Guesthouses Tampa

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1,356 guest houses

Close to Siesta key with hot tub, fire pit and butterfly garden

Gulf Gate Estates guest house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Rental types Beach or lakeside relaxation Fishing

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Price per night from

$193

ROYAL REXHOST RESORTS – Madeira Beach Yacht Club (MBYCC)

Madeira Beach guest house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Rental types Beach or lakeside relaxation Fishing

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Price per night from

$172

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Lido Sunshine L

Lido Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

2 of 3 match: Rental types, Beach or lakeside relaxation, Fishing

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Price per night from

$171

Charming Lido Key Beach House 5 min Walk to Beach!

Sarasota house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

2 of 3 match: Rental types, Beach or lakeside relaxation, Fishing

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Price per night from

$410

Huge Renovated pool Home By Lake 10 mins to the Beach

St. Petersburg house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 3 match: Rental types, Beach or lakeside relaxation, Fishing

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Price per night from

$229

#6 Boutique Beach Retreat, Heated Pool, Private Room Outside Access/Corridor

Treasure Island hotel apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 5

2 of 3 match: Rental types, Beach or lakeside relaxation, Fishing

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Price per night from

$345

#11 Boutique Beach Retreat, Heated Pool, Private Room Outside Access/Corridor

Treasure Island hotel apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 7

2 of 3 match: Rental types, Beach or lakeside relaxation, Fishing

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Price per night from

$459

Downtown Largo Cottage

Largo house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

2 of 3 match: Rental types, Beach or lakeside relaxation, Fishing

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Price per night from

$218

Renovated Beachside Condo

Belleair Beach condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

2 of 3 match: Rental types, Beach or lakeside relaxation, Fishing

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Price per night from

$252

Steps to the Beach! Your Beach Getaway Awaits! Your Search Is Over!!

Indian Shores condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 3 hours 36 minutes

2 of 3 match: Rental types, Beach or lakeside relaxation, Fishing

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Price per night from

$458

MODERN CONDO IN GATED COMMUNITY MINUTE FROM BEACH

Clearwater condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

“Great condo” The condo was clean and very well appointed. Edith was reachable and a good communicator. Convenient location to Publix, restaurants, etc. The pool was nice, and gym was basic but usable. I would give the unit itself a 5 rating. However, there were two disappointments with the facility, neither of which has to do with the unit, but impacted our use. Although the pool says they are open dawn to dusk, the gates are locked with chains and padlocks until someone gets there to open it, so swimming and using the gym early in the morning was not an option. Frustrating if you prefer an early workout.

2 of 3 match: Rental types, Beach or lakeside relaxation, Fishing

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Price per night from

$126

Beachfront Condo Steps to Beach! Incredible View of the Gulf of Mexico!

Indian Shores condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 36 minutes

2 of 3 match: Rental types, Beach or lakeside relaxation, Fishing

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Price per night from

$716

The Anchor- A two bedroom cottage minutes walking to beach.

Bradenton Beach cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

2 of 3 match: Rental types, Beach or lakeside relaxation, Fishing

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Price per night from

$373

Bianco Sands - 2 Bedroom - Poolside: By Beachside Management

Siesta Key villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

2 of 3 match: Rental types, Beach or lakeside relaxation, Fishing

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Price per night from

$331

Bianco Sands - 1 Bedroom 1 Bath: By Beachside Management

Siesta Key villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

2 of 3 match: Rental types, Beach or lakeside relaxation, Fishing

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Price per night from

$228

Amazing 2BR Townhome, 2 min walk to beach! Spacious Patio, a Tropical Paradise!

Indian Shores condo

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 36 minutes

2 of 3 match: Rental types, Beach or lakeside relaxation, Fishing

2 of 3 filters match

Price per night from

$373

Bianco Sands - 3 Bedroom 2 Bath: By Beachside Management

Siesta Key villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 3 match: Rental types, Beach or lakeside relaxation, Fishing

2 of 3 filters match

Price per night from

$308

Perfecto's Retreat Unit #1

St. Petersburg cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

2 of 3 match: Rental types, Beach or lakeside relaxation, Fishing

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Price per night from

$343

Sunshine's Hideaway - Beachfront with Private Pool

Indian Rocks Beach house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 14

2 of 3 match: Rental types, Beach or lakeside relaxation, Fishing

2 of 3 filters match

Price per night from

$1,449

3 Palms Retreat - Beachfront

Indian Rocks Beach house

  • 7 bedrooms
  • 4 bathrooms
  • sleeps 16

2 of 3 match: Rental types, Beach or lakeside relaxation, Fishing

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Price per night from

$1,584

Best IRB Location-Close to Restaurants and Shops 2

Indian Rocks Beach apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

“Very lovely place” Large, well-appointed condo with easy walk to gulf. Had all we could ask for, including beach chairs, kids' beach toys and even a wagon to haul the gear. Lovely sitting out at night on the porch. Highlt recommended.

2 of 3 match: Rental types, Beach or lakeside relaxation, Fishing

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Price per night from

$224

Beautiful 2 bedroom condo,mins. drive to beach, pool

Clearwater apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 3 match: Rental types, Beach or lakeside relaxation, Fishing

2 of 3 filters match

Price per night from

$207

One Of The Last One Story Beach Houses

Indian Shores house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

2 of 3 match: Rental types, Beach or lakeside relaxation, Fishing

2 of 3 filters match

Price per night from

$329

Reserve now! Beautiful Siesta key Beach

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 3 match: Rental types, Beach or lakeside relaxation, Fishing

2 of 3 filters match

Price per night from

$345

Waterfront Home away from Home

Dunedin apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 2 hours 35 minutes

2 of 3 match: Rental types, Beach or lakeside relaxation, Fishing

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Price per night from

$109

Cozy carriage apartment in Tarpon Springs

Tarpon Springs apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

“Great stay in Tarpon Springs” What a gem of a place. We had two bedrooms, full kitchen, living area and sun deck. What more could you want! gulf beaches, restaurants etc are all nearby. Super clean with all the necessary amenities including beach chairs, towels etc. The neighborhood is super quiet with lots of old Florida charm. It was three of us traveling including a friend and my husband. We felt right at home! Would highly recommend this place.

Responds fast! avg. 43 minutes

2 of 3 match: Rental types, Beach or lakeside relaxation, Fishing

2 of 3 filters match

Price per night from

$150

Comfy Cozy Cul de Sac Home in Beacon Woods East

Hudson house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 3 match: Rental types, Beach or lakeside relaxation, Fishing

2 of 3 filters match

Price per night from

$135

Jacaranda Artist Retreat

Anna Maria house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 3 match: Rental types, Beach or lakeside relaxation, Fishing

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Price per night from

$219

Waterfront Penthouse Condo on Intercoastal Across from Beach

Indian Shores condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Great views” Great place in a good location and awesome views of the intercoastal. Enjoyed sitting on the patio and watching the boats go by. Would definitely stay there again if i am in the area.

2 of 3 match: Rental types, Beach or lakeside relaxation, Fishing

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Price per night from

$224

“Perfect, as seen on the pics” Was a great pleasure to be there and very helpful information from the owners side. Easy to book and friendly service. We will be back one day, for sure.

2 of 3 match: Rental types, Beach or lakeside relaxation, Fishing

2 of 3 filters match

Price per night from

$328

beautiful condo with magnificent views of mandalay

Clearwater apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

2 of 3 match: Rental types, Beach or lakeside relaxation, Fishing

2 of 3 filters match

Price per night from

$153

A Siesta Tropical Retreat - Island Pool Oasis in Village & 2 blocks to Beach

Siesta Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 9

“Your best choice for location!” We stayed for 10 lovely days in this home and I have to say It was an even better location than I expected. Everything you could want to do is in walking distance or you can walk to the village (maybe a 3 minute walk)and hop in a free taxi . The house is well appointed and beds are very comfortable. We traveled with a 10 yr.old, 11yr. old , and 15 yr. old my 15 yr. old niece slept in the trundle bed and commented on how comfortable the bed was. In the kitchen you will find a drawer full of menus for the many nearby restaurants and information for water activities. I highly recommend parasailing while your there ! Considering how close everything is the street is very quiet and the owners were great to deal with. Thanks Kathi and Grant!

2 of 3 match: Rental types, Beach or lakeside relaxation, Fishing

2 of 3 filters match

Price per night from

$501

Crystal Sands Unit 308 Siesta Key, Florida

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Great Vacation Rental” We have been coming to Siesta Key for our Vacations for years... We have stayed at a number of Units at Crystal Sands, Crescent arms and El Presidente... Crystal Sands Unit 308 is one of the best Units we have stayed at... It has a great view of the Beach and Pool... You can watch the Sunsets and Moonsets right from the Lanai... The Unit is Roomy, Clean and had all the appliances, Dishes and Linens we needed... The Washer\Dryer in the Unit is very convenient... It has a New 60" Hdtv in the Living Room with an incredible picture... Jim left printed instructions for the Hdtv, Washer and Dryer which made it very easy to use the appliances in the Unit... We are looking forward to staying in Crystal Sands Unit 308 again for our next trip to Siesta Key...

2 of 3 match: Rental types, Beach or lakeside relaxation, Fishing

2 of 3 filters match

Price per night from

$431

Home Away Villa

Davenport house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 12

2 of 3 match: Rental types, Beach or lakeside relaxation, Fishing

2 of 3 filters match

Price per night from

$230

Best IRB Location - Close to Restaurants and Shops

Indian Rocks Beach apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

2 of 3 match: Rental types, Beach or lakeside relaxation, Fishing

2 of 3 filters match

Price per night from

$224

Intracoastal Indian Rocks Beach House

Indian Rocks Beach house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

2 of 3 match: Rental types, Beach or lakeside relaxation, Fishing

2 of 3 filters match

Price per night from

$459

Cocoa Villa

Haines City villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

“Vacation to remember” beautiful home, beautiful neighborhood, security guards were very nice, always smiling and greeting us as we enter and exit, The pest control guy was very informative and nice, seems to love his job. The maintenance guy answer questions and followed up on our concerns immediately. Overall I enjoyed our home and would be interested in leasing property out there. Very convenient to all stores and dinning areas

2 of 3 match: Rental types, Beach or lakeside relaxation, Fishing

2 of 3 filters match

Price per night from

$122

Sundown Palm

Kissimmee villa

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 13

2 of 3 match: Rental types, Beach or lakeside relaxation, Fishing

2 of 3 filters match

Price per night from

$345

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