Search Results - Vacation Rentals

Estero, Florida Vacation Rentals

134 listings found
About Estero, Florida

A vacation rental in beautiful Estero will be just the place for you and your family to enjoy a memorable Florida vacation. Estero resorts, Estero condo rentals and vacation houses in Estero are plentiful, and here you are sure to find just what you are looking for in a Florida vacation destination!

Scenic Estero Rentals!

Estero, Florida began as a citrus community on the western gulf coast, and has evolved into a center for recreation and culture.  Located on the beautiful Estero River, many Estero vacation rentals overlook its calm shining waters.  Sit out on the front porch of a luxurious condominium in Estero and watch the boaters and kayakers glide by.  Join them by heading to a marina conveniently close to Estero house rentals and hopping in your own rented pleasure craft, or take a guided tour along Estero’s beautiful waterways.  Take a day trip a short distance from your condo in Estero and experience the beautiful beaches along the crystal waters of the Gulf of Mexico.  There you can fish, SCUBA dive or snorkel before heading back to your Estero house rental.  Explore the area’s many scenic walking and biking trails and see a part of unspoiled Florida as it used to be, only steps from the door of your Estero resort. It will be hard to miss Mound Key, the mangrove covered island in Estero Bay, which can be viewed from many condominiums in Estero. Estero condos and vacation houses in Estero are close to some of the most scenic and pristine beaches that Florida has to offer. You and your family will enjoy lazy days of fun in the sun before you return to your cozy Estero condo for an evening of relaxation on the beautiful shores of Estero Bay.

Venture Out!

 Estero rentals in the center of lots of action—the cities of Naples to the south and Ft. Myers to the north offer year-round sightseeing and cultural activities. You will find plenty to do in the area around Estero condo rentals to suit every member of your family.  For the sports lover in your group, check out the Florida Everglades Hockey team or catch an exciting Florida Firecats Arena Football game.  A family trip from your Estero house rental to Mound Key Archeological park is a must.  You and your family can immerse yourself in the lush tropical outdoors as you learn about the Florida of thousands of years ago.  Explore the Trail of Florida’s Indian Heritage, which is a collection of Florida’s ancient Indian sites.  Near Estero condos and Estero resorts there are also a variety of eclectic shops and restaurants that will help you pass an afternoon.  Naples and Ft. Myers are also home to various art festivals and celebrations throughout the year.  Whatever season you vacation in, there will be sure to plenty to choose from in the area near Estero rentals and vacation houses in Estero.

An Estero vacation has everything you and your family need for a perfect Florida vacation.  Whether you choose a condo in Estero or an Estero house rental, everything you need to have a wonderful Estero vacation is within your reach.  It’s up to you to pack book your Estero vacation rental, pack your bags and start making memories on your fabulous Estero vacation!

LEARN MORESHOW LESS
Rate & Availability Disclaimer
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.

Blue Lagoon Estate

Blue Starfish Estate

Nature View #3

Nature View #2

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!

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

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

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

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

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

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

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

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

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!

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!

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

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!

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!

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

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 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!

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!

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

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

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

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

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

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

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

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