Search Results - Vacation Rentals

Waterway Estates, Florida Vacation Rentals

146 listings found
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Base rates (EXCLUDING any applicable taxes, fees, and promotions) are displayed as provided by rental managers and are not guaranteed. Rates are based on the start date or arrival date selected in the search and may vary on subsequent days. Properties marked ‘Available’ or ‘Booked’ are done so based on information provided by the rental manager and are not guaranteed. For completed details (including minimum stay length, full availability information, approved arrival days and other booking rules for the property) select ‘Book Now” (on available properties) or ‘Check Availability’ (booked properties) to be directed to the rental manager’s website or click “Contact” to send them a specific request.

Nature View #3

Nature View #2

Blue Starfish Estate

Blue Lagoon Estate

Orchid Estate #1

Orchid Estate #2

Orchid Estates

Venice Villas * Villa Laguna #28

Venice Villas * Studio #69

Venice Villas * Poolside #41

Venice Villas * Villa San Marco #33

Venice Villas * Studio #74

Venice Villas * Villa San Marco #31

Venice Villas * Villa Regina #1

Venice Villas * Villa San Marco #34

Venice Villas * Villa San Marco #37

Venice Villas * Villa San Marco #38

Venice Villas * Studio #49

Venice Villas * Villa Paradiso #12

Venice Villas * Unit #45

Venice Villas * Villa Paradiso #13

Venice Villas * Studio #76

Venice Villas * Studio #51

Venice Villas * Villa Regina #6

Venice Villas * Villa San Marco #32

Venice Villas * Villa Laguna #27

Venice Villas * Villa Regina #5

Venice Villas * Studio #78

Venice Villas * Studio #58

Venice Villas * Studio #53

Venice Villas * Studio #61

Venice Villas * Villa Paradiso #14

Venice Villas * Villa Paradiso #18

Cozy 2BR Florida Home Near the Shore!

King Bed & Patio, Minutes to the Beach

Turtle Bay Hideaway | Large Pet Friendly Home on Siesta Key w/ Private Pool & Spa, Beach Access

Casita Sun Star | Pet Friendly Home on Siesta Key, Heated Pool, Walk to Beach & South Village!

Casita Morning Star | Pet Friendly Home on Siesta Key, Heated Pool, Walk to Beach & South Village!

The Solaster | Pet Friendly Home on Siesta Key w/ 2 Heated Pools, Walk to Beach & South Village!

Seahorse Cabana | Pet Friendly Home on Siesta Key w/ Heated Pool, Short Walk to Beach!

Sandy Seahorse Cottage | Pet Friendly Home on Siesta Key w/ Private Pool, Short Walk to Beach

Sandy Rocks | Ultimate Bundle: 2 Private Pet Friendly Homes, 2 Private Heated Pools, Walk to Beach!

Sandy Cabana | Pet Friendly Home on Siesta Key w/ Heated Pool, Short Walk to Beach!

Crescent Cottage | Private Pool, Lounging Area, Short Walk to Crescent Beach

Serenity Cottage | Multilevel Home on Siesta Key w/ Private Pool & Spa, Short Walk to Beach!

Fiesta Playa | Luxury Home on Siesta Key w/ Private Elevator, 2 Minute Walk to Crescent Beach!

Topsail Cottage | Luxury Home on Siesta Key w/ Heated Pool & Rooftop View of Gulf, Walk to Beach!

Casa Coquina | Pet Friendly Home on Siesta Key w/ Private Heated Pool & Elevator, Steps to Beach!

The Conch | Luxury Pet Friendly Home on Siesta Key, 2 Heated Pools, 2 Elevators, Steps to Beach!

Casa Antilles | Pet Friendly Home on Siesta Key w/ Private Heated Pool & Elevator, Steps to Beach!

Casa Bella Vita | Luxury Home w/ Heated Pool, Ping Pong Table, & Walking Distance to Crescent Beach!

Casa Eulimia | Pet Friendly Home on Siesta Key w/ Private Heated Pool & Elevator, Steps to Beach!

Casa Junonia | Pet Friendly Home on Siesta Key w/ Private Heated Pool & Elevator, Steps to Beach!

The Abalone | Luxury Pet Friendly Home on Siesta Key, 2 Heated Pools, 2 Elevators, Steps to Beach!

Casa Stolida | Pet Friendly Home on Siesta Key w/ Private Heated Pool & Elevator, Steps to Beach!

The Nautilus | Luxury Pet Friendly Home on Siesta Key, 2 Heated Pools, 2 Elevators, Steps to Beach!

Casa Tegula | Pet Friendly Home on Siesta Key w/ Private Heated Pool & Elevator, Steps to Beach!

Sandpiper Cottage | Pet Friendly Home in Sarasota w/ Private Pool, 2 Story Loft, Close to Siesta Key

New Listing | Gulf Birdie | Waterfront Home on Siesta Key, w/ Private Heated Pool & Hot Tub!

La Contento Casa | Pet Friendly, Waterfront Home on Siesta Key w/ Private Heated Pool & Kayaks!

Sand Dollar Cottage | Waterfront Home w/ Private Pool & Kayaks! Minutes to Siesta Key Beach!

Admirals Watch | Ocean View w/ Spacious Balcony, Heated Pool, & Walking Distance to Siesta Key Beach

Villa Vista Mare | Gorgeous Home w/ Views of Gulf, Heated Pool, & Across From Siesta Key Beach!

Beach Palm Villa | Private Heated Pool, Fire Pit, & Spacious Outdoor Lounging Area

Beach Dream | Home w/ Ocean Views, 2 Private Pools, & Rooftop Lookout! Steps to Siesta Key Beach

Silver Shore | Home w/ Ocean Views, Private Pool, & Rooftop Lookout! Steps to Siesta Key Beach

Crystal Sands | Home w/ Ocean Views, Private Pool, & Rooftop Lookout! Steps to Siesta Key Beach

Island Escape | Home on Siesta Key w/ Private Heated Pool & Ping Pong Table!

New Listing! Don't Be Salty | Gorgeous Modern Home w/ Private Heated Pool & Spa, Near Beach!

The Sun Dial | Waterfront Home on Siesta Key w/ Private Pool & Large Backyard, Close to Beach!

Casa De Mariposa | Ocean Views, Spacious Balcony, Private Heated Pool, & Steps to Siesta Key Beach!

Peacock Villa | Spacious Outdoor Area, Cabana Room, Heated Pool, & Steps to Siesta Key Beach!

Monarch Villa | Ocean Views, Cabana Room, Heated Pool, & Steps to Siesta Key Beach!

Seaside Cottage | Pet Friendly Siesta Key Home w/ Private Pool, Across From Beach Access 9!

Seas the Day | Canal Front Home on Siesta Key w/ Private Heated Pool & Kayaks, Walk to Beach!

Isla Amor | Waterfront Home on Siesta Key w/ Private Heated Pool, Fire Pit, Walk to Beach!

Siesta Sunset | Luxurious Beach Front Penthouse w/ Views of Gulf, Minutes to Siesta Key Village

New Listing! Avanti Villa | Hot Tub, Walk to Siesta Beach and Village, Beach Views

Endless Views | Walking Distance To Siesta Key Beach + Village, Panoramic Views

Sophie's Cottage | Pet Friendly, Waterfront Home w/ Private Pool & Kayaks! Beach & Village Close!

Beach Walk Cottage | Pet Friendly Home on Palm Island, Private Pool, Ping Pong Table, Walk to Beach!

Villa Champagne | Pet Friendly Waterfront Home w/ Private Pool & Spa, Close to Beach & Village!

Sophie's Quartier | Siesta Bundle, 2 Pet Friendly Waterfront Homes w/ 2 Private Pools, Near Village

Latitude Adjustment | Waterfront Home w/ Private Heated Pool! Walk to Siesta Village & Beach!

The Key Canal - Spacious Waterfront Home w/ Rooftop Deck, Walk to Siesta Beach & Village

New Listing | Pet Friendly Home on Siesta Key w/ Outdoor Patio & Private Screened-In Heated Pool!

New Listing! The Birdhouse | Private Siesta Key Home w/ Heated Pool, Minutes Away From Beach!

Luna Flores | Pet Friendly Home in Sarasota w/ 2 Private Heated Pools & Screened-In Porches

Villa Las Flores | Pet Friendly Home in Sarasota w/ Private Heated Pool & Screened-In Porch

Luna Nueva | Pet Friendly Home in Sarasota w/ Private Heated Pool & Screened-In Porch

Sea Esta | Walking Distance to Siesta Key Beach & Village w/ Heated Pool & Outdoor Dining

Siesta Salt Life | Walking Distance to Siesta Key Beach & Village w/ Private Heated Pool!

The Palms Cottage | Pet Friendly Home w/ Private Pool & Spa, Walking Distance to Siesta Key Beach!

Sea la Vie | Walking Distance to Siesta Key Beach & Village w/ Heated Pool & Outdoor Dining

Caribbean Dream | Luxury Condo on Siesta Key w/ Heated Pool, Walking Distance to Beach & Village!

Siesta Villa | Luxury Condo in Siesta Village w/ Heated Pool, Walking Distance to Beach & Village!

Siesta Breeze Retreat | Walk to Beach, Siesta Village, Shared Pool!

At Sun Sea Terrace | Luxury Siesta Key Condo w/ Heated Pool, Short Walk to Beach and Village!

Bali Hai House | Luxury Waterfront Home on Siesta Key w/ Large Private Heated Pool & Outdoor Patio!

Vinca | Pet Friendly Home Located in Siesta Key Village w/ Heated Pool, Walk to Beach!

Honeysuckle | Pet Friendly Home Located in Siesta Key Village w/ Heated Pool, Walk to Beach!

Mandevilla | Pet Friendly Home Located in Siesta Key Village w/ Heated Pool, Walk to Beach!

Plumbago | Pet Friendly Home Located in Siesta Key Village w/ Heated Pool, Walk to Beach!

Lantana | Pet Friendly Home Located in Siesta Key Village w/ Heated Pool, Walk to Beach!

Mimosa | Pet Friendly Home Located in Siesta Key Village w/ Heated Pool, Walk to Beach!

The Hummingbird | Pet Friendly Home Located in Siesta Key Village w/ Private Pool, Walk to Beach!

Siesta Soul | Multilevel Home Located in Siesta Key Village w/ Private Pool, Fire Pit, Walk to Beach

Casa Ohana | Pet Friendly Home on Siesta Key w/ Private Heated Pool, Steps to Beach & Village!

The Big Kahuna | Luxury Pet Friendly Home on Siesta Key, 2 Heated Pools, Steps to Beach & Village!

Casa Mahalo | Pet Friendly Home on Siesta Key w/ Private Heated Pool, Steps to Beach & Village!

Villa Castile | Pet Friendly Home on Siesta Key w/ Private Heated Pool, Walk to Beach & Village!

Villa Fiesta | Pet Friendly Home In Siesta Village, Heated Pool and Hot Tub, Walk to the Beach!

Casa De Siesta | Pet Friendly Home In Siesta Village, Private Pool and Hot Tub, Walk to the Beach!

Villa Margarita | Pet Friendly Home In Siesta Village, Heated Pool and Hot Tub, Walk to the Beach!

Blu Sky Cottage | Pet Friendly, Canal Front Home on Siesta Key w/ Private Heated Pool & Spa, Kayaks!

Hidden Treasure | Located on Siesta Key w/ Private Heated Pool/Hot Tub & Spacious Outdoor Area

Tropical Oasis | Luxury Home on Siesta Key w/ Private Heated Pool/ Spa, Steps to Beach & Village!

Sea Foam | Pet Friendly, Located in Siesta Key Village, Steps to Siesta Key Beach!

Sea Angel | Pet Friendly, Located in Siesta Key Village, Steps to Siesta Key Beach!

Sea Breeze | Pet Friendly, Located in Siesta Key Village, Steps to Siesta Key Beach!

Sea Coast | Pet Friendly, Located in Siesta Key Village, Steps to Siesta Key Beach!

The Beachy Keen | Pet Friendly, Located in Siesta Key Village, Steps to Siesta Key Beach!

CJs on Siesta | Pet Friendly, Located in Siesta Key Village, Steps to Siesta Key Beach!

The Coral Reef! | Pet Friendly, Located in Siesta Key Village, Steps to Siesta Key Beach!

Sea Escape | Pet Friendly, Located in Siesta Key Village, Steps to Siesta Key Beach!

Sea Dream | Pet Friendly, Located in Siesta Key Village, Steps to Siesta Key Beach!

Ventana Rosa | Beautiful Sarasota Home Near Siesta Key w/ Private Pool & Large Outdoor Space

Villa De Paradisio | Waterfront Home w/ Private Pool, Fishing Dock, Close to Beach & Village!

Casamigos | West of the Trail - Private Home with Tiki Bar, Heated Pool, and Spa, Near Siesta Key!

Ocean Sky | Pet Friendly Home in Sarasota w/ Private Heated Pool & Fire Pit!

New Listing! Sunburst Courtyard | Pet Friendly Waterfront Home, Walk to Siesta Key Beach & Village!

New Listing! Island Sol | Private Pool, Pet Friendly, Minutes from Siesta Beach

Coral Breeze | Siesta Home, Heated Pool & Spa, Minutes to Village and Beach!

The Pearl on the Bay | Luxury Water Front Home Near Siesta Key, Gorgeous Views & Private Pool!

New Listing! Siesta Dolce | Luxury Siesta Key Home w/ Private Heated Pool, Close To Beach!

Baydream Bungalow | Pet Friendly Home w/ Private Heated Screened-In Pool

Casa Leone | Pet Friendly Home on Siesta Key w/ Private Heated Pool & Putting Green!

Hemingway House | Beautiful Traditional Home w/ Spacious Outdoor Dining Area & Lush Landscaping

Bay Isle Bliss | Pet Friendly Home w/ Private Pool & Walking Distance to Shell Beach

Palm Paradise | Pet Friendly Home on Siesta Key w/ Large Heated Private Pool & Outdoor Area!

Floritas Key | Pet Friendly Home on Siesta Key w/ Large Heated Private Pool & Outdoor Area!

New Listing! Mermaids Oasis | Private Pool, 5 Minute Walk to St. Armands Circle!

Coconut Cottage | Home on Lido Key w/ Private Heated Pool/Spa, Walk to Lido Beach & St. Armands!

New Listing! Manatee Cove | Waterfront Home on Lido Key, 30 Second Walk to St. Armands Circle!

Sunset Heaven | St Armands - Lido Key Home w/ Water Views, Dock Access, Private Heated Pool & Spa!

Florida Retreat Nr Lakewood Ranch Sports Campus