Beachfront vacation rentals in Caspersen Beach

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Top-rated beachfront rentals in Caspersen Beach

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Guest favorite

Apartment in Siesta Key

4.99 out of 5 average rating, 142 reviews

Siesta Key #1 Beach, pickle ball & tennis paradise

Beautiful Apartment w/ Hotel Services, at Siesta Key Beach. Totally remodeled. Fully equipped to spend the best holidays with family or friends. Condo hotel, on the best beach in Siesta. Beach pool, shade pool (heated), gym, 3 tennis courts on site (2 clay, 1 hard) and 2 pickle ball courts. Master bedroom with King bed. The Mattress is a SAATVA ORGANIC. 2nd room with 2 single beds, and a queen sofa bed, in the living room. Pack n Play 600 MB Wifi. HD TV. 70” Smart TV Nesspreso, Keurig Machines

Oct 4 – 11

G$94,637 GYD per night

Guest favorite

Home in Englewood

5.0 out of 5 average rating, 25 reviews

"Lost Loon" Oceanfront Cottage by Roxy Rentals

Located right on the Gulf, our renovated beach cottage is equipped with everything you need for a relaxing getaway. With private beach access and outdoor dining area, take in the views and enjoy with your family, friends or a solo trip to reset with a little R&R. This 2-bedroom, 2-bath bungalow has all the accoutrements for your a home-away-from-home, complete with beach chairs, boogie boards, beach games and of course, sun tan lotion. Come for some fun in the sun, your beachfront oasis awaits!

Sep 23 – 30

G$96,482 GYD per night

Superhost

Guesthouse in Englewood

4.93 out of 5 average rating, 235 reviews

Gulf front romantic cottage in paradise

Gated and surrounded by lush scenery you will feel like you have suddenly escaped to the caribbean! The pressures of the world melt away as you get your first glimpse of the Gulf of Mexico. Eclectic design with mostly Caribbean influences. Marble floors, tile counter tops and a large shower with a sit down bench. Walk the custom pathways which reveal beautiful orchids and exotic plants. Go kayaking, fish off the beach or look for sharks teeth. Take a swim in the pool or work on your tan.

Jan 23 – 30

G$69,246 GYD per night

Guest favorite

Island in Sarasota

4.97 out of 5 average rating, 303 reviews

*NEW May 17 CX 30% OFF! Sarasota #1 Luxury Villa*

Check our nearby sister properties for 2024 dates by clicking our host picture, then click picture again or "contact host". Or BOOK 2024 NOW, stay in Style magazines exclusive beachfront gem! This property OWNS THE BEACH!! UNIQUE PRIVATE POOL & BEACH combo is HEAVEN! Private ELEVATOR! 32,000/gl FREEFORM POOL, with 4 WATERFALLS, HOT GROTTO with HOT falls! NEW BBQ PIT AREA, BIKES, KAYAKS, and PADDLEBOARDS! WRAPAROUND BALCONY, CHEF kitchen. Hosted CELEBS! SHOPPING, FINE DINING, watch our VIDEOS!

Nov 3 – 10

G$131,629 GYD per night

Guest favorite

Condo in Venice

4.87 out of 5 average rating, 141 reviews

The Studio at the Beach 56

This is a studio first floor apartment, only 50 feet from the oversize pool and approximately 300 steps to the beach! Quick bike ride or a 20 to 25 minute walk to all of downtown Venice has to offer. About the same to Sharkeys and the fishing pier. Inside you will find all you would expect from a very nicely appointed studio. Efficiency kitchen new appliances and everything you need to prepare a simple meal. Lots of pillows super comfy brand new queen bed will ensure a restful nights sleep.

May 19 – 26

G$26,530 GYD per night

Guest favorite

Condo in Longboat Key

4.93 out of 5 average rating, 145 reviews

Beachfront Resort, Ocean View, Pool, Tennis, Gym

Beachfront on beautiful Longboat Key, this condominium offers all the amenities of a resort with the privacy and seclusion that has Silver Sands Beach Resort guests returning each year. Enjoy a coffee on your private patio looking at the Gulf of Mexico and the beach. Relax on our private beach, walk on our soft white sand, take a dip in our heated beachside pool, or enjoy complimentary chaise lounges and beach umbrellas while breathing in the fresh air. You can't get closer to the beach.

Nov 6 – 13

G$64,186 GYD per night

Guest favorite

Condo in Longboat Key

4.97 out of 5 average rating, 149 reviews

Charming Condo on the Coast!

This sublime oceanfront studio is directly on the pristine white sands and serene blue waters of the Gulf of Mexico in exclusive Longboat Key, Florida! Located on the second floor, overlooking the heated pool and ocean, this dreamy studio condo is optimal for sunset viewing from a private lanai. Take a 30-second walk to the pool and onward to the secluded beach with complimentary chairs and umbrellas. Enjoy a relaxing vacation at our peaceful condo at The Beach on Longboat Key Resort!

Nov 22 – 29

G$65,998 GYD per night

Guest favorite

Condo in Venice

4.82 out of 5 average rating, 219 reviews

Updated beachy condo - ready for you!

Conveniently located on Venice Island. This recently renovated, cozy, light an bright beachside condo has everything you need for your vacation. We have beach chairs, umbrella, towels and cooler. The efficiency unit has a full size frige, stovetop, microwave and convection oven. Comfy queen bed, Xfinity cable TV & Wifi in the condo. Park right in front of your unit, 1st floor - no stairs! Kayak rentals at the beach, bike rentals nearby. Bring your flip flops and sun tan lotion!

Dec 12 – 19

G$27,679 GYD per night

Guest favorite

Condo in Englewood

4.94 out of 5 average rating, 116 reviews

Gulf Side Condo Englewood Florida

A cozy 2 bed 2 bath condo with a full kitchen, dining area, living room, a king size master bedroom and a small 2nd bedroom. The coastal decor and furnishings create the ambiance of an island home. The condo opens onto a wide porch which has beautiful views of the Gulf of Mexico. Wander down the sandy path to a private beach and the turquoise waters of the Gulf. Enjoy sunsets from the porch or the beach. Unwind and let all of your cares float away on the Gulf breezes.

Dec 21 – 28

G$47,065 GYD per night

Superhost

Home in Englewood

4.89 out of 5 average rating, 9 reviews

Quaint Surf Cottage on Beach

This quaint surf cottage sits right on the beach, and it has all the amenities necessary for a comfortable extended stay. Situated right on the ocean, you will fall asleep every night to the sound of the waves. Enjoy time in your screen-porch with tables and chairs or a patio with chaise lounges where you can soak up the sun and witness some of the most spectacular sunsets on the Gulf coast. The Surf Cottage generally see repeat customers who love its convenience and privacy.

Dec 1 – 8

G$54,251 GYD per night

Guest favorite

Apartment in Englewood

4.92 out of 5 average rating, 125 reviews

Shoreview Beach House, Unit A

Relax at our Manasota Key beachfront getaway, while you enjoy the magnificent gulf and sunset views. This lovely triplex is GULF FRONT on a laid back stretch of beautiful Manasota Key, between Englewood Public Beach and Stump Pass. Our units have a beach cottage feel, and have beachfront views from the living areas. Enjoy your morning breakfast, while watching dolphins pass you by or a dinner watching the sunset from the patio.

Jan 4 – 11

G$39,890 GYD per night

Guest favorite

Condo in Siesta Key

4.93 out of 5 average rating, 181 reviews

Siesta key getaway!

perfect and very comfortable 4th floor condo with elevator, screened in lanai, fully stocked kitchen and full bath. laundry facilities on the premises, a tennis court. We supply beach chairs, umbrellas, a rolling cooler and big beach bag. There is a beautiful dock on the intercoastal side of us with picnic chairs, grills, and you may even see dolphins playing !

Jul 4 – 11

G$30,980 GYD per night