Vacation Rentals & Beach Rentals in Siesta Key

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1,839 beach rentals

From $100/NT,1.5 Mile to Disney ,1808 sq ft 4br/3ba townhome with lake view

Kissimmee apartment

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

“Great location” We had great times in Oakwater, all was perfect! The house is fully equipped, all is clean, new and works perfect!It is an ideal location, close to everything. Near the home are so many great restaurants such as: Bonefish, Longhorn, Golden Corral, Ihop, Bahama Breeze, Buffalo Wild Wings, Flippers Pizza*, Red Lobster and lots more! The super target is within 2 min as well as the Publix.It is also located in very quiet area. There are great sports facilities, tennis court, and the pool area itself is fantastic. We enjoyed it very much and the pool s huge and warm !!! We loved it and will definitely recommend to our friends and family!

Responds fast! avg. 1 hour 27 minutes

Match: Shared outdoor pool (heated) Trampoline

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Price per night from

$121

From $120/nt,5br/3ba townhome with hot tub,Close Disney,Seaworld,Convention Ctr

Kissimmee townhouse

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 12

“Excellent” The house was perfect for our families. Every thing was great. Except the sliding door lock is broken, the glass table is unstable if you have kids and the folding table in the kitchen doesn't have the hinges to be unfolded. I love the house and will return there and refer it to my friends without hesitation.

Responds fast! avg. 1 hour 27 minutes

Match: Shared outdoor pool (heated) Trampoline

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Price per night from

$150

Four Seasons 2 bedroom suite

Miami apartment

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Shared outdoor pool (heated) Trampoline

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Price per night from

$982

ROYAL REXHOST RESORTS – Madeira Beach Yacht Club (MBYCC)

Madeira Beach guest house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Shared outdoor pool (heated) Trampoline

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Price per night from

$173

These homes match some but not all of your filters. Clear all filters

My Orlando home

Celebration apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Trampoline, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$180

Executive Bay Club- great unit, great location!,

Islamorada villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 20 minutes

1 of 2 match: Trampoline, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$206

Fort Myers, Lake View, 2Br $ 2BA, Best Beaches

Iona apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Trampoline, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$81

Royal Harbor - downtown Naples condo

Naples condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Trampoline, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$249

Welcome to our charming and stylish home located at Windsor at westside

Kissimmee house

  • 8 bedrooms
  • 6 bathrooms
  • sleeps 16

1 of 2 match: Trampoline, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$402

Modern, chic & cozy 2br 2ba apartment in Wynwood

Miami apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Trampoline, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$184

COZY RETREAT modern condo near Gulf of Mexico beaches

Clearwater condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

“Fabulous!” Owner was great! Condo is everything you need or want. Every detail is perfect. Pool was just steps away.

1 of 2 match: Trampoline, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$161

Bonita Isles spectacular Hidden Gem in the heart of Bonita Springs/Naples Fl.

Bonita Springs villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Trampoline, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$115

2 bedroom Condo Bay Oaks Siesta Key

Sarasota condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 3

1 of 2 match: Trampoline, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$574

Treviso Bay - Luxury Resort Style Golf Community

Naples apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Trampoline, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$253

Beautiful Lakeview Condo at Falling Waters (Davis Blvd) in Naples Florida

Naples apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 57 minutes

1 of 2 match: Trampoline, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$176

The Vue at Downtown Orlando

Orlando condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Trampoline, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$138

Gorgeous Water View, Condo!Completely Renovated 2015,Wifi

Tierra Verde condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Trampoline, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$201

Direct Beachfront 2 BR Condo on Florida’S Beautiful Gulf Coast!

Holmes Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Trampoline, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$431

Spacious 2nd floor coach home!

Naples condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Trampoline, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$230

Beautiful Secluded Island Home, Great Fishing

Everglades City house

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Trampoline, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$173

Friends and Family close to beaches and more

Fort Myers house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Trampoline, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$127

Beachfront Condo With Weekly Rentals

Fort Myers Beach condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

“Estero Sands was PERFECT!!” Estero Sands was a great place for our family! We've stayed in Ft. Myers many times and this stay was one of the best. The owners that were on site were very nice. The grounds were very well kept. Literally steps to the beach!!! Loved it!!

1 of 2 match: Trampoline, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$327

Vacation Villa EE12

Kissimmee villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Trampoline, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$247

Royal Paradise - Avalon at Clearwater | Minutes to Clearwater Beach

Clearwater apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Trampoline, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$195

1 of 2 match: Trampoline, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$295

Direct Ocean View 2 Bedroom / 2 Bath Condo On Cocoa Beach

Cocoa Beach condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

1 of 2 match: Trampoline, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$210

Vanderbilt Beach Condo Available for the month of April

Vanderbilt Beach condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Trampoline, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$345

Kima 204 Direct Gulf Front in Madeira Beach

Madeira Beach condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

1 of 2 match: Trampoline, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$287

Waterfront Condo

Vero Beach condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Trampoline, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$81

☀Across from Resident's Beach☀2/2 Marco Condo☀

Marco Island condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Trampoline, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$84

“Great stay in Sarasota” My husband and our two daughters spent a wonderful four days in Sarasota. The townhome we stayed in was beautiful and had all the amenities we needed. We spent every day at the beach and relaxed at the townhome in the evenings. We would definitely stay here again and have recommended this place to our family and friends. Thanks Louie!

Responds fast! avg. 2 hours 32 minutes

1 of 2 match: Trampoline, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$435

1 bedroom single story condo near pool

Longboat Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Trampoline, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$295

2 bedroom poolside condo steps from ocean beach and dock on bay

Longboat Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Trampoline, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$426

Key west style unit

Jensen Beach house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Trampoline, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$77

THE CONDO HAS BEEN SEVERELY DAMAGED BY HURRICANE IAN AND IS TEMPORARILY CLOSED.

Sanibel Island condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Trampoline, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$345

THE CONDO HAS BEEN SEVERELY DAMAGED BY HURRICANE IAN AND IS TEMPORARILY CLOSED

Sanibel Island condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Trampoline, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$345

1 bedroom single story ocean view

Longboat Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Trampoline, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$361

Nice St Pete Beach Condo steps from beach and near restaurants

St. Pete Beach condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Trampoline, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$137

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rentals in Siesta Key

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