Search Results - Vacation Rentals

Cumberland Estates, Florida Vacation Rentals

89 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

TampaGolfVillas by AmericanVacationLiving 7 Room

TampaGolfVillas by AmericanVacationLiving 5 Room

Florida Retreat Nr Lakewood Ranch Sports Campus

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

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

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!

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

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

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

Casa De Siesta | Pet Friendly Home In Siesta Village, Private 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

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!

Windsor Island Resort 9br Theater Pool Spa Disney

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

Windsor Island Resort 10br Jurassic Pool Spa Disney

Luxury Windsor Island 7br Pool Spa near Disney

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

Championsgate 6 Bedroom House Pool Spa near Disney

Windsor Island Resort 10br Private Pool Spa Disney

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

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

ChampionsGate 5br Pool Home Near Disney

Windsor island 5BR Pool Game room Disney Area

THEMED Windsor Island 7BR w Pool SPA Loft

Steps to Clubhouse Family Reunion 5BR Home

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

Windsor Island Resort 5br Private Pool Disney Area

Greenview Luxury Home near Disney Pool spa loft

Greenview Pool 8br Villa Theater Game near Disney

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

Luxury Town Home With Splash Pool in Solara Resort

Fabulous 7BR PRIVATE Pool SPA near Disney World

Jurassic 9br Game Room Villa Pool Spa by Disney

Striking 9BR Pond view Pool SPA near Disney World

Solara Resort 7br Disney themed rooms Pool Spa Villa

Extraordinary 7br Private Pool/Spa near Disney

Family Kissimmee 5BR Home Pool Loft Tub

Luxury 9BR Villa with Pool Spa No rear neighbor

Lakefront 8Br Villa Pool Spa Steps to Clubhouse

Cozy 4BR Town Home with POOL Close to Disney!

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

7br Disney Getaway w/Games Projector Pool Spa

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!

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

Newly upgraded modern 4BR/3BA private pool TH

Solterra Resort 5br Pool Spa Near Disney

Amazing Townhouse close Disney 3 bedrooms OBA62000

Solterra resort 5br Private Pool near Disney World

Extraordinary 5BR Private Pool/Spa Disney Area

Solterra 7BR Family Reunion pool home near Disney

5 Beds Description Luxury Townhome with Pool OBA61

3 Bedroom,3 Bath Townhouse in Gate Resort

Close to Disney Condo 3 Bed / 2 Bath

6 Bed Close to Disney in a Gated Resort Community

Spectacular 5BR House - South Facing Pool & Spa

Private Theater Cozy 6br Home Pool Spa By Disney

Striking 5BR villa private pool spa near Disney

Luxurious 6BR Pool Villa,2.5 Miles to Disney

Relaxing Getaway at 6BR Clubhouse Villa Pool&SPA

Firework view 6br Disney Villa Pool/spa

Windsor Hills Resort 6br Villa, Pool/Spa, by Disney

Lake view 5BR 5B Private Pool Spa luxury villa

3 BR * 2 Miles to Disney, pool, free WiFi and more

DisneyMansionEstate by AmericanVacationLiving 22BR

No Rear Neighbor/Themed 12br Villa Pool Spa Disney

Storey Lake Apartment with 3 bed,2 Bath - Oba59

Specious Game room Lakeview 12br Villa Pool Spa Near Disney

Children world 12br Fancy Themed Rooms w/ Pool Spa Disney

Stylish Themed 12br Villa Pool Spa w/ Disney

Brand New Home 4 bedrooms 2,5baths OBA5100

BRAND NEW townhome wih resort OBA21000

Movie World 9br Villa w/Pool Spa Near Disney

Veranda Palms Lakeview 9br Pool Villa Near Disney

Fabulous 10BR Greenview Pool Spa Disney Area

Storey Lake Resort 8br Family Villa Pool by Disney

Stylish 10BR Private Pool Spa near Disney

Storey Lake 10br villa pool spa game room Disney

Venice Villas * Villa Laguna #28

Venice Villas * Studio #69

Venice Villas * Poolside #41

Venice Villas * Villa San Marco #33

Venice Villas * Studio #74

Vista Cay Luxury 4 bedroom condo (#3099)

Vista Cay Standard 3 bedroom condo (#3104)

Vista Cay Standard 2 bedroom condo (#3102)