Guesthouses Tampa

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1,128 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 Water sports

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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 Water sports

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Price per night from

$172

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Perfecto's Retreat Unit #1

St. Petersburg cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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

2 of 3 filters match

Price per night from

$343

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, Water sports

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Price per night from

$344

La Buena Vida II at Captains Cove, Indian Shores, Florida - Come, relax, enjoy!

Indian Shores apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Very clean and comfortable. Walking distance to everywhere and a great view” Great place to stay. I felt very comfortable and relaxed, this place has a very beachy relaxing vibe in a prime location. You literally do not have to drive anywhere while you're here, everything I wanted was in walking distance!

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

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Price per night from

$172

Jacaranda Artist Retreat

Anna Maria house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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

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Price per night from

$218

Geodesic Dome

Holiday apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

“Will and already have recomend to others.” Lots of fun places to see and eat at nearby. Sharon and Ralph made sure we had everything we needed.

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

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Price per night from

$230

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, Water sports

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Price per night from

$430

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, Water sports

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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, Water sports

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Price per night from

$207

1 Bedroom Madeira Beach Cottage

Madeira Beach condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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

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Price per night from

$155

4 Bedroom 3 bath Luxury Villa

Davenport villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

“Amazing” Our stay at this property was perfect. Loved the pool and games room. The house was the perfect size for our group.

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

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Price per night from

$174

IRB Getaway - Cute Private 1/2 a duplex steps from the beach

Indian Rocks Beach apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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

2 of 3 filters match

Price per night from

$195

Westgate Town Center

Kissimmee hotel apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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

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Price per night from

$201

Peace and Quiet in Gated Community on Boca Ciega Bay

Gulfport apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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

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Price per night from

$77

BEACH FRONT, GROUND FLOOR CONDO #1, 1 BDRM , PRIVATE, W/LARGE PATIO AND GARDEN

Treasure Island condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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

2 of 3 filters match

Price per night from

$327

Beach Front 3 Bedroom Condo with Beautiful Ocean Views

Indian Rocks Beach condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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

2 of 3 filters match

Price per night from

$516

Apartment close to Disney parks

Kissimmee apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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

2 of 3 filters match

Price per night from

$183

Holiday Inn Club Vacations At Orange Lake Resort

Orlando villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

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

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Price per night from

$215

September Fall Fun in the Sun Mickeys Place - Wiltshire Villa

Loughman house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

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

2 of 3 filters match

Price per night from

$213

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

2 of 3 filters match

Price per night from

$402

Flamingo Love Apartment by the beach

Treasure Island house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 2 hours 3 minutes

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

2 of 3 filters match

Price per night from

$183

Stunning Beach View From Private Deck

Indian Rocks Beach condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 2 hours 3 minutes

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

2 of 3 filters match

Price per night from

$458

Stylish Mystic Home I Hot tub, Patio, Grill, Beach

Largo house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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

2 of 3 filters match

Price per night from

$127

Dream beach, pool/spa retreat!

Siesta Key house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 9

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

2 of 3 filters match

Price per night from

$344

Four Shores # 4 2,000 SqFt Condo w/ Private Indoor Poolside Cabana

Indian Shores condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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

2 of 3 filters match

Price per night from

$602

Pelican Cove

Indian Rocks Beach house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

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

2 of 3 filters match

Price per night from

$274

BEACH-FRONT! July- Aug 2024 Availability!

Clearwater condo

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

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

2 of 3 filters match

Price per night from

$84

SPECIAL! $650 8/24 - 8/31. PRIME LOCATION AMI DIRECTLY ON BEACH HEATED POOL

Bradenton Beach house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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

2 of 3 filters match

Price per night from

$287

Steps to the Beach

Holmes Beach condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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

2 of 3 filters match

Price per night from

$164

SPECTACULAR OCEAN VIEW WITH BALCONY

Indian Rocks Beach condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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

2 of 3 filters match

Price per night from

$401

TRANQUIL WHILE BEAUTIFUL CONDO - Close to Bucs stadium

Tampa condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 2 hours 7 minutes

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

2 of 3 filters match

Price per night from

$229

Elegant Waterfront Condo La Bella Vita

Tampa condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 2 hours 7 minutes

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

2 of 3 filters match

Price per night from

$230

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

2 of 3 filters match

Price per night from

$333

Gorgeous house in the heart of St. Pete Beach!

St. Pete Beach house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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

2 of 3 filters match

Price per night from

$127

Lido Beach Villa, 1.2k sf, 1 block to the beach

Lido Key villa

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

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

2 of 3 filters match

Price per night from

$184

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, Water sports

2 of 3 filters match

Price per night from

$501

Casa Del Mar - Tampa/ Rocky Point

Tampa condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 2 hours 7 minutes

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

2 of 3 filters match

Price per night from

$229

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