Fitness-friendly vacation rentals in Osprey

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Top-rated fitness-friendly rentals in Osprey

Guests agree: these fitness-friendly rentals are highly rated for location, cleanliness, and more.

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Guest favorite

Apartment in Siesta Key

4.99 out of 5 average rating, 143 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

Nov 19 – 26

G$94,501 GYD per night

Guest favorite

Guest suite in North Port

4.86 out of 5 average rating, 29 reviews

Plant Lovers Tranquil Paradise

A newly renovated, fully furnished studio in a house, with own private entrance, surrounded by a tropical garden in a safe and quiet neighborhood. Private bathroom with shower and oversized bathtub, walk-in closet with additional folding bed. Kitchenette comes equipped with a small fridge, microwave,hot plate,coffee maker, teapot,toaster,slow cooker,dishes,pots and pans. At the screened lanai there is a table with chairs where you can have a cup of coffee in the early morning with birdsongs.

Jun 12 – 19

G$14,089 GYD per night

Guest favorite

Home in Sarasota

4.87 out of 5 average rating, 133 reviews

5 minutes to private Siesta Key Beach + 2 pools

Best getaway, beach vacation, and staycation! The luxurious condo is on the 1st. floor and located on Siesta Key in a tropical setting. It is kid-friendly and has private access to its private beach on Siesta Key Beach within 5 minutes of walking distance (the Best Beach in the U.S.A.) with crystal white sand and turquoise waters of the Gulf of Mexico. There are two heated pools, barbeque areas, lighted pickleball and tennis courts, a fishing pier, a gym, and a sauna, all for your enjoyment.

Aug 23 – 30

G$65,134 GYD per night

Guest favorite

Condo in Venice

4.95 out of 5 average rating, 43 reviews

Lovely large one+ in the heart of downtown Venice

Large, quaint, quiet condo in the heart of downtown Venice Island. Short walking distance to all the idyllic downtown shops, restaurants, entertainment, bars, arts & a quick bike ride to an amazing beach. Bikes included. Very spacious & well equipped rental suitable for short or long-term visits. Large fully equipped kitchen. Lots of amenities & beach gear! Comfy king bed. Free parking. Venice Beach 1.1 miles / Sharkey's Restaurant & Pier 1.7 miles / Coffee shop & downtown just 3 blocks away.

Jul 11 – 18

G$27,050 GYD per night

Guest favorite

Condo in Siesta Key

4.96 out of 5 average rating, 276 reviews

On the Beach; Siesta Key SunBum Studio

STEPS TO YOUR OWN PRIVATE BEACH!! NO TRICKS or GIMMICKS LIKE OTHER LISTINGS on the KEY. This is the only studio in the Palm Bay Club tower on ground level with breathtaking views of the white sand and gulf waters. The Palm Bay Club offers 2 pools, hot tub, new gym, boat docks, fishing pier, outdoor grills, tennis/pickle ball courts; not to mention FREE parking+ beach lounge chairs. Enjoy 2 free bikes day rental with booking! You are sure to enjoy your time here on the #1 U.S. Beach.

Apr 3 – 10

G$95,448 GYD per night

Guest favorite

Condo in Siesta Key

4.83 out of 5 average rating, 122 reviews

Sarasota Surf & Racquet Club Siesta Key Condo

Sarasota Surf and Racquet Club is located on Siesta Key's award winning Crescent Beach. Our condo unit has all of the amenities of home for your convenience. The master bedroom has a king sized bed and it's own ensuite with walk-in shower. The second bedroom has 2 double beds and a large closet for all of your belongings. The complex has two heated pools, multiple charcoal grills and just steps away from the unit are 3 tennis courts and 2 pickle ball courts. Restaurants and shopping close by

Jan 12 – 19

G$85,319 GYD per night

Guest favorite

Home in Sarasota

4.98 out of 5 average rating, 144 reviews

Stunning home near Siesta w/ incredible pool area!

Welcome to The Palmieri - the ideal Sarasota family vacation destination! Minutes from DT, Siesta & Lido beach, our beautifully styled home features an incredible backyard with a heated saltwater pool, hot tub, fire pit, playland, and a shaded lounge. Spacious and open inside, with a fully equipped kitchen, and all the cozy feels of home. The finished garage houses beach supplies for your convenience, and thoughtful touches throughout combine comfort & luxury for an unforgettable experience.

Jul 11 – 18

G$104,294 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.

Dec 7 – 14

G$64,093 GYD per night

Superhost

Home in Nokomis

5.0 out of 5 average rating, 5 reviews

Sandy Beaches Minutes Away! Fun in the sun Resort

Only 3 miles from the beaches of tropical Nokomis Florida and right on Donna Bay! This resort features a BEAUTIFUL pool area, fitness center, dock for fishing, tennis, shuffle board, basket ball, volleyball and pickle ball courts, kayak rental for Donna Bay, mini golf, horse shoes, dog park, and bike trails. House has a cozy feel with an attached lanai and picnic table in the yard. Close to Nokomis beach, Siesta Key Americas #1 beach and Venice beach (shark tooth capital of the world).

Jun 21 – 28

G$23,811 GYD per night

Guest favorite

Condo in Siesta Key

4.96 out of 5 average rating, 104 reviews

2 Bed/2 Bath Condo Resort View on Siesta Key Beach

Amazing 2nd floor unit in building C at the Sarasota Surf & Racquet Club. This fully furnished 2 bed/ 2 bath condo offers a resort view and just steps away from the white sands of Siesta Key Beach. This unit is recently updated with an open floor plan, featuring stainless steel appliances, granite counter tops, kitchen bar with stools, living room, and dining room. This unit has flat screen tv's, ceiling fans, and maid service including linens and bath towels.

Sep 27 – Oct 4

G$74,610 GYD per night

Guest favorite

Guesthouse in Sarasota

4.88 out of 5 average rating, 96 reviews

Guest house w/heated salt water pool and Game Room

This special place is close to everything, 10 min to Beautiful Siesta Key and 15 to Longboat key. Brand new UTC mall is a 10 min drive. Be the first to enjoy our new renovations and upgrades!! Private free parking on property. Heated salt water pool and game room! Covered BBQ area with seating, bluetooth speakers, TV and Free wifi. Host can also decorate room for special occasions... birthdays, anniversary, valentines, etc...

Sep 14 – 21

G$21,518 GYD per night

Superhost

Apartment in Sarasota

4.84 out of 5 average rating, 116 reviews

Downtown Apartment w/ Pool Deck, Gym, & Coworking

This new construction apartment features an oversized kitchen island and a slider with views of Downtown Sarasota. Shared amenities include: a gym; sunset deck; massive roof deck with a pool; gazebo with big-screen TV, fireplace, and wet bar; a dog run; and access to the adjacent Cowork office space. Also on-site is Motoneko Cafe, a full-service coffee/ramen shop that also serves tea, espresso drinks, and snacks.

Dec 6 – 13

G$46,551 GYD per night