Search Results - Vacation Rentals

Belleair, Florida Vacation Rentals

246 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.

New centrally located chic family home in Tampa

New Listing! | Beach a la Mode | Luxury Canal Front Home on Anna Maria Island!

New Listing! | Front Row Seat | Luxury Beachfront Home Located On Anna Maria Island!

TampaGolfVillas by AmericanVacationLiving 7 Room

TampaGolfVillas by AmericanVacationLiving 5 Room

Florida Retreat Nr Lakewood Ranch Sports Campus

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

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

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

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

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

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!

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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!

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

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

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!

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

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

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

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!

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

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 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!

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

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

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

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!

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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!

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

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

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

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!

Casa Stolida | 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 Eulimia | 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 Coquina | 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!

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

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

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

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

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!

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!

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

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

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

Cozy 2BR Florida Home Near the Shore!

King Bed & Patio, Minutes to the Beach

Venice Villas * Villa Paradiso #18

Venice Villas * Villa Paradiso #14

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

DisneyEstate by AmericanVacationLiving 14 room 30p

DisneyEstate by AmericanVacationLiving 14 room 30p

DisneyMansion by AmericanVacationLiving 11BR - 30p

DisneyMansionEstate by AmericanVacationLiving 22BR

40% OFF Last Minute Deal 9BR home with pool spa, Disney

Cozy 8BR Champions Gate Theater Pool SPA

Beautiful 4 Bedroom 3 Bathroom pool & spa Villa

Spacious Davenport 8 BR Home w Pool Theater Loft

8BR Disney Home w Pool SPA Theater Near Clubhouse

8BD 5BA Spacious Home w Pool SPA Theater Game Room

Avatar Theater 8br home w/ Pool Spa Greenview Walk to Waterpark

Solana Resort 5br Family Villa Pool Spa Disney

South Pool Game Room Theater Steps to Clubhouse

ChampionsGate 10br 28ppl Pool Spa Villa by Disney

Striking ChampionsGate 10br villa pool spa Disney

Private Theater Pool Spa in Windsor Island Resort

ChampionsGate 5br Pool Home Near Disney

Championsgate 6 Bedroom House Pool Spa near Disney

ChampionsGate 5br Pool Spa Villa Near Disney

Minecraft Game Room 10br Villa w/Pool Spa Disney

ChampionsGate 5br Modern Townhome w/Pool by Disney

Cozy 5BR townhome private pool Near Disney Park

Disney Vacation 10br themed Villa w/ Pool Spa

Windsor Island Resort 7Br private Pool/spa Disney

ChampionsGate 5br Pool Home Near Disney

No Rear neighbor 6br private Home Pool Spa Disney

Windsor Island Resort 9br Theater Pool Spa Disney

Windsor Island 10br Iron Man Pool Spa Disney

BRIGHT 2BR Home in Champions Gate resort near Disney

Fabulous 9br Windsor Island Villa Pool/Spa Near Disney Sleep 26

Windsor Island Resort 5br Villa Pool Near Disney

Family Gathering Windsor Island new 7BR home w Pool

Extraordinary 10BR Private Pool Spa Near Disney

VR/Loft Theater/Game room 10br Villa w/Pool Spa

Avatar Gameroom10br 30ppl Villa w/ Pool Spa Disney

Avatar Theater 9br home w/ Pool Spa Near Disney

Loft Theater/Game Room 10br Villa w/ Pool Spa

Windsor Island Resort 10br Villa Pool Spa Near Disney

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8903Oba Champions Gate 6 Bedroom 5 Bathroom Villa

Windsor Island Resort 10BR pool spa Disney Area

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Windsor Island Resort 10br Jurassic Pool Spa Disney

9BR Pool/SPA/Game, Close to Disney

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Windsor Island Resort 7br Villa Pool Spa Near Disney

Perfect 5 Bed Villa just for you and your family

8BR Family Home w/POOL+Theater close to Disney

Greenview Luxury Home near Disney Pool spa loft

Greenview 8BR Davenport villa w theater pool SPA

OBA63 Windsor 5 Beds 4 Baths Townhome whit pool

NFL Game room 7br Villa w/ Private Pool Spa Disney

Windsor Island Resort 7br 16 people Pool Spa Disney

Greenview 8BR Theater Pool SPA Loft Game room

Fabulous 9BR Greenview Pool SPA near Disney World

Spacious 6BR Pool/SPA with a stunning Greenview

Iron Man Game Room 7br Villa Pool Spa by Disney

Specious 7br Kids World Villa w/ Pool Spa Disney

Avengers Game Room 10br Villa w/Private Pool Spa

Spacious 8BR Villa w pool spa Game room Greenview

Disney 9BR Vacation Home Theater Pool Spa

Mario Game Room Theater Loft w/ Pool Spa Disney

No Rear Neighbors 10br Villa Pool Spa Disney

Hall of Famous Game Room 10br Villa Pool Spa Disney

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8BR Family Disney Getaway w Theatre Pool Spa

ChampionsGate Greenview Pool Villa near Disney

Greenview Pool 8br Villa Theater Game near Disney

Windsor Island Resort 5br Private Pool, Disney Area

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Fantastic 8br Villa Resort Pool spa Near Disney

Extraordinary 7BR Private Pool spa Disney Area

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Perfect for Family Reunion Stunning 9BR Home with Pool SPA

Brand New 5br Home w/Pool Near Disney area

Steps to Clubhouse Family Reunion 5BR Home

Windsor Island Resort 5br Villa Pool near Disney

WINDSOR ISLAND resort spacious 9BR home Pool SPA

Windsor island 5BR Pool Game room Disney Area

THEMED Windsor Island 7BR w Pool SPA Loft

Modern Family 6BR Home w Pool close to Disney

Fireworks View Sunrise luxury Home Pool/SPA/Loft

ChampionsGate 5br Pool spa Home Near Disney

Windsor Island Resort 5br Private Pool Disney Area

SPACIOUS Davenport10BR w Pool SPA Loft near DISNEY

Ultimate 9BR Greenview Pool SPA near Disney World

World Class 8 Bedroom private pool/spa villa near Disney

Windsor Island Resort 8br Villa Pool Spa Near Disney

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Lake View 9BR Villa Pool Spa Near Disney World

Resort 9BR Greenview Pool Villa Disney Area

Spacious Villa w/ South Pool/Game/Near Clubhouse

Golf Course View 9BR Luxury Villa with Pool/SPA

No Rear neighbor 8br private Home Pool Spa Disney

Champions Gate 9br Lake Villa Pool Spa Near Disney

No Rear Neighbors 8br Villa w/Private Pool Spa

Luxury Town Home With Splash Pool in Solara Resort

Solara Resort Brand New 4 Bed 4.5 Bath Townhome

Ultimate 9br Chef's Kitchens Pool/Spa Disney Area

Modern 9BR Family Villa close Disney w POOL SPA