Vacation Rentals & Beach Rentals in Siesta Key

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500 beach rentals

Four Seasons 2 bedroom suite

Miami apartment

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Sea view Trampoline

All filters match

Price per night from

$981

ROYAL REXHOST RESORTS – Madeira Beach Yacht Club (MBYCC)

Madeira Beach guest house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Sea view Trampoline

All filters match

Price per night from

$172

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Paradise On Lake Harris Apt #102

Leesburg apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Sea view, Trampoline

1 of 2 filters match

Price per night from

$214

Paradise On Lake Harris Apt #201

Leesburg apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Sea view, Trampoline

1 of 2 filters match

Price per night from

$202

Paradise On Lake Harris Apt #101

Leesburg apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Sea view, Trampoline

1 of 2 filters match

Price per night from

$239

Paradise On Lake Harris Apt #202

Leesburg apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Sea view, Trampoline

1 of 2 filters match

Price per night from

$225

Paradise On Lake Harris # R.V.

Leesburg caravan/mobile home

  • 1 bedroom
  • 2 bathrooms
  • sleeps 10

1 of 2 match: Sea view, Trampoline

1 of 2 filters match

Price per night from

$167

SunnyDay

Kissimmee apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 5

Responds fast! avg. 16 minutes

1 of 2 match: Sea view, Trampoline

1 of 2 filters match

Price per night from

$132

The Harmony Oaks Homestead - Florida Cottage Rental

Brooksville cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 23 minutes

1 of 2 match: Sea view, Trampoline

1 of 2 filters match

Price per night from

$206

Luxury Miami Oasis Villa (Near Beach & Airport)

Kendall West house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

1 of 2 match: Sea view, Trampoline

1 of 2 filters match

Price per night from

$689

Enchanted Hideaway: 20 Min Away from Disney World and Unforgettable Experiences!

Intercession City house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

1 of 2 match: Sea view, Trampoline

1 of 2 filters match

Price per night from

$230

Casa de Cox

Southwest Ranches house

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 14

1 of 2 match: Sea view, Trampoline

1 of 2 filters match

Price per night from

$802

Vacation Rental Near Hard Rock Hollywood

Hollywood house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Sea view, Trampoline

1 of 2 filters match

Price per night from

$401

Near Disney, 5 Star Princess Themed Home and Resort

Kissimmee house

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 14

1 of 2 match: Sea view, Trampoline

1 of 2 filters match

Price per night from

$658

BEST PARADAISE ORLANDO

Clermont house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

1 of 2 match: Sea view, Trampoline

1 of 2 filters match

Price per night from

$264

172 VD - Blissful Haven: Serene Retreat

Loughman house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

Responds fast! avg. 3 hours 40 minutes

1 of 2 match: Sea view, Trampoline

1 of 2 filters match

Price per night from

$89

BSV3225 PROMO Luxury 9 Bed 6 Bath in Windsor Island

Four Corners house

  • 9 bedrooms
  • 6 bathrooms
  • sleeps 19

1 of 2 match: Sea view, Trampoline

1 of 2 filters match

Price per night from

$205

Beach Dreams "Tangerine Dreams Villa "

Bradenton Beach cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

1 of 2 match: Trampoline, Sea view

1 of 2 filters match

Price per night from

$344

Beach Dreams "DreamBoat Villa"

Bradenton Beach apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 5

1 of 2 match: Trampoline, Sea view

1 of 2 filters match

Price per night from

$487

Windsor Palms 4/3 Pr. Pl., Hot Tub, Jacuzzi/Games

Kissimmee house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

“Amazing house!” We have amazing family time! This house is excellent with great location! We'll be back soon! I recommend

1 of 2 match: Sea view, Trampoline

1 of 2 filters match

Price per night from

$177

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

1 of 2 match: Sea view, Trampoline

1 of 2 filters match

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

1 of 2 match: Sea view, Trampoline

1 of 2 filters match

Price per night from

$150

New Luxury Villa Europa with Pool Theater /10 min to Disney

Kissimmee house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

1 of 2 match: Sea view, Trampoline

1 of 2 filters match

Price per night from

$345

⭐Spacious and Comfy 8 Bedroom & Near Disney⭐

Kissimmee villa

  • 8 bedrooms
  • 6 bathrooms
  • sleeps 18

1 of 2 match: Sea view, Trampoline

1 of 2 filters match

Price per night from

$408

⭐Miles from Disney World - Gorgeous 8 Bedrooms w/ Pool⭐

Kissimmee villa

  • 8 bedrooms
  • 6 bathrooms
  • sleeps 18

1 of 2 match: Sea view, Trampoline

1 of 2 filters match

Price per night from

$408

Anna Maria Island/ IMG Academy/ Beach/ HotTub/ Bikes/ Kayaks/ Golf/ Fishing

Bradenton house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Sea view, Trampoline

1 of 2 filters match

Price per night from

$287

Luxury upgraded home with lakeview, salt water heated pool 4 Mi from the beach

Jensen Beach house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 12

1 of 2 match: Sea view, Trampoline

1 of 2 filters match

Price per night from

$652

Luxury Ranch House w/ Private Tennis Court and Pool

Southwest Ranches house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 16

1 of 2 match: Sea view, Trampoline

1 of 2 filters match

Price per night from

$1,145

*9332 SH - Champions Gate Unique Luxury 7BR

Reunion house

  • 7 bedrooms
  • 5 bathrooms
  • sleeps 21

Responds fast! avg. 3 hours 40 minutes

1 of 2 match: Sea view, Trampoline

1 of 2 filters match

Price per night from

$378

NEWLY LISTED DIRECT VIEW OF ULTRA 3br/2ba

Miami apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Trampoline, Sea view

1 of 2 filters match

Price per night from

$2,295

Tiny Home Camping Experience

St. Petersburg yurt

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

1 of 2 match: Trampoline, Sea view

1 of 2 filters match

Price per night from

$287

Paridise Found

Tavernier house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 13

1 of 2 match: Trampoline, Sea view

1 of 2 filters match

Price per night from

$764

Gulf Resort

Fort Myers Beach apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Trampoline, Sea view

1 of 2 filters match

Price per night from

$522

Gulf Resort

Fort Myers Beach apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Trampoline, Sea view

1 of 2 filters match

Price per night from

$627

Gulf Resort

Fort Myers Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Trampoline, Sea view

1 of 2 filters match

Price per night from

$959

Gulf Resort

Fort Myers Beach apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Trampoline, Sea view

1 of 2 filters match

Price per night from

$522

Gulf Resort

Fort Myers Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Trampoline, Sea view

1 of 2 filters match

Price per night from

$959

Gulf Resort

Fort Myers Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Trampoline, Sea view

1 of 2 filters match

Price per night from

$905

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