Sarasota Area Rentals
- From $292 per night (USD)
VRBO
Gulf View from Lanai or Master - B308 with Boat Dock & Free WiFi
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This lovely and colorful 3rd floor unit has an incredible view of the Gulf of Mexico to enjoy with your family members f ...
From $292 per night (USD)VRBO
- From $161 per night (USD)
Expedia
Extraordinary Beach view! 2b\/1b Fully Renovated, Walk in shower, Custom Kitchen
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Now with private WiFi. Your perfect vacation awaits in this Two Bedroom/One Bath condo right next to the famous Siesta K ...
From $161 per night (USD)Expedia
- From $263 per night (USD)
VRBO
Corner Unit, Privacy and Gulf front, First Floor - B114, Free Boat Docks & WiFi
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
High demand upgraded first floor corner unit which sleeps 6 features a king, twins and sleeper sofa. The south end offer ...
From $263 per night (USD)VRBO
- From $334 per night (USD)
Expedia
Lower Pricing! Private Beach, Pools, Bay Sunrises
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Vacation like a King and Queen in one of Siesta Key's most luxurious resorts, The Palm Bay Club! This beach to bay reso ...
From $334 per night (USD)Expedia
- From $263 per night (USD)
VRBO
Turtle Beach, A105 - Gulf front - perfect for couples! Free Boat Docks & WiFi
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This first floor colorful unit sleeps 6 and you will love the sandy beach just outside the lanai door with comfortable p ...
From $263 per night (USD)VRBO
- From $292 per night (USD)
Expedia
Beach View with Boat Docks, Lovely Condo - B203, Free Boat Docks & WiFi
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to Fisherman's Cove unit B203, this cozy beach house awaits your visit! Magnificent view of the Gulf of Mexico a ...
From $292 per night (USD)Expedia
- From $292 per night (USD)
VRBO
Beach front Fisherman's Cove - A109, 1st floor, Free Boat Dock & WiFi
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Newly remodeled kitchen with stainless appliances. Freshly painted throughout and casual furnishings for your family to ...
From $292 per night (USD)VRBO
- From $292 per night (USD)
Expedia
First Class with Gulf View & Sunsets - B213, Free Boat Docks & WiFi
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Gorgeous unit and beautifully furnished with an incredible 2nd floor view of the Gulf of Mexico. Sleeps six comfortably ...
From $292 per night (USD)Expedia
- From $292 per night (USD)
VRBO
Siesta Sand & Sunsets-Breathtaking Beach Views-B204-2 BR, 2 BA condo
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Enjoy the unrestricted views (no sea oats or berm) of the ocean and sunsets from our beach front condo just steps away f ...
From $292 per night (USD)VRBO
- From $292 per night (USD)
Expedia
Corner Unit, Gulf Front on 2nd floor - A214, Free Boat Docks & WiFi
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
A beautiful gulf view with wrap around, all screened sliding doors to enjoy the gulf breeze. This unit is on the south ...
From $292 per night (USD)Expedia
- From $660 per night (USD)
VRBO
Villa Vista Mare | Gorgeous Home w\/ Views of Gulf, Heated Pool, & Across From Siesta Key Beach!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to Villa Vista Mare, located just steps away from the world-renowned Siesta Key Beach! This 3 bedroom, 3 bathroo ...
From $660 per night (USD)VRBO
- From $263 per night (USD)
Expedia
Siesta Key Gulf Front-2 BR-B103, Beautiful Sunsets + Water Views
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Just bring your swimsuits, flip flops, and some groceries…everything that you might need is located in this totally upda ...
From $263 per night (USD)Expedia
- From $227 per night (USD)
VRBO
Beach Condo on Siesta Key Beach w\/ Heated Pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
If you are going to visit the #1 beach in the country, then stay on the #1 beach! This two bedroom, two full bathroom be ...
From $227 per night (USD)VRBO
- From $149 per night (USD)
Expedia
POOL VIEW King bed Walk to beach Covered porch overlooks pool DAILY RATES
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
We are a small resort on Siesta Key offering daily rentals Pool view is a 1 bedroom 1 bathroom ground floor rental wit ...
From $149 per night (USD)Expedia
- From $497 per night (USD)
VRBO
Crescent Cottage | Pet Friendly 🐶 w\/ Private Pool, Lounging Area,Short Walk to Crescent Beach
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Welcome to Crescent Cottage, a charming villa nestled on the southern end of Siesta Key. With its luxurious backyard oas ...
From $497 per night (USD)VRBO
- From $644 per night (USD)
Expedia
Sand Dollar Cottage | Waterfront Home w\/ Private Pool & Kayaks! Minutes to Siesta Key Beach!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to Sand Dollar Cottage, your ideal vacation rental home located on the tropical island of Siesta Key! This beaut ...
From $644 per night (USD)Expedia
- From $722 per night (USD)
VRBO
Villa Champagne | Pet Friendly Waterfront Home w\/ Private Pool & Spa, Close to Beach & Village!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to Villa Champagne! This enchanting 4 bedroom/3.5 bathroom cottage is a short walk to Siesta Key Village and jus ...
From $722 per night (USD)VRBO
- From $571 per night (USD)
Expedia
Sandy Seahorse Cottage | Pet Friendly Home on Siesta Key w\/ Private Pool, Short Walk to Beach
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 16
Welcome to Sandy Seahorse Cottage, a beautiful home nestled between the quiet streets of south Siesta Key. This charming ...
From $571 per night (USD)Expedia
- From $314 per night (USD)
VRBO
Updated and clean, two heated pool, tennis, and beach access
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Enjoy this updated townhome within walking distance to Siesta Key's main beach. The property is located within a resort ...
From $314 per night (USD)VRBO
- From $483 per night (USD)
Expedia
Seaside Cottage | Pet Friendly Siesta Key Home w\/ Private Pool, Across From Beach Access 9!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 11
Welcome to Seaside Cottage, a charming coastal retreat that promises an unforgettable vacation experience on Siesta Key. ...
From $483 per night (USD)Expedia
- From $162 per night (USD)
VRBO
Enjoy the Siesta Key Beach Life to the fullest! Beach AND Pool Access
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
*** NEW *** Siesta Key beach has become known world wide for its incredible miles of soft white sand beaches and small v ...
From $162 per night (USD)VRBO
- From $542 per night (USD)
Expedia
Sarasota House w\/ Backyard Oasis: 6 Mi to Beach!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Soak up the Sunshine State from this 2-bedroom, 2-bathroom Sarasota vacation rental. The home boasts a private backyard ...
From $542 per night (USD)Expedia
- From $168 per night (USD)
VRBO
Boat Day Included! Waterfront Pool Home with Dock - Amazing Sunsets Included
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
SPECIAL OFFER! Rent this home and get a day out on a beautiful 35' Sea Ray. Additional details below. Beautiful proper ...
From $168 per night (USD)VRBO
- From $288 per night (USD)
Expedia
Well Appointed Home with Heated Pool Just Off Siesta Key Close Gulf Gate Area
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Come enjoy the relaxed but vibrant vibe of Sarasota, Florida. The beautiful white sand beaches of Siesta Key, named #1 b ...
From $288 per night (USD)Expedia
- From $173 per night (USD)
VRBO
Oceanfront Home w\/ Sunset Views of Sarasota Bay - Snowbirds Welcome, Dogs OK
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Sunsetter on Sapphire Shores Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply ...
From $173 per night (USD)VRBO
- From $335 per night (USD)
Expedia
Walk to the Village or the Beach, Everything is in Reach from this SK Rental
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Enjoy this upscale townhome located within walking distance of Siesta Key Village and Siesta Key beaches. It features a ...
From $335 per night (USD)Expedia
- From $275 per night (USD)
VRBO
The Coral Cottage close to all that Sarasota has to offer
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
We are Matt and Val, and we purchased this home with a vision to create a warm, inviting space for individuals, couples ...
From $275 per night (USD)VRBO
- From $115 per night (USD)
Expedia
Hidden Paradise Among Tropical Landscape on Lakefront Property on Siesta Key
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
This is a one bedroom one bathroom unit furnished with king-size bed in the private bedroom and queen-size sleeper sofa ...
From $115 per night (USD)Expedia
- From $105 per night (USD)
VRBO
Siesta Key Lakefront Hidden Paradise Among Tropical Landscape W\/ Heated Pool
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
This is a one bedroom one bathroom unit furnished with king-size bed in the private bedroom and queen-size sleeper sofa ...
From $105 per night (USD)VRBO
- From $175 per night (USD)
Expedia
Lakefront Siesta Key Vacation Rental Home within Small Private Resort W\/ Pool
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
This is a three bedroom two bathroom single family home furnished with king-size bed in the private master bedroom with ...
From $175 per night (USD)Expedia
- From $286 per night (USD)
VRBO
Spacious Renovated 1 Bedroom Siesta Key Beachside Vacation Rental Getaway
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Want to stay in a prime location and stay within budget? America's #1 rated beach is just a stones through away located ...
From $286 per night (USD)VRBO
- Click For Pricing
Expedia
Siesta Key Beach Townhouse with Heated Pool and Accommodates up to 7 Guests
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Service Highlights: - Professionally laundered linens & towels with each reservation. - Guaranteed clean - No keys to pi ...
Click For PricingExpedia
- Click For Pricing
VRBO
Veranda Beach Club, ( Week 2 ) Jan. 11 to 18, 2020
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Beautifully furnished beach front property, Second floor corner garden unit with two balconies. Private beach with umbr ...
Click For PricingVRBO
- From $177 per night (USD)
Expedia
Great place to see the dolphins! And less than half a mile from Turtle Beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Sunrise Bay is a 2BR, 1.5 bath, second floor apartment, in a 4-plex apartment property. It faces east and is on the wat ...
From $177 per night (USD)Expedia
- From $129 per night (USD)
VRBO
POOL VIEW V5 Luxury King Bedroom Siesta Key Walk to beach DAILY SPECIALS
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
We are a small resort on Siesta Key offering daily rentals Villa 5 is a ground floor luxury studio suite The entire stud ...
From $129 per night (USD)VRBO
- From $239 per night (USD)
Expedia
Siesta Key For Me @ The Palm Bay Club
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Inter-coastal & Ocean Front Property, 2 Pools, 1 Hot Tub, Private Beach ⭐⭐⭐⭐⭐average reviews. This Bayside Suite has be ...
From $239 per night (USD)Expedia
- From $419 per night (USD)
VRBO
Adorable Lido Beach Home- walk to beach and St. Armand's
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Enjoy a morning stroll on the beach collecting sea shells, walk to St. Armand's to experience great restaurants and shop ...
From $419 per night (USD)VRBO
- Click For Pricing
Expedia
Sea Side Vacation Home - By 5 beaches
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Our remodeled Tropical Vacation Home has everything for your living needs. 3 Bedroom with Office/Den. We are only 5 mi ...
Click For PricingExpedia
- From $147 per night (USD)
VRBO
Charming Beach Cottage
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 7
LOCATION!!! 3D Matterport scan of the house available!!! Getaway from the fast paced, high pressure life and slip on som ...
From $147 per night (USD)VRBO
- From $730 per night (USD)
Expedia
Casa Eulimia | Pet Friendly, Ping Pong Table, Private Heated Pool, Elevator, Steps to Beach!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
Welcome to Casa Eulimia, a gorgeous vacation home located on the Southern end of Siesta Key. This spacious and airy prop ...
From $730 per night (USD)Expedia
- From $554 per night (USD)
VRBO
Sophie's Cottage | Pet Friendly, Waterfront Home w/ Private Pool & Kayaks! Beach & Village Close!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to Sophie's Cottage, a picturesque waterfront retreat nestled on the canals of Siesta Key. This charming 2-bedro ...
From $554 per night (USD)VRBO
- From $301 per night (USD)
Expedia
Seahorse Cabana | Pet Friendly Home on Siesta Key w\/ Heated Pool, Short Walk to Beach!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to Seahorse Cottage, a beautiful home nestled between the quiet streets of south Siesta Key. This charming duple ...
From $301 per night (USD)Expedia
- From $760 per night (USD)
VRBO
Casa Ohana | Pet Friendly, Ping Pong Table, Private Heated Pool, Elevator, Steps to Beach!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
Welcome to Casa Ohana, a stunning vacation home that promises to exceed all your expectations. Nestled in the heart of S ...
From $760 per night (USD)VRBO
- From $668 per night (USD)
Expedia
Casa Tegula | Pet Friendly 🐶 Ping Pong Table, Private Heated Pool, Elevator, Steps to Beach!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
Welcome to Casa Tegula, your luxurious tropical oasis on the Southern end of Siesta Key. This stunning beach house offer ...
From $668 per night (USD)Expedia
- From $728 per night (USD)
VRBO
Casa Antilles | Pet Friendly, Ping Pong Table, Private Heated Pool, Elevator, Steps to Beach!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
Welcome to Casa Antilles, a hidden gem located on the Southern end of Siesta Key. As you enter the property, the open la ...
From $728 per night (USD)VRBO
- From $699 per night (USD)
Expedia
Casa Junonia | Pet Friendly, Ping Pong Table, Private Heated Pool, Elevator, Steps to Beach!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
Welcome to Casa Junonia, a gorgeous vacation home located on the Southern end of Siesta Key. This spacious and airy prop ...
From $699 per night (USD)Expedia
- From $917 per night (USD)
VRBO
Admirals Watch | Ocean View w\/ Spacious Balcony, Heated Pool, & Walking Distance to Siesta Key Beach
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Imagine waking up to the gentle sound of waves crashing against the shore, and looking out to see the shimmering turquoi ...
From $917 per night (USD)VRBO
- From $798 per night (USD)
Expedia
La Contento Casa | Pet Friendly, Waterfront Home on Siesta Key w\/ Private Heated Pool & Kayaks!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to La Contento Casa, a stunning waterfront retreat that promises nothing less than a memorable vacation experien ...
From $798 per night (USD)Expedia
- From $876 per night (USD)
VRBO
The Solaster | Pet Friendly Home on Siesta Key w\/ 2 Heated Pools, Walk to Beach & South Village!
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 20
Escape to The Solaster, a magnificent retreat that offers nothing but luxury and relaxation. This coastal villa can be r ...
From $876 per night (USD)VRBO
- From $1451 per night (USD)
Expedia
The Abalone | Luxury Pet Friendly Home, 2 Heated Pools, Elevators, Ping Pong Tables Steps to Beach!
- Bedrooms:
- 6
- Bathrooms:
- 8
- Sleeps:
- 24
Welcome to The Abalone, a gorgeous vacation home located on the Southern end of Siesta Key. This spacious and airy prope ...
From $1451 per night (USD)Expedia
- From $386 per night (USD)
VRBO
Peacock Villa | Spacious Outdoor Area, Cabana Room, Heated Pool, & Steps to Siesta Key Beach!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to Peacock Villa, an exquisite Siesta Key retreat that offers a unique opportunity for a customizable vacation e ...
From $386 per night (USD)VRBO
- From $715 per night (USD)
Expedia
Casa Coquina | Pet Friendly, Ping Pong Table, Private Heated Pool, Elevator, Steps to Beach!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 14
Welcome to Casa Coquina, a hidden gem located on the Southern end of Siesta Key. As you enter the property, the open lay ...
From $715 per night (USD)Expedia
- From $1416 per night (USD)
VRBO
The Nautilus | Luxury Pet Friendly Home, 2 Heated Pools, Elevators, Ping Pong Tables Steps to Beach!
- Bedrooms:
- 6
- Bathrooms:
- 8
- Sleeps:
- 24
Welcome to the Nautilus, your luxurious tropical oasis on the Southern end of Siesta Key. This stunning beach house offe ...
From $1416 per night (USD)VRBO
- From $367 per night (USD)
Expedia
Casita Sun Star | Pet Friendly Home on Siesta Key, Heated Pool, Walk to Beach & South Village!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 10
Escape to Casita Sun Star, a magnificent retreat that offers nothing but luxury and relaxation. This coastal villa can b ...
From $367 per night (USD)Expedia
- From $815 per night (USD)
VRBO
Casa De Mariposa | Ocean Views, Spacious Balcony, Private Heated Pool, & Steps to Siesta Key Beach!
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 16
Welcome to Casa De Mariposa, an exquisite Siesta Key retreat that offers a unique opportunity for a customizable vacatio ...
From $815 per night (USD)VRBO
- From $1645 per night (USD)
Expedia
Sophie's Quartier | Siesta Bundle, 2 Pet Friendly Waterfront Homes w/ 2 Private Pools, Near Village
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 14
Welcome to Sophie's Quartier, a breathtaking waterfront retreat that offers not just one, but two separate private homes ...
From $1645 per night (USD)Expedia
- From $751 per night (USD)
VRBO
Villa De Paradisio | Waterfront Home w\/ Private Pool, Fishing Dock, Close to Beach & Village!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 12
Experience the epitome of waterfront luxury at Villa De Paradisio, a magnificent retreat nestled on the canals of Siesta ...
From $751 per night (USD)VRBO
- From $951 per night (USD)
Expedia
Casa Mahalo | Pet Friendly, Ping Pong Table, Private Heated Pool, Elevator, Steps to Beach!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
Welcome to Casa Mahalo, a stunning vacation home that promises to exceed all your expectations. Nestled in the heart of ...
From $951 per night (USD)Expedia
- From $266 per night (USD)
VRBO
Sandy Cabana | Pet Friendly Home on Siesta Key w\/ Heated Pool, Short Walk to Beach!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to Sandy Cabana, a beautiful home nestled between the quiet streets of south Siesta Key. This charming duplex of ...
From $266 per night (USD)VRBO
- From $494 per night (USD)
Expedia
The Palms Cottage | Pet Friendly Home w\/ Private Pool & Spa, Walking Distance to Siesta Key Beach!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Welcome to The Palms Cottage, a charming retreat nestled in the prestigious neighborhood of Palm Island on Siesta Key! ...
From $494 per night (USD)Expedia
- From $1953 per night (USD)
VRBO
The Big Kahuna | SK Village, Pet Friendly, 2 Heated Pools, Elevator, Ping Pong Tables Steps to Beach
- Bedrooms:
- 6
- Bathrooms:
- 8
- Sleeps:
- 24
Welcome to The Big Kahuna, a stunning vacation home that promises to exceed all your expectations. Nestled in the heart ...
From $1953 per night (USD)VRBO
- From $627 per night (USD)
Expedia
Serenity Cottage | Multilevel Home on Siesta Key w\/ Private Pool & Spa, Short Walk to Beach!
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to Serenity Cottage, a tranquil cottage located on the southern end of Siesta Key. This remarkable vacation home ...
From $627 per night (USD)Expedia
- From $1457 per night (USD)
VRBO
The Conch | Luxury Pet Friendly Home, 2 Heated Pools, Elevators, Ping Pong Tables Steps to Beach!
- Bedrooms:
- 6
- Bathrooms:
- 8
- Sleeps:
- 26
Welcome to The Conch, a hidden gem located on the Southern end of Siesta Key. As you enter the property, the open layout ...
From $1457 per night (USD)VRBO
- From $699 per night (USD)
Expedia
Casa Stolida | Pet Friendly 🐶 Ping Pong Table, Private Heated Pool, Elevator, Steps to Beach!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
Welcome to Casa Stolida, your luxurious tropical oasis on the Southern end of Siesta Key. This stunning beach house offe ...
From $699 per night (USD)Expedia
- From $383 per night (USD)
VRBO
Casita Morning Star | Pet Friendly Home on Siesta Key, Heated Pool, Walk to Beach & South Village!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 10
Escape to Casita Morning Star, a magnificent retreat that offers nothing but luxury and relaxation. This coastal villa c ...
From $383 per night (USD)VRBO
- From $452 per night (USD)
Expedia
Monarch Villa | Ocean Views, Cabana Room, Heated Pool, & Steps to Siesta Key Beach!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to Monarch Villa, an exquisite Siesta Key retreat that offers a unique opportunity for a customizable vacation e ...
From $452 per night (USD)Expedia
- From $631 per night (USD)
VRBO
Topsail Cottage | Luxury Home on Siesta Key w\/ Heated Pool & Rooftop View of Gulf, Walk to Beach!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 12
Welcome to Topsail Cottage, a luxurious condo located on the southern end of Siesta Key. This exquisite 4-bedroom, 4-bat ...
From $631 per night (USD)VRBO
- From $1816 per night (USD)
Expedia
AMAZING 4 level SIESTA KEY home on large water with dock, crows nest, spa\/pool
- Bedrooms:
- 7
- Bathrooms:
- 5
- Sleeps:
- 10
Indulge in unbeatable waterfront living in this breathtaking Siesta Key vacation rental, nestled on the serene waters of ...
From $1816 per night (USD)Expedia
- From $250 per night (USD)
VRBO
Siesta Key Condo Escapes, *Pool and Beach Access*
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 7
The Space Find yourself steps from the powdery white sands of Siesta Key and the #1 beach in the USA in this beautifully ...
From $250 per night (USD)VRBO
- From $873 per night (USD)
Expedia
Luxe Beachfront Villa with Indoor Pool & Gulf View
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Pack your bags for a lavish getaway and stay at this chic oceanfront vacation rental in Englewood! Resting on a stunning ...
From $873 per night (USD)Expedia
- From $127 per night (USD)
VRBO
2 Bedroom 2 Bath home near Siesta Key Beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 7
Right over the South Bridge from Siesta Key Beach - #1 Beach in the USA - A newly renovated 2 Bedroom 2 Bathroom modular ...
From $127 per night (USD)VRBO
- From $75 per night (USD)
Expedia
Adorable 1 Bedroom 1 Apartment
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Very nice and spacious 1 bedroom 1 bath apartment with a comfortable setting. Perfectly located only 3 min walking dista ...
From $75 per night (USD)Expedia
- From $556 per night (USD)
VRBO
Crystal Sands Tower Unit 903 - Beachfront
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Breathtaking, unobstructed, North to South, panoramic views of the Gulf of Mexico on renowned Crescent Beach; located o ...
From $556 per night (USD)VRBO
- From $415 per night (USD)
Expedia
Crystal Sands Tower Unit 1206 - Beachfront
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Penthouse Condo - Direct Beachfront -Million Dollar View This condo is in the most requested part of the Crystal Sands c ...
From $415 per night (USD)Expedia
- From $230 per night (USD)
VRBO
Spectacular penthouse view over downtown Sarasota plus private beach access
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to paradise on Siesta Key! You will find this penthouse condo inviting and comfortable with everything you need ...
From $230 per night (USD)VRBO
- From $399 per night (USD)
Expedia
\"Safe & Clean\" Key West Suite , only 60 steps to the Siesta Key Public Beach -
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Next to the Siesta Key Public Beach, 60 steps only! This amazing recently updated and newly refurbished 2 bedroom apartm ...
From $399 per night (USD)Expedia
- From $154 per night (USD)
VRBO
Waterfront house with a park and restaurant
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
The tan house on Myakka River provides access to the river with a beautiful view. This property has units; 1st floor an ...
From $154 per night (USD)VRBO
- From $171 per night (USD)
Expedia
Cute House near Downtown
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
CALL US FOR OUR WEEKLY RATES!!! Cute house near Downtown Sarasota offers convenience, quietness and ability to enjoy Sa ...
From $171 per night (USD)Expedia
- Click For Pricing
VRBO
Adorable Home w\/Pool, Close to Siesta Key Beach, FREE WiFi, Dog* (See Note)...
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
**ASK ABOUT LAST MINUTE DEALS! Are the art, theater, and dining opportunities in Sarasota tempting, but you ...
Click For PricingVRBO
- From $200 per night (USD)
Expedia
VILLA DEL SOL 🌞💥🥂🌴🌴🌴🌴🍸🍸
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to Villa Del Sol, our sunny piece of paradise. From the time you arrive at the Villa, you will feel the sunshin ...
From $200 per night (USD)Expedia
- Click For Pricing
Expedia
Beautiful West of The Trail Home
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 10
Exquisite West of Trail home in Granada is a quiet, private neighborhood with easy access to all amenities. 4 Bedrooms 3 ...
Click For PricingExpedia
- From $314 per night (USD)
VRBO
Exquisitely renovated Gulf Front, First Floor A108, Siesta Key
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
The uniqueness of this gorgeous first floor unit will make you say WOW! Walk out the front door and onto your boat docke ...
From $314 per night (USD)VRBO
- From $379 per night (USD)
VRBO
Luxury Beach Condo on Crescent Beach #1 Beach in USA
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 4
Discover your dream vacation rentals at Crescent Siesta Key - Prime Location: Situated on the pristine Crescent Beach, ...
From $379 per night (USD)VRBO
- From $85 per night (USD)
Expedia
COZY GUEST HOUSE, 15 MINUTES FROM SIESTA KEY BEACH!!!!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Come and enjoy this cozy guest house perfect for a romantic and relaxing getaway. 1 bedroom, 1 bath, comfy loveseat, 1 ...
From $85 per night (USD)Expedia
- From $225 per night (USD)
VRBO
Private beach getaway near point of rocks
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Beautiful 2nd-floor family-friendly beachside condo. Located on the world-famous crescent beach. 1 private parking space ...
From $225 per night (USD)VRBO
- From $196 per night (USD)
Expedia
Resort-Style Siesta Key Condo: Walk to Beach!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Built with couples and small families in mind, this Siesta Key vacation rental offers 2 heated pools, a gym, beach acces ...
From $196 per night (USD)Expedia
- From $350 per night (USD)
VRBO
Family getaway 5 miles to Siesta Beach. Heated private Pool, bicycles.Sleep 10.
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Welcome to our Blue Beach House! Look no further, you have found the ideal rental for relaxing in the Florida sun! This ...
From $350 per night (USD)VRBO
- From $292 per night (USD)
Expedia
'Casa Bella' Florida Getaway w\/Heated Spa & Grill
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 7
Treat yourself to “Casa Bella” on your next trip to Florida’s beautiful west coast. A private and relaxing home with ple ...
From $292 per night (USD)Expedia
- From $202 per night (USD)
VRBO
Villa Las Flores | Pet Friendly Home in Sarasota w\/ Private Heated Pool & Screened-In Porch
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to Villa Las Flores, a magnificent retreat that can be rented out separately or combined with its sister unit Lu ...
From $202 per night (USD)VRBO
- From $202 per night (USD)
Expedia
Luna Nueva | Pet Friendly Home in Sarasota w\/ Private Heated Pool & Screened-In Porch
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to Luna Nueva, a magnificent retreat that can be rented out separately or combined with its sister unit Villa La ...
From $202 per night (USD)Expedia
- From $404 per night (USD)
VRBO
Luna Flores | Pet Friendly Home in Sarasota w\/ 2 Private Heated Pools & Screened-In Porches
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 16
Welcome to Luna Flores, a magnificent retreat that combines the best of two homes, Luna Nueva and Villa Las Flores. Whet ...
From $404 per night (USD)VRBO
- From $143 per night (USD)
Expedia
Renovated retreat - dog-friendly yard, AC & W\/D - snowbirds welcome
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Alta Vista Respite Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $143 per night (USD)Expedia
- From $454 per night (USD)
VRBO
***Walk to Beach 5min. Waterfront Grand Canal~PrivatePOOL\/HotTub,Kayaks,Bikes**
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Great location! Walk to beach!! 5 minutes, Siesta Village- 15 minutes. Waterfront property-125' on Grand Canal. Walk m ...
From $454 per night (USD)VRBO
- From $300 per night (USD)
Expedia
Steps away from the #1 beach! Spectacular views on the GIANT balcony!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Jamaica Royale's private BEACH FRONT community is just steps away from the soft white quartz sand of Siesta Key Beach wh ...
From $300 per night (USD)Expedia
- From $220 per night (USD)
VRBO
Elegant - Spacious - Private Townhome - steps aways from Siesta Key Beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
It is with gratitude that we share that this condominium complex and specifically this property was not damaged by hurri ...
From $220 per night (USD)VRBO
- From $116 per night (USD)
Expedia
Near Siesta Key - single story pet friendly
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Newly renovated home in Sarasota. All new ceramic floors with new kitchen including granite counter tops, dishwasher, mi ...
From $116 per night (USD)Expedia
- From $248 per night (USD)
VRBO
Charming Florida Pool home 8 minutes from Siesta Key
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
Your perfect Florida vacation is waiting for you at this well-appointed 3-bedroom, 2-bathroom home in Sarasota. Start yo ...
From $248 per night (USD)VRBO
- From $310 per night (USD)
Expedia
3-BR with Pool & hot tub, 2 min to Siesta Key Beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 12
Embark on a getaway to sunny Florida and discover this unique vacation home in an excellent location just across the str ...
From $310 per night (USD)Expedia
- From $133 per night (USD)
VRBO
2\/2 Ground Unit 10 Min to beach on golf course
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This Venice vacation rental ground floor condo has 2 bedrooms, 2 baths and room for 6 guests It features 2 separate lan ...
From $133 per night (USD)VRBO
- From $400 per night (USD)
Expedia
2 Cottages Rented Together | Pool | Near Beaches
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
Summary: Bring your friends, family and loved ones to enjoy an unforgettable escape at this unique property which comfor ...
From $400 per night (USD)Expedia