From $351 per night (USD)
Expedia
Gorgeous Sunset Views from Sand Castle 3 Condo. 3/2, heated pool, beachfront
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Our condo was fully renovated in 2015 with a refresh in 2025: Tile floors throughout living area and primary bedroom, ne ...
From $351 per night (USD)Expedia
- From $551 per night (USD)
VRBO
Cozy and friendly. All is Well - no damage
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
This quaint two-bedroom 'home away from home' is on a residential street, just 75 steps off the serene, white sands of N ...
From $551 per night (USD)VRBO
- From $412 per night (USD)
Expedia
Dog-Friendly Home with High-Speed WiFi and Central AC - Snowbird-Friendly
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Sol Mate Beach Cottage Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter ...
From $412 per night (USD)Expedia